WO2015046826A1 - 역 파장 분산성 화합물, 이를 포함하는 역 파장 분산성 조성물 및 광학 이방체 - Google Patents
역 파장 분산성 화합물, 이를 포함하는 역 파장 분산성 조성물 및 광학 이방체 Download PDFInfo
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
- C07C69/84—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring
- C07C69/86—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring with esterified hydroxyl groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
- C07C69/94—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of polycyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of six-membered aromatic rings
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- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Definitions
- Reverse wavelength dispersible compound, reverse wavelength dispersible composition and optically anisotropic body comprising same
- the present invention relates to a reverse wavelength dispersible compound, a reverse wavelength dispersible composition and an optically anisotropic body comprising the same.
- LCDs liquid crystal displays
- LEDs organic light emitting diodes
- OLED displays are gaining attention as the displays of the future because they are superior to LCDs in various fields such as thickness, power consumption, speed of response, viewing angle, and can be used for various purposes such as transparent and flexible products.
- OLEDs have a short lifespan and a low luminous efficiency, and thus are still limited in size.
- OLEDs are difficult to realize perfect black due to interference of external light.
- the present invention and the reverse wavelength dispersion composition comprising the compound It is for providing an optically anisotropic body.
- A is a carbocyclic or heterocyclic group having 5 to 8 carbon atoms, or an aromatic or heteroaromatic group having 6 to 20 carbon atoms;
- E 1 , E 2 , D 1 , and D 2 are each independently a single bond or a divalent linking group
- R 1 and R 2 are each independently —H or alkyl having 1 to 12 carbon atoms;
- n 1 to 5;
- each repeating unit of two or more repeating-(D 1 -G 1 )-or-(G 2 -D 2 )- may be the same or different from each other;
- G 1 and G 2 are each independently a non-aromatic carbocyclic or heterocyclic group having 5 to 8 carbon atoms, or an aromatic or heteroaromatic group having 6 to 20 carbon atoms, wherein at least one of G 1 and G 2 increases A carbocyclic or heterocyclic group, and any one of the hydrogens contained in the carbocyclic or heterocyclic group is substituted with a group represented by the following Chemical Formula 2:
- ⁇ is an integer of 1 to 10, and if ⁇ is 2 or more, each repeating unit of-(Q 1 )-repeated two or more times may be the same or different from each other,
- ⁇ ( ⁇ ) means specific birefringence at wavelength ⁇ .
- ⁇ ( ⁇ ) means specific birefringence at wavelength ⁇ .
- the meaning of “comprising” embodies a particular characteristic, region, integer step, operation, element, or component, and excludes the addition of other specific characteristics, region, integer, step, operation, element, or component. It is not.
- the "reverse wavelength dispersible compound” itself shows liquid crystallinity and reverse wavelength dispersibility, or does not itself show liquid crystallinity, but is polymerized or crosslinked with any liquid crystal compound so that the liquid crystal compound is reverse wavelength. It means a compound that can exhibit dispersibility. Specifically, after orienting a composition containing the reverse wavelength dispersible compound or the reverse wavelength dispersible compound and a liquid crystal compound (for example, a semi-ungsogenic mesogenic compound having liquid crystallinity) in a liquid crystal state, the state When irradiating active energy rays, such as an ultraviolet-ray, can obtain the superposition
- active energy rays such as an ultraviolet-ray
- the polymer obtained in this way has anisotropy of physical properties such as refractive index, dielectric constant, magnetization rate, elastic modulus, thermal expansion rate, and the like, so that it can be applied as an optical anisotropic body such as a retardation plate, a polarizing plate polarizing prism, a brightness enhancing film, and an optical fiber coating material. .
- phase difference value in the wavelength ⁇ of transmitted light passing through the optical film, and may be represented by ⁇ ( ⁇ ).
- mesogenic group means a group having the ability to induce liquid crystal phase behavior.
- spacer groups are known to those of ordinary skill in the art, for example in C. Tschierske, G. Pelzl, S. Diele, Angew. Chem. 2004, 116, 6340-6368.
- the spacer group refers to a flexible organic group connecting the mesogenic group and the polymerizable group.
- “carbyl groups” comprise one or more carbon atoms (eg, —C ⁇ C—) free of any non-carbon atoms, or optionally one or more non-carbon atoms (eg, N, O, S, P At least one carbon atom in combination with Si Carbonyl), meaning any monovalent or polyvalent organic radical moiety.
