WO2019003934A1 - Composition de cristaux liquides polymérisable, et film optique l'utilisant et son procédé de production - Google Patents
Composition de cristaux liquides polymérisable, et film optique l'utilisant et son procédé de production Download PDFInfo
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- WO2019003934A1 WO2019003934A1 PCT/JP2018/022688 JP2018022688W WO2019003934A1 WO 2019003934 A1 WO2019003934 A1 WO 2019003934A1 JP 2018022688 W JP2018022688 W JP 2018022688W WO 2019003934 A1 WO2019003934 A1 WO 2019003934A1
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- 0 COC(C1(*)C(C2)C=CC2C1)=O Chemical compound COC(C1(*)C(C2)C=CC2C1)=O 0.000 description 3
- KOUXLNFYDZKAKO-UHFFFAOYSA-N CC(CC1=C)[U]C1=O Chemical compound CC(CC1=C)[U]C1=O KOUXLNFYDZKAKO-UHFFFAOYSA-N 0.000 description 1
- CZNIMHHTXVHMGF-UHFFFAOYSA-N COC(C1C(C2)C=CC2C1)=[U] Chemical compound COC(C1C(C2)C=CC2C1)=[U] CZNIMHHTXVHMGF-UHFFFAOYSA-N 0.000 description 1
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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
- 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
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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
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- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- 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
- G02F1/13363—Birefringent elements, e.g. for optical compensation
Definitions
- the present invention is useful as a liquid crystal device, a display, an optical component, a colorant, a marking for security, a member for laser emission, or an optical anisotropic member used for optical compensation of a liquid crystal display or the like, a reflective polarizing element, a component
- the present invention relates to a polymerizable liquid crystal composition, an optical film made of the composition, and an image display device using the optical film.
- the polymerizable liquid crystal composition is useful as a component of an optical anisotropic member, and the optical anisotropic member is applied to various liquid crystal displays as an optical film such as a polarizing film and a retardation film, for example.
- a polymerizable liquid crystal composition is applied to a substrate, and after drying the solvent, heating or active energy ray is performed in a state where the polymerizable liquid crystal composition is oriented by an alignment film or the like. It can be obtained by curing the polymerizable liquid crystal composition by irradiation.
- the liquid crystal panel itself is generally exposed to a high temperature of about 50 to 60 ° C. when the liquid crystal display is used, even if the initial color purity can be increased.
- the selective reflection wavelength range shifts to the minus side or the plus side with the use of the liquid crystal display, and the problem of the initial loss of color reproducibility occurs.
- the heat resistance is an important index showing the durability of the optical element, and it has been required that the selective reflection wavelength does not change after being left at high temperature.
- the adhesion of the anisotropic member to the substrate is also required without causing peeling from the substrate during transportation or cutting of the film.
- the problem to be solved by the present invention is a polymerizable liquid crystal composition suitable for an optical film excellent in adhesion to a base material and excellent in heat resistance with a small shift of selected wavelength due to heat history, and an optical film using the same It is an object of the present invention to provide a method of manufacturing the same and an image display apparatus using the optical film.
- the present inventors polymerize the polymerizable liquid crystal composition containing a specific bifunctional polymerizable liquid crystal compound, a chiral compound, and an oxime ester type polymerization initiator. It has been found that the cholestick liquid crystal film obtained by the present invention exhibits excellent heat resistance, and the present invention has been completed.
- P 121 and P 122 each independently represent a polymerizable functional group
- Sp 121 and Sp 122 each independently represent an alkylene group having 1 to 18 carbon atoms or a single bond
- the alkylene one -CH 2 in the group - or nonadjacent two or more -CH 2 - -COO are each independently -, - OCO- or --OCO-O-may be substituted by, said alkylene
- One or more hydrogen atoms of the group may be substituted by a halogen atom (a fluorine atom, a chlorine atom, a bromine atom, an iodine atom) or a CN group
- X 121 and X 122 each independently represent -O-, -S-, -OCH 2- , -CH 2 O-, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O- , -CO-
- A1, A2 and A3 are each independently 1,4-phenylene, 1,4-cyclohexylene, 1,4-cyclohexenyl, tetrahydropyran-2, 5-diyl group, 1,3-dioxane-2,5-diyl group, tetrahydrothiopyran-2,5-diyl group, 1,4-bicyclo (2,2,2) octylene group, decahydronaphthalene-2, 6-diyl group, pyridine-2,5-diyl group, pyrimidine-2,5-diyl group, pyrazine-2,5-diyl group, thiophene-2,5-diyl group-, 1,2,3,4- Tetrahydronaphthalene-2,6-diyl group, 2,6-naphthylene group, phenanthrene-2,7-diyl group, 9,10-dihydrophen
- P 221 represents a polymerizable functional group
- Sp 221 represents an alkylene group having 1 to 18 carbon atoms
- one —CH 2 — or two or more non-adjacent ones in the alkylene group -CH 2 - may be independently substituted by -O-, -COO-, -OCO- or -OCO-O-
- one or more hydrogen atoms of the alkylene group are halogens It may be substituted by an atom (a fluorine atom, a chlorine atom, a bromine atom, an iodine atom) or a CN group
- X 221 is -O-, -S-, -OCH 2- , -CH 2 O-, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -SCH 2- , -CH
- P 211 represents a polymerizable functional group
- a 211 and A 212 are each independently 1,4-phenylene, 1,4-cyclohexylene, bicyclo [2.2.2] octane-1,4-diyl, pyridine-2,5-diyl Group, pyrimidine-2,5-diyl group, naphthalene-2,6-diyl group, naphthalene-1,4-diyl group, tetrahydronaphthalene-2,6-diyl group, decahydronaphthalene-2,6-diyl group or Represents a 1,3-dioxane-2,5-diyl group, which may be unsubstituted or substituted by one or more substituents L, L represents a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorosul
- the present invention further relates to an optical film composed of a cured product of the polymerizable liquid crystal composition.
- the present invention further relates to a method for producing an optical film, which comprises applying the above-mentioned polymerizable liquid crystal composition onto a substrate, drying it, and then irradiating it with ultraviolet light.
- the present invention further relates to an image display device using the optical film.
- a polymerizable liquid crystal composition suitable for an optical film excellent in adhesion to a substrate and having a small shift of a selected wavelength due to thermal history and excellent in heat resistance, an optical film using the same, and a method for producing the same can provide an image display device using the optical film.
- FIG. 1 is a schematic view showing the concept of the central value ( ⁇ ) of the selective reflection wavelength and the half width ( ⁇ ) thereof by measuring the spectral transmittance.
- the “liquid crystal” of the polymerizable liquid crystal composition is a state in which the organic liquid is removed after the polymerizable liquid crystal composition is applied to a substrate. Is intended to exhibit liquid crystallinity.
- “liquid crystal” of the polymerizable liquid crystal compound is a compound of only one kind of polymerizable liquid crystal compound to be used, and when it is intended to exhibit liquid crystallinity or mixed with other liquid crystal compounds Is intended to exhibit liquid crystallinity.
- the polymerizable liquid crystal composition can be polymerized (filmized) by performing polymerization treatment by irradiation with light such as ultraviolet light, heating, or a combination thereof.
- (Bifunctional polymerizable liquid crystal compound) (Bifunctional Polymerizable Liquid Crystal Compound Represented by General Formula (I-2))
- the bifunctional polymerizable liquid crystal compound used in the present invention is represented by the following general formula (I-2).
- P 121 and P 122 each independently represent a polymerizable functional group
- Sp 121 and Sp 122 each independently represent an alkylene group having 1 to 18 carbon atoms or a single bond
- the alkylene one -CH 2 in the group - or nonadjacent two or more -CH 2 - -COO are each independently -, - OCO- or --OCO-O-may be substituted by, said alkylene
- One or more hydrogen atoms of the group may be substituted by a halogen atom (preferably a fluorine atom, a chlorine atom, a bromine atom, an iodine atom) or a CN group
- X 121 and X 122 are each independently -O-, -S-, -OCH 2- , -CH 2 O-, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO- O-, -CO
- formula (P-1), formula (P-2), formula (P-3), formula (P-4), formula (P-8), formula (P) -10), formula (P-12) or formula (P-15) is preferable, and formula (P-1), formula (P-2), formula (P-3), formula (P-4), formula (P-4) P-8) or Formula (P-10) is more preferable, Formula (P-1), Formula (P-2) or Formula (P-3) is more preferable, and Formula (P-1) or Formula (P-) 2) is particularly preferred.
