WO2011078055A1 - 広帯域コレステリック液晶フィルムの製造方法 - Google Patents
広帯域コレステリック液晶フィルムの製造方法 Download PDFInfo
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- WO2011078055A1 WO2011078055A1 PCT/JP2010/072664 JP2010072664W WO2011078055A1 WO 2011078055 A1 WO2011078055 A1 WO 2011078055A1 JP 2010072664 W JP2010072664 W JP 2010072664W WO 2011078055 A1 WO2011078055 A1 WO 2011078055A1
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- WIPO (PCT)
- Prior art keywords
- liquid crystal
- cholesteric liquid
- crystal film
- thermal polymerization
- broadband cholesteric
- Prior art date
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- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920006393 polyether sulfone Polymers 0.000 description 1
- 229920002530 polyetherether ketone Polymers 0.000 description 1
- 229920001601 polyetherimide Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 239000011112 polyethylene naphthalate Substances 0.000 description 1
- 229920001470 polyketone Polymers 0.000 description 1
- 229920000306 polymethylpentene Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920006324 polyoxymethylene Polymers 0.000 description 1
- 229920006380 polyphenylene oxide Polymers 0.000 description 1
- 229920000069 polyphenylene sulfide Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- OPQYOFWUFGEMRZ-UHFFFAOYSA-N tert-butyl 2,2-dimethylpropaneperoxoate Chemical compound CC(C)(C)OOC(=O)C(C)(C)C OPQYOFWUFGEMRZ-UHFFFAOYSA-N 0.000 description 1
- SWAXTRYEYUTSAP-UHFFFAOYSA-N tert-butyl ethaneperoxoate Chemical compound CC(=O)OOC(C)(C)C SWAXTRYEYUTSAP-UHFFFAOYSA-N 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
-
- 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
- G02F1/133528—Polarisers
Definitions
- the present invention relates to a method for producing a broadband cholesteric liquid crystal film.
- it is related with the manufacturing method of the broadband cholesteric liquid crystal film whose reflection bandwidth is 300 nm or more.
- a cholesteric liquid crystal having a circularly polarized light separation function has a selective reflection characteristic that reflects only circularly polarized light whose wavelength is the helical pitch of the liquid crystal, with the rotational direction of the liquid crystal spiral and the circular polarization direction coincident. Due to this selective reflection characteristic, cholesteric liquid crystals are used for brightness enhancement films and color filters.
- the selective reflection characteristic of cholesteric liquid crystal is limited to a specific wavelength band, and it is difficult to cover the entire visible light range.
- the selective reflection wavelength region width ⁇ is widened, but ne-no is usually 0.3 or less. If this value is increased, other functions as liquid crystal (alignment characteristics, liquid crystal temperature, etc.) become insufficient, making practical use difficult. Therefore, in practice, the selective reflection wavelength region width ⁇ is about 150 nm at the maximum. Many of the practically usable cholesteric liquid crystals are about 30 to 100 nm at present.
- the pitch length is increased by a method of laminating a plurality of layers having different selective reflection center wavelengths (for example, refer to Patent Documents 1 and 2) or by ultraviolet polymerization under special conditions.
- a method has been proposed in which the presence distribution of the selective reflection center wavelength itself is formed by continuously changing the direction (for example, see Patent Document 3).
- the method of forming the existence distribution of the selective reflection center wavelength itself by continuously changing the pitch length in the thickness direction by ultraviolet polymerization under special conditions is performed when the cholesteric liquid crystal composition is cured by ultraviolet exposure.
- a difference in the exposure intensity between the surface side and the exit surface side and a difference in the polymerization rate are provided to change the composition ratio of the liquid crystal compositions having different reaction rates in the thickness direction.
- this method requires long-time ultraviolet irradiation, a main curing step in which high-intensity ultraviolet irradiation is performed after broadening the band in a semi-cured state, and further heating during curing by ultraviolet irradiation is required. There arises a problem that the manufacturing process becomes complicated. Moreover, yellowing occurs in the film obtained by ultraviolet irradiation, and the problem that an external appearance worsens arises.
- the production method of the present invention comprises: A method for producing a broadband cholesteric liquid crystal film having a reflection bandwidth of 300 nm or more, Applying a liquid crystal composition containing a polymerizable mesogenic compound (a), a polymerizable chiral agent (b), and a thermal polymerization initiator (c) onto an alignment substrate, and broadening the band of the liquid crystal composition by thermal polymerization Including a process,
- the content of the thermal polymerization initiator (c) in the liquid crystal composition is 0.2 to 4 parts by weight based on 100 parts by weight of the total of the polymerizable mesogenic compound (a) and the polymerizable chiral agent (b). is there.
- the pitch length of the broadband cholesteric liquid crystal film changes so as to be continuously reduced from the alignment substrate side.
