WO2019159886A1 - Composition - Google Patents

Composition Download PDF

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Publication number
WO2019159886A1
WO2019159886A1 PCT/JP2019/004843 JP2019004843W WO2019159886A1 WO 2019159886 A1 WO2019159886 A1 WO 2019159886A1 JP 2019004843 W JP2019004843 W JP 2019004843W WO 2019159886 A1 WO2019159886 A1 WO 2019159886A1
Authority
WO
WIPO (PCT)
Prior art keywords
liquid crystal
group
film
cured film
crystal cured
Prior art date
Application number
PCT/JP2019/004843
Other languages
English (en)
Japanese (ja)
Inventor
辰昌 葛西
伸行 幡中
Original Assignee
住友化学株式会社
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from JP2019007267A external-priority patent/JP7398868B2/ja
Application filed by 住友化学株式会社 filed Critical 住友化学株式会社
Priority to KR1020207024308A priority Critical patent/KR20200120653A/ko
Priority to CN201980011836.2A priority patent/CN111712740B/zh
Publication of WO2019159886A1 publication Critical patent/WO2019159886A1/fr

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    • 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
    • C08F20/38—Esters containing sulfur
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/30—Polarising elements
    • G—PHYSICS
    • G09—EDUCATION; CRYPTOGRAPHY; DISPLAY; ADVERTISING; SEALS
    • G09F—DISPLAYING; ADVERTISING; SIGNS; LABELS OR NAME-PLATES; SEALS
    • G09F9/00—Indicating arrangements for variable information in which the information is built-up on a support by selection or combination of individual elements
    • G09F9/30—Indicating arrangements for variable information in which the information is built-up on a support by selection or combination of individual elements in which the desired character or characters are formed by combining individual elements
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
    • H05B33/00—Electroluminescent light sources
    • H05B33/02—Details
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
    • H10K59/80—Constructional details
    • H10K59/8791—Arrangements for improving contrast, e.g. preventing reflection of ambient light