- Sp 121 and Sp 122 preferably each independently represent an alkylene group having 1 to 15 carbon atoms, and one —CH 2 — or adjacent group in the alkylene group
- Two or more non-substituted -CH 2 - may each independently be substituted by -COO-, -OCO- or -OCO-O-, and one or more hydrogen atoms of the alkylene group May be substituted by a halogen atom (preferably a fluorine atom, a chlorine atom, a bromine atom, an iodine atom) or a CN group
- Sp 11 and Sp 12 each independently represent an alkylene group having 1 to 12 carbon atoms it is more preferable that represents, one -CH 2 in the alkylene group - or nonadjacent two or more -CH 2 - are each independently -O -, - COO -, - OCO- or -O O-O-by may be substituted.
- A1, A2 and A3 are each independently 1,4-phenylene, 1,4-cyclohexylene, 1,4-cyclohexenyl, tetrahydropyran-2, 5-diyl group, 1,3-dioxane-2,5-diyl group, tetrahydrothiopyran-2,5-diyl group, 1,4-bicyclo (2,2,2) octylene group, decahydronaphthalene-2, 6-diyl group, pyridine-2,5-diyl group, pyrimidine-2,5-diyl group, pyrazine-2,5-diyl group, thiophene-2,5-diyl group-, 1,2,3,4- Tetrahydronaphthalene-2,6-diyl group, 2,6-naphthylene group, phenanthrene-2,7-diyl group, 9,10-dihydrophen
- A1, A2 and A3 are each independently 1,4-phenylene, 1,4-cyclohexylene, 2,6-naphthylene (the 1,4-phenylene, 2,6-naphthylene) Preferably represents a substituent L 2 ).
- P 121 , Sp 121 , X 121 , q 121 , X 122 , Sp 122 , q 122 and P 122 each represent the same as the definition of the general formula (I-2) above
- A11, A12 and A13, A2 and A3 represent the same as the definitions of A1 to A3 in the general formula (I-2-b), and they may be the same or different
- Z11, Z12, Z13 and Z2 respectively represent the same as the definitions of Z1 and Z2 in the general formula (I-2-b), and they may be the same or different.
- the compounds represented by the above general formulas (I-2-1) to (I-2-4) include the following general formula (I-2-1-1) to general formulas (I-2-1-21) Examples of the compound represented by) are listed, but not limited thereto.
- R d and R e each independently represent a hydrogen atom or a methyl group
- the cyclic group is one or more of F, Cl, CF 3 , OCF 3 , CN, an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, and 1 to 8 carbon atoms as a substituent.
- Alkanoyl group C 1 -C 8 alkanoyl group, C 1 -C 8 alkoxycarbonyl group, C 2 -C 8 alkenyl group, C 2 -C 8 alkenyloxy group, carbon atom And may have an alkenoyl group of 2 to 8 and an alkenoyl group of 2 to 8 carbon atoms, m1, m2, m3 and m4 each independently represent an integer of 0 to 18, but each independently preferably represents an integer of 0 to 8, and n1, n2, n3 and n4 each independently represent 0 or 1 Represent.
- the bifunctional polymerizable liquid crystal compound represented by the above general formula (I-2) may be used singly or in combination, but the total of the bifunctional polymerizable liquid crystal compounds represented by the general formula (I-2)
- the content is preferably 0 to 50% by mass, and more preferably 0 to 30% by mass, of the total amount of polymerizable liquid crystal compounds used in the polymerizable liquid crystal composition.
- a chiral compound when added to the polymerizable liquid crystal composition, the compound has an asymmetric structure or has a substituent in the mesogen skeleton to facilitate the development of a twisted nematic phase or a cholesteric phase.
- the compounds represented by the general formula (I-2-1-1) to the general formula (I-2-1-21) have the following general formula (I-2-2-1) to the general formula Examples of the compound represented by (I-2-2-24) can be mentioned, but the present invention is not limited thereto.
- the bifunctional polymerizable liquid crystal compound represented by the above general formula (I-2) may be used singly or in combination, but the total of the bifunctional polymerizable liquid crystal compounds represented by the general formula (I-2)
- the content is preferably 5 to 50% by mass, more preferably 5 to 40% by mass, and particularly preferably 5 to 30% by mass, from the viewpoint of adhesion and heat resistance. It is most preferable to contain mass%.
- Bifunctional Polymerizable Liquid Crystal Compound Represented by General Formula (I-1) Among the compounds represented by the general formula (1-2) described above, the polymerizable liquid crystal compound represented by the following general formula (I-1) is more preferable.
- P 111 and P 112 each independently represent a polymerizable functional group
- Sp 111 and Sp 112 represents an alkylene group or a single bond of 1 to 18 carbon atoms independently, one -CH 2 in the alkylene group - or nonadjacent two or more -CH 2 -
- Each may be independently substituted by -COO-, -OCO- or -OCO-O-, and one or more hydrogen atoms possessed by the alkylene group are substituted by a halogen atom or a CN group
- X 111 and X 112 are each independently -O-, -S-, -OCH 2- , -CH 2 O-, -CO-, -COO-, -OCO-, -CO-S-, -S -CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -SCH 2- , -CH 2 S-, -CF 2 O-, -OC
- formula (P-1), formula (P-2), formula (P-3), formula (P-4), formula (P-8), formula (P) -10), formula (P-12) or formula (P-15) is preferable, and formula (P-1), formula (P-2), formula (P-3), formula (P-4), formula (P-4) P-8) or Formula (P-10) is more preferable, Formula (P-1), Formula (P-2) or Formula (P-3) is more preferable, and Formula (P-1) or Formula (P-) 2) is particularly preferred.
- q111 and q112 each independently represent 0 or 1, but 1 is particularly preferable.
- Sp 111 and Sp 112 each independently represent an alkylene group having 1 to 18 carbon atoms or a single bond, and one —CH 2 — in the alkylene group or adjacent thereto Two or more -CH 2 -may be each independently substituted by -COO-, -OCO- or -OCO-O-, and one or more hydrogen atoms of the alkylene group are And may be substituted by a halogen atom (preferably a fluorine atom, a chlorine atom, a bromine atom, an iodine atom) or a CN group.
- a halogen atom preferably a fluorine atom, a chlorine atom, a bromine atom, an iodine atom
- Sp 111 and Sp 112 each independently represent an alkylene group having 1 to 12 carbon atoms, and one —CH 2 — or two or more not adjacent to each other in the alkylene group.
- -CH 2 - may be independently substituted by -COO-, -OCO- or -OCO-O-.
- Sp 111 and Sp 112 each independently represent an alkylene group having 1 to 8 carbon atoms.
- each of A 11 and A 12 independently represents a 1,4-phenylene group, a 1,4-cyclohexylene group, bicyclo [2.2.2] octane-1,4-diyl Group, pyridine-2,5-diyl group, pyrimidine-2,5-diyl group, naphthalene-2,6-diyl group, naphthalene-1,4-diyl group, tetrahydronaphthalene-2,6-diyl group, decahydro It represents a naphthalene-2,6-diyl group or a 1,3-dioxane-2,5-diyl group, which may be unsubstituted or substituted by one or more substituents L.
- a 11 and A 12 may each be independently unsubstituted or may be substituted by one or more substituents L, 1, 4 -Phenylene group, 1,4-cyclohexylene group, bicyclo [2.2.2] octane-1,4-diyl group, naphthalene-2,6-diyl group or naphthalene-1,4-diyl group
- substituents L 1, 4 -Phenylene group, 1,4-cyclohexylene group, bicyclo [2.2.2] octane-1,4-diyl group, naphthalene-2,6-diyl group or naphthalene-1,4-diyl group
- each of Formulas (A-1) to (A-16) below independently represents
- each of A 11 and A 12 independently represents a group selected from the above formulas (A-1) to (A-7) and (A-10). It is further preferred that each of A 11 and A 12 present be independently and even more preferably represent a group selected from Formulas (A-1) to (A-7) above, A 11 and A 12 present It is particularly preferable that each independently represents a group selected from the above formulas (A-1) to (A-4). In the case where A 11 there are a plurality thereof may be different even in the same, A 12 may be those when there are multiple different be the same.
- L represents a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorosulfuranyl group, a nitro group, a cyano group, an isocyano group, an amino group, a hydroxyl group, a mercapto group, methyl Amino group, dimethylamino group, diethylamino group, diisopropylamino group, trimethylsilyl group, dimethylsilyl group, thioisocyano group, phenyl group which may be substituted, phenylalkyl group which may be substituted, cyclohexyl which may be substituted
- the substituent L is a fluorine atom, a chlorine atom, a pentafluorosulfuranyl group, a nitro group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, or any group
- m111 and m112 each independently represent an integer of 0 to 2, but m111 + m112 is preferably 1 or 2, m111 + m112 is more preferably 2, and both m111 and m112 are 1 Being particularly preferred.