- the production method of the present invention also includes A method for producing a broadband cholesteric liquid crystal film having a reflection bandwidth of 300 nm or more, Applying a liquid crystal composition containing a polymerizable mesogenic compound (a), a polymerizable chiral agent (b), and a thermal polymerization initiator (c) onto an alignment substrate, and broadening the band of the liquid crystal composition by thermal polymerization Including a process,
- the thermal polymerization is performed in an inert gas atmosphere containing oxygen having an oxygen concentration of 5% by volume or less at a heating temperature of 70 to 150 ° C.
- the pitch length of the broadband cholesteric liquid crystal film changes so as to be continuously reduced from the alignment substrate side.
- a method for producing a broadband cholesteric liquid crystal film having a reflection bandwidth of 300 nm or more comprising a simplified process and capable of producing a broadband cholesteric liquid crystal film having a good appearance without yellowing.
- a method for producing a broadband cholesteric liquid crystal film can be provided.
- the production method of the present invention is a method for producing a broadband cholesteric liquid crystal film.
- the broadband cholesteric liquid crystal film obtained by the production method of the present invention has a reflection bandwidth of 300 nm or more and has a very wide reflection bandwidth.
- the reflection bandwidth of the broadband cholesteric liquid crystal film obtained by the production method of the present invention is preferably 350 nm or more, more preferably 400 to 800 nm.
- the production method of the present invention comprises a step of applying a liquid crystal composition comprising a polymerizable mesogenic compound (a), a polymerizable chiral agent (b), and a thermal polymerization initiator (c) on an alignment substrate, and the liquid crystal mixture. And a broadening process by thermal polymerization.
- any appropriate polymerizable mesogenic compound may be employed as the polymerizable mesogenic compound (a).
- polymerizable mesogenic compounds described in JP-T-2002-533742 WO 00/37585
- EP 358208 US 5118877
- EP 66137 US 4388453
- WO 93/22397 EP 0261712, DE 19504224, DE 4408445, and GB2280445
- Specific examples of such a polymerizable mesogenic compound include, for example, trade name LC242 of BASF, trade name E7 of Merck, and trade name LC-Silicon-CC3767 of Wacker-Chem.
- polymerizable mesogenic compound (a) for example, liquid crystal monomers described in paragraphs 0035 to 0047 of JP-A No. 2003-287623 can be suitably used.
- polymerizable mesogenic compound (a) only one type may be used, or two or more types may be used in combination.
- the content of the polymerizable mesogen compound (a) in the liquid crystal composition is preferably 75 to 98% by weight, more preferably 80 to 98.5% by weight, and still more preferably 85 to 98% by weight. is there.
- the content of the polymerizable mesogenic compound (a) in the liquid crystal composition is less than 75% by weight, the composition may not exhibit a sufficient liquid crystal state, and as a result, cholesteric alignment may not be sufficiently formed. is there.
- the content ratio of the polymerizable mesogen compound (a) in the liquid crystal composition exceeds 98% by weight, the content of the polymerizable chiral agent (b) decreases, and the twist is not sufficiently imparted. In some cases, the cholesteric orientation is not sufficiently formed.
- the twisting force of such a chiral agent is preferably 1 ⁇ 10 ⁇ 6 nm ⁇ 1 ⁇ (wt%) ⁇ 1 or more, more preferably 1 ⁇ 10 ⁇ 5 nm ⁇ 1 ⁇ (wt%) ⁇ . 1 to 1 ⁇ 10 ⁇ 2 nm ⁇ 1 ⁇ (wt%) ⁇ 1 , and most preferably 1 ⁇ 10 ⁇ 4 nm ⁇ 1 ⁇ (wt%) ⁇ 1 to 1 ⁇ 10 ⁇ 3 nm ⁇ 1 ⁇ (wt %) -1 .
- the helical pitch of the cholesteric alignment solidified layer can be controlled within a desired range, and as a result, the wavelength range of selective reflection can be controlled within a desired range. Can do.
- the polymerizable chiral agent (b) for example, the chiral agents described in paragraphs 0048 to 0056 of JP-A-2003-287623 can be suitably used.
- the polymerizable chiral agent (b) may be used alone or in combination of two or more.
- the content of the polymerizable chiral agent (b) in the liquid crystal composition is preferably 1 to 20% by weight, more preferably 1.5 to 15% by weight, and further preferably 2 to 10% by weight. is there.
- the content of the polymerizable chiral agent (b) in the liquid crystal composition is less than 1% by weight, the twist is not sufficiently imparted, so that the cholesteric alignment may not be sufficiently formed.
- the content of the polymerizable chiral agent (b) in the liquid crystal composition exceeds 20% by weight, the temperature range exhibiting a liquid crystal state becomes very narrow.
- thermal polymerization initiator can be adopted as the thermal polymerization initiator (c).