- “Hydrocarbyl group” means a carbyl group that additionally contains one or more H atoms and optionally one or more heteroatoms (eg, N, 0, S, P, Si).
- Dispersible compounds are pore:
- A is a carbocyclic or heterocyclic group having 5 to 8 carbon atoms, or an aromatic or heteroaromatic group having 6 to 20 carbon atoms;
- E 1 , E 2 , D 1 , and D 2 are each independently a single bond or a divalent linking group
- R 1 and R 2 are each independently -H or alkyl having 1 to 12 carbon atoms;
- n are each independently an integer from 1 to 5; M or n is
- each repeating unit of two or more repeating-(D 1 -G 1 )-or-(G 2 -D 2 )- may be the same or different from each other;
- G 1 and G 2 are each independently a non-aromatic carbocyclic or heterocyclic group having 5 to 8 carbon atoms, or an aromatic or heteroaromatic group having 6 to 20 carbon atoms, wherein at least one of G 1 and G 2 is A carbocyclic or heterocyclic group, and any one of the hydrogens contained in the carbocyclic or heterocyclic group is substituted with a group represented by the following Chemical Formula 2:
- p is an integer of 1 to 10, and if p is 2 or more, each repeating unit of-(Q 1 )-which is repeated two or more times may be the same or different from each other,
- the compounds having the structure represented by the formula (1) surprisingly exhibits liquid crystallinity and reverse wavelength dispersion, or do not show liquid crystallinity by themselves but are polymerized with arbitrary liquid crystal compounds or It was confirmed that crosslinking can exhibit reverse wavelength dispersion, thereby providing an optically anisotropic body having a thin thickness and excellent optical properties.
- the compound represented by the formula (1) is a mesogenic group (particularly, L 1-
- the bridging group HQ 1 ] P -B 1 ) of the conjugated structure having high polarization at any one of (D 1 -G 1 ) m -group and-(G 2 -D 2 ) n -L 2 group) is in the vertical direction. It has a T-shaped structure connected in (axial direction).
- the reverse wavelength dispersible compound has an asymmetric structure in the form of ⁇ . Accordingly, the compound of Formula 1 may exhibit stable reverse wavelength dispersion by the bridging group having a high polarization vertically and excellent orientation by the asymmetric mesogenic group in the T-shape.
- A is a carbocyclic or heterocyclic group having 5 to 8 carbon atoms, or an aromatic or heteroaromatic group having 6 to 20 carbon atoms.
- the carbocyclic or heterocyclic group in A is a 5-membered ring (e.g. cyclopentane, tetrahydrofuran, tetrahydrothiofuran, pyridine; 6-membered ring (e.g. cyclonucleic acid, silinane, cyclonuxene, Tetrahydropyran, tetrahydrothiopyran, 1,3-dioxane, 1,3-dithiane, piperidine); 7-membered ring (e.g. cycloheptane); or fused group (e.g.
- the aromatic group in A is benzene, biphenylene, triphenylene, naphthalene, anthracene, binaphthylene, phenanthrene, pyrene, dihydropyrene, chrysene, perylene, tetracene, pentacene, benzpyrene Fluorene, indene, indenofluorene, spirobifluorene, and the like.
- the heteroaromatic groups in A, G 1 and G 2 are 5-membered rings (e.g., blood, pyrazole, imidazole, 1,2,3-triazole, 1,2,4-triazole, tetrazole). , Furan, thiophene, selenophene, oxazole, isoxazole, ⁇ thiazole, ⁇ thiazole, ⁇ oxadiazole, 2,4-oxadiazole,
- Y 1 and Y 2 are each independently —H, —F, —CI, —CN, or —R 1 , and R 1 and R 2 are each independently —H or alkyl having 1 to 12 carbon atoms. . '
- L 1 and L 2 are alkyl having 1 to 20 carbon atoms, oxaalkyl having 1 to 20 carbon atoms, alkoxy having 1 to 20 carbon atoms, alkenyl having 2 to 20 carbon atoms, alkynyl having 2 to 20 carbon atoms, and having 1 to C carbon atoms.
- S p is -Xp----
- Y 1 and Y 2 are each independently —H, —F, —CI, —CN, or —R 1 , and R 1 and R 2 are each independently —H or alkyl having 1 to 12 carbon atoms. .
- m and n may have the same or different values, and may each independently be an integer of 1 to 5.
- each repeating unit of-(D 1 -G 1 )-or-(G 2 -D 2 )-that is repeated two or more times may be the same or different from each other.