- each of R 1 and R 2 independently represents a hydrogen atom, a fluorine atom, a cyano group, a hydroxyl group, a nitro group, an alkyl group having 1 to 10 carbon atoms, or 1 carbon atom
- any one of R 1 and R 2 represents other than a hydrogen atom.
- a preferable group other than a hydrogen atom a fluorine atom, a cyano group, a hydroxyl group, a nitro group, an alkyl group having 1 to 6 carbon atoms, or an alkoxy group having 1 to 6 carbon atoms is more preferable.
- R 1 or R 2 represents other than a hydrogen atom, it is preferable that one of R 1 and R 2 represents a hydrogen atom, and the other represents a non-hydrogen atom.
- R 2 is preferably linked to a substituent L which A 12 present adjacently has, to thereby represent a cyclic group.
- R e and R d each independently represent a hydrogen atom or a methyl group
- m 1 and m 2 are each independently N1 and n2 each independently represent 0 or 1.
- the compounds of the general formula (1-1-1) are most preferable.
- the bifunctional polymerizable liquid crystal compound represented by the above general formula (I-1) may be used alone or in combination, but the total of the bifunctional polymerizable liquid crystal compounds represented by the general formula (I-1)
- the content is preferably 5 to 50% by mass, more preferably 5 to 40% by mass, and more preferably 5 to 30% by mass, based on the total amount of polymerizable liquid crystal compounds used in the polymerizable liquid crystal composition. It is particularly preferable to do it, and it is most preferable to contain 5 to 20% by mass.
- a bifunctional polymerizable liquid crystal compound represented by the above general formula (I-2) preferably a bifunctional polymerizable liquid crystal compound represented by the general formula (I-1)
- a monofunctional polymerizable liquid crystal compound represented by the following general formula (II-2) as a second component is used in combination.
- P 221 represents a polymerizable functional group
- Sp 221 represents an alkylene group having 1 to 18 carbon atoms
- one —CH 2 — or two or more non-adjacent groups in the alkylene group CH 2 - may be each independently substituted by -O-, -COO-, -OCO- or -OCO-O-
- one or more hydrogen atoms of the alkylene group are halogen atoms (Fluorine atom, chlorine atom, bromine atom, iodine atom) or CN group may be substituted
- X 221 is -O-, -S-, -OCH 2- , -CH 2 O-, -CO-,- COO -, - OCO -, - CO-S -, - S-CO -, - OCO-O -, - CO-NH -, - NH-CO -, - SCH 2 -, - CH 2 S
- P 221 represents a polymerizable functional group, but the following formulas (P-1) to (P-17)
- formula (P-1), formula (P-2), formula (P-3), formula (P-4), formula (P-8), formula (P) -10), formula (P-12) or formula (P-15) is preferable, and formula (P-1), formula (P-2), formula (P-3), formula (P-4), formula (P-4) P-8) or Formula (P-10) is more preferable, Formula (P-1), Formula (P-2) or Formula (P-3) is more preferable, and Formula (P-1) or Formula (P-) 2) is particularly preferred.
- Sp 221 preferably represents an alkylene group having 1 to 8 carbon atoms, and one —CH 2 — or two or more nonadjacent groups in the alkylene group CH 2 -may be each independently substituted by -O-, -COO-, -OCO- or -OCO-O-, and one or more hydrogen atoms of the alkylene group are halogen atoms (Fluorine atom, chlorine atom, bromine atom, iodine atom) or CN group may be substituted.
- halogen atoms Fluorine atom, chlorine atom, bromine atom, iodine atom
- MG 221 represents a mesogenic group, and is represented by general formula (II-2-b)
- A1, A2 and A3 are each independently 1,4-phenylene, 1,4-cyclohexylene, 1,4-cyclohexenyl, tetrahydropyran-2,5-diyl, 1, 3-Dioxane-2,5-diyl group, tetrahydrothiopyran-2,5-diyl group, 1,4-bicyclo (2,2,2) octylene group, decahydronaphthalene-2,6-diyl group, pyridine- 2,5-diyl group, pyrimidine-2,5-diyl group, pyrazine-2,5-diyl group, thiophene-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
- P 221 , Sp 221 , X 221 and R 221 each represent the same as the definition of the above general formula (II-2), A11, A12, A13, A2 and A3 represent the same as the definitions of A1 to A3 in the general formula (II-2-b), and they may be the same or different, Z11, Z12, Z13 and Z2 represent the same as the definitions of Z1 to Z3 in the general formula (II-2-b), and they may be the same or different,
- the compounds represented by the above general formulas (II-2-1) to (II-2-4) include the following general formulas (II-2-1-1) to (II-2-1-26) Examples of the compound represented by) are listed, but not limited thereto.
- R c represents a hydrogen atom or a methyl group
- m represents an integer of 1 to 8
- n is 0 or represents 1
- R 221 is the same meaning as defined in formula (II-2-1) ⁇ (II -2-4)
- R 221 represents a hydrogen atom, a halogen atom (fluorine atom, chlorine Atom, bromine atom, iodine atom), cyano group, one -CH 2 -may be substituted by -O-, -CO-, -COO-, -OCO-, having 1 to 6 carbon atoms It preferably represents a linear alkyl group or a linear alkenyl group having 1 to 6 carbon atoms.
- the cyclic group is one or more of F, Cl, CF 3 , OCF 3 , CN group as a substituent, Alkyl group having 1 to 8 carbon atoms, alkoxy group having 1 to 8 carbon atoms, alkanoyl group having 1 to 8 carbon atoms, alkanoyloxy group having 1 to 8 carbon atoms, alkoxycarbonyl having 1 to 8 carbon atoms Group, alkenyl group having 2 to 8 carbon atoms, alkenyloxy group having 2 to 8 carbon atoms, alkenoyl group having 2 to 8 carbon atoms, and alkenoyl group having 2 to 8 carbon atoms good.
- the monofunctional polymerizable liquid crystal compound represented by the above general formula (II-2) may be used alone or in combination, but the total of monofunctional polymerizable liquid crystal compounds represented by the general formula (II-2)
- the content is preferably 30 to 90% by mass, more preferably 40 to 90% by mass, and more preferably 45 to 90% by mass, of the total amount of polymerizable liquid crystal compounds used in the polymerizable liquid crystal composition. It is particularly preferable to do it, and it is most preferable to contain 50 to 90% by mass.
- the half width ( ⁇ ) of the wavelength which is expressed by the relation and shows selective reflection is expressed by the product of the birefringence anisotropy ( ⁇ n) of the polymerizable liquid crystal composition and p.
- the polymerizable liquid crystal composition When the polymerizable liquid crystal composition is polymerized by containing a polymerizable liquid crystal compound having one polymerizable functional group, the mesogen skeleton portion present in the polymerizable liquid crystal compound represented by each of the general formulas is partially contained.
- the alignment property is not uniform, and a polymer having a low alignment order can be obtained, so that the birefringence anisotropy ( ⁇ n) can be suppressed low, and the wavelength width ( ⁇ ) of selective reflection can be reduced.
- P 211 represents a polymerizable functional group
- a 211 and A 212 each independently represent a 1,4-phenylene group, a 1,4-cyclohexylene group, or a bicyclo [2.
- formula (P-1), formula (P-2), formula (P-3), formula (P-4), formula (P-8), formula (P) -10), formula (P-12) or formula (P-15) is preferable, and formula (P-1), formula (P-2), formula (P-3), formula (P-4), formula (P-4) P-8) or Formula (P-10) is more preferable, Formula (P-1), Formula (P-2) or Formula (P-3) is more preferable, and Formula (P-1) or Formula (P-) 2) is particularly preferred.
- each of A 211 and A 212 independently represents a 1,4-phenylene group, a 1,4-cyclohexylene group, a bicyclo [2.2.2] octane-1,4-diyl Group, pyridine-2,5-diyl group, pyrimidine-2,5-diyl group, naphthalene-2,6-diyl group, naphthalene-1,4-diyl group, tetrahydronaphthalene-2,6-diyl group, decahydro It represents a naphthalene-2,6-diyl group or a 1,3-dioxane-2,5-diyl group, which may be unsubstituted or substituted by one or more substituents L.
