WO2015046825A2 - Composé à cristaux liquides polymérisable, composition à cristaux liquides et film optique le contenant - Google Patents

Composé à cristaux liquides polymérisable, composition à cristaux liquides et film optique le contenant Download PDF

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WO2015046825A2
WO2015046825A2 PCT/KR2014/008750 KR2014008750W WO2015046825A2 WO 2015046825 A2 WO2015046825 A2 WO 2015046825A2 KR 2014008750 W KR2014008750 W KR 2014008750W WO 2015046825 A2 WO2015046825 A2 WO 2015046825A2
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compound
synthesis
liquid crystal
group
carbon atoms
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Korean (ko)
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WO2015046825A3 (fr
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이민형
송영지
전성호
서경창
장형빈
최지영
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주식회사 엘지화학
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Priority claimed from KR1020140124469A external-priority patent/KR101614524B1/ko
Application filed by 주식회사 엘지화학 filed Critical 주식회사 엘지화학
Priority to JP2016545679A priority Critical patent/JP6431078B2/ja
Priority to CN201480053838.5A priority patent/CN105593339B/zh
Priority to US14/914,567 priority patent/US9505979B2/en
Publication of WO2015046825A2 publication Critical patent/WO2015046825A2/fr
Publication of WO2015046825A3 publication Critical patent/WO2015046825A3/fr

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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
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/32—Non-steroidal liquid crystal compounds containing condensed ring systems, i.e. fused, bridged or spiro ring systems
    • C09K19/322—Compounds containing a naphthalene ring or a completely or partially hydrogenated naphthalene ring
    • 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
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
    • C09K19/20—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers
    • 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
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
    • C09K19/3001—Cyclohexane rings
    • C09K19/3066—Cyclohexane rings in which the rings are linked by a chain containing carbon and oxygen atoms, e.g. esters or ethers
    • C09K19/3068—Cyclohexane rings in which the rings are linked by a chain containing carbon and oxygen atoms, e.g. esters or ethers chain containing -COO- or -OCO- groups
    • 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
    • C09K2019/0444—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit characterized by a linking chain between rings or ring systems, a bridging chain between extensive mesogenic moieties or an end chain group
    • 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
    • C09K2019/0444—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit characterized by a linking chain between rings or ring systems, a bridging chain between extensive mesogenic moieties or an end chain group
    • C09K2019/0448—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit characterized by a linking chain between rings or ring systems, a bridging chain between extensive mesogenic moieties or an end chain group the end chain group being a polymerizable end group, e.g. -Sp-P or acrylate
    • 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
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
    • C09K19/20—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers
    • C09K19/2007—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers the chain containing -COO- or -OCO- groups
    • C09K2019/2078—Ph-COO-Ph-COO-Ph

Definitions

  • the present invention relates to a polymerizable liquid crystal compound, a liquid crystal composition comprising the same, and an optical film.
  • LCDs liquid crystal displays
  • LEDs organic light emitting diodes
  • OLED displays are gaining attention as future displays because they are superior to LCDs in various fields such as thickness, power consumption, response speed, and viewing angle, and can be used for various purposes such as transparent products 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 is to provide a polymerizable liquid crystal compound that can be used more suitably for anti-radiation films and the like by enabling formation of a liquid crystal layer having high alignment stability.
  • the present invention is a polymerizable liquid crystal composition comprising the compound and It is for providing an optical film.
  • a polymerizable liquid crystal compound o represented by the following Chemical Formula 1 is provided:
  • A, 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;
  • 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-(D 1 -G 1 )-or-(G 2 -D 2 )-repeated two or more times may be the same or different from each other;
  • a polymerizable liquid crystal composition comprising the compound represented by Chemical Formula 1 is provided.
  • the optical film formed using the said polymeric liquid crystal composition is provided.
  • a polymerizable liquid crystal compound, a composition including the same, and an optical film according to embodiments of the present invention will be described.
  • Polymerizable liquid crystal compound means a liquid crystal compound having at least one polymerizable functional group. After aligning the composition containing the polymerizable liquid crystal compound in a liquid crystal state, and irradiating active energy rays such as ultraviolet rays in that state, a polymer obtained by fixing the alignment structure of the liquid crystal molecules can be obtained.
  • the resulting composite has anisotropy in physical properties such as refractive index, dielectric constant, susceptibility modulus, thermal expansion coefficient, and the like, and thus can be used as an optical anisotropic body such as a retardation plate, a polarizing plate, a polarizing prism, a brightness enhancement film, and an optical fiber covering. Do.
  • meogenic 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, see 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 group” comprises one or more carbon atoms (eg, -c ⁇ c—) free of any non-carbon atoms, or optionally one or more non-carbon atoms (eg, N, 0, S, P , Si) means any monovalent or polyvalent organic radical moiety comprising one or more carbon atoms (eg carbonal).
  • hydrocarbyl group is meant a carbyl group which additionally contains one or more H atoms and optionally one or more heteroatoms (eg, N, 0, S, P, Si).
  • a polymerizable compound represented by the following Chemical Formula 1 is provided:
  • A, 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;
  • 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-(D 1 -G 1 )-or-(G 2 -D 2 )-repeated two or more times may be the same or different from each other;
  • the polymerizable liquid crystal compound having the structure of Chemical Formula 1 enables formation of a liquid crystal layer having higher orientation stability.
  • the conventional liquid crystal compound has a limitation in that the alignment collapses when the alignment is high because the interaction between molecules is weak.
  • the polymerizable liquid crystal compound represented by Chemical Formula 1 has a structure in which at least two functional groups are introduced into the molecule to enable intermolecular interaction. Accordingly, the polymerizable liquid crystal compound represented by Chemical Formula 1 enables the formation of a liquid crystal layer having high orientation stability due to relatively strong interaction between molecules.
  • the functional group that enables the intermolecular interactions in Formula 1 A, E 1 , E 2 , D 1 , D 2 , G 1 , G 2 , L 1 , and L 2 contained in sp 2 can be introduced to the two or more common activated carbon-common activated carbon and sp 3.
  • A, G 1 and G 2 are each independently an aromatic 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, G 1 and G 2 is a 5-membered ring (eg cyclopentane, tetrahydrofuran, tetrahydrothiofuran, pyridine; 6-membered ring (eg 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 groups in A, G 1 and G 2 are 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,
  • A, G 1 and G 2 may be each independently a cyclonucleic acid ring, cyclonucleene ring, benzene ring, naphthalene ring, or phenanthrene ring. More preferably, A, G 1 and G 2 are each independently composed of trans-1,4-cyclonuylene, 1,4-phenylene, 1,5-naphthylene, and 2,6-naphthylene Can be selected from the group.
  • m and n may be each independently an integer of 1 to 5.
  • each repeating unit of-(D -G 1 )-or-(G 2 -D 2 )-which is repeated two or more times may be the same or different from each other.
  • D 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.
  • the polymerizable liquid crystal compound represented by Chemical Formula 1 has at least two functional groups that enable intermolecular interactions in a molecule.
  • the polymerizable liquid crystal compound may exhibit improved orientation stability through interaction with other molecules as it includes functional groups that enable intermolecular interactions.
  • two or more functional groups are introduced into the polymerizable liquid crystal compound to enable the intermolecular interaction.
  • the position at which the functional group enabling the intermolecular interaction is introduced is not particularly limited, and may vary depending on the design of the length of the polymerizable liquid crystal compound and the kind of functional groups constituting the polymerizable liquid crystal compound.
  • sp 2 -generated carbon and sp 3 -generated carbon contained in A, E, E 2 , D 1 , D 2 , G 1 , G 2 , L 1 , and L 2 Two of the bound hydrogens The above may be substituted with a functional group that enables the intermolecular interaction. More preferably, the functional group that enables the intermolecular interaction may be introduced into A and G 1 , or A and G 2 , or A, G 1 and G 2 in Formula 1.
  • the polymerizable liquid crystal compound of Chemical Formula 1 may include compounds represented by RD-01 to RD-30 according to embodiments to be described below.
  • the polymerizable liquid crystal compound is not limited to the compounds of RD-1 to RD-30, but may be implemented in various combinations in the above-described range.
  • the polymerizable liquid crystal compound represented by Chemical Formula 1 may be synthesized by applying known reactions, and a more detailed synthesis method will be described through Examples.
  • a polymerizable liquid crystal composition comprising the compound represented by the formula (1).
  • the polymerizable liquid crystal composition may be a composition obtained by dissolving the compound represented by Chemical Formula 1 in a solvent together with a polymerization initiator.
  • the compound represented by Formula 1 may be included in the composition alone or in combination of two or more.
  • 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 polymerizable liquid crystal compound.
  • the polymerization initiator may be included in 10% by weight or less, preferably 0.5 to 8% by weight 0 /.
  • 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 polymerizable liquid crystal composition may further include a sensitizer, such as Xanthone, thioxanthone, chlorothioxanthone, phenothiazine, anthracene, diphenylanthracene, and the like, if necessary.
  • a sensitizer such as Xanthone, thioxanthone, chlorothioxanthone, phenothiazine, anthracene, diphenylanthracene, and the like, if necessary.
  • the polymerizable liquid crystal composition may optionally contain quaternary ammonium salts, alkylamine oxides, polyamine derivatives, polyoxyethylene-polyoxypropylene condensates, sodium lauryl sulfate, ammonium lauryl sulfate, and alkyl-substituted aromatic sulfonates.
  • Surfactants such as alkyl phosphate and perfluoroalkyl sulfonate; Storage stabilizers such as hydroquinone, hydroquinone monoalkyl ethers, pyrogallols, 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, pyrogallols, thiophenols, 2-naphthylamines and 2-hydroxynaphthalenes
  • Antioxidants such as 2,6-di-t-butyl-P-cresol and triphenylphosphite
  • UV absorbers such
  • the polymerizable liquid crystal composition may further include particulate matter for selectively adjusting optical anisotropy or improving the strength of the polymerized film as necessary.
  • the particulate matter may be a nucleite, montmorillonite, kaolinite, ZnO, TiO 2 , CeO 2 , AI 2 O 3 , Fe 2 O 3) ZrO 2 , MgF 2 , Si0 2l SrC0 3 , Ba (OH) 2 , Ca (OH) Inorganic particulate matters such as 2 , Ga (OH) 3 , AI (OH) 3 , Mg (OH) 2 and Zr (OH) 4 ; Organic particulate matter such as carbon nanotubes, fullerene dendrimers, polyvinyl alcohol, polymethacrylate, polyimide, and the like.
  • the polymerizable liquid crystal composition may further include any liquid crystal compound in addition to the compound represented by Chemical Formula 1.
  • Any of the above The liquid crystal compound may be polymerizable or non-polymerizable.
  • the liquid crystal compound which has an ethylenically unsaturated bond, the compound which has an optical active group, a rod-shaped liquid crystal compound, etc. are mentioned.
  • any of the liquid crystal compounds may be mixed in an appropriate amount according to their structure, preferably, the compound represented by the formula (1) is included in 20 weight 0 / ° or more, or 50 weight% or more of the total weight of the liquid crystal compound It may be advantageous in view of achieving the above object.
  • an optical film formed using the polymerizable liquid crystal composition there is provided an optical film formed using the polymerizable liquid crystal composition.
  • the optical film may include a liquid crystal layer having a high alignment stability according to i formed by using a liquid crystal compound the above-mentioned polymerizable group.
  • the said optical film can be obtained by apply
  • 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, or the like may be used.
  • a polyimide alignment layer or a polyvinyl alcohol alignment layer may be preferably used on the support substrate.
  • a known method may be used. For example, a roll 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 0 . It can be selected in the range of 01 to 100.
  • the method of performing a pre-orientation process on a support substrate is mentioned as a non-limiting example.
  • various polyimide-based alignment films or polyvinyl alcohol-based The liquid crystal aligning side containing an oriented film is formed on a support substrate, and the method of processing, such as rubbing, is mentioned.
  • the method of applying a magnetic field or electric field etc. to the composition on a support substrate is mentioned.
  • the method of polymerizing the polymerizable liquid crystal composition may be a known method using light, heat, or electromagnetic waves.
  • the optical film may be used in a retardation film, a polarizing element, an antireflection film, a selective radiation film, a viewing angle compensation film of a liquid crystal display or an OLED display.
  • the optical film formed using the composition is applied to an OLED display, the interference by external light can be minimized, so that more perfect black can be realized.
  • the polymerizable liquid crystal compound according to the present invention has at least two functional groups that enable intermolecular interactions in a molecule, and thus, it is possible to form a liquid crystal layer having high orientation stability when coating a composition including the same.
  • a liquid crystal layer having high orientation stability when coating a composition including the same.
  • interference by external light can be minimized, thereby enabling a more perfect black.
  • 1A and 8B show a scheme for synthesizing a polymerizable liquid crystal compound according to an embodiment of the present invention, respectively.
  • Compound RD-01 was prepared according to the scheme shown in FIGS. 1a and 1b. Synthesized.
  • Compound RD-02 was synthesized according to the scheme shown in FIGS. 1a and 1b.
  • Compound RD-02 was obtained by the same method as the synthesis of Compound RD-1 of Example 1, except that Compound 9-2 was used instead of Compound 9-1.
  • compound 10 (4- (4-hydroxyphenyl) cyclohexanone) was dissolved in about 120 g of ⁇ , ⁇ -diisopropylethylamine ( ⁇ , ⁇ -diisopropylethylamine) in dichloromethane, and then about 50 g of methylchloromethyl ether at room temperature. (methyl chlo ⁇ ethyl ether) was slowly added dropwise. It was stirred for about 2 hours and then extracted with dichloromethane and water. Then, the extracted organic layer was chemically dried, the solvent was removed, and purified by column chromatography to obtain about 120 g of Compound 11.
  • Compound RD-06 was synthesized according to the scheme shown in FIG. That is, the compound of Example 4, except that compound 7-3 ((1 r, 4r) -4-(((8- (acryloyloxy) octyl) oxy) carbonyl) cyclohexanecarboxylic acid) was used instead of the compound 7-1. About 100 g of Compound RD-06 was obtained by the same method as the synthesis of RD-04.
  • Compound RD-08 was obtained by the same method as the synthesis of Compound RD-07 of Example 7, except that Compound 20-2 was used instead of Compound 20-1.
  • Compound RD-09 was obtained by the same method as the synthesis of Compound RD-07 of Example 7, except that Compound 20-3 was used instead of Compound 20-1.
  • Compound RD-10 was obtained by the same method as the synthesis of Compound RD-01 of Example 1, except that Compound Compound 25-1 was used instead of Compound 9-1.
  • Compound 24-3 was obtained by the same method as the synthesis of Compound 8-1 of Example 1, except that Compound 23 was used instead of Compound 6 and Compound 7-3 was used instead of Compound 7-1.
  • Compound RD-12 was obtained by the same method as the synthesis of Compound RD-0.1 of Example 1, except that Compound 25-3 was used instead of Compound 9-1.
  • Example 13 Synthesis of Compound RD-13 Eu ⁇ 0,: according to the Scheme illustrated in ⁇ 0 ⁇ oo Figures 5a and 5b was synthesized from the compound RD-13.
  • Compound RD-14 was synthesized according to the scheme shown in FIGS. 5a and 5b.
  • Compound 29-2 was obtained by the same method as the synthesis of Compound 29-1 of Example 13, except that Compound 28-2 was used instead of Compound 28-1.
  • Compound RD-14 was obtained by the same method as the synthesis of Compound RD-01 of Example 1, except that Compound 33-2 was used instead of Compound 9-1.
  • Compound RD-15 was synthesized according to the scheme shown in FIGS. 5a and 5b.
  • Compound RD-15 was obtained by the same method as the synthesis of Compound RD-01 of Example 1, except that Compound 33-3 was used instead of Compound 9-1.
  • Compound RD-16 was synthesized according to the scheme shown in FIGS. 5a and 5b.
  • Compound RD-17 was synthesized according to the scheme shown in FIGS. 5a and 5b.
  • Compound 32-5 was obtained by the same method as the synthesis of Compound 8-1 of Example 1, except that (acryloyloxy) hexyl) oxy) carbonyl) cyclohexanecarboxylic acid was used.
  • Compound RD-17 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 9-1.
  • Compound RD-18 was synthesized according to the scheme shown in FIGS. 5a and 5b.
  • Compound 32-6 was obtained by the same method as the synthesis of Compound 8-1 of Example 1, except that (acryloyloxy) hexyl) oxy) carbonyl) cyclohexanecarboxylic acid was used.
  • Compound RD-18 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 9-1.
  • Compound RD-19 was synthesized according to the scheme shown in FIGS. 5a and 5b.
  • Compound 32-7 was obtained by the same method as the synthesis of Compound 8-1 of Example 1, except that (acryloyloxy) octyl) oxy) carbonyl) cyclohexanecarboxylic acid was used.
  • Compound RD-19 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 9-1.
  • Compound RD-20 was synthesized according to the scheme shown in FIGS. 5a and 5b.
  • Compound 32-8 was obtained by the same method as the synthesis of Compound 8-1 of Example 1, except that (acryloyloxy) octyl) oxy) carbonyl) cyclohexanecarboxylic acid was used.
  • Compound RD-20 was obtained by the same method as the synthesis of Compound RD-01 of Example 1, except that Compound 33-8 was used instead of Compound 9-1.
  • Compound RD-21 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 9-1.
  • Compound RD-23 was obtained by the same method as the synthesis of Compound RD-01 of Example 1, except that Compound 36-2 was used instead of Compound 9-1.
  • Compound RD-24 was obtained by the same method as the synthesis of Compound RD-01 of Example 1, except that Compound 36-3 was used instead of Compound 9-1.
  • Compound RD-25 was obtained by the same method as the synthesis of Compound RD-01 of Example 1, except that Compound 39-1 was used instead of Compound 9-1.
  • Example 3 except that compound 38-2 was used instead of compound 8-1.
  • About 70 g of Compound 39-2 was obtained by the same method as the synthesis of Compound 9-1.
  • Compound RD-28 was synthesized according to the scheme shown in FIGS. 8a and 8b.
  • Compound 41 was obtained by the same method as the synthesis of Compound 4 of Example 1, except that Compound 40 (6-hydroxy-4-iodo-2-naphthoic acid) was used instead of Compound 3.
  • Compound RD-28 was obtained by the same method as the synthesis of Compound RD-01 of Example 1, except that Compound 45-1 was used instead of Compound 9-1.
  • Compound RD-30 was synthesized according to the scheme shown in FIGS. 8a and 8b.
  • Compound 44-3 was obtained by the same method as the synthesis of Compound 8-1 of Example 1, except that Compound 43 was used instead of Compound 6 and Compound 7-3 was used instead of Compound 7-1.
  • Compound RD-30 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 9-1.
  • Example RD-1 compound according to 1 about 90 weight 0 /., To about 2 weight percent mesogenic compound represented by the mesogenic compound about 5 weight 0/0, the formula b represented by the formula a, initiator (Irgacure 907 , Ciba-Geigy Co.) about 1 part by weight 0/0, and an antioxidant (Irganox 1076, Ciba-Geigy Co.) about 1 part by weight 0/0, and a fluorine-containing surfactant (FC-
  • the composition was coated on a TAC film coated with a cinnamate photo-alignment material by a roll coating method, and then dried at about 50 ° C. for 2 minutes to align the liquid crystal molecules. Thereafter, a retardation film was prepared by irradiating non-polarized UV light having a high pressure mercury lamp of 200 mVWcirf 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, the An d (550 nm) value was found to be about 212, and the An (450 nm) / An (550 nm) value was about 1.000.
  • a liquid crystal compound in the RD-1 compound about 80 weight 0 /., The formula a compound of about 12 increased 0 / in., And except for using about 5 parts by weight 0 /.
  • the compound of Formula b a method similar to that of Example 1 A retardation film was produced.
  • 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.
  • An An d (550 nm) value of about 250 An (450 nm) / An (550 nm) value of about 1.0 was confirmed. Comparative Production Example 1
  • a liquid crystal compound without using the RD-1 compound except that approximately 5 parts by weight with 0 /.
  • the compound of formula (a) compound of about 92 parts by weight 0/0, and the formula b of the phase difference in the same manner as in Preparation Example 1 A film was prepared.
  • 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, the value of An d (550 nm) was about 210, and the value of An (450 nm) / An (550 nm) was about 1.09.

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  • Chemical & Material Sciences (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Abstract

Cette invention concerne un composé à cristaux liquides polymérisable, une composition à cristaux liquides et un film optique le contenant. Le composé à cristaux liquides polymérisable selon l'invention comporte au moins deux groupes fonctionnels qui permettent une interaction intermoléculaire entre des molécules, et après application de la composition le contenant, une couche à cristaux liquides présentant une stabilité d'alignement élevée peut être formée. Le film optique formé à l'aide de la composition peut par conséquent être utilisé de manière convenable dans des films antiréfléchissants, etc. pour affichages à cristaux liquides ou affichages OLED.
PCT/KR2014/008750 2013-09-30 2014-09-19 Composé à cristaux liquides polymérisable, composition à cristaux liquides et film optique le contenant WO2015046825A2 (fr)

Priority Applications (3)

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JP2016545679A JP6431078B2 (ja) 2013-09-30 2014-09-19 重合性液晶化合物、これを含む液晶組成物および光学フィルム
CN201480053838.5A CN105593339B (zh) 2013-09-30 2014-09-19 可聚合液晶化合物、包含所述化合物的液晶组合物以及包含所述组合物的光学膜
US14/914,567 US9505979B2 (en) 2013-09-30 2014-09-19 Polymerizable liquid crystal compounds, liquid crystal composition comprising the compounds, and optical film comprising the composition

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KR10-2013-0116535 2013-09-30
KR20130116535 2013-09-30
KR10-2014-0124469 2014-09-18
KR1020140124469A KR101614524B1 (ko) 2013-09-30 2014-09-18 중합성 액정 화합물, 이를 포함하는 액정 조성물 및 광학 필름

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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20020019619A (ko) * 2000-07-20 2002-03-13 플레믹 크리스티안 중합성 메소제닉 톨란
KR20080054383A (ko) * 2005-10-17 2008-06-17 아사히 가라스 가부시키가이샤 중합성 액정 화합물, 액정 조성물, 광학 이방성 재료, 및광학 소자
KR20100085929A (ko) * 2007-09-25 2010-07-29 메르크 파텐트 게엠베하 메소젠 이량체
JP2010241791A (ja) * 2009-03-18 2010-10-28 Chisso Corp 重合性液晶化合物、重合性液晶組成物およびその重合体
JP2011148762A (ja) * 2009-12-22 2011-08-04 Jnc Corp 重合性液晶化合物、重合性液晶組成物および異方性ポリマー

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20020019619A (ko) * 2000-07-20 2002-03-13 플레믹 크리스티안 중합성 메소제닉 톨란
KR20080054383A (ko) * 2005-10-17 2008-06-17 아사히 가라스 가부시키가이샤 중합성 액정 화합물, 액정 조성물, 광학 이방성 재료, 및광학 소자
KR20100085929A (ko) * 2007-09-25 2010-07-29 메르크 파텐트 게엠베하 메소젠 이량체
JP2010241791A (ja) * 2009-03-18 2010-10-28 Chisso Corp 重合性液晶化合物、重合性液晶組成物およびその重合体
JP2011148762A (ja) * 2009-12-22 2011-08-04 Jnc Corp 重合性液晶化合物、重合性液晶組成物および異方性ポリマー

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