WO2022168607A1 - 重合性液晶混合物、重合性液晶組成物 - Google Patents

重合性液晶混合物、重合性液晶組成物 Download PDF

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WO2022168607A1
WO2022168607A1 PCT/JP2022/001808 JP2022001808W WO2022168607A1 WO 2022168607 A1 WO2022168607 A1 WO 2022168607A1 JP 2022001808 W JP2022001808 W JP 2022001808W WO 2022168607 A1 WO2022168607 A1 WO 2022168607A1
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group
liquid crystal
polymerizable liquid
carbon atoms
crystal compound
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PCT/JP2022/001808
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English (en)
French (fr)
Japanese (ja)
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真之介 吉岡
憲之 飛田
啓貴 中田
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住友化学株式会社
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Priority to KR1020237022392A priority Critical patent/KR20230138450A/ko
Priority to CN202280009560.6A priority patent/CN116745664A/zh
Publication of WO2022168607A1 publication Critical patent/WO2022168607A1/ja

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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
    • C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
    • C09K19/3491—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having sulfur as hetero atom
    • C09K19/3497—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having sulfur as hetero atom the heterocyclic ring containing sulfur and nitrogen atoms
    • 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
    • C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
    • C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
    • C08F20/10—Esters
    • C08F20/34—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate
    • C08F20/36—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate containing oxygen in addition to the carboxy oxygen, e.g. 2-N-morpholinoethyl (meth)acrylate or 2-isocyanatoethyl (meth)acrylate
    • 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
    • C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
    • C08F222/10—Esters
    • C08F222/1006—Esters of polyhydric alcohols or polyhydric phenols
    • C08F222/102—Esters of polyhydric alcohols or polyhydric phenols of dialcohols, e.g. ethylene glycol di(meth)acrylate or 1,4-butanediol dimethacrylate
    • 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
    • C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
    • C08F222/10—Esters
    • C08F222/1006—Esters of polyhydric alcohols or polyhydric phenols
    • C08F222/106—Esters of polycondensation macromers
    • 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
    • C09K19/2021—Compounds containing at least one asymmetric carbon atom
    • C09K19/2028—Compounds containing at least one asymmetric carbon atom containing additionally a linking group other than -COO- or -OCO-, e.g. -CH2-CH2-, -CH=CH-, -C=C-; containing at least one additional carbon atom in the chain containing -COO- or -OCO- groups, e.g. -COO-CH*-CH3
    • 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
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/30—Polarising elements
    • 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
    • C09K2019/2035—Ph-COO-Ph
    • 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
    • C09K2019/3069—Cy-COO-Cy

Definitions

  • the groups represented by A 11 , A 12 , B 11 , B 12 , E 11 , E 12 , F 11 , F 12 , G 11 , G 12 , P 11 and P 12 in formula (1) are , respectively, groups represented by A 21 , A 22 , B 21 , B 22 , E 21 , E 22 , F 21 , F 22 , G 21 , G 22 , P 21 and P 22 in formula (2); [4] or [5] above, wherein the groups represented by Ar 11 and Ar 12 in formula (1) are the same as the groups represented by Ar 21 in formula (2).
  • the polymerizable liquid crystal composition according to 1.
  • a hydrogen atom contained in the divalent aliphatic hydrocarbon group having 3 to 13 carbon atoms may be replaced with a substituent.
  • M in formula (1) is a divalent aliphatic hydrocarbon group of 3 to 13 having a substituent, it is preferred that there is no cyclic structure in M including the substituent.
  • the polymerizable liquid crystal compound (1) of the present invention is represented by the group Ar 11 in the structure represented by -(Ar 11 -O-CO-M-CO-O)- in formula (1). It does not contain a cyclic structure other than an alicyclic hydrocarbon group or an aromatic hydrocarbon group.
  • the total number of ⁇ electrons contained in the optionally substituted divalent aromatic groups represented by Ar 11 and Ar 12 N ⁇ is preferably 8 or more and more Preferably 12 or more, particularly preferably 16 or more, particularly preferably 20 or more. Also, it is preferably 36 or less, more preferably 32 or less, still more preferably 30 or less, particularly preferably 26 or less, and most preferably 24 or less.
  • Y 1 represents an alkyl group having 1 to 6 carbon atoms, an optionally substituted aromatic hydrocarbon group or an aromatic heterocyclic group.
  • Y 2 represents a CN group or an optionally substituted alkyl group having 1 to 12 carbon atoms.
  • a hydrogen atom contained in the alkyl group may be substituted with a halogen atom, and -CH 2 - contained in the alkyl group is -O-, -CO-, -O-CO- or - It may be substituted with CO--O--.
  • U 1 represents an organic group having 2 to 30 carbon atoms and having an aromatic hydrocarbon group. Any carbon atom of the aromatic hydrocarbon group may be substituted with a heteroatom, and U 1 has at least one aromatic ring selected from the group consisting of aromatic hydrocarbon rings and aromatic heterocycles , is an organic group having 2 to 30 carbon atoms.
  • the aromatic hydrocarbon group may be substituted with one or more of said substituents X3 .
  • E 31 , A 31 , B 32 , F 32 and P 32 are defined in the same manner as E 11 , A 11 , B 11 , F 11 and P 11 in formula (1), respectively, and E 11 , A 11 , B 11 , F 11 and P 11 may be the same or different; q represents an integer of 0 to 4; may be different.
  • *-O-CO-G 11 -E 11 -(A 11 -B 11 ) k11 -F 11 -P 11 and *-O-CO-G 12 -E 12 -(A 12 -B 12 ) k12 -F 12 -P 12 include structures represented by formulas (R-1) to (R-100).
  • * represents a bond to Ar 11 or Ar 12
  • n represents an integer of 2-12.
  • the cyclohexane ring may be trans-form or cis-form, but preferably trans-form.
  • k21 and k22 each independently represent an integer of 1 or more;
  • the method for producing the polymerizable liquid crystal compound (1) and the polymerizable liquid crystal compound (2) that constitute the polymerizable liquid crystal composition of the present invention is not particularly limited, and they are Methoden der Organischen Chemie, Organic Reactions, Organic Syntheses, and Comprehensive Organic Synthesis, respectively. , known organic synthesis reactions described in New Experimental Chemistry Course (e.g., condensation reaction, esterification reaction, Williamson reaction, Ullmann reaction, Wittig reaction, Schiff base formation reaction, benzylation reaction, Sonogashira reaction, Suzuki -Miyaura reaction, Negishi reaction, Kumada reaction, Hiyama reaction, Buchwald-Hartwig reaction, Friedel-Crafts reaction, Heck reaction, Aldol reaction, etc.) can be appropriately combined according to the structure.
  • Methoden der Organischen Chemie Organic Reactions, Organic Syntheses, and Comprehensive Organic Synthesis, respectively.
  • known organic synthesis reactions described in New Experimental Chemistry Course e.g., condensation reaction, esterification reaction, Williamson reaction, Ullmann reaction
  • the polymerizable liquid crystal compound (2) can be produced, for example, by reacting the compound (1-1) with the compound (1-3).
  • the polymerizable liquid crystal compound constituting the polymerizable liquid crystal composition is preferably substantially composed of a polymerizable liquid crystal compound having a structure similar to that of the polymerizable liquid crystal compound (1).
  • the above-mentioned “similar” means, for example, —O—CO—G 11 —E 11 —(A 11 —B 11 ) k11 —F 11 —P 11 , —O—CO of the polymerizable liquid crystal compound (1).
  • the polymerizable liquid crystal composition does not contain polymerizable liquid crystal compounds other than the polymerizable liquid crystal compound (1) and the polymerizable liquid crystal compound (2).
  • the polymerizable liquid crystal composition of the present invention contains, in addition to the polymerizable liquid crystal compound (1) and the polymerizable liquid crystal compound (2), an organic solvent, a photopolymerization initiator, a polymerization inhibitor, a photosensitizer, a leveling agent, and the like. It may further contain additives. Each of these components may be used alone or in combination of two or more.
  • solvents can be used alone or in combination of two or more.
  • organic solvents are preferred, and alcohol solvents, ester solvents, ketone solvents, chlorine-containing solvents, amide solvents and aromatic hydrocarbon solvents are more preferred.
  • methyl ethyl ketone, methyl isobutyl ketone, cyclopentanone , cyclohexanone and N-methylpyrrolidone is more preferred.
  • the polymerizable liquid crystal composition of the invention preferably contains a photopolymerization initiator.
  • a photopolymerization initiator is a compound capable of generating a reactive species by the contribution of light and initiating a polymerization reaction of a polymerizable liquid crystal or the like.
  • reactive species include active species such as radicals, cations, and anions.
  • a photopolymerization initiator that generates radicals by light irradiation is preferable from the viewpoint that reaction control is easy.
  • As a photoinitiator only 1 type may be used and you may use it in combination of 2 or more type.
  • Irgacure (registered trademark) 907, Irgacure 184, Irgacure 651, Irgacure 819, Irgacure 250, Irgacure 369, Irgacure 379, Irgacure 127, Irgacure 2959, Irgacure 754, Irgacure 379EG (above, BASF Japan Corporation ), Seikuol BZ, Seikuol Z, Seikuol BEE (manufactured by Seiko Chemical Co., Ltd.), Kayacure BP100 (manufactured by Nippon Kayaku Co., Ltd.), Kayacure UVI-6992 (manufactured by Dow), Adeka Optomer SP- 152, Adeka Optomer SP-170, Adeka Optomer N-1717, Adeka Optomer N-1919, Adeka Arkles NCI-831, Adeka Arkles NCI-9
  • the photopolymerization initiator can fully utilize the energy emitted from the light source and is excellent in productivity, it is preferable that the maximum absorption wavelength is 300 nm to 400 nm, more preferably 300 nm to 380 nm. Polymerization initiators and oxime photopolymerization initiators are preferred.
  • the polymerizable liquid crystal composition of the present invention comprises a polymerizable liquid crystal compound (1) and a polymerizable liquid crystal compound (2), optionally a solvent, a photopolymerization initiator, a polymerization inhibitor, a photosensitizer or a leveling agent. It can be prepared by adding additives such as and stirring and mixing at a predetermined temperature.
  • nx represents the principal refractive index at the wavelength ⁇ nm in the direction parallel to the plane of the liquid crystal cured film in the refractive index ellipsoid formed by the liquid crystal cured film
  • ny represents the liquid crystal cured film formed In the refractive index ellipsoid, it is parallel to the plane of the liquid crystal cured film and represents the refractive index at the wavelength ⁇ nm in the direction perpendicular to the direction of the nx
  • Cyclic olefin-based resins manufactured by Kagaku Co., Ltd. can be mentioned.
  • a commercially available cyclic olefin resin base material can also be used.
  • Examples of commercially available cyclic olefin resin substrates include cyclic olefin resin substrates manufactured by Sekisui Chemical Co., Ltd. such as “Escina (registered trademark)” and “SCA40 (registered trademark)”; Optes Co., Ltd. cyclic olefin resin base material such as "; JSR Co., Ltd. cyclic olefin resin base material such as "Arton Film (registered trademark)".
  • the silane compound is a nonionic silane compound
  • a silane compound having an alkyl group at the molecular end is preferable, and a silane compound having an alkyl group having 3 to 30 carbon atoms is more preferable, from the viewpoint of easily increasing the vertical alignment control force.
  • a film obtained by forming such a polyvinyl alcohol resin is used as a raw film for a polarizing film.
  • the method of forming the polyvinyl alcohol-based resin into a film is not particularly limited, and the film can be formed by a known method.
  • the film thickness of the polyvinyl alcohol-based raw film can be, for example, about 10 to 150 ⁇ m.
  • the polarizing film may be obtained by laminating a transparent protective film via an adhesive on at least one surface of the polarizer thus obtained.
  • a transparent protective film a transparent film similar to the resin film exemplified above as the base material that can be used in the production of the cured liquid crystal film can be preferably used.
  • Example 2 As the polymerizable liquid crystal compound, 510 mg of the liquid crystal mixture (2) of the polymerizable liquid crystal compound (1-1-2) obtained in Synthesis Example 3 and the polymerizable liquid crystal compound (2-1-1), and the liquid crystal mixture (2) obtained in Synthesis Example 1 A polymerizable liquid crystal composition (2) was obtained in the same manner as in Example 1, except that 490 mg of the compound (2-1-1) was mixed and used. Using the obtained polymerizable liquid crystal composition (2), HPLC analysis was performed under the above measurement conditions, and the sum of the polymerizable liquid crystal compound (2-1-1) and the polymerizable liquid crystal compound (1-1-2) was determined. The area percentage value of the polymerizable liquid crystal compound (1-1-2) based on the amount was calculated.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Materials Engineering (AREA)
  • Engineering & Computer Science (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • General Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Polarising Elements (AREA)
PCT/JP2022/001808 2021-02-05 2022-01-19 重合性液晶混合物、重合性液晶組成物 WO2022168607A1 (ja)

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KR1020237022392A KR20230138450A (ko) 2021-02-05 2022-01-19 중합성 액정 혼합물, 중합성 액정 조성물
CN202280009560.6A CN116745664A (zh) 2021-02-05 2022-01-19 聚合性液晶混合物、聚合性液晶组合物

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JP2021-017702 2021-02-05
JP2021017702A JP2022120659A (ja) 2021-02-05 2021-02-05 重合性液晶混合物、重合性液晶組成物

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Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2010100541A (ja) * 2008-10-21 2010-05-06 Asahi Glass Co Ltd アクリル酸誘導体化合物、液晶性組成物、高分子液晶、光学素子および光ヘッド装置
JP2017197602A (ja) * 2016-04-25 2017-11-02 住友化学株式会社 液晶組成物及びその製造方法、並びに該液晶組成物から構成される位相差フィルム
WO2018123586A1 (ja) * 2016-12-27 2018-07-05 日本ゼオン株式会社 重合性化合物、重合性液晶混合物、高分子、光学フィルム、光学異方体、偏光板、表示装置、反射防止フィルム、および化合物
WO2018168778A1 (ja) * 2017-03-17 2018-09-20 日本ゼオン株式会社 重合性化合物、重合性液晶混合物、高分子、光学フィルム、光学異方体、偏光板、表示装置、反射防止フィルム、および化合物
JP2019191504A (ja) * 2018-04-27 2019-10-31 住友化学株式会社 光学異方性膜
JP2020041026A (ja) * 2018-09-07 2020-03-19 大日本印刷株式会社 重合性組成物、位相差フィルム及びその製造方法、転写用積層体、光学部材及びその製造方法、並びに表示装置

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR102477376B1 (ko) 2014-12-04 2022-12-13 스미또모 가가꾸 가부시키가이샤 조성물 및 광학 필름 그리고 조성물 및 광학 필름의 제조 방법
JP2019156733A (ja) 2018-03-08 2019-09-19 Dic株式会社 混合物及び光学異方体

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2010100541A (ja) * 2008-10-21 2010-05-06 Asahi Glass Co Ltd アクリル酸誘導体化合物、液晶性組成物、高分子液晶、光学素子および光ヘッド装置
JP2017197602A (ja) * 2016-04-25 2017-11-02 住友化学株式会社 液晶組成物及びその製造方法、並びに該液晶組成物から構成される位相差フィルム
WO2018123586A1 (ja) * 2016-12-27 2018-07-05 日本ゼオン株式会社 重合性化合物、重合性液晶混合物、高分子、光学フィルム、光学異方体、偏光板、表示装置、反射防止フィルム、および化合物
WO2018168778A1 (ja) * 2017-03-17 2018-09-20 日本ゼオン株式会社 重合性化合物、重合性液晶混合物、高分子、光学フィルム、光学異方体、偏光板、表示装置、反射防止フィルム、および化合物
JP2019191504A (ja) * 2018-04-27 2019-10-31 住友化学株式会社 光学異方性膜
JP2020041026A (ja) * 2018-09-07 2020-03-19 大日本印刷株式会社 重合性組成物、位相差フィルム及びその製造方法、転写用積層体、光学部材及びその製造方法、並びに表示装置

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JP2022120659A (ja) 2022-08-18
TW202242075A (zh) 2022-11-01

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