- a 211 and A 212 may each be independently unsubstituted or may be substituted by one or more substituents L, 1, 4 -Phenylene group, 1,4-cyclohexylene group, bicyclo [2.2.2] octane-1,4-diyl group, naphthalene-2,6-diyl group or naphthalene-1,4-diyl group
- substituents L 1, 4 -Phenylene group, 1,4-cyclohexylene group, bicyclo [2.2.2] octane-1,4-diyl group, naphthalene-2,6-diyl group or naphthalene-1,4-diyl group
- each of Formulas (A-1) to (A-16) below independently represents
- At least one of A 211 and A 212 represents a group selected from Formula (A-2) or Formula (A-10) above, and the remainder is More preferably, each independently represents a group selected from the above formulas (A-1) to (A-7) and (A-10), and at least one of A 211 and A 212 is any of the above It is still more preferable to represent a group represented by Formula (A-2), and the remaining each independently represent a group selected from Formula (A-1) to Formula (A-7) above, A 211 and At least one of A 212 represents a group represented by Formula (A-2) above, and the rest each independently represent a group selected from Formula (A-1) to Formula (A-4) above. It is particularly preferred to represent. In addition, when two or more A 212 exists, they may be same or different.
- L represents a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorosulfuranyl group, a nitro group, a cyano group, an isocyano group, an amino group, a hydroxyl group, a mercapto group, a methyl group Amino group, dimethylamino group, diethylamino group, diisopropylamino group, trimethylsilyl group, dimethylsilyl group, thioisocyano group, phenyl group which may be substituted, phenylalkyl group which may be substituted, cyclohexyl which may be substituted
- the substituent L is a fluorine atom, a chlorine atom, a pentafluorosulfuranyl group, a nitro group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, or any group
- m211 represents an integer of 1 to 3, but m211 preferably represents 1 or 2, and m211 preferably represents 1.
- T 211 is a hydrogen atom, -OH group, -SH group, -CN group, -COOH group, -NH 2 group, -NO 2 group, -COCH 3 group, -O ( CH 2 ) n CH 3 or-(CH 2 ) n CH 3 (n represents an integer of 0 to 20), but T 211 is a hydrogen atom, -O (CH 2 ) n CH 3 or-( It is more preferable to represent CH 2 ) n CH 3 (n represents an integer of 0 to 10), and T 211 is —O (CH 2 ) n CH 3 or — (CH 2 ) n CH 3 (n is It is particularly preferred to represent an integer of 0-8.
- the monofunctional polymerizable liquid crystal compound represented by the above general formula (II-1) may be used alone or in combination of two or more, but from the viewpoint of adhesion, a monofunctional polymerization represented by the general formula (II-1)
- the total content of the functional liquid crystal compounds is preferably 5 to 50% by mass, more preferably 5 to 40% by mass, of the total amount of polymerizable liquid crystal compounds used in the polymerizable liquid crystal composition. It is particularly preferable to contain up to 40% by mass, and it is most preferable to contain 15 to 35% by mass.
- the compound represented by the general formula (I-1) is used as the bifunctional polymerizable liquid crystal compound, and the compound represented by the general formula (II-1) and the general as the monofunctional polymerizable liquid crystal compound.
- the compound represented by the formula (II-2) is used in combination, and in this case, the compound represented by the general formula (II) is a monofunctional component in the total amount of the polymerizable liquid crystal compound used in the polymerizable liquid crystal composition.
- the total of the compounds represented by formula (II-2) is in the range of 50 to 95% by mass, in the range of 60 to 95% by mass, particularly in the range of 70 to 95% by mass. It is preferable from the point of adhesiveness and heat resistance.
- the polymerizable liquid crystal composition of the present invention may contain a polymerizable liquid crystal compound having three or more polymerizable functional groups in the molecule, as long as the physical properties are not impaired.
- Examples of the polymerizable liquid crystal compound having three or more polymerizable functional groups in the molecule include compounds represented by the following general formula (III-1) and general formula (III-2).
- P 31 to P 35 each independently represent a polymerizable functional group
- Sp 31 to S 35 each independently represent an alkylene group having 1 to 18 carbon atoms or a single bond
- the alkylene one -CH 2 in the group - or nonadjacent two or more -CH 2 - are each independently -O -, - COO -, - OCO- or --OCO-O-substituted by
- one or more hydrogen atoms of the alkylene group may be substituted by a halogen atom (preferably a fluorine atom, a chlorine atom, a bromine atom, an iodine atom) or a CN group
- X 31 to X 35 Are each independently -O-, -S-, -OCH 2- , -CH 2 O-, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-,- O-CO-O-, -
- formulas (P-2-1), (P-2-2), (P-2-7), (P-2-12), ( P-2-13) is preferable, and formulas (P-2-1) and (P-2-2) are more preferable.
- Sp 31 to Sp 35 each preferably independently represent an alkylene group having 1 to 15 carbon atoms, and it is preferable that 1 to 15 carbon atoms be contained in the alkylene group.
- number of -CH 2 - or nonadjacent two or more -CH 2 - are each independently -O -, - COO -, - OCO- or --OCO-O-may be substituted by, said alkylene
- One or more hydrogen atoms of the group may be substituted by a halogen atom (preferably a fluorine atom, a chlorine atom, a bromine atom, an iodine atom) or a CN group
- Sp 31 to Sp 35 are each independently Te, more preferably represents an alkylene group having 1 to 12 carbon atoms, one -CH 2 in the alkylene group - or nonadjacent two or more -CH 2 - are each independently -O -,- OO -,
- A1, A2 and A3 are each independently 1,4-phenylene, 1,4-cyclohexylene, 1,4-cyclohexenyl, tetrahydropyran-2,5-diyl, 1,3 -Dioxane-2,5-diyl group, tetrahydrothiopyran-2,5-diyl group, 1,4-bicyclo (2,2,2) octylene group, decahydronaphthalene-2,6-diyl group, pyridine-2 , 5-diyl group, pyrimidine-2,5-diyl group, pyrazine-2,5-diyl group, thiophene-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
- A1, A2 and A3 each independently represent a 1,4-phenylene group, a 1,4-cyclohexylene group or a 2,6-naphthylene group.
- Examples of the general formula (III) include the following general formula (III-1-1) to general formula (III-1-8) and general formula (III-2-1) to general formula) III-2-2)
- the compound represented can be mentioned, it is not necessarily limited to the following general formula.
- P 31 to P 35 , Sp 31 to Sp 35 , X 31 to X 35 and q 31 to q 39 MG 31 are respectively the same as the definitions of the general formula (III-1) to the general formula (III-2)
- Z11, Z12, Z13 and Z2 respectively represent the same as the definitions of Z1 and Z2 in the general formula (III-A), and they may be the same or different.
- Examples of the compounds represented by the above general formula (III-1-1) to general formula (III-1-8), general formula (III-2-1) and general formula (III-2-2) include the following:
- the compounds represented by the general formulas (III-9-1) to (III-9-6) are exemplified, but not limited thereto.
- R f , R g and R h each independently represent a hydrogen atom or a methyl group
- R i , R j and R k Each independently represents a hydrogen atom, a halogen atom (preferably a fluorine atom, a chlorine atom, a bromine atom, an iodine atom), an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, or a cyano group
- Group is an alkyl group having 1 to 6 carbon atoms or an alkoxy group having 1 to 6 carbon atoms, all of which are unsubstituted or one or more halogen atoms (preferably a fluorine atom or a chlorine atom)
- the cyclic group may be substituted by one or more of F, Cl, CF 3 , OCF 3 , CN, an alkyl group having 1 to 8 carbon atoms, Alkoxy
- the polyfunctional polymerizable liquid crystal compound having three or more polymerizable functional groups can be used alone or in combination.
- the total content of the polyfunctional polymerizable liquid crystal compound having three polymerizable functional groups in the molecule is contained in the range of 20% by mass or less based on the total amount of the polymerizable liquid crystal compound used for the polymerizable liquid crystal composition In particular, the content is preferably 10% by mass or less, particularly preferably 5% by mass or less.
- the polymerizable liquid crystal composition of the present invention may be added with a compound containing a mesogenic group not having a polymerizable group, and a normal liquid crystal device such as STN (super twisted nematic) liquid crystal, The compound used for TN (twisted nematic) liquid crystal, TFT (thin film transistor) liquid crystal etc. is mentioned.
- the compound containing a mesogenic group having no polymerizable functional group is preferably a compound represented by the following general formula (5).
- the mesogenic group or mesogenic supporting group represented by MG3 has the general formula (5-b)
- a 1 d , A 2 d and A 3 d are each independently a 1,4-phenylene group, a 1,4-cyclohexylene group, a 1,4-cyclohexenyl group, a tetrahydropyran-2,5-diyl group 1,3-Dioxane-2,5-diyl group, tetrahydrothiopyran-2,5-diyl group, 1,4-bicyclo (2,2,2) octylene group, decahydronaphthalene-2,6-diyl group , Pyridine-2,5-diyl group, pyrimidine-2,5-diyl group, pyrazine-2,5-diyl group, thiophene-2,5-diyl group-, 1,2,3,4-tetrahydronaphthalene-2 , 6-diyl group, 2,6-naphthylene group, phenanthrene-2,
- Ra and Rb each independently represent a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, an alkenyl group having 1 to 6 carbon atoms, or a cyano group, and these groups each have 1 carbon atom
- an alkyl group of -6 or an alkoxy group having 1 to 6 carbon atoms all may be unsubstituted or substituted by one or more halogen atoms.