- G 1 or G 1 included in each repeating unit of-(D 1 -G 1 )-(D 1 -G 1 )- is the same as or different from each other in the aforementioned range.
- G 1 and G 2 are each independently a non-aromatic carbocyclic or heterocyclic group having 5 to 8 carbon atoms, or an aromatic or heteroaromatic group having 6 to 20 carbon atoms, wherein the G 1 and At least one of G 2 is the carbocyclic or heterocyclic group.
- the carbocyclic group, heterocyclic group, aromatic group, and heteroaromatic group in G 1 and G 2 are replaced with the definitions for A.
- At least one of the G 1 and G 2 is the carbocyclic or heterocyclic group, any one hydrogen contained in the carbocyclic or heterocyclic group is represented by the formula It is substituted with a group represented by:
- p is an integer of 1 to 10, and if p is 2 or more, each repeating unit of-(Q 1 )-which is repeated two or more times may be the same or different from each other,
- -[Q 1 ] p - may be composed of at least one subgroup Q 1 selected from the group consisting of a pi-conjugated linear group, an aromatic group and a heteroaromatic group.
- -[Q 1 ] p - may be composed of one or more subgroups Q 1 selected from the group having a coupling angle of 120 degrees or more, preferably 180 degrees.
- p is an integer of 1 to 10, and if p is 2 or more, each repeating unit of-(Q 1 )-repeated two or more times may be the same or different from each other.
- such subgroup Q 1 is a divalent aromatic group connected to an adjacent group in the para-position (eg 1,4-phenylene, naphthalene-2,6-diyl, indan-2,6-diyl, Thieno [3,2-b] thiophene-2,5-diyl) or a group comprising sp-splended carbon atoms (eg, -C ⁇ C-).
- Y 1 and ⁇ 2 are each independently —H, —F, —CI, —CN, or —R 1
- R 1 and R 2 are each independently —H or alkyl having 1 to 12 carbon atoms. .
- -[Q 1 ] P - is selected from the group consisting of -C ⁇ C-, substituted or unsubstituted 1,4-phenylene, and substituted or unsubstituted 9H-fluorene-2,7-diyl. It may include one or more groups. At this time, the H atom in the 9-position in the fluorene group may be replaced with a carbyl or hydrocarbyl group.
- P 2 as defined in Formula 1, an alkenyl group having 2 to 6 carbon atoms, an alkynyl group having 2 to 6 carbon
- R ⁇ 1> and R ⁇ 2> is respectively independently -H or C1-C12 alkyl.
- B 1 is selected from the group consisting of a pi-conjugated linear group, an aromatic group and a heteroaromatic group such that the bridging group of Formula 2 has a conjugated structure among the above-described exemplary groups. It may be preferable to be the above group (for example, the group referred to above Q 1 ).
- the reverse wavelength dispersible compound of Chemical Formula 1 compounds represented by RD-01 to RD-42 according to embodiments to be described later may be exemplified.
- the reverse wavelength dispersible compound is not limited to the compounds of RD-01 to RD-42, and may be implemented in various combinations in the above-described range.
- reverse wavelength dispersion compound represented by Chemical Formula 1 may be synthesized by applying known reactions, and a more detailed synthesis method will be described through examples. II. Reverse wavelength dispersion composition
- a reverse wavelength dispersion composition comprising the compound represented by the formula (1).
- the reverse wavelength dispersible composition may be a composition in which the compound represented by Chemical Formula 1 is dissolved in a solvent together with a polymerization initiator.
- the composition represented by Formula 1 may be included alone or in combination of two or more kinds.
- the polymerization initiator radical polymerization initiators conventional in the art to which the present invention pertains may be used.
- the content of the polymerization initiator may be determined in a conventional range capable of efficiently eliciting the polymerization reaction of the reverse wavelength dispersible compound.
- the polymerization initiator may comprise from 10 parts by weight 0/0, preferably 0.5 to 8 parts by weight 0 /, based on the total weight of the composition.
- the solvent is benzene, toluene, xylene, mesitylene, n-butylbenzene, diethylbenzene, tetralin, methoxybenzene, 1,2-dimethoxybenzene, ethylene glycol dimethyl Ether, diethylene glycol dimethyl ether, acetone, Methyl ethyl ketone, methyl isobutyl ketone, cyclopentanone, cyclonucleanone, ethyl acetate, methyl lactate, ethyl lactate,. Ethylene glycol monomethyl ether acetate, propylene glycol monomethyl ether acetate,
- a boiling point of 60 to 250 ° C. is advantageous for forming a uniform film thickness at the time of application of the composition, and is advantageous for minimizing the residual of the solvent and the deterioration of the orientation.