Definitions

  • the present invention relates to a composition, a vertically aligned liquid crystal cured film, a laminate, an elliptically polarizing plate, and an organic EL display device.
  • the carbon atoms contained in the divalent aromatic group and the divalent alicyclic hydrocarbon group may each independently be substituted with an oxygen atom, a sulfur atom, or a nitrogen atom, * Represents a bond]
  • at least one selected from the group consisting of a nonionic silane compound and an ionic compound and includes both the nonionic silane compound and the ionic compound. Is preferred.
  • composition of the present invention may further contain additives such as a solvent, a photopolymerization initiator, a polymerization inhibitor, a photosensitizer, a leveling agent, and an adhesion improver as other components as necessary. Good. These additives may be used individually by 1 type, or may be used in combination of 2 or more type.
  • Alcohol solvents such as ethyl acetate, butyl acetate, ethylene glycol methyl ether acetate, ⁇ -butyrolactone, propylene glycol methyl ether acetate and ethyl lactate; acetone, methyl ethyl ketone, cyclopentanone, cyclohexanone, 2-heptanone, and methyl Ketone solvents such as isobutyl ketone; aliphatic hydrocarbon solvents such as pentane, hexane, and heptane; Cycloaliphatic hydrocarbon solvents such as cyclohexane; aromatic hydrocarbon solvents such as toluene and xylene; nitrile solvents such as acetonitrile; ether solvents such as tetrahydrofuran and dimethoxyethane; chlorine-containing solvents such as chloroform and chlorobenzene Amide solvents such as dimethylacetamide, dimethyl
  • solvent may be used individually by 1 type, or may be used in combination of 2 or more type.
  • solvents alcohol solvents, ester solvents, ketone solvents, chlorine-containing solvents, amide solvents, and aromatic hydrocarbon solvents are preferable.
  • solvent may be used individually by 1 type, or may be used in combination of 2 or more type.
  • composition of the present invention comprises, for example, the liquid crystal compound (I) -1, one or both of a nonionic silane compound and an ionic compound, and an additive to be added as necessary at a predetermined temperature.
  • a nonionic silane compound and an ionic compound By stirring or the like, these components can be obtained by dispersing or dissolving them substantially uniformly.
  • the vertically aligned liquid crystal cured film is used from the viewpoint of suppressing a decrease in ellipticity when viewed from the oblique side on the short wavelength side in the elliptically polarizing plate including the vertically aligned liquid crystal cured film.
  • RthC (450) represents the retardation value in the thickness direction at a wavelength of 450 nm of the vertically aligned liquid crystal cured film
  • RthC (550) represents the retardation in the thickness direction of the vertically aligned liquid crystal cured film at a wavelength of 550 nm. Show value] It is preferable to satisfy.
  • the vertical alignment film is composed of Si element and C element as constituent elements from the viewpoint of easily reducing the surface tension and improving the adhesion with the layer adjacent to the vertical alignment film.
  • membrane containing the compound containing is preferable, and a silane compound can be used conveniently.
  • the silane compound the nonionic silane compound described above or a silane-containing ionic compound exemplified in the section of the ionic compound can be used.
  • the vertical alignment is regulated. You can increase your power.
  • These silane compounds may be used individually by 1 type, may be used in combination of 2 or more type, and may be used in mixture with other materials.
  • the horizontally aligned liquid crystal cured film included in the laminate of the present invention is referred to as a horizontally aligned liquid crystal cured film A
  • the horizontally aligned liquid crystal cured film included in the polarizing film of the polarizing plate described later is horizontally aligned liquid crystal cured.
  • membranes B are distinguished from each other.
  • the horizontal alignment film constituting the laminate is represented by the following relational expression (3) from the viewpoint of suppressing a decrease in ellipticity on the short wavelength side in the elliptically polarizing plate provided with the laminate.
  • ReA (450) / ReA (550) ⁇ 1 (3) [In the relational expression (3), ReA (450) represents the in-plane retardation value at a wavelength of 450 nm of the film oriented in the horizontal direction with respect to the in-plane direction of the vertically aligned liquid crystal cured film, and ReA (550) In-plane retardation value at a wavelength of 550 nm of a film oriented in the horizontal direction with respect to the in-plane direction of the vertically aligned liquid crystal cured film] It is preferable to satisfy.
  • the manufacturing method of the laminated body of this invention includes a vertical alignment liquid crystal cured film formation process.
  • the vertical alignment liquid crystal cured film forming step may be the above-described method for manufacturing a vertical alignment liquid crystal cured film.
  • a laminate composed of a substrate and a vertically aligned liquid crystal cured film, and a laminate composed of the substrate, the alignment film, and the vertically aligned liquid crystal cured film can be produced. it can.
  • Examples of the polymer of a monomer having a protonic functional group such as a hydroxyl group, a carboxyl group or an amino group and an ethylenically unsaturated group include, for example, an ethylene-maleic acid copolymer, an itaconic acid copolymer, and an acrylic acid copolymer. , Acrylamide copolymer, saponified polyvinyl acetate, and polyvinyl alcohol resin.
  • the horizontally aligned liquid crystal cured film B is preferably a cured film in which the polymerizable liquid crystal compound (B) is cured in a smectic phase aligned in the horizontal direction with respect to the in-plane direction of the film. That is, when the polymerizable liquid crystal compound (B) is a thermotropic liquid crystal, it may be a thermotropic liquid crystal compound showing a nematic liquid crystal phase or a thermotropic liquid crystal compound showing a smectic liquid crystal phase. .
  • the liquid crystal state exhibited by the polymerizable liquid crystal compound is preferably a smectic phase, and a higher order smectic phase is more preferable from the viewpoint of high performance.
  • higher-order smectic liquid crystal compounds that form a smectic B phase, a smectic D phase, a smectic E phase, a smectic F phase, a smectic G phase, a smectic H phase, a smectic I phase, a smectic J phase, a smectic K phase, or a smectic L phase.
  • Xan-1,4-diyl group when Y 1 and Y 2 have the same structure, it is preferable that at least one of X 1 , X 2 and X 3 is a different structure. When at least one of X 1 , X 2 and X 3 has a different structure, smectic liquid crystallinity tends to be easily exhibited.
  • R 16 to R 23 each independently represents a hydrogen atom, —R x , —NH 2 , —NHR x , —NR x 2 , —SR x , or a halogen atom.
  • R x represents an alkyl group having 1 to 4 carbon atoms or an aryl group having 6 to 12 carbon atoms.
  • examples of the alkyl group having 1 to 4 carbon atoms represented by R x include a methyl group, an ethyl group, a propyl group, A butyl group, a pentyl group, and a hexyl group are mentioned.
  • examples of the aryl group having 6 to 12 carbon atoms represented by R x include a phenyl group, a toluyl group, a xylyl group, And a naphthyl group.
  • D 1 and D 2 each independently represent a group represented by any one of formulas (2-12a) to (2-12d).
  • n5 represents an integer of 1 to 3.
  • D 3 and D 4 each independently represent a group represented by any one of formulas (2-13a) to (2-13h).
  • iodine When iodine is used as the dichroic dye, a method of dyeing a polyvinyl alcohol-based resin film in an aqueous solution containing iodine and potassium iodide is usually employed.
  • the iodine content in this aqueous solution is usually about 0.01 to 1 part by mass per 100 parts by mass of water.
  • the content of potassium iodide is usually about 0.5 to 20 parts by mass per 100 parts by mass of water.
  • the temperature of the aqueous solution used for dyeing is usually about 20 to 40 ° C.
  • the immersion time (dyeing time) in this aqueous solution is usually about 20 to 1,800 seconds.
  • the maximum absorption wavelength of the liquid crystal compound A in the region of a wavelength of 260 nm or more and 400 nm or less was read from the obtained absorption spectrum.
  • the wavelength having the highest absorbance among the plurality of maximum absorption wavelengths is defined as ⁇ max .
  • the obtained maximum absorption wavelength is shown in Table 1.
  • Example 1 the sample for an optical characteristic measurement was produced by the method similar to Example 1, and the phase difference value, the average refractive index, and orientation were evaluated. Further, the ratio between the maximum absorption wavelength and the maximum absorbance of the liquid crystal compound (A) -3 was also calculated in the same manner as in Example 1. The results are shown in Table 1.
  • the liquid crystal compound (A) -4 was prepared with reference to JP2011-207765A.
  • the liquid crystal compound (A) -4 is represented by the following formula (A) -4.
  • Example 16> [Production of Polarizing Film A] After immersing a polyvinyl alcohol film (average polymerization degree of about 2,400, saponification degree of 99.9 mol% or more, thickness of 75 ⁇ m) in pure water at 30 ° C., the mass ratio of iodine / potassium iodide / water is 0. Iodine dyeing was carried out by dipping in a 0.02 / 2/100 aqueous solution at 30 ° C. (iodine dyeing step).
  • composition for forming horizontally aligned liquid crystal cured film A Liquid crystal compound A and liquid crystal compound B were mixed at a mass ratio of 90:10 to obtain a mixture. For 100 parts by mass of the resulting mixture, 1.0 part of a leveling agent (“F-556” manufactured by DIC) and 2-dimethylamino-2-benzyl-1- (4-morpholinophenyl) as a polymerization initiator ) 6 parts of butan-1-one (“Irgacure (registered trademark) 369 (Irg369)” manufactured by BASF Japan Ltd.) was added. Further, N-methyl-2-pyrrolidone (NMP) was added so that the solid content concentration was 13%.
  • the composition for horizontal alignment liquid crystal cured film A formation was obtained by stirring at 80 degreeC for 1 hour.
  • the “addition amount” of the column silane compound and the “addition amount” of the ionic compound respectively indicate the addition amount (unit: wt%) with respect to the composition for forming a vertically aligned liquid crystal cured film.
  • the number of the ratio of the column liquid crystal compound and the alphabet in parentheses indicate the ratio of the added amount of the added liquid crystal compound.
  • 90/10 (A / B) indicates a mass ratio (liquid crystal compound A / liquid crystal compound B) 90/10.