- the total content of the compounds having a mesogenic group is preferably 0% by mass or more and 20% by mass or less with respect to the total amount of the polymerizable liquid crystal composition, and when used, preferably 1% by mass or more, 2 The content is preferably 5% by mass or more, preferably 15% by mass or less, and more preferably 10% by mass or less.
- the polymerizable liquid crystal composition in the present invention contains a chiral compound which may exhibit liquid crystallinity or non-liquid crystallinity in order to impart cholesteric liquid crystallinity to the obtained optical film. Among the chiral compounds, it is preferable to use a polymerizable chiral compound having a polymerizability.
- the polymerizable chiral compound used in the present invention preferably has one or more polymerizable functional groups.
- a compound for example, JP-A-11-193287, JP-A-2001-158788, JP-A-2006-52669, JP-A-2007-269639, JP-A-2007-269640, 2009
- JP-84178 and the like which contain a chiral saccharide such as isosorbide, isomannitol, glucoside and the like, and a rigid site such as 1,4-phenylene group 1,4-cyclohexene group, and a vinyl group
- a polymerizable chiral compound having a polymerizable functional group such as an acryloyl group, a (meth) acryloyl group, or a maleimide group
- a polymerizable chiral compound comprising a terpenoid derivative as described in JP-A-8-239666; NATURE VOL 35 467-469 pages (
- the following general formula (3-1) to general formula (3-4) can be mentioned as large chiral compounds of helical twisting power (HTP), and general formulas (3-1) to general formula It is more preferable to use a chiral compound selected from (3-3), and among chiral compounds selected from general formula (3-1) to general formula (3-3), a compound represented by the following general formula (3-a) It is particularly preferable to use a polymerizable chiral compound having a polymerizable group that is represented, and a compound in which R 3a and R 3b in the general formula (3-1) are (P1) is particularly preferable.
- HTP helical twisting power
- Sp 3a and Sp 3b each independently represent an alkylene group having 0 to 18 carbon atoms
- the alkylene group is a carbon atom having one or more halogen atoms, a CN group, or a polymerizable functional group may be substituted by an alkyl group having 1 to 8, two or more of CH 2 groups, independently of one another each of the present in the radical is not one CH 2 group or adjacent, each other oxygen atom -O-, -S-, -NH-, -N (CH 3 )-, -CO-, -COO-, -OCO-, -OCOO-, -SCO-, -COS- in a form not directly bound to Or -C ⁇ C- may be substituted
- A1, A2, A3, A4, A5 and A6 are each independently a 1,4-phenylene group, a 1,4-cyclohexylene group, a 1,4-cyclohexenyl group, a tetrahydropyran
- A1, A2, A3, A4, A5 and A6 each preferably independently represent a 1,4-phenylene group, a 1,4-cyclohexylene group or a 2,6-naphthylene group, and one or more as a substituent F, CN, an alkyl group having 1 to 8 carbon atoms, or an alkoxy group having 1 to 8 carbon atoms.
- n, l, k and s each independently represent 0 or 1;
- R 3a and R 3b each represent a hydrogen atom, a halogen atom, a cyano group or an alkyl group having 1 to 18 carbon atoms, and
- P 3a represents a polymerizable functional group
- P 3a preferably represents a substituent selected from polymerizable groups represented by the following formulas (P-1) to (P-20).
- formula (P-1) or formula (P-2), (P-7), (P-12), (P-13) are preferred, and formulas (P-1), (P-7) and (P-12) are more preferred.
- polymerizable chiral compound may include compounds (3-5) to (3-26), but are not limited to the following compounds.
- m, n, k and l each independently represent an integer of 1 to 18, R 1 to R 4 each independently represent a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or 1 to 6 carbon atoms And an alkoxy group, a carboxy group or a cyano group.
- R 1 to R 4 each independently represent a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or 1 to 6 carbon atoms And an alkoxy group, a carboxy group or a cyano group.
- these groups are an alkyl group having 1 to 6 carbon atoms or an alkoxy group having 1 to 6 carbon atoms, all may be unsubstituted or may be substituted by one or more halogen atoms. .
- polymerizable chiral compounds represented by the above general formulas (3-5) to (3-26) as a large chiral compound having a helical twisting power (HTP), a general formula (3-5) to a general formula ( 3-9), General Formula (3-12) to General Formula (3-14), General Formula (3-16) to General Formula (3-18), (3-25), and (3-26) It is particularly preferable to use the polymerizable chiral compounds that are represented, and it is even more preferable to use the polymerizable chiral compounds that are represented by (3-8), (3-25), and (3-26).
- HTP helical twisting power
- the above-mentioned chiral compound is used for the polymerizable liquid crystal composition in order to give cholesteric property to the obtained optical film and obtain an optical film having good transparency. It is preferable to use 0.5 to 20 parts by mass, more preferably 1 to 15 parts by mass, and particularly preferably 1.5 to 10 parts by mass with respect to 100 parts by mass of the total of the compounds.
- the polymerizable liquid crystal composition in the present invention preferably contains a photopolymerization initiator.
- a photopolymerization initiator is preferably an acylphosphine oxide type photopolymerization initiator or an ⁇ -aminoalkylphenone type initiator from the viewpoint of heat resistance.
- a photopolymerization initiator specifically, as an acylphosphine oxide photopolymerization initiator, 2,4,6-trimethylbenzoyl-diphenyl-phosphine oxide ("IRGACURE TPO” manufactured by BASF Corp.), bis (2,4,6-trimethylbenzoyl) -phenyl phosphine oxide (“IRGACURE 819” manufactured by BASF Corp.), and as an ⁇ -aminoalkylphenone initiator, 2-methyl-1- (4-methylthiophenyl) -2 -Morpholinopropan-1-one ("IRGACURE 907" manufactured by BASF), 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butanone-1 (“IRGACURE 369E” manufactured by BASF), 2- (Dimethylamino) -2-[(4-methylphenyl) methyl] -1- [4- (4-) Ruhoriniru) phenyl]
- photopolymerization initiators may be used in combination, and as such photopolymerization initiators, "Lucirin TPO", “Darocure 1173", “Darocure MBF” or “Esacure 1001M” manufactured by LAMBSON, “Esacure” KIP150 “,” Speed Cure BEM “,” Speed Cure BMS “,” Speed Cure MBP “,” Speed Cure PBZ “,” Speed Cure ITX “,” Speed Cure DETX “,” Speed Cure EBD “,” Speed Cure MBB “ , “Speed Cure BP” or “Kaya Cure DMBI” manufactured by Nippon Kayaku Co., Ltd., “TAZ-A” manufactured by Nippon Shiber Hegner (now DKSH), "ADEKA OPTOMER SP-152” manufactured by ADEKA, “ADEKA OPTO” Mer SP-170, "Adeka Optomer N-1414", “Adé Optomer N-1606 “,” Adeka Opto
- the amount of the photopolymerization initiator used is preferably 0.1 to 10 parts by mass, and more preferably 0.5 to 7 parts by mass with respect to 100 parts by mass of the polymerizable liquid crystal compound contained in the polymerizable liquid crystal composition. Is particularly preferred. In order to enhance the curability of the optically anisotropic member, it is preferable to use 3 parts by mass or more of a photopolymerization initiator per 100 parts by mass of the polymerizable liquid crystal compound. These may be used alone or in combination of two or more, and may be added with a sensitizer and the like.
- Organic solvent may be added to the polymerizable liquid crystal composition in the present invention.
- the organic solvent to be used is not particularly limited, but preferred is an organic solvent in which the polymerizable liquid crystal compound exhibits good solubility, and is preferably an organic solvent which can be dried at a temperature of 100 ° C. or less.
- solvents examples include aromatic hydrocarbons such as toluene, xylene, cumene and mesitylene, ester solvents such as methyl acetate, ethyl acetate, propyl acetate and butyl acetate, methyl ethyl ketone (MEK), methyl isobutyl ketone MIBK), ketone solvents such as cyclohexanone and cyclopentanone, ether solvents such as tetrahydrofuran, 1,2-dimethoxyethane and anisole, amide solvents such as N, N-dimethylformamide and N-methyl-2-pyrrolidone And propylene glycol monomethyl ether acetate, diethylene glycol monomethyl ether acetate, ⁇ -butyrolactone, chlorobenzene and the like. These can be used alone or as a mixture of two or more, but any one of ketone solvents, ether solvents, ester solvents and aromatic hydrocarbon solvents
- the composition used in the present invention can be applied to a substrate when it is a solution using an organic solvent.
- the proportion of the organic solvent used in the polymerizable liquid crystal composition is not particularly limited as long as the coated state is not significantly impaired, but the total amount of organic solvents in the solution containing the polymerizable liquid crystal composition is 10 to 95% by mass Is preferable, 12 to 90% by mass is more preferable, and 15 to 85% by mass is particularly preferable.
- the heating temperature at the time of heating and stirring may be appropriately adjusted in consideration of the solubility of the composition to be used in the organic solvent, but is preferably 15 ° C. to 110 ° C., more preferably 15 ° C. 15 ° C. to 100 ° C. is more preferable, and 20 ° C. to 90 ° C. is particularly preferable.
- a dispersion stirrer when adding a solvent, it is preferable to stir and mix by a dispersion stirrer.
- a disperser having a stirring blade such as a disper, a propeller and a turbine blade, a paint shaker, a planetary stirrer, a shaker, a shaker or a rotary evaporator can be used.
- an ultrasonic irradiation device can be used.
- the stirring rotation speed at the time of adding the solvent is preferably adjusted appropriately according to the stirring apparatus used, but in order to obtain a uniform polymerizable liquid crystal composition solution, the stirring rotation speed is preferably 10 rpm to 1000 rpm, and 50 rpm to It is more preferable to set 800 rpm, and it is particularly preferable to set 150 rpm to 600 rpm.
- a polymerization inhibitor a phenol type compound, a quinone type compound, an amine type compound, a thioether type compound, a nitroso compound, etc. are mentioned.
- Phenolic compounds include p-methoxyphenol, cresol, t-butyl catechol, 3.5-di-t-butyl-4-hydroxytoluene, 2.2′-methylenebis (4-methyl-6-t-butylphenol) 2.2′-methylenebis (4-ethyl-6-t-butylphenol), 4.4′-thiobis (3-methyl-6-t-butylphenol), 4-methoxy-1-naphthol, 4,4′- Dialkoxy-2,2'-bi-1-naphthol and the like can be mentioned.
- quinone compounds include hydroquinone, methylhydroquinone, tert-butylhydroquinone, p-benzoquinone, methyl-p-benzoquinone, tert-butyl-p-benzoquinone, 2,5-diphenylbenzoquinone and 2-hydroxy-1,4-naphthoquinone.
- 1,4-naphthoquinone, 2,3-dichloro-1,4-naphthoquinone, anthraquinone, diphenoquinone and the like are examples of quinone compounds.
- amine compounds include p-phenylenediamine, 4-aminodiphenylamine, N. N'-diphenyl-p-phenylenediamine, Ni-propyl-N'-phenyl-p-phenylenediamine, N- (1.3-dimethylbutyl) -N'-phenyl-p-phenylenediamine, N.I. N′-di-2-naphthyl-p-phenylenediamine, diphenylamine, N-phenyl- ⁇ -naphthylamine, 4.4′-dicumyl-diphenylamine, 4.4′-dioctyl-diphenylamine and the like.
- thioether compounds include phenothiazine and distearylthiodipropionate.
- the nitroso compounds include N-nitrosodiphenylamine, N-nitrosophenylnaphthylamine, N-nitrosodinaphthylamine, p-nitrosophenol, nitrosobenzene, p-nitrosodiphenylamine, ⁇ -nitroso- ⁇ -naphthol, etc., N, N-dimethyl p-Nitrosoaniline, p-nitrosodiphenylamine, p-nitrone dimethylamine, p-nitrone-N, N-diethylamine, N-nitrosoethanolamine, N-nitrosodi-n-butylamine, N-nitroso-Nn-butyl- 4-butanolamine, N-nitroso-diisopropanolamine, N-nitroso-N-ethyl-4-butanolamine, 5-nitroso-8-hydroxyquinoline, N-nitrosomorpholine, N-nitros
- the addition amount of the polymerization inhibitor is preferably 0.01 to 1.0% by mass, and more preferably 0.05 to 0.5% by mass with respect to the polymerizable liquid crystal composition.
- a thermal polymerization initiator may be used in combination with the photopolymerization initiator.
- thermal polymerization initiator known conventional ones can be used, and examples thereof include methylacetoacetoate peroxide, cumene hydroperoxide, benzoyl peroxide, bis (4-t-butylcyclohexyl) peroxydicarbonate, t-butyl Peroxybenzoate, methyl ethyl ketone peroxide, 1,1-bis (t-hexylperoxy) 3,3,5-trimethylcyclohexane, p-pentahydroperoxide, t-butylhydroperoxide, dicumyl peroxide, isobutyl Organic peroxides such as peroxide, di (3-methyl-3-methoxybutyl) peroxydicarbonate, 1,1-bis (t-butylperoxy) cyclohexane, 2,2'-azobisisobutyronitrile , 2,2'-azobis (2,4 Azonitrile compounds such as dimethylvaleronitrile), azoamidines
- V-40 and “VF-096” manufactured by Wako Pure Chemical Industries, Ltd., “Per hexil D” by Nippon Oil and Fats Co. (now Nippon Oil Co., Ltd.), “Per hexil I” Etc.
- the amount of the thermal polymerization initiator used is preferably 0.1 to 10 parts by mass and particularly preferably 0.5 to 5 parts by mass with respect to 100 parts by mass of the polymerizable liquid crystal compound contained in the polymerizable liquid crystal composition. . These can be used alone or in combination of two or more.
- the polymerizable liquid crystal composition in the present invention may contain at least one surfactant in order to reduce the film thickness unevenness in the case of forming an optically anisotropic material.
- Surfactants that can be contained include alkyl carboxylates, alkyl phosphates, alkyl sulfonates, fluoroalkyl carboxylates, fluoroalkyl phosphates, fluoroalkyl sulfonates, polyoxyethylene derivatives, fluoro Examples thereof include alkyl ethylene oxide derivatives, polyethylene glycol derivatives, alkyl ammonium salts, fluoroalkyl ammonium salts and the like, and fluorine-based and acrylic surfactants are particularly preferable.
- the surfactant is not an essential component, but when it is added, the addition amount of the surfactant is 0. 0 to 100 parts by mass of the content of the polymerizable liquid crystal compound contained in the polymerizable liquid crystal composition.
- the amount is preferably in the range of 01 to 2 parts by mass, and more preferably 0.05 to 0.5 parts by mass.
- the tilt angle at the air interface can be effectively reduced by using the surfactant.
- the polymerizable liquid crystal composition according to the present invention has the effect of effectively reducing the tilt angle of the air interface when it is made an optically anisotropic member, and as other than the above-mentioned surfactant, it has a repetition represented by the following general formula (7)
- the compound which has a weight average molecular weight which has a unit is 100 or more is mentioned.
- R 11 , R 12 , R 13 and R 14 each independently represent a hydrogen atom, a halogen atom or a hydrocarbon group having 1 to 20 carbon atoms, and one or more hydrogen atoms in the hydrocarbon group It may be substituted by a halogen atom of
- Examples of suitable compounds represented by the general formula (7) include polyethylene, polypropylene, polyisobutylene, paraffin, liquid paraffin, chlorinated polypropylene, chlorinated paraffin, chlorinated liquid paraffin and the like.
- the addition amount of the compound represented by the general formula (7) is preferably 0.01 to 1 part by mass with respect to 100 parts by mass of the content of the polymerizable liquid crystal compound contained in the polymerizable liquid crystal composition, More preferably, it is 0.05 to 0.5 parts by mass.
- a compound having a polymerizable group but not a liquid crystal compound can also be added. Such compounds can be used without particular limitation as long as they are generally recognized as polymerizable monomers or polymerizable oligomers in this technical field.
- the addition amount of the non-liquid crystal compound having a polymerizable group is preferably 0.01 to 15 parts by mass with respect to 100 parts by mass of the content of the polymerizable liquid crystal compound contained in the polymerizable liquid crystal composition,
- the content is more preferably in the range of 0.05 to 10 parts by mass, and particularly preferably 0.05 to 5 parts by mass.
- Triacrylates such as diacrylates, trimethylolpropane tri (meth) acrylates, ethoxylated isocyanuric acid triacrylates, pentaerythritol tri (meth) acrylates, ⁇ -caprolactone modified tris- (2-acryloyloxyethyl) isocyanurate, etc.