- azo compounds such as 2,2-azobisisobutyronitrile and 2,2-azobis (2,4-dimethylvaleronitrile); diacyl peroxides such as benzoyl peroxide, lauroyl peroxide, and disuccinic acid peroxide
- Dialkyl peroxides such as di-t-butyl peroxide, t-butyl cumyl peroxide, dicumyl peroxide; t-butyl peroxyacetate, t-butyl peroxypivalate, t-butyl peroxybenzoate, t
- Organic peroxides such as peroxyesters such as butyl maleic acid hemiperester; hydroperoxides such as t-butyl hydroperoxide and cumene hydroperoxide; ketone peroxides such as methyl ethyl ketone peroxide; And the like.
- the content ratio of the thermal polymerization initiator (c) in the liquid crystal composition is preferably 0.2 to 4% by weight with respect to 100 parts by weight of the total of the polymerizable mesogenic compound (a) and the polymerizable chiral agent (b). Part, more preferably 0.3 to 4 parts by weight, still more preferably 0.5 to 3.5 parts by weight, and particularly preferably 0.5 to 3 parts by weight.
- the content ratio of the thermal polymerization initiator (c) is less than 0.2 parts by weight with respect to 100 parts by weight of the total of the polymerizable mesogenic compound (a) and the polymerizable chiral agent (b), the radical during heating There is a risk that the curing will not proceed because of the insufficient amount of.
- the content ratio of the thermal polymerization initiator (c) exceeds 4 parts by weight with respect to 100 parts by weight of the total of the polymerizable mesogenic compound (a) and the polymerizable chiral agent (b), the temperature range exhibiting a liquid crystal state is In addition to being narrow and easily clouded, the amount of radicals generated increases, so that the curing speed increases, and there is a possibility that the diffusion of monomers necessary for broadening the band becomes insufficient.
- the liquid crystal composition does not contain a photopolymerization initiator.
- the liquid crystal composition may contain any appropriate additive as long as the effects of the present invention are not impaired.
- the additive include an antioxidant, a modifier, a surfactant, a dye, a pigment, a discoloration inhibitor, and an ultraviolet absorber. These additives may be used alone or in combination of two or more. More specifically, examples of the anti-aging agent include phenol compounds, amine compounds, organic sulfur compounds, and phosphine compounds. Examples of the modifier include glycols, silicones, and alcohols.
- the surfactant is added, for example, to smooth the surface of the optical compensation layer, and examples thereof include silicone-based, acrylic-based, and fluorine-based surfactants.
- the liquid crystal composition may be applied as it is on the alignment substrate, or may be applied to the alignment substrate after being dissolved or dispersed in a solvent.
- solvents include halogenated hydrocarbons such as chloroform, dichloromethane, carbon tetrachloride, dichloroethane, tetrachloroethane, methylene chloride, trichloroethylene, tetrachloroethylene, chlorobenzene, orthodichlorobenzene, phenol, p-chlorophenol, o- Phenolic compounds such as chlorophenol, m-cresol, o-cresol, p-cresol, aromatic hydrocarbons such as benzene, toluene, xylene, methoxybenzene, 1,2-dimethoxybenzene, acetone, methyl ethyl ketone (MEK), methyl Ketone solvents such as isobutyl ketone, cyclohe
- any appropriate substrate capable of aligning liquid crystal can be adopted.
- various plastic films are mentioned.
- the plastic include polyolefins such as triacetyl cellulose (TAC), polyethylene, polypropylene, poly (4-methylpentene-1), polyimide, polyimide amide, polyether imide, polyamide, polyether ether ketone, polyether ketone, Polyketone sulfide, polyethersulfone, polysulfone, polyphenylene sulfide, polyphenylene oxide, polyethylene terephthalate, polybutylene terephthalate, polyethylene naphthalate, polyacetal, polycarbonate, polyarylate, acrylic resin, polyvinyl alcohol, polypropylene, cellulosic plastics, epoxy resin, phenol Examples thereof include resins.
- TAC triacetyl cellulose
- polyethylene polypropylene
- poly (4-methylpentene-1 polyimide
- polyimide amide polyether imide
- polyamide polyamide
- stretched these plastics is also mentioned.
- seats on the surfaces such as metal board
- the thickness of the alignment substrate is preferably 5 ⁇ m to 500 ⁇ m, more preferably 10 ⁇ m to 200 ⁇ m, and most preferably 15 ⁇ m to 150 ⁇ m. If it is such thickness, since it has sufficient intensity
- any appropriate application method can be adopted for applying the liquid crystal composition onto the alignment substrate.
- the casting method etc. are mentioned.