- the reverse wavelength dispersion composition may optionally further include a sensitizer such as xanthone, thioxanthone, chlorothioxanthone, phenothiazine, anthracene, diphenylanthracene, and the like.
- a sensitizer such as xanthone, thioxanthone, chlorothioxanthone, phenothiazine, anthracene, diphenylanthracene, and the like.
- the reverse wavelength dispersion composition may optionally contain quaternary ammonium salts, alkylamine oxides, polyamine derivatives, polyoxyethylene-polyoxypropylene condensates, sodium lauryl sulfate, ammonium lauryl sulfate, and alkyl-substituted aromatic sulfonic acids.
- Surfactants such as salts, alkyl phosphates and perfluoroalkyl sulfonates; Storage stabilizers such as hydroquinone, hydroquinone monoalkyl ethers, pyrogalls, thiophenols, 2-naphthylamines, and 2-hydroxynaphthalenes; Antioxidants such as 2,6-di-t-butyl-P-cresol and triphenylphosphite; UV absorbers such as salicylic acid ester compounds, benzophenol compounds, benzotriazole compounds, cyanoacrylate compounds, and nickel complex salt compounds may be further included.
- Storage stabilizers such as hydroquinone, hydroquinone monoalkyl ethers, pyrogalls, thiophenols, 2-naphthylamines, and 2-hydroxynaphthalenes
- Antioxidants such as 2,6-di-t-butyl-P-cresol and triphenylphosphite
- the reverse wavelength dispersion composition may further include particulate matter for selectively adjusting optical anisotropy or improving the strength of the polymerized film as necessary.
- the particulate matter is hacklite, montmorillonite, kallinite, ZnO, TiO 2 , Ce0 2 , Al 2 0 3 , Fe 2 O 3 , Zr0 2 , MgF 2 , SiO 2 , SrCO 3 , Ba (OH) 2 , Ca
- Inorganic particulate matters such as (OH) 2 , Ga (OH) 3 , AI (OH) 3 , Mg (OH) 2 , Zr (OH) 4 ;
- Organic particulate matter such as carbon nanotubes, fullerenes, dendrimers, polyvinyl alcohols, polymethacrylates, and polyimides.
- the reverse wavelength dispersion composition may further include any liquid crystal compound.
- the arbitrary liquid crystal compound may be polymerized or not.
- the liquid crystal compound which has an ethylenically unsaturated bond, the compound which has an optical active group, a rod-like liquid crystal compound, etc. are mentioned.
- the liquid crystal compound of any will be heunhap in appropriate amounts depending on their structure, the preferably the compound is the total compound weight of the 20 parts by weight 0/0 or more of the formula (1), or 50 parts by weight 0/0 or more It may be advantageous to be included in terms of achieving the above object.
- an optically anisotropic body formed using the reverse wavelength dispersion composition.
- the optically anisotropic substance may exhibit reverse wavelength dispersibility satisfying the following Formulas I and II.
- the optically anisotropic body applies the above-mentioned reverse wavelength dispersible composition to a support substrate, and the reverse wavelength dispersible composition It is possible to obtain by desolventing the liquid crystal compound in the oriented state, and then irradiating and polymerizing the energy ray.
- the support substrate is not particularly limited, but a preferred example is a glass plate, polyethylene terephthalate film, polyimide film, polyamide film, polymethyl methacrylate film, polystyrene film, polyvinyl chloride film, polytetrafluoroethylene film , Cellulose-based film, silicon film and the like can be used. And, a polyimide alignment film or on the support substrate What gave polyvinyl alcohol the alignment film can be used preferably.
- a known method may be used. For example, a coating method, a spin coating method, a bar coating method, a dip coating method, a spray coating method, or the like may be applied. And, the thickness of the film formed by the composition may vary depending on the use, preferably may be selected in the range of 0.01 to 100.
- the method of performing a pre-orientation process on a support substrate is mentioned as a non-limiting example.
- a method of performing an orientation process the method of forming the liquid crystal aligning side containing various polyimide oriented films or polyvinyl alcohol-type oriented films on a support substrate, and performing a process, such as rubbing, is mentioned.
- the method of applying a magnetic field, an electric field, etc. to the composition on a support substrate is mentioned.