- Tetra (meth) acrylates such as meta) acrylate, pentaerythritol tetra (meth) acrylate, ditrimethylolpropane tetra (meth) acrylate, etc., dipentaerythritol hexa (meth) acrylate , Oligomeric (meth) acrylates, various urethane acrylates, various macromonomers, ethylene glycol diglycidyl ether, diethylene glycol diglycidyl ether, propylene glycol diglycidyl ether, neopentyl glycol diglycidyl ether, 1,6-hexanediol diglycidyl Epoxy compounds such as ether, glycerin diglycidyl ether, bisphenol A diglycidyl ether, etc., maleimide and the like can be mentioned.
- Chain transfer agent It is also preferable to add a chain transfer agent to the polymerizable liquid crystal composition of the present invention in order to further improve the adhesion to the substrate when it is made an optically anisotropic material.
- the chain transfer agent is preferably a thiol compound, more preferably a monothiol, dithiol, trithiol or tetrathiol compound, and still more preferably a trithiol compound.
- compounds represented by the following formulas (8-1) to (8-13) are preferable.
- ⁇ -methylstyrene dimer is also suitably used as a chain transfer agent other than thiol.
- the addition amount of the chain transfer agent is preferably 0.5 to 10 parts by mass with respect to 100 parts by mass of the polymerizable liquid crystal compound contained in the polymerizable liquid crystal composition, and is preferably 1.0 to 5.0. More preferably, it is part by mass.
- the polymerizable liquid crystal composition of the present invention may contain a dye, if necessary.
- the dye to be used is not particularly limited, and may contain commonly known ones as long as the orientation is not disturbed.
- the dye examples include dichroic dyes and fluorescent dyes.
- examples of such dyes include polyazo dyes, anthraquinone dyes, cyanine dyes, phthalocyanine dyes, perylene dyes, perinone dyes, squarylium dyes, etc.
- the dyes are preferably dyes exhibiting liquid crystallinity.
- dichroic dye for example, the following formulas (d-1) to (d-8)
- the addition amount of the dye such as the dichroic dye is preferably 0.001 to 10 parts by mass, and preferably 0.01 to 5 parts by mass, with respect to 100 parts by mass of the total of the polymerizable liquid crystal compounds contained in the powder mixture. It is more preferable that it is a part.
- the polymerizable liquid crystal composition of the present invention can contain a filler, if necessary.
- the filler to be used is not particularly limited, and may contain known and conventional ones as long as the thermal conductivity of the obtained polymer does not decrease.
- inorganic fillers such as alumina, titanium white, aluminum hydroxide, talc, clay, mica, barium titanate, zinc oxide and glass fibers, metal powders such as silver powder and copper powder, aluminum nitride, boron nitride, etc.
- Thermally conductive fillers such as silicon nitride, gallium nitride, silicon carbide, magnesia (aluminum oxide), alumina (aluminum oxide), crystalline silica (silicon oxide), fused silica (silicon oxide), silver nanoparticles, etc. .
- the optical film of the present invention is composed of the cured product of the polymerizable liquid crystal composition described above in detail. Specifically as a method of manufacturing an optical film from the polymeric liquid crystal composition of this invention, after making a polymeric liquid crystal composition apply
- the substrate used for the optical film of the present invention is a substrate usually used for liquid crystal devices, displays, optical parts and optical films, and withstands heating during drying after application of the polymerizable liquid crystal composition of the present invention
- a substrate include organic materials such as a glass substrate, a metal substrate, a ceramic substrate, and a plastic substrate.
- the substrate is an organic material, cellulose derivatives, polyolefins, polyesters, polycarbonates, polyacrylates (acrylic resins), polyarylates, polyether sulfones, polyimides, polyphenylene sulfides, polyphenylene ethers, nylons, polystyrenes, etc.
- plastic substrates such as polyester, polystyrene, polyacrylate, polyolefin, cellulose derivative, polyarylate and polycarbonate are preferable, substrates such as polyester, polyacrylate, polyolefin and cellulose derivative are more preferable, and PET (polyethylene terephthalate) is preferable as polyester. It is particularly preferable to use COP (cycloolefin polymer) as the polyolefin, use TAC (triacetylcellulose) as the cellulose derivative, and use PMMA (polymethyl methacrylate) as the polyacrylate. As a shape of a base material, it may have a curved surface other than a flat plate. These substrates may have an electrode layer, an antireflective function, and a reflective function, as necessary.
- These substrates may be subjected to surface treatment to improve the coatability and adhesion of the polymerizable liquid crystal composition of the present invention.
- surface treatment ozone treatment, plasma treatment, corona treatment, silane coupling treatment and the like can be mentioned.
- an organic thin film, an inorganic oxide thin film, a metal thin film, etc. are provided on the substrate surface by a method such as vapor deposition, or to add optical value.
- the material may be a pickup lens, a rod lens, an optical disc, a retardation film, a light diffusion film, a color filter, or the like.
- a pickup lens, a retardation film, a light diffusion film and a color filter which have higher added value, are preferable.
- an alignment film is provided on the glass substrate alone or on the substrate so that the polymerizable liquid crystal composition is oriented when the polymerizable liquid crystal composition of the present invention is applied and dried.
- orientation treatment include stretching treatment, rubbing treatment, polarized ultraviolet visible light irradiation treatment, ion beam treatment and the like.
- hydrophilic polymers include polyvinyl alcohol, polyacrylic acid, sodium polyacrylate, polymethacrylic acid, sodium polyalginate, polycarboxymethyl cellulose soda, pullulan and polystyrene sulfonic acid.
- hydrophilic inorganic compounds include oxides such as Si, Al, Mg, and Zr, and inorganic compounds such as fluoride.
- a hydrophilic substrate is preferred to obtain an optical anisotropy of a positive C plate, as it is effective to orient the optical axis of the optically anisotropic body approximately parallel to the normal to the substrate.
- the rubbing process adversely affects the vertical alignment in the hydrophilic polymer layer, which is preferable in order to obtain an optical film of a positive C plate. Absent.
- an applicator method As a method of applying the polymerizable liquid crystal composition of the present invention to the above-mentioned substrate, an applicator method, bar coating method, spin coating method, roll coating method, direct gravure coating method, reverse gravure coating method, flexo coating method, inkjet Methods known in the art such as die coating method, cap coating method, dip coating method and slit coating method can be used.
- the solvent contained in the polymerizable liquid crystal composition is heated and dried as required.
- the polymerization operation of the polymerizable liquid crystal composition of the present invention is generally performed by irradiation with light such as ultraviolet light or heating in a state where the liquid crystal compound in the polymerizable liquid crystal composition is cholesterically aligned with the substrate.
- light irradiation specifically, it is preferable to irradiate ultraviolet light of 390 nm or less, and it is most preferable to irradiate light having a wavelength of 250 to 370 nm.
- the polymerizable liquid crystal composition causes decomposition or the like by ultraviolet light of 390 nm or less, it may be preferable to carry out the polymerization treatment with ultraviolet light of 390 nm or more.
- the light is preferably diffused light and unpolarized light.
- Polymerization method As a method of polymerizing the polymerizable liquid crystal composition of the present invention, a method of irradiating an active energy ray, a thermal polymerization method, etc. may be mentioned, but heating is not necessary and the reaction proceeds at room temperature. A method of irradiation is preferable, and among them, a method of irradiating light such as ultraviolet light is preferable because the operation is simple.
- the temperature at the time of irradiation is preferably a temperature at which the polymerizable liquid crystal composition of the present invention can maintain the liquid crystal phase and 50 ° C. or less as much as possible in order to avoid induction of thermal polymerization of the polymerizable liquid crystal composition.
- the irradiation intensity and the irradiation energy greatly affect the heat resistance of the obtained optical film.
- the irradiation intensity or the irradiation energy is too weak, a part of the polymerization reaction is not generated, which affects the heat resistance, and even if the irradiation intensity or the irradiation energy is too strong, the degree of polymerization in the layer depth direction Differences arise and likewise affect the heat resistance.
- the irradiation intensity is preferably 30 to 2,000 mW / cm 2 of UVA light (UVA is ultraviolet light of 315 to 380 nm), preferably 50 to 1,500 mW / cm 2 of UVA light It is more preferable to irradiate UV light of UVA light of 120 to 1,000 mW / cm 2 , and more preferable to irradiate UV light of 250 to 1,000 mW / cm 2. Most preferred.
- the irradiation energy is preferably 100 to 5,000 mJ / cm 2 of UVA light, more preferably 150 to 4,000 mJ / cm 2 of UVA light, more preferably 200 to 500 mJ / cm 2.
- the UV irradiation may be performed a plurality of times, but the first irradiation intensity is preferably the above-mentioned UV intensity, and more preferably the first irradiation energy is the above-mentioned UV irradiation energy.
- the bifunctional polymerizable liquid crystal compound represented by the general formula (I-1) and the monofunctional polymerizable liquid crystal compound represented by the general formula (II-1) on a mass basis
- UVA ultraviolet radiation is applied at a dose of 300 to 1,000 mJ / cm 2 It is preferable from the point that heat resistance becomes favorable.