- the coating thickness of the liquid crystal composition is preferably from 3 to 20 ⁇ m, more preferably from 3 to 15 ⁇ m, even more preferably from 3 to 10 ⁇ m, and particularly preferably from 4 to 4 as the thickness of the resulting broadband cholesteric liquid crystal film. 10 ⁇ m. If the thickness is less than 3 ⁇ m, the resulting broadband cholesteric liquid crystal film may not be able to form a spiral pitch sufficient to make the reflection bandwidth 300 nm or more. If the thickness is larger than 20 ⁇ m, the alignment regulating force cannot sufficiently act and there is a possibility that alignment failure occurs.
- the production method of the present invention includes a broadening step by thermal polymerization of the liquid crystal composition.
- the heating temperature in the thermal polymerization is preferably 70 to 150 ° C, more preferably 80 to 140 ° C, and further preferably 80 to 130 ° C.
- the heating temperature in the thermal polymerization is lower than 70 ° C., there is little generation of radicals due to the thermal polymerization initiator, and curing may not proceed. If the heating temperature in the thermal polymerization is higher than 150 ° C., the liquid crystal may transition to an isotropic phase and may not exhibit selective reflection.
- the heating time for the thermal polymerization is preferably 2 minutes or more, more preferably 2 to 30 minutes, and further preferably 2 to 20 minutes. If the heating time in the thermal polymerization is shorter than 2 minutes, the amount of radicals generated from the thermal polymerization initiator may be insufficient. Moreover, when the heating time in the said thermal polymerization is too long, a manufacturing process will become long and there exists a possibility that it may not be suitable for a roll-to-roll.
- the thermal polymerization is preferably performed in an inert gas atmosphere containing oxygen having an oxygen concentration of 5% by volume or less.
- This oxygen concentration is more preferably 4% by volume or less, further preferably 3% by volume or less, particularly preferably 2.5% by volume or less, and most preferably 2% by volume or less.
- the lower limit of the oxygen concentration is preferably a value exceeding 0% by volume. If the oxygen concentration exceeds 5% by volume, radicals generated from the thermal polymerization initiator may be trapped by oxygen and curing may not proceed. On the other hand, when the oxygen concentration is 0% by volume, there is no inhibition of oxygen on the air surface, so that a difference in reaction rate with the substrate surface is difficult to occur, and there is a possibility that a broad band will not occur.
- any appropriate inert gas can be adopted as the inert gas.
- nitrogen, argon, helium, neon, xenon, krypton, and the like can be given.
- nitrogen is preferable because it has the highest versatility.
- the wide-band cholesteric liquid crystal film obtained by the production method of the present invention preferably has a pitch length that changes continuously from the alignment substrate side.
- the pitch length is preferably such that the difference between the alignment substrate side and the opposite side is at least 250 nm, more preferably at least 300 nm.
- the pitch length can be read from a cross-sectional TEM image of the broadband cholesteric liquid crystal film.
- the broadband cholesteric liquid crystal film obtained by the production method of the present invention preferably has a Grandjean structure in which the pitch length is changed continuously from one side.
- On the long pitch length side it is preferable to have a helical structure having a pitch length exhibiting reflection in the infrared region, or a layer in which the spiral is substantially eliminated, continuously or discontinuously.
- the long pitch length spiral structure or the layer in which the spiral is substantially eliminated has an optical retardation value of 50 to 450 nm with respect to incident light from the front. A retardation layer is preferred.
- the broadband cholesteric liquid crystal film obtained by the production method of the present invention preferably has a Grand Jean structure, has a portion exhibiting selective reflection in the visible region (380 to 780 nm) as a cholesteric liquid crystal, and selective reflection.
- a layer having a pitch completely different from that of the portion showing is provided on the long pitch long side.
- This layer can be a retardation layer as an optical property.
- the phase difference value is preferably controllable between 50 and 450 nm. For example, when the retardation value is 100 to 160 nm, the visible light passing through the cholesteric liquid crystal film can exhibit linearly polarized light.
- the phase difference value when the phase difference value is 200 to 400 nm, it can be converted into a circularly polarized state of rotation opposite to the circularly polarized state transmitted through the cholesteric liquid crystal.
- the polarization state of transmitted light can be freely controlled by the retardation value of the retardation layer of the broadband cholesteric liquid crystal film. Therefore, the broadband cholesteric liquid crystal film obtained by the production method of the present invention can be used as a polarizing plate in accordance with the mode of the liquid crystal display to be used.
- Example 1-1 97.5 parts by weight of LC242 (manufactured by BASF) as the polymerizable mesogenic compound (a), 2.5 parts by weight of LC756 (manufactured by BASF) as the polymerizable chiral agent (b), and V as the thermal polymerization initiator (c)
- the above solution was cast on a stretched polyethylene terephthalate base material and subjected to thermal polymerization at 100 ° C. for 10 minutes in a nitrogen gas atmosphere containing oxygen having an oxygen concentration of 0.5 vol% to produce a broadband cholesteric liquid crystal film (1-1) Got.
- Table 1 The results are shown in Table 1.
- Example 1-2 A broadband cholesteric liquid crystal film (1-2) was obtained in the same manner as in Example 1 except that the amount of the thermal polymerization initiator (c) was 1.0 part by weight. The results are shown in Table 1.
- Example 1-3 A broadband cholesteric liquid crystal film (1-3) was obtained in the same manner as in Example 1 except that the amount of the thermal polymerization initiator (c) was 2.0 parts by weight. The results are shown in Table 1.
- Example 1-4 A broadband cholesteric liquid crystal film (1-4) was obtained in the same manner as in Example 1 except that the amount of the thermal polymerization initiator (c) was changed to 3.0 parts by weight. The results are shown in Table 1.
- Example 1-1 A broadband cholesteric liquid crystal film (C1-1) was obtained in the same manner as in Example 1 except that the thermal polymerization initiator (c) was not used. The results are shown in Table 2.
- Example 1-2 A broadband cholesteric liquid crystal film (C1-2) was obtained in the same manner as in Example 1 except that the amount of the thermal polymerization initiator (c) was 0.1 parts by weight. The results are shown in Table 2.
- Example 1-3 A broadband cholesteric liquid crystal film (C1-3) was obtained in the same manner as in Example 1 except that the amount of the thermal polymerization initiator (c) was 5.0 parts by weight. The results are shown in Table 2.
- Example 2-1 97.5 parts by weight of LC242 (manufactured by BASF) as the polymerizable mesogenic compound (a), 2.5 parts by weight of LC756 (manufactured by BASF) as the polymerizable chiral agent (b), and V as the thermal polymerization initiator (c)
- LC242 manufactured by BASF
- LC756 manufactured by BASF
- V the thermal polymerization initiator
- a cyclopentanone solution (30 wt% solid content) of a mixture consisting of 1.0 part by weight of ⁇ 65 (manufactured by Wako Pure Chemical Industries, Ltd.) was prepared.
- the above-mentioned solution was cast on a stretched polyethylene terephthalate substrate and subjected to thermal polymerization at 100 ° C. for 10 minutes in a nitrogen gas atmosphere containing oxygen having an oxygen concentration of 0.2% by volume to produce a broadband cholesteric liquid crystal film (2-1) Got.
- Table 3 The results are shown in Table 3.
- Example 2-2 A broadband cholesteric liquid crystal film (2-2) was obtained in the same manner as in Example 2-1, except that the oxygen concentration in the nitrogen gas was changed to 0.5% by volume. The results are shown in Table 3.
- Example 2-3 A broadband cholesteric liquid crystal film (2-3) was obtained in the same manner as in Example 2-1, except that the oxygen concentration in the nitrogen gas was 1.0% by volume. The results are shown in Table 3.
- Example 2-4 A broadband cholesteric liquid crystal film (2-4) was obtained in the same manner as in Example 2-1, except that the oxygen concentration in the nitrogen gas was 0% by volume. The results are shown in Table 3.
- Example 2-5 A broadband cholesteric liquid crystal film (2-5) was obtained in the same manner as in Example 2-1, except that the oxygen concentration in nitrogen gas was changed to 3.0% by volume. The results are shown in Table 3.
- Example 2-6 A broadband cholesteric liquid crystal film (2-6) was obtained in the same manner as in Example 2-3 except that the polymerization temperature was 80 ° C. The results are shown in Table 4.
- Example 2-7 A broadband cholesteric liquid crystal film (2-7) was obtained in the same manner as in Example 2-3 except that the polymerization temperature was 120 ° C. The results are shown in Table 4.
- Example 2-8 A broadband cholesteric liquid crystal film (2-8) was obtained in the same manner as in Example 2-5 except that the polymerization temperature was 80 ° C. The results are shown in Table 4.
- Example 2-9 A broadband cholesteric liquid crystal film (2-9) was obtained in the same manner as in Example 2-5 except that the polymerization temperature was 120 ° C. The results are shown in Table 4.
- Example 2-1 A broadband cholesteric liquid crystal film (C2-1) was obtained in the same manner as in Example 2-1, except that the oxygen concentration in the nitrogen gas was 7.0% by volume. The results are shown in Table 5.
- Example 2-2 A broadband cholesteric liquid crystal film (C2-2) was obtained in the same manner as in Example 2-1, except that the oxygen concentration in the nitrogen gas was changed to 10% by volume. The results are shown in Table 5.
- Example 2-3 A broadband cholesteric liquid crystal film (C2-3) was obtained in the same manner as in Example 2-1, except that the oxygen concentration in the nitrogen gas was changed to 21% by volume. The results are shown in Table 5.
- Example 2-4 A broadband cholesteric liquid crystal film (C2-4) was obtained in the same manner as in Example 2-3 except that the polymerization temperature was 50 ° C. The results are shown in Table 5.
- Example 2-6 A broadband cholesteric liquid crystal film (C2-6) was obtained in the same manner as in Example 2-5 except that the polymerization temperature was 50 ° C. The results are shown in Table 5.
- Example 2-7 A broadband cholesteric liquid crystal film (C2-7) was obtained in the same manner as in Example 2-5 except that the polymerization temperature was 160 ° C. The results are shown in Table 6.
- Example 2-10 A broadband cholesteric liquid crystal film (C2-10) was obtained in the same manner as in Example 2-1, except that the oxygen concentration in nitrogen gas was 10% by volume and the polymerization temperature was 160 ° C. The results are shown in Table 6.
- the broadband cholesteric liquid crystal film obtained by the production method of the present invention is suitably used for an IR filter, a bandpass filter, a UV reflection film, a brightness enhancement film, a light control film, a retardation plate, a notch filter, and the like.
Abstract
Description
△λ=2λ・(ne-no)/(ne+no)
no:コレステリック液晶分子の正常光に対する屈折率
ne:コレステリック液晶分子の異常光に対する屈折率
λ:選択反射の中心波長
で表され、コレステリック液晶そのものの分子構造に依存する。
λ=(ne+no)P/2
P:コレステリック液晶一回転ねじれに要する螺旋ピッチ長
で表され、ピッチ一定であれば液晶分子の平均屈折率とピッチ長に依存する。
反射帯域巾が300nm以上である広帯域コレステリック液晶フィルムの製造方法であって、
重合性メソゲン化合物(a)、重合性カイラル剤(b)、および熱重合開始剤(c)を含む液晶組成物を配向基材上に塗布する工程と、該液晶組成物の熱重合による広帯域化工程とを含み、
該液晶組成物中の該熱重合開始剤(c)の含有割合が、重合性メソゲン化合物(a)および重合性カイラル剤(b)の合計100重量部に対して0.2~4重量部である。
好ましい実施形態においては、上記広帯域コレステリック液晶フィルムのピッチ長が、上記配向基材側から連続的に小さくなるように変化している。
反射帯域巾が300nm以上である広帯域コレステリック液晶フィルムの製造方法であって、
重合性メソゲン化合物(a)、重合性カイラル剤(b)、および熱重合開始剤(c)を含む液晶組成物を配向基材上に塗布する工程と、該液晶組成物の熱重合による広帯域化工程とを含み、
該熱重合を、加熱温度が70~150℃において、酸素濃度5体積%以下の酸素を含有する不活性ガス雰囲気下で行う。
好ましい実施形態においては、上記広帯域コレステリック液晶フィルムのピッチ長が、上記配向基材側から連続的に小さくなるように変化している。
得られたコレステリック液晶フィルムをガラスに転写して測定用サンプルとし、日立ハイテク社製のU-4100を用いて測定した。
<黄変の評価>
日立ハイテク社製のU-4100を用い、YI値を測定した。YI値が1以下の場合を黄変なしと判断した。
<窒素ガス中の酸素濃度の調整>
金属製の密閉可能な容器の開口部から、酸素濃度計のセンサー部を差込み、窒素ガスを封入しながら容器内の酸素濃度を測定した。所望の酸素濃度まで低下したところで、センサーを抜き、窒素ガスの封入をやめ、開口部を閉じた。
重合性メソゲン化合物(a)としてLC242(BASF社製)97.5重量部、重合性カイラル剤(b)としてLC756(BASF社製)2.5重量部、および熱重合開始剤(c)としてV-65(和光純薬工業社製)0.5重量部からなる混合物のシクロペンタノン溶液(30重量%固体含有量)を調製した。
上記溶液を延伸ポリエチレンテレフタレート基材にキャストし、酸素濃度0.5体積%の酸素を含有する窒素ガス雰囲気下で、100℃で10分間、熱重合を行い、広帯域コレステリック液晶フィルム(1-1)を得た。
結果を表1に示した。
熱重合開始剤(c)の量を1.0重量部とした以外は、実施例1と同様に行い、広帯域コレステリック液晶フィルム(1-2)を得た。
結果を表1に示した。
熱重合開始剤(c)の量を2.0重量部とした以外は、実施例1と同様に行い、広帯域コレステリック液晶フィルム(1-3)を得た。
結果を表1に示した。
熱重合開始剤(c)の量を3.0重量部とした以外は、実施例1と同様に行い、広帯域コレステリック液晶フィルム(1-4)を得た。
結果を表1に示した。
熱重合開始剤(c)を用いなかった以外は、実施例1と同様に行い、広帯域コレステリック液晶フィルム(C1-1)を得た。
結果を表2に示した。
熱重合開始剤(c)の量を0.1重量部とした以外は、実施例1と同様に行い、広帯域コレステリック液晶フィルム(C1-2)を得た。
結果を表2に示した。
熱重合開始剤(c)の量を5.0重量部とした以外は、実施例1と同様に行い、広帯域コレステリック液晶フィルム(C1-3)を得た。
結果を表2に示した。
重合性メソゲン化合物(a)としてLC242(BASF社製)97.5重量部、重合性カイラル剤(b)としてLC756(BASF社製)2.5重量部、および光重合開始剤としてIRGACURE907(チバ・ジャパン社製)5.0重量部からなる混合物のシクロペンタノン溶液(30重量%固体含有量)を調製した。
上記溶液を延伸ポリエチレンテレフタレート基材にキャストし、100℃で2分間乾燥させて溶媒を除去した。その後、100℃に加熱しながら、配向基材側より、酸素濃度21体積%の酸素を含有する窒素ガス雰囲気下で、紫外線を6mW/cm2で5分間照射し、広帯域コレステリック液晶フィルム(C1-4)を得た。
結果を表2に示した。
重合性メソゲン化合物(a)としてLC242(BASF社製)97.5重量部、重合性カイラル剤(b)としてLC756(BASF社製)2.5重量部、および熱重合開始剤(c)としてV-65(和光純薬工業社製)1.0重量部からなる混合物のシクロペンタノン溶液(30重量%固体含有量)を調製した。
上記溶液を延伸ポリエチレンテレフタレート基材にキャストし、酸素濃度0.2体積%の酸素を含有する窒素ガス雰囲気下で、100℃で10分間、熱重合を行い、広帯域コレステリック液晶フィルム(2-1)を得た。
結果を表3に示した。
窒素ガス中の酸素濃度を0.5体積%とした以外は、実施例2-1と同様に行い、広帯域コレステリック液晶フィルム(2-2)を得た。
結果を表3に示した。
窒素ガス中の酸素濃度を1.0体積%とした以外は、実施例2-1と同様に行い、広帯域コレステリック液晶フィルム(2-3)を得た。
結果を表3に示した。
窒素ガス中の酸素濃度を0体積%とした以外は、実施例2-1と同様に行い、広帯域コレステリック液晶フィルム(2-4)を得た。
結果を表3に示した。
窒素ガス中の酸素濃度を3.0体積%とした以外は、実施例2-1と同様に行い、広帯域コレステリック液晶フィルム(2-5)を得た。
結果を表3に示した。
重合温度を80℃とした以外は、実施例2-3と同様に行い、広帯域コレステリック液晶フィルム(2-6)を得た。
結果を表4に示した。
重合温度を120℃とした以外は、実施例2-3と同様に行い、広帯域コレステリック液晶フィルム(2-7)を得た。
結果を表4に示した。
重合温度を80℃とした以外は、実施例2-5と同様に行い、広帯域コレステリック液晶フィルム(2-8)を得た。
結果を表4に示した。
重合温度を120℃とした以外は、実施例2-5と同様に行い、広帯域コレステリック液晶フィルム(2-9)を得た。
結果を表4に示した。
窒素ガス中の酸素濃度を7.0体積%とした以外は、実施例2-1と同様に行い、広帯域コレステリック液晶フィルム(C2-1)を得た。
結果を表5に示した。
窒素ガス中の酸素濃度を10体積%とした以外は、実施例2-1と同様に行い、広帯域コレステリック液晶フィルム(C2-2)を得た。
結果を表5に示した。
窒素ガス中の酸素濃度を21体積%とした以外は、実施例2-1と同様に行い、広帯域コレステリック液晶フィルム(C2-3)を得た。
結果を表5に示した。
重合温度を50℃とした以外は、実施例2-3と同様に行い、広帯域コレステリック液晶フィルム(C2-4)を得た。
結果を表5に示した。
重合温度を160℃とした以外は、実施例2-3と同様に行い、広帯域コレステリック液晶フィルム(C2-5)を得た。
結果を表5に示した。
重合温度を50℃とした以外は、実施例2-5と同様に行い、広帯域コレステリック液晶フィルム(C2-6)を得た。
結果を表5に示した。
重合温度を160℃とした以外は、実施例2-5と同様に行い、広帯域コレステリック液晶フィルム(C2-7)を得た。
結果を表6に示した。
重合温度を50℃とした以外は、実施例2-4と同様に行い、広帯域コレステリック液晶フィルム(C2-8)を得た。
結果を表6に示した。
重合温度を160℃とした以外は、実施例2-4と同様に行い、広帯域コレステリック液晶フィルム(C2-9)を得た。
結果を表6に示した。
窒素ガス中の酸素濃度を10体積%とし、重合温度を160℃とした以外は、実施例2-1と同様に行い、広帯域コレステリック液晶フィルム(C2-10)を得た。
結果を表6に示した。
重合性メソゲン化合物(a)としてLC242(BASF社製)97.5重量部、重合性カイラル剤(b)としてLC756(BASF社製)2.5重量部、および光重合開始剤としてIRGACURE907(チバ・ジャパン社製)5.0重量部からなる混合物のシクロペンタノン溶液(30重量%固体含有量)を調製した。
上記溶液を延伸ポリエチレンテレフタレート基材にキャストし、100℃で2分間乾燥させて溶媒を除去した。その後、100℃に加熱しながら、配向基材側より、酸素濃度21体積%の酸素を含有する窒素ガス雰囲気下で、紫外線を6mW/cm2で5分間照射し、広帯域コレステリック液晶フィルム(C2-11)を得た。
結果を表6に示した。
Claims (4)
- 反射帯域巾が300nm以上である広帯域コレステリック液晶フィルムの製造方法であって、
重合性メソゲン化合物(a)、重合性カイラル剤(b)、および熱重合開始剤(c)を含む液晶組成物を配向基材上に塗布する工程と、該液晶組成物の熱重合による広帯域化工程とを含み、
該液晶組成物中の該熱重合開始剤(c)の含有割合が、重合性メソゲン化合物(a)および重合性カイラル剤(b)の合計100重量部に対して0.2~4重量部である、