- the method of polymerizing the reverse wavelength dispersion composition may be a known method using light, heat, or electromagnetic waves.
- the optically anisotropic body may be used in a retardation film, a polarizing element, an antireflection film, a selective emission film, a viewing angle compensation film, or the like of a liquid crystal display or an OLED display.
- a retardation film a polarizing element
- an antireflection film a selective emission film
- a viewing angle compensation film or the like of a liquid crystal display or an OLED display.
- interference by external light can be minimized, thereby enabling a more perfect black.
- the reverse wavelength dispersion compound according to the present invention can provide a stronger and more stable reverse wavelength dispersion, thereby providing an optically anisotropic body having excellent optical properties.
- FIG. 1 a to. 10 illustrates a scheme for synthesizing a reverse wavelength dispersion compound according to one embodiment of the present invention, respectively.
- Compound RD-01 was synthesized according to the scheme shown in FIGS. 1a to 1c.
- K 2 CO 3 potassium carbonate
- Compound RD-02 was synthesized according to the scheme shown in FIGS. 1 a to 1 c.
- Example 55 except that about 55 g of Compound 11-2 ((1 r, 4r) -4-(((6- (acryloyloxy) hexyl) oxy) carbonyl) cyclohexanecarboxylic acid) was used instead of Compound 11-1.
- About 100 g of Compound 12-2 was obtained by the same method as the synthesis of Compound 12-1.
- Compound 15-2 was obtained by the same method as the synthesis of Compound 15-1 of Example 1, except that Compound 14-2 was used instead of Compound 14-1.
- Compound RD-03 was prepared according to the scheme shown in FIGS. 1a to 1c.
- Example 1 except that about 60 g of Compound 11-3 ((1 r, 4r) -4-(((8- (acr loyloxy) octyl) oxy) carbonyl) cyclohexanecarboxylic acid) was used instead of Compound 11-1. About 100 g of Compound 12-3 was obtained by the same method as the synthesis of Compound 12-1.
- Compound 15-3 was obtained by the same method as the synthesis of Compound 15-1 of Example 1, except that Compound 14-3 was used instead of Compound 14-1.
- Compound RD-03 was obtained by the same method as the synthesis of Compound RD-1 of Example 1, except that Compound 15-3 was used instead of Compound 15-1.
- Compound RD-04 was synthesized according to the scheme shown in FIGS. 2a and 2b.
- Compound RD-05 was synthesized according to the scheme shown in FIGS. 2a and 2b.
- Compound 24-2 was obtained by the same method as the synthesis of Compound 24-1 of Example 4, except that Compound 23-2 was used instead of Compound 23-1.
- Compound RD-05 was obtained by the same method as the synthesis of Compound RD-04 of Example 4, except that Compound 24-2 was used instead of Compound 24-1.
- Compound RD-06 was synthesized according to the scheme shown in FIGS. 2a and 2b.
- Compound RD-06 was obtained by the same method as the synthesis of Compound RD-04 of Example 4, except that Compound 24-3 was used instead of Compound 24-1.
- Compound RD-08 was synthesized according to the scheme shown in FIGS. 3a and 3b.
- Compound 28-2 was obtained by the same method as the synthesis of Compound 28-1 of Example 7, except that ((hexyloxy) carbonyl) cyclohexanecarboxylic acid] was used. .
- Compound RD-09 was synthesized according to the scheme shown in FIGS. 3a and 3b.
- Compound 28-3 was obtained by the same method as the compound phase of Compound 28-1 of Example 7, except that ((octyloxy) carbonyl) cyclohexanecarboxylic acid] was used.
- Compound RD-10 was synthesized according to the scheme shown in FIGS. 3a and 3b.
- Compound RD-10 was obtained by the same method as the synthesis of Compound RD-01 of Example 1, except that Compound 33-4 was used instead of Compound 1 5-1.
- Compound RD-11 was synthesized according to the scheme shown in FIGS. 3a and 3b.
- Compound RD-11 was obtained by the same method as the synthesis of Compound RD-01 of Example 1, except that Compound 33-5 was used instead of Compound 15-1.
- Compound RD-12 was synthesized according to the scheme shown in FIGS. 3a and 3b.
- Compound 32-6 was obtained by the same method as the synthesis of Compound 12-1 of Example 1, except that (acryloyloxy) hexyl) oxy) carbonyl) cyclohexanecarboxylic acid was used.
- Compound RD-12 was obtained by the same method as the synthesis of Compound RD-01 of Example 1, except that Compound 33-6 was used instead of Compound 15-1.
- Compound RD-13 was synthesized according to the scheme shown in FIGS. 3a and 3b.
- Compound 33-7 was obtained by the same method as the synthesis of Compound 15-1 of Example 1, except that Compound 32-7 was used instead of Compound 14-1.
- Compound RD-13 was obtained by the same method as the synthesis of Compound RD-01 of Example 1, except that Compound 33-7 was used instead of Compound 15-1.
- About 80 g of Compound 32-9 was obtained by the same method as the synthesis of Compound 12-1 of Example 1, except that octyl) oxy) carbonyl) cyclohexanecarboxylic acid was used.
- Compound RD-15 was obtained by the same method as the synthesis of Compound RD-01 of Example 1, except that Compound 33-9 was used instead of Compound 15-1.
- Compound RD-16 was synthesized according to the scheme shown in FIGS. 4a and 4b.
- Compound RD-16 was obtained by the same method as the synthesis of Compound RD-01 of Example 1, except that Compound 40-1 was used instead of Compound 15-1.
- Compound RD-17 was synthesized according to the scheme shown in FIGS. 4a and 4b.
- compound 39-2 was obtained by the same method as the synthesis of Compound 12-1 of Example 1, except.
- Compound 40-2 was obtained by the same method as the synthesis of Compound 15-1 of Example 1, except that Compound 39-2 was used instead of Compound 14-1 and Compound 35 was used instead of Compound 6. .
- Compound RD-17 was obtained by the same method as the synthesis of Compound RD-01 of Example 1, except that Compound 40-2 was used instead of Compound 15-1.
- Compound RD-18 was synthesized according to the scheme shown in FIGS. 4a and 4b.
- Compound 39-3 was obtained by the same method as the synthesis of Compound 12-1 of Example 1, except that (acryloyloxy) octyl) oxy) carbonyl) cyclohexanecarboxylic acid] was used.
- Compound 40-3 was obtained by the same method as the synthesis of Compound 15-1 of Example 1, except that Compound 39-3 was used instead of Compound 14-1 and Compound 35 was used instead of Compound 6. .
- Compound RD-18 was obtained by the same method as the synthesis of Compound RD-01 of Example 1, except that Compound 40-3 was used instead of Compound 15-1.
- Compound RD-20 was synthesized according to the scheme shown in FIGS. 5a and 5b.
- Compound RD-20 was obtained by the same method as the synthesis of Compound RD-04 of Example 4, except that Compound 41-2 was used instead of Compound 24-1.
- Compound RD-21 was synthesized according to the scheme shown in FIGS. 5a and 5b.
- Compound RD-23 was synthesized according to the scheme shown in FIGS. 6a and 6b.
- Compound RD-23 was obtained by the same method as the synthesis of Compound RD-01 of Example 1, except that Compound 42-2 was used instead of Compound 15-1.
- Compound RD-26 was synthesized according to the scheme shown in FIGS. 6a and 6b.
- Compound RD-26 was obtained by the same method as the synthesis of Compound RD-01 of Example 1, except that Compound 42-5 was used instead of Compound 15-1.
- Compound RD-27 was obtained by the same method as the synthesis of Compound RD-01 of Example 1, except that Compound 42-6 was used instead of Compound 15-1.
- Compound RD-28 was synthesized according to the scheme shown in FIGS. 6a and 6b.
- Compound RD-29 was synthesized according to the scheme shown in FIGS. 6a and 6b.
- Compound RD-30 was synthesized according to the scheme shown in FIGS. 6a and 6b.
- Compound RD-30 was obtained by the same method as the synthesis of Compound RD-01 of Example 1, except that Compound 42-9 was used instead of Compound 15-1.
- Compound RD-31 was synthesized according to the scheme shown in FIGS. 7a and 7b.
- Compound RD-32 was synthesized according to the scheme shown in FIGS. 7a and 7b.
- Compound 44-2 was obtained by the same method as the synthesis of Compound 12-1 of Example 1, except that (methacryloyloxy) hexyl) oxy) carbonyl) cyclohexanecarboxylic acid was used.
- Compound RD-32 was obtained by the same method as the synthesis of Compound RD-01 of Example 1, except that Compound 45-2 was used instead of Compound 15-1.
- Compound RD-33 was synthesized according to the scheme shown in FIGS. 7a and 7b.
- Compound 44-3 was obtained by the same method as the synthesis of Compound 12-1 of Example 1, except that (methacryloyloxy) octyl) oxy) carbonyl) cyclohexanecarboxylic acid was used.
- Compound RD-33 was obtained by the same method as the synthesis of Compound RD-01 of Example 1, except that Compound 45-3 was used instead of Compound 15-1.
- Compound RD-34 was synthesized according to the scheme shown in FIGS. 8a and 8b.
- Compound RD-34 was obtained by the same method as the synthesis of Compound RD-01 of Example 1, except that Compound 48-1 was used instead of Compound 15-1.
- Compound RD-35 was synthesized according to the scheme shown in FIGS. 8a and 8b.
- Compound 47-2 was obtained by the same method as the synthesis of Compound 12-1 of Example 1, except that (cinnamoyloxy) hexyl) oxy) carbonyl) cyclohexanecarboxylic acid] was used.
- Example 1 except that compound 47-2 was used instead of compound 14-1.
- Compound RD-35 was obtained by the same method as the synthesis of Compound RD-01 of Example 1, except that Compound 48-2 was used instead of Compound 15-1.
- Compound RD-36 was synthesized according to the scheme shown in FIGS. 8a and 8b.
- Compound RD-36 was obtained by the same method as the synthesis of Compound RD-01 of Example 1, except that Compound 48-3 was used instead of Compound 15-1.
- Compound RD-37 was synthesized according to the scheme shown in FIGS. 9a and 9b.
- Compound 50 was obtained by the same method as the synthesis of Compound 8 of Example 1, except that Compound 49 (6-hydroxy-2-naphthoic acid) was used instead of Compound 7.
- Compound 53-1 was obtained by the same method as the synthesis of Compound 12-1 of Example 1, except that Compound 52 was used instead of Compound 10.
- Compound RD-39 was obtained by the same method as the synthesis of Compound RD-01 of Example 1, except that Compound 54-3 was used instead of Compound 15-1.
- Compound RD-40 was synthesized according to the scheme shown in FIG. 10. That is, the same as the synthesis of Compound 15-1 of Example 1, except that Compound 39-1 according to Example 16 was used instead of Compound 14-1, and about 10 g of iodobenzene was used instead of Compound 6. By method, about 30 g of compound RD-40 was obtained.
- RD-18 compound About 100 parts by weight of the RD-18 compound according to Example 18, about 12: 5 parts by weight of the mesogenic compound represented by Formula (a), about 37.5 parts by weight of the mesogenic compound represented by Formula (b), and initiator (Irgacure 907 , Ciba-Geigy) about 12.5 parts by weight, antioxidant (Irganox 1076, Ciba-Geigy) about 0.27 parts by weight, fluorine-based surfactant (FC-171, 3M) about 3.33 parts by weight, and about 1000 parts by weight of In combination, a composition for an optical device (solid content of about 21% by weight) was prepared.
- a retardation film was prepared by irradiating non-polarized UV light having a high pressure mercury lamp of 200 mW / citf as a light source to fix the alignment state of the liquid crystal.
- the quantitative retardation value of the prepared retardation film was measured using Axoscan (manufactured by Axomatrix Co., Ltd.). At this time, the thickness was measured independently, and the retardation value (Arvd) was obtained from the obtained value.
- Arrd (450 nm) An d (550 nm) and Arvd (650 nm) were measured to be 103, 1 10, and 1 14, respectively. Therefore, An (450 nm) / An (550 nm) value is 0.94, An (650 nm) / An (550 nm) value is 1.0, it was confirmed that the conditions according to the formulas I and I I above.
- composition is coated with a norbornene-based photo-alignment material, by the coating method
- a retardation film was prepared by a method of fixing non-polarized UV light having a high pressure mercury lamp of 200 mW / cuf as a light source to the film to fix the alignment state of the liquid crystal.
- the quantitative retardation value of the prepared retardation film was measured using Axoscan (manufactured by Axomatrix Co., Ltd.). At this time, the thickness was measured independently, and the retardation value (Arvd) was obtained from the obtained value. As a result, zovd (450 nm), An d (550 nm), and An'd (650 nm) were measured to be 115, 120, and 124, respectively. Therefore, it was confirmed that the value of ⁇ (450 ⁇ ) / ⁇ (550 ⁇ ) was 0.96, and the value of An (650nm) / An (550nm) was 1.03, which satisfies the conditions according to the above formulas I and II.
- the composition was coated on a TAC film coated with a norbornene-based photo-alignment material by a roll coating method, and then dried at about 80 ° C. for 2 minutes to align the liquid crystal molecules. Thereafter, a retardation film was produced by irradiating non-polarized UV light having a high pressure mercury lamp of 200 mW / cuf as a light source to fix the alignment state of the liquid crystal.
- the quantitative retardation value of the prepared retardation film was measured using Axoscan (manufactured by Axomatrix Co., Ltd.). At this time, the thickness was measured independently, and the retardation value (Aird) was obtained from the obtained value. As a result, An'd (450 nm), An d (550 nm), and An d (650 nm) were measured to be 1 10, 1 13, and "5. Therefore, the value of An (450 nm) / An (550 nm) was 0.97 and An (650 nm) / An (550 nm) value of 1.0, which was confirmed to satisfy the conditions according to the formula (I) and formula (II).
- the composition was coated on a TAC film coated with a norbornene-based photoalignment material by a roll coating method, and then dried at about 80 ° C. for 2 minutes to form a liquid crystal.
- the molecules were allowed to be oriented. Thereafter, a retardation film was produced by irradiating non-polarized UV light having a high pressure mercury lamp of 200 mW / cuf as a light source to fix the alignment state of the liquid crystal.
- the quantitative retardation value of the prepared retardation film was measured using Axoscan (manufactured by Axomatrix Co., Ltd.). At this time, the thickness was measured independently, and the retardation value (Arvd) was obtained from the obtained value. As a result, An d (450 nm), An d (550 nm), and An d (650 nm) were measured to be 125, 126, and 127, respectively. Thus, the ⁇ (450 ⁇ ) / ⁇ (550 ⁇ ) values are 0.99 and the An (650 nm) / An (550 nm) values are
- composition by the coating method, the norbornene-based photo-alignment material is coated
- a retardation film was produced by irradiating non-polarized UV light having a high pressure mercury lamp of 200 mW / cuf as a light source to fix the alignment state of the liquid crystal.
- the quantitative retardation value of the prepared retardation film was measured using Axoscan (manufactured by Axomatrix Co., Ltd.). At this time, the thickness was measured independently, and the retardation value (An.d) was obtained from the obtained value. As a result, ⁇ ⁇ ⁇ (450 ⁇ ), An d (550 nm), and An d (650 nm) were measured at 225, 210, and 203, respectively. Therefore, the An (450nm) / An (550nm) value is 1.07, and the An (650nm) / An (550nm) value is 0.96, and the positive wavelength that does not satisfy the conditions according to Equation & Equation It was confirmed to exhibit dispersion.
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US14/913,589 US9850196B2 (en) | 2013-09-30 | 2014-09-19 | Compounds having negative optical dispersion, negative optical dispersion composition comprising the compounds, and optically anisotropic body comprising the composition |
CN201480054163.6A CN105593204B (zh) | 2013-09-30 | 2014-09-19 | 有负光色散性的化合物、含该化合物的负光色散性组合物和含该组合物的光学各向异性体 |
JP2016518722A JP6397004B2 (ja) | 2013-09-30 | 2014-09-19 | 逆波長分散性化合物、これを含む逆波長分散性組成物および光学異方体 |
EP14847655.9A EP3053909B1 (en) | 2013-09-30 | 2014-09-19 | Inverse-wavelength dispersible compound, and inverse-wavelength dispersible composition and optically anisotropic body comprising same |
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KR20100130179A (ko) * | 2008-01-11 | 2010-12-10 | 메르크 파텐트 게엠베하 | 반응성 메소젠 화합물 및 혼합물 |
KR20110043776A (ko) * | 2008-08-18 | 2011-04-27 | 메르크 파텐트 게엠베하 | 디스코틱 및 칼라미틱 기를 포함하는 메소젠 화합물 |
-
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Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR20100016054A (ko) * | 2007-03-30 | 2010-02-12 | 메르크 파텐트 게엠베하 | 음성 광학 분산도를 갖는 복굴절성 중합체 필름 |
KR20100130179A (ko) * | 2008-01-11 | 2010-12-10 | 메르크 파텐트 게엠베하 | 반응성 메소젠 화합물 및 혼합물 |
KR20110043776A (ko) * | 2008-08-18 | 2011-04-27 | 메르크 파텐트 게엠베하 | 디스코틱 및 칼라미틱 기를 포함하는 메소젠 화합물 |
Non-Patent Citations (1)
Title |
---|
C. TSCHIERSKE; G. PELZL; S. DIELE, ANGEW. CHEM., vol. 116, 2004, pages 6340 - 6368 |
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