- the optical film obtained by polymerizing the polymerizable liquid crystal composition of the present invention can be peeled off from the substrate and used alone as an optical film, or can be used directly as an optical film without peeling from the substrate.
- it since it is hard to contaminate other members, it is useful when using it as a lamination
- the optical film thus obtained can exhibit excellent color purity as a cholesteric reflection film.
- a cholesteric reflection film a negative C plate in which a rod-like liquid crystalline compound is cholesteric-aligned to a substrate, a selective reflection film (band stop filter) which reflects light of a specific wavelength, and a rod-like liquid crystalline compound as a substrate It can be used as a twisted positive A plate which is horizontally oriented and twisted in orientation.
- DBEF double brightness enhancement film
- the optical film of the present invention is used for liquid crystal devices, displays, optical elements, optical components, colorants, markings for security, members for laser emission, optical films, compensation films, etc. in addition to the cholesteric reflection film. Accordingly, it can be used in various applications in a form suitable for the application, and can also be used as, for example, a brightness enhancement film, a reflective polarizing plate, and a viewing angle compensation film.
- the optical film of the present invention when using the optical film of the present invention as a brightness enhancement film, it is a brightness enhancement film having a ⁇ / 4 plate and a reflective polarizer, and the reflective polarizer reflects the first light from the ⁇ / 4 plate side.
- Layer, a second light reflecting layer and a third light reflecting layer in this order, and the first light reflecting layer, the second light reflecting layer and the third light reflecting layer are all from the optical film of the present invention What will be mentioned.
- a blue light having a peak of reflectance whose reflection center wavelength is 380 to 499 nm and whose half width is 100 nm or less among any of the first light reflection layer, the second light reflection layer, and the third light reflection layer It is a light reflection layer, any one of which is a green light reflection layer having a reflectance peak having a reflection center wavelength of 500 to 599 nm and a half width of 200 nm or less, and any one is a reflection center wavelength of 600 to 750 nm, a half width of 150 nm.
- Layer a layer that is a red light reflection layer having a peak of reflectance that is the following, or change the pitch of the cholesteric liquid crystal above and below the layer, and one or two layers with a half width of 200 to 400 nm It is a laminated film.
- the optical film of the present invention is used as a reflective polarizing plate, it is a reflective polarizing plate in which a cholesteric reflective film, an adhesive layer, and a linear polarizing film are sequentially laminated, and the cholesteric reflective film is the one of the present invention.
- a cholesteric reflection film is used.
- one or more retardation films may be provided in the reflective polarizing plate, and the retardation films may be retardation films different in retardation.
- the lamination of the retardation film is carried out by bonding an adhesive or an adhesive film to the obtained retardation film, and then using the cholesteric reflection film of the present invention and the retardation film as an adhesive or an adhesive film. It is obtained by pasting.
- an adhesive or an adhesive film is used, as the adhesive and the adhesive film, known and commonly used optical film applications are used.
- Irgacure 907 (manufactured by BASF)
- E-1 Irgacure 819 (manufactured by BASF)
- E-2) P-Methoxyphenol (F-1) Trimethylolpropane tris (made by Sakai Chemical Co., Ltd.)
- G-1) Alpha methyl styrene dimer (manufactured by Goi Chemical Co., Ltd.)
- Megafuck F-554 made by DIC)
- H-1) Toluene S-1) Methyl ethyl ketone (S-2)
- Example 1 Measurement of selective reflection wavelength
- the prepared polymerizable liquid crystal composition (1) is rubbed on a glass substrate with polyimide for horizontal alignment (SE-6414 manufactured by Nissan Chemical Co., Ltd.) by spin coating at a rotational speed of 800 rpm for 15 seconds at room temperature (25 ° C.) After coating and drying at 60 ° C for 2 minutes and then standing at 25 ° C for 1 minute, UVA with a maximum illuminance of 300 mW / cm 2 at room temperature is applied at 420 mJ / cm 2 using a conveyor type metal halide lamp By doing this, the thin film of Example 1 was obtained.
- the cross-cut test JIS K5400 was performed on the obtained thin film.
- the spectral transmittance of the obtained thin film is measured with a UV-visible spectrophotometer V-560 (manufactured by JASCO Corporation), from which the central value ( ⁇ ) of the selective reflection wavelength shown in FIG. 1 and its half width ( ⁇ ) was determined. After leaving the thin film in an oven at 85 ° C. for 24 hours, ( ⁇ ) and ( ⁇ ) were similarly determined. (Examples 2 to 20 and Comparative Examples 1 to 4) Similarly, thin films were similarly produced for the polymerizable liquid crystal compositions (2) to (16), and ( ⁇ ) and ( ⁇ ) before and after heating were determined.
- the maximum illumination intensity of the UVA is irradiated 90 mJ / cm 2 UV light of 120 mW / cm 2
- the UV radiation maximum illuminance of UVA changes the UV light of 1000 mW / cm 2 to 2,500 mJ / cm 2 a method of irradiating.
- compositions of the examples have less change in the selective reflection wavelength ( ⁇ ) before and after heating at 85 ° C. for 24 hours and are excellent in adhesion as compared with the compositions of the comparative examples.
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- Crystallography & Structural Chemistry (AREA)
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Abstract
La présente invention répond au problème de fourniture : d'une composition de cristaux liquides polymérisable qui est appropriée pour un film optique ayant une excellente adhérence à un matériau de base, est réduite dans le degré de décalage d'une longueur d'onde sélectionnée associée à un historique thermique, et a une excellente résistance à la chaleur ; un film optique utilisant la composition de cristaux liquides polymérisable ; un procédé de production du film optique ; et un dispositif d'affichage d'image équipé du film optique. Il est démontré qu'un film de cristaux liquides cholestériques produit par polymérisation d'une composition de cristaux liquides polymérisable contenant un composé de cristaux liquides polymérisable bifonctionnel spécifique, un composé chiral spécifique et un initiateur de polymérisation de type ester d'oxime spécifique peuvent présenter une excellente résistance à la chaleur, et cette découverte conduit à la réalisation de la présente invention.
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Cited By (6)
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CN111171202A (zh) * | 2020-01-12 | 2020-05-19 | 湘潭大学 | 一种侧链型手性发光液晶聚合物及其制备方法 |
CN111187374A (zh) * | 2020-01-12 | 2020-05-22 | 湘潭大学 | 一种含薄荷醇手性结构的发光液晶聚合物及其制备方法 |
CN112029512A (zh) * | 2019-06-04 | 2020-12-04 | Dic株式会社 | 液晶组合物和液晶显示元件 |
CN112779023A (zh) * | 2019-11-05 | 2021-05-11 | Dic株式会社 | 高频装置用液晶化合物 |
CN114605350A (zh) * | 2022-03-23 | 2022-06-10 | 江苏创拓新材料有限公司 | 可聚合化合物及含有其的可聚合组合物和光学各向异性体 |
CN116444732A (zh) * | 2023-04-27 | 2023-07-18 | 成都瑞波科材料科技有限公司 | 可聚合组合物、相位差膜、制备方法以及显示器件 |
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US20240117095A1 (en) * | 2022-09-21 | 2024-04-11 | Vadient Optics, Llc | Grin lenses made by 3d printing monomer-based inks |
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CN112029512B (zh) * | 2019-06-04 | 2024-04-26 | Dic株式会社 | 液晶组合物和液晶显示元件 |
CN112779023A (zh) * | 2019-11-05 | 2021-05-11 | Dic株式会社 | 高频装置用液晶化合物 |
CN112779023B (zh) * | 2019-11-05 | 2024-03-01 | Dic株式会社 | 高频装置用液晶化合物 |
CN111171202A (zh) * | 2020-01-12 | 2020-05-19 | 湘潭大学 | 一种侧链型手性发光液晶聚合物及其制备方法 |
CN111187374A (zh) * | 2020-01-12 | 2020-05-22 | 湘潭大学 | 一种含薄荷醇手性结构的发光液晶聚合物及其制备方法 |
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CN114605350A (zh) * | 2022-03-23 | 2022-06-10 | 江苏创拓新材料有限公司 | 可聚合化合物及含有其的可聚合组合物和光学各向异性体 |
CN116444732A (zh) * | 2023-04-27 | 2023-07-18 | 成都瑞波科材料科技有限公司 | 可聚合组合物、相位差膜、制备方法以及显示器件 |
CN116444732B (zh) * | 2023-04-27 | 2024-04-05 | 成都瑞波科材料科技有限公司 | 可聚合组合物、相位差膜、制备方法以及显示器件 |
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