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  • Physics & Mathematics (AREA)
  • Chemical & Material Sciences (AREA)
  • General Physics & Mathematics (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Optics & Photonics (AREA)
  • Engineering & Computer Science (AREA)
  • Theoretical Computer Science (AREA)
  • Liquid Crystal (AREA)
  • Polarising Elements (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

L'invention concerne une composition qui contient : un composé cristallin liquide possédant une structure représenté par la formule （Ｉ）－１ [Dans la formule （Ｉ）－１, Ar représente un groupe divalent possédant au moins deux structures cycliques, l'une de ces structures cycliques consistant en un cycle à 6 chaînons, Ｌ１ et Ｌ２ sont liés en position 1 ou position 4 du cycle à 6 chaînons, Ｌ１ et Ｌ２ représentent chacun indépendamment une liaison simple ou un groupe de liaison divalent, Ｇ１ et Ｇ２ représentent chacun indépendamment un groupe aromatique divalent ou un groupe hydrocarbure alicyclique divalent, et * représente une liaison atomique], et au moins un élément choisi dans un groupe constitué d'un composé silane non-ionique et d'un composé ionique.
PCT/JP2019/004843 2018-02-14 2019-02-12 Composition WO2019159886A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
KR1020207024308A KR20200120653A (ko) 2018-02-14 2019-02-12 조성물
CN201980011836.2A CN111712740B (zh) 2018-02-14 2019-02-12 组合物

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
JP2018024566 2018-02-14
JP2018-024566 2018-02-14
JP2019-007267 2019-01-18
JP2019007267A JP7398868B2 (ja) 2018-02-14 2019-01-18 組成物

Publications (1)

Publication Number Publication Date
WO2019159886A1 true WO2019159886A1 (fr) 2019-08-22

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PCT/JP2019/004843 WO2019159886A1 (fr) 2018-02-14 2019-02-12 Composition

Country Status (1)

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WO (1) WO2019159886A1 (fr)

Citations (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2007225912A (ja) * 2006-02-23 2007-09-06 Fujifilm Corp 液晶表示装置
JP2008020904A (ja) * 2006-06-13 2008-01-31 Dainippon Printing Co Ltd 液晶組成物、カラーフィルタ及び液晶表示装置
JP2009040984A (ja) * 2007-08-13 2009-02-26 Dainippon Printing Co Ltd 液晶組成物、該液晶組成物を用いた位相差制御部材、及び、液晶表示装置
JP2011207765A (ja) * 2009-03-16 2011-10-20 Sumitomo Chemical Co Ltd 化合物、光学フィルム及び光学フィルムの製造方法
WO2014054769A1 (fr) * 2012-10-04 2014-04-10 富士フイルム株式会社 Plaque polarisante circulaire et procédé de production de ladite plaque, corps stratifié optique
JP2015043073A (ja) * 2013-07-25 2015-03-05 富士フイルム株式会社 位相差フィルム、偏光板および液晶表示装置
JP2016098258A (ja) * 2014-11-18 2016-05-30 日本ゼオン株式会社 重合性液晶組成物、高分子、光学異方体、及び偏光板
JP2017014381A (ja) * 2015-06-30 2017-01-19 Jnc株式会社 重合性液晶化合物、組成物およびその重合体
JP2017068005A (ja) * 2015-09-30 2017-04-06 富士フイルム株式会社 光学異方性層の製造方法および偏光板の製造方法
JP2017167517A (ja) * 2016-03-15 2017-09-21 住友化学株式会社 楕円偏光板
JP2018022152A (ja) * 2016-07-21 2018-02-08 住友化学株式会社 楕円偏光板
WO2018123551A1 (fr) * 2016-12-28 2018-07-05 富士フイルム株式会社 Film optique, son procédé de fabrication, plaque de polarisation et dispositif d'affichage

Patent Citations (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2007225912A (ja) * 2006-02-23 2007-09-06 Fujifilm Corp 液晶表示装置
JP2008020904A (ja) * 2006-06-13 2008-01-31 Dainippon Printing Co Ltd 液晶組成物、カラーフィルタ及び液晶表示装置
JP2009040984A (ja) * 2007-08-13 2009-02-26 Dainippon Printing Co Ltd 液晶組成物、該液晶組成物を用いた位相差制御部材、及び、液晶表示装置
JP2011207765A (ja) * 2009-03-16 2011-10-20 Sumitomo Chemical Co Ltd 化合物、光学フィルム及び光学フィルムの製造方法
WO2014054769A1 (fr) * 2012-10-04 2014-04-10 富士フイルム株式会社 Plaque polarisante circulaire et procédé de production de ladite plaque, corps stratifié optique
JP2015043073A (ja) * 2013-07-25 2015-03-05 富士フイルム株式会社 位相差フィルム、偏光板および液晶表示装置
JP2016098258A (ja) * 2014-11-18 2016-05-30 日本ゼオン株式会社 重合性液晶組成物、高分子、光学異方体、及び偏光板
JP2017014381A (ja) * 2015-06-30 2017-01-19 Jnc株式会社 重合性液晶化合物、組成物およびその重合体
JP2017068005A (ja) * 2015-09-30 2017-04-06 富士フイルム株式会社 光学異方性層の製造方法および偏光板の製造方法
JP2017167517A (ja) * 2016-03-15 2017-09-21 住友化学株式会社 楕円偏光板
JP2018022152A (ja) * 2016-07-21 2018-02-08 住友化学株式会社 楕円偏光板
WO2018123551A1 (fr) * 2016-12-28 2018-07-05 富士フイルム株式会社 Film optique, son procédé de fabrication, plaque de polarisation et dispositif d'affichage

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