広帯域コレステリック液晶フィルムの製造方法。 - 前記広帯域コレステリック液晶フィルムのピッチ長が、前記配向基材側から連続的に小さくなるように変化している、請求項1に記載の製造方法。
- 反射帯域巾が300nm以上である広帯域コレステリック液晶フィルムの製造方法であって、
重合性メソゲン化合物(a)、重合性カイラル剤(b)、および熱重合開始剤(c)を含む液晶組成物を配向基材上に塗布する工程と、該液晶組成物の熱重合による広帯域化工程とを含み、
該熱重合を、加熱温度が70~150℃において、酸素濃度5体積%以下の酸素を含有する不活性ガス雰囲気下で行う、
広帯域コレステリック液晶フィルムの製造方法。 - 前記広帯域コレステリック液晶フィルムのピッチ長が、前記配向基材側から連続的に小さくなるように変化している、請求項3に記載の製造方法。
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EP10839288A EP2518540A1 (en) | 2009-12-24 | 2010-12-16 | Process for production of broad-band cholesteric liquid crystal film |
KR1020127016306A KR101381026B1 (ko) | 2009-12-24 | 2010-12-16 | 광대역 콜레스테릭 액정 필름의 제조 방법 |
US13/505,521 US20120219707A1 (en) | 2009-12-24 | 2010-12-16 | Process for production of broad-band cholesteric liquid crystal film |
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JP2009-293790 | 2009-12-25 | ||
JP2009293790A JP5153762B2 (ja) | 2009-12-25 | 2009-12-25 | 広帯域コレステリック液晶フィルムの製造方法 |
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JP6486116B2 (ja) * | 2014-10-31 | 2019-03-20 | 富士フイルム株式会社 | 光学部材および光学部材を有する画像表示装置 |
WO2016093290A1 (ja) * | 2014-12-11 | 2016-06-16 | 富士フイルム株式会社 | 光学部材および光学部材を有する画像表示装置 |
JP6630438B2 (ja) * | 2016-07-01 | 2020-01-15 | 富士フイルム株式会社 | イメージセンサー用カラーフィルター、イメージセンサーおよびイメージセンサー用カラーフィルターの製造方法 |
CN110582721B (zh) * | 2017-05-01 | 2022-09-20 | 金泰克斯公司 | 具有可切换的白天和夜晚模式的成像装置 |
WO2020080216A1 (ja) * | 2018-10-19 | 2020-04-23 | 富士フイルム株式会社 | 硬化膜の製造方法、樹脂組成物、硬化膜、積層体の製造方法および半導体デバイスの製造方法 |
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JP2004258405A (ja) | 2003-02-26 | 2004-09-16 | Nitto Denko Corp | コレステリック液晶積層体、それを用いた広帯域円偏光板、直線偏光子および液晶表示装置 |
JP2009283246A (ja) * | 2008-05-21 | 2009-12-03 | Dainippon Printing Co Ltd | エレクトロルミネッセント素子に用いられる光学部材およびそれを備えたエレクトロルミネッセント素子 |
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WO2015092867A1 (ja) | 2013-12-17 | 2015-06-25 | パイオニア株式会社 | 虚像生成素子及びヘッドアップディスプレイ |
JPWO2015092867A1 (ja) * | 2013-12-17 | 2017-03-16 | パイオニア株式会社 | 虚像生成素子及びヘッドアップディスプレイ |
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TW201142378A (en) | 2011-12-01 |
US20120219707A1 (en) | 2012-08-30 |
KR20140009549A (ko) | 2014-01-22 |
KR20120096038A (ko) | 2012-08-29 |
EP2518540A1 (en) | 2012-10-31 |
KR101413824B1 (ko) | 2014-07-01 |
KR101381026B1 (ko) | 2014-04-04 |
TWI437289B (zh) | 2014-05-11 |
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