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WO2007111356A1 - Composition de résine photosensible, matière de transfert photosensible, paroi de séparation et procédé de formation de celle-ci, dispositif optique et procédé de fabrication de celui-ci et affichage - Google Patents

Composition de résine photosensible, matière de transfert photosensible, paroi de séparation et procédé de formation de celle-ci, dispositif optique et procédé de fabrication de celui-ci et affichage Download PDF

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Publication number
WO2007111356A1
WO2007111356A1 PCT/JP2007/056735 JP2007056735W WO2007111356A1 WO 2007111356 A1 WO2007111356 A1 WO 2007111356A1 JP 2007056735 W JP2007056735 W JP 2007056735W WO 2007111356 A1 WO2007111356 A1 WO 2007111356A1
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WO
WIPO (PCT)
Prior art keywords
photosensitive resin
group
resin layer
layer
photosensitive
Prior art date
Legal status (The legal status 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 status listed.)
Ceased
Application number
PCT/JP2007/056735
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English (en)
Japanese (ja)
Inventor
Daisuke Arioka
Takeshi Ando
Hiroki Sasaki
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Fujifilm Corp
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Fujifilm Corp
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Filing date
Publication date
Application filed by Fujifilm Corp filed Critical Fujifilm Corp
Priority to CN200780010889XA priority Critical patent/CN101410758B/zh
Priority to JP2008507522A priority patent/JP5159608B2/ja
Publication of WO2007111356A1 publication Critical patent/WO2007111356A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
    • G03F7/0382—Macromolecular compounds which are rendered insoluble or differentially wettable the macromolecular compound being present in a chemically amplified negative photoresist composition
    • 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
    • C08F220/00—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
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/04—Acids; Metal salts or ammonium salts thereof
    • C08F220/06—Acrylic acid; Methacrylic acid; Metal salts or ammonium salts thereof
    • 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
    • C08F220/00—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
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/12—Esters of monohydric alcohols or phenols
    • C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
    • C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
    • 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
    • C08F220/00—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
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/12—Esters of monohydric alcohols or phenols
    • C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
    • C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
    • C08F220/1807—C7-(meth)acrylate, e.g. heptyl (meth)acrylate or benzyl (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
    • C08F220/00—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
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/40—Esters of unsaturated alcohols, e.g. allyl (meth)acrylate
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/0046—Photosensitive materials with perfluoro compounds, e.g. for dry lithography
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • G03F7/032—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders
    • G03F7/033—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders the binders being polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. vinyl polymers
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
    • G03F7/11—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers having cover layers or intermediate layers, e.g. subbing layers

Definitions

  • Photosensitive resin composition Photosensitive transfer material, partition wall and method for forming the same, optical element and method for manufacturing the same, and display device
  • the present invention relates to a photosensitive resin composition and a photosensitive transfer material suitable for production of a display element such as a color filter, a partition using the photosensitive transfer material, a method of forming the same, an optical element and its
  • the present invention relates to a manufacturing method, a display device such as a liquid crystal display and a liquid crystal color television.
  • a water-soluble polymer material layer which is a dyeing material, is formed on a transparent substrate, and this is patterned into a desired shape by a photolithographic process.
  • a colored pattern is obtained by immersion in By repeating this process three times, three colored layers of R (red), G (green), and B (blue) can be formed.
  • the pigment dispersion method has been widely used in recent years, and a single layer is formed by forming a photosensitive resin layer in which a pigment is dispersed on a transparent substrate and patterning the formed photosensitive resin layer. Pattern is obtained. By repeating this process three times, three colored layers of R, G, and B can be formed.
  • a transparent electrode is patterned on a transparent substrate and immersed in an electrodeposition coating solution containing a pigment, a resin, an electrolytic solution, etc., and a colored layer is formed by electrodeposition. This process is repeated three times to form three colored layers of R, G, and B, and finally fired.
  • thermosetting resin a pigment is dispersed in a thermosetting resin, and printing is repeated three times to separate R, G, and B, and then a colored layer is formed by thermosetting the resin.
  • pixels can be formed by sequentially applying colored inks of R, G, and B colors to the recesses surrounded by the black matrix, and the manufacturing process can be simplified. There is an advantage that low cost can be achieved.
  • the ink jet method can be applied not only to the production of a color filter but also to the production of other optical elements such as an electoluminescence element.
  • An electoluminescence device has a configuration in which a thin film containing a fluorescent inorganic or organic compound is sandwiched between a cathode and an anode, and recombines by injecting electrons and holes into the thin film.
  • This is an element that generates excitons by means of, and emits light by using emission of fluorescence or phosphorescence when the excitons are deactivated.
  • Each color fluorescent material used for such an electroluminescent device can be applied to a substrate on which an element such as a TFT is formed by an ink jet method to form a light emitting layer to constitute the element.
  • the method of applying droplets such as the ink jet method can simplify the manufacturing process and reduce the cost, so that it can be used to manufacture optical elements such as color filters and electoluminescence elements. Applied.
  • Color mixing is a phenomenon in which overflowing ink mixes between adjacent colored areas. If ink color mixing occurs when ink is applied by the ink jet method, it may cause display defects such as color unevenness in the produced color filter or reduction in contrast of the display image.
  • a silicone rubber layer that has water and oil repellency can be put into a partition wall for preventing color mixing (for example, see Patent Document 1), or a silicone rubber layer is formed on a black matrix that serves as a light shielding layer.
  • a method of using as a partition wall for preventing color mixture for example, see Patent Documents 2 to 3) has been proposed.
  • ink repellent treatment is performed by this method, there is a drawback that white spots are likely to occur because the ink mixing between adjacent pixels is effectively prevented. This is a problem that occurs because the ink repellent treatment is not limited to the upper surface of the partition wall but also extends to the side surface of the partition wall. Another problem was that a large capital investment was required to perform the plasma treatment.
  • any of these methods has to provide a dedicated process for the ink repellent treatment, which has been a cost burden.
  • a technique in which a partition is formed using a transfer film having a first layer having ink repellency and a second ink-philic transfer layer on the base film (for example, And Patent Document 6).
  • a color filter is disclosed in which a resin layer containing a fluorine-containing compound or the like is laminated on a light shielding layer provided on a transparent substrate constituting the color filter (for example, Patent Document 7). reference).
  • a fluorine-containing co-polymer is used in order to improve the processability (development latitude) when developing a lithographic printing plate precursor coated with an infrared-sensitive composition using a fatigue developer.
  • a technique using a polymer is disclosed (for example, see Patent Document 8).
  • Patent Document 1 Japanese Patent Laid-Open No. 4-123005
  • Patent Document 2 Japanese Patent Laid-Open No. 5-241011
  • Patent Document 3 Japanese Patent Laid-Open No. 5-241012
  • Patent Document 4 Japanese Patent Laid-Open No. 2003-344640
  • Patent Document 5 JP-A-9-127327
  • Patent Document 6 Japanese Patent Laid-Open No. 2002-139612
  • Patent Document 7 Japanese Patent Laid-Open No. 7-35916
  • Patent Document 8 Japanese Unexamined Patent Publication No. 2003-248301
  • the method of forming the silicone rubber layer as described above is insufficient as the repellency of the partition wall surface.
  • a fluorine-based material such as a fluorine-containing compound, which has been known in the past, has an ink repellency that does not have sufficient ink repellency.
  • the cell gap is regulated by a spacer material.
  • the cell gap is not fixed and display unevenness is caused. Easy to wake up.
  • the present invention has been made in view of the above, and a cured pattern comprising a highly photosensitive resin composition having a liquid contact angle (for example, ink repellency) after curing, and a transferred photosensitive resin layer.
  • a liquid contact angle for example, ink repellency
  • the liquid contact angle of a light shielding film such as a black matrix E.g., ink repellency
  • flatness of the pixel when used as an optical element and a photosensitive transfer material having a uniform photosensitive resin layer in which the occurrence of repelling (repel) during application is suppressed, Partition and the method for forming the same, and an optical element capable of displaying a good image without display unevenness or a decrease in contrast, a method for manufacturing the same, and a display
  • the object is to provide an apparatus and to achieve the object.
  • the fluorine-containing compound when contained in a layer adjacent to the photosensitive resin layer, it is photosensitive that polyethylene oxide or polypropylene oxide is introduced into the side chain of the fluorine-containing compound. It is effective in preventing repelling when a liquid for forming a resin layer is applied (for example, applied) on a fluorine-containing compound-containing layer, and the effect of improving the liquid contact angle after curing is high. Based on this knowledge, it has been achieved!
  • R 5 each independently represents a hydrogen atom or an alkyl group having 1 to 5 carbon atoms.
  • L 3 each independently represents a divalent linking group which may be a single bond.
  • X 1 represents an ester group, an amide group, or an arylene group
  • X 2 Represents an ether group, an ester group, an amide group, an arylene group, or a heterocyclic residue.
  • Rf represents a substituent containing fluorine.
  • n represents an integer of 2 to 20
  • a, b, and c each represent a mass ratio, a represents 0 to 40, b represents 1 to 40, and c represents 20 to 98.
  • the surface-treated layer is a photosensitive transfer material containing at least a resin represented by the following structural formula (1).
  • R 4 and R 5 each independently represents a hydrogen atom or an alkyl group having 1 to 5 carbon atoms.
  • L 3 each independently represents a divalent linking group which may be a single bond.
  • X 1 represents an ester group, an amide group, or an arylene group
  • X 2 represents an ether group, an ester group, an amide group, an arylene group, or a heterocyclic residue.
  • n represents an integer of 2 to 20
  • a, b, and c each represent a mass ratio
  • a represents 0 to 40
  • b represents 1 to 40
  • c represents 20 to 98.
  • ⁇ 4> (a) a pressure-bonding step in which the photosensitive transfer material according to ⁇ 2> or ⁇ 3> is pressure-bonded to the transfer target so that the photosensitive resin layer is in contact with the transfer target; (b) An exposure step of exposing the photosensitive resin layer of the photosensitive transfer material pressure-bonded to the transfer medium in a pattern (at least through or without a surface treatment layer); and (c) the exposed Photosensitive resin And a development step of developing the layer.
  • the (c) development step is the method for forming a partition wall according to ⁇ 4> or ⁇ 5>, wherein the surface treatment layer is removed.
  • ⁇ 7> A partition formed by the method for forming a partition according to any one of ⁇ 4> to ⁇ 6>.
  • the surface of the photosensitive resin layer on the transferred body opposite to the side in contact with the transferred body is fluorinated by the surface treatment layer, and the fluorinated surface is exposed ⁇ 7>.
  • the partition according to any one of the above ⁇ 7> to ⁇ 9> partitions the transferred body, and droplets are applied to the recessed portions on the partitioned transferred body by an ink jet method. This is a method for manufacturing an optical element that forms an image region.
  • the liquid droplets contain a colorant, and the image area is colored!
  • a display device comprising the optical element according to ⁇ 12>.
  • a cured liquid resin composition having a liquid contact angle (for example, ink repellency) after curing, and a pattern (for example, a color filter) comprising a transferred photosensitive resin layer is prepared.
  • the liquid contact angle (for example, ink repellency) of the black matrix and the like is maintained, and the flatness of the pixel when used as an optical element is maintained, and the occurrence of flipping (repel) during formation is suppressed.
  • Photosensitive transfer material having a photosensitive resin layer, good ink repellency, partition walls capable of good ink application by the ink jet method, a method for forming the same, and a good image with no decrease in contrast of display display Displayable optical element and manufacturing method thereof
  • a display device can be provided.
  • FIG. 1 is a conceptual diagram for explaining a state in which ink overflows, color mixture, and white spots occur in a conventional color filter.
  • FIG. 2 is a cross-sectional view showing an example of a three-layer photosensitive transfer material.
  • FIG. 3 is a cross-sectional view showing an example of a photosensitive transfer material having a four-layer structure.
  • FIG. 4 is a cross-sectional view schematically showing a color filter (for LCD) according to the present invention.
  • the photosensitive resin composition of the present invention contains at least one resin represented by the following structural formula (1) (hereinafter sometimes referred to as “fluorine-based resin according to the present invention”). However, if necessary, it can be constituted using other components.
  • a resin represented by the following structural formula (1) (1) an alkali-soluble binder, (2) a monomer and Z or an oligomer, and (3) a photopolymerization initiator and Z or a photopolymerization initiation system are used to form a photosensitive resin composition. Furthermore, from the viewpoint of imparting light shielding properties, (4) a colorant is preferably included.
  • the light-shielding property is useful for forming a partition that separates each colored region (colored pixel) of a pixel group constituting a color filter, such as a black matrix.
  • the photosensitive resin composition of the present invention is suitable for forming a cured pattern by performing pattern exposure and development, and can form a pattern with a high liquid contact angle after curing.
  • the photosensitive resin composition of the present invention is used to form partition walls (such as a black matrix) on a desired substrate, and droplets are applied to the recesses surrounded by the formed partition walls by an inkjet method.
  • partition walls such as a black matrix
  • droplets are applied to the recesses surrounded by the formed partition walls by an inkjet method.
  • an optical element including a color filter
  • an optical element that maintains high ink repellency on the upper surface of the partition wall (upper surface 4 of the partition wall in Fig. 4) and suppresses the occurrence of ink overflow and color mixing is manufactured. can do.
  • R 5 each independently represents a hydrogen atom or an alkyl group having 1 to 5 carbon atoms.
  • Examples of the alkyl group having 1 to 5 carbon atoms represented by Ri to R 5 include a methyl group, an ethyl group, a propyl group, a butyl group, and a pentyl group.
  • An alkyl group of 3 is preferred, and a methyl group is particularly preferred.
  • R 4 and R 5 are preferably a hydrogen atom or a methyl group.
  • ⁇ L 2 and L 3 each independently represent a single bond or a divalent linking group.
  • Examples of the divalent linking group represented by L 1 include an alkylene group having at least one of a hydroxy group, an ether bond, and an ester bond, or at least one of a hydroxy group, an ether bond, and an ester bond.
  • the arylene group having is preferable.
  • Examples of the divalent linking group represented by L 2 chromatic alkyl group having a substituent, mono-ether bond gesture et preferred is Ariru group to have a substituent group, an ester bond, a etc. urethane bond You may do it.
  • Examples of the divalent linking group represented by L 3, hydroxy groups, ether linkages, and ester le bond in the alkylene group contains at least one or a hydroxy group, an ether bond, and ester bond of at least a It may be an arylene group containing one. More preferably, it is more preferably a single bond, the following group or a group having the following structure.
  • X 1 represents an ester group, an amide group, or an arylene group
  • X 2 represents an ether group, an ester group, an amide group, an arylene group, or a heterocyclic residue.
  • the arylene group represented by X 1 or X 2 is preferably an arylene group having a total carbon number of 6 to 20, and examples thereof include phenylene, naphthylene, anthracene, and biphenylene. May be o-, p-, m-substitution. Of these, an arylene group having 6 to 12 carbon atoms is more preferable, and phenylene and biphenylene are particularly preferable.
  • Examples of the heterocyclic residue represented by X 2 include a 5-membered ring containing a nitrogen atom or an oxygen atom as a ring member, or a pyridine ring, a pyrimidine ring, a pyrazine ring, preferably a 6-membered ring.
  • Thiazole ring, benzothiazole ring, oxazole ring, benzoxazole ring, isoxazole ring, pyrazole ring, imidazole ring, quinoline ring, thiadiazole ring and the like S are preferable, and pyridine ring and thiadiazole ring are more preferable.
  • X 1 is preferably the following linking group or a linking group having the following structure.
  • R represents a hydrogen atom, an alkyl group having 1 to 12 carbon atoms in total, or an aryl group having 6 to 20 carbon atoms in total.
  • alkyl group having 1 to 12 carbon atoms in total examples include unsubstituted alkyl groups such as a methyl group, an ethyl group, a propyl group, a butyl group, a hexyl group, an octyl group, and a dodecyl group, as well as an ether group, a thioether group, Examples thereof include substituted alkyl groups having substituent groups such as ester groups, amide groups, amino groups, urethane groups, and hydroxy groups. Of these, a methyl group, a butyl group, and an octyl group are preferred, where an alkyl group having 1 to 8 carbon atoms is preferred.
  • aryl group having 6 to 20 carbon atoms in total examples include phenyl group, naphthyl group, methylphenyl group, methoxyphenyl group, and norphenyl group. Of these, a aryl group having a total carbon number of 6 to 15 is preferred, and a phenol group and a norphenol group are preferred.
  • X 2 is preferably the following coupler or a linking group having the following structure.
  • R here is synonymous with R above.
  • Rf represents a group containing fluorine.
  • group containing fluorine the following fluorine-containing groups or fluorine-containing groups having the following structures are suitable.
  • m in the fluorine group represents an integer of 1 to 20
  • 1 represents an integer of 1 to 10
  • n represents an integer of 1 to 20.
  • n represents an integer of 2 to 20, preferably 4 to 12.
  • A, b and c each represents a mass ratio, a is 0 to 40 (preferably 0 to 20), b is 1 to 40 (preferably 5 to 20), and c is 20-98 (preferably 30-80)
  • R 5 is a hydrogen atom
  • R 2 force methyl group
  • L 1 is a single bond
  • L 2 is —CONHCH CH—
  • L 3 is —CH CH—.
  • X 1 is one OCO—
  • X 2 is one COO—
  • Rf is one CF, one CF, one C
  • F is M
  • M is the following group (R 4 is a hydrogen atom), and n is 7 to 9 is preferable.
  • the molecular weight of the fluorinated resin according to the present invention is preferably 1000 to 200,000 in weight average molecular weight (Mw), more preferably 4000 to 50,000! When the Mw force is within the above range, it is stably present in the surface treatment layer and is effective in terms of transition to the partition wall layer.
  • Mw weight average molecular weight
  • MEK methyl ethyl ketone
  • Step 2> Introduction of a double bond to rosin A1
  • MEK methyl ethyl ketone
  • Step 2> Introduction of a double bond into slag B1
  • the weight average molecular weight (GPC, THF, polystyrene conversion) Mw of the exemplary coconut resin b was 12,000. [0065] [Chemical 16]
  • MEK methyl ethyl ketone
  • the weight average molecular weight (GPC, THF, polystyrene conversion) of the exemplary coconut c is Mw is 11, 000.
  • MEK methyl ethyl ketone
  • FAC8 2- (perfluorooctyl) ethyl acrylate
  • PE200, NOF Corporation polyethylene oxide monomer
  • V601, manufactured by Wako Pure Chemical Industries, Ltd. 0.15 g (0.000 mol) lmol
  • MEK methyl ethyl ketone
  • FAC8 2- (perfluorooctyl) ethyl acrylate
  • PP500 polypropylene oxide monomer
  • V601 manufactured by Wako Pure Chemical Industries, Ltd.
  • MEK methyl ethyl ketone
  • the weight average molecular weight (GPC THF, converted to polystyrene) Mw of the exemplary coconut resin f was 13,000.
  • MEK methyl ethyl ketone
  • the weight average molecular weight (GPC, THF, polystyrene conversion) Mw of the exemplary coconut resin g was 13,000.
  • MEK methyl ethyl ketone
  • Step 2> Introduction of a double bond to rosin HI
  • the mixture was stirred for 8 hours, and it was confirmed by NMR that atariloyloxetyl isocyanate had disappeared, and the following exemplified fats h were obtained.
  • the weight average molecular weight (GPC, THF, Polystyrene conversion) Mw was 8,200.
  • MEK methyl ethyl ketone
  • FAAC6 perfluorinated hexyl ethyl acrylate
  • PE350 polyethylene oxide monomer
  • AA acrylic acid
  • MEK methyl ethyl ketone
  • FAAC4 perfluorobutyl ethyl acrylate
  • PE350 polyethylenoxide monomer
  • AA acrylic acid
  • Step. 1> Synthesis of rosin K1 Under a nitrogen stream, 15 g of methyl ethyl ketone (MEK) was placed in a 300 ml three-necked flask equipped with a condenser and heated to 70 ° C in a water bath.
  • MEK methyl ethyl ketone
  • MEK20g is mixed with 2- (perfluohexyl) 1-ethyl acrylate (FAAC6, manufactured by Ryutech) 10.0 g (0.026 mol) and polyethylene oxide monomer (PE350, NOF Corporation) 12.5 g (0.029 mol) and acrylic acid (AA) 2.5 g (0.045 mol) in solution and MEK15 g in 2,2'-azobis (isobutyric acid) dimethyl (V601, Wako Pure) A solution in which 0.145 g (0.OOlmol) was dissolved was added dropwise with a plunger pump over 2 hours. After completion of dropping, the mixture was stirred for 5 hours.
  • FAC6 perfluohexyl) 1-ethyl acrylate
  • PE350 polyethylene oxide monomer
  • AA acrylic acid
  • V601 2,2'-azobis (isobutyric acid) dimethyl
  • the content of the fluorinated resin in the photosensitive resin composition according to the present invention is preferably 0.01 to 5 gZm 2 with respect to the total solid content of the composition 0.05 to 4 gZm. 2 is more preferable, and 0.1 to 4 g / m 2 is particularly preferable.
  • the content of the fluorinated resin is within the above range, the liquid contact angle on the surface of the pattern after curing can be increased.
  • ink is applied to the recesses between the partition walls such as black bear tritus formed in advance.
  • an optical element such as a color filter is produced by forming a colored region, it is possible to effectively prevent ink from overflowing and color mixing, and to improve display characteristics when displaying an image.
  • components (1) to (4) will be described in detail as components other than the fluorinated resin according to the present invention constituting the photosensitive resin composition.
  • binder As the alkali-soluble binder (hereinafter sometimes simply referred to as “binder”), a polymer having a polar group such as a carboxylic acid group or a carboxylic acid group in the side chain is preferred. Examples include JP-A-59-44615, JP-B-54-34327, JP-B-58 12577, JP-B-54-25957, JP-A-59-53836, and JP-A-59-53836.
  • cell mouth derivatives having a carboxylic acid group in the side chain can also be mentioned.
  • a polymer having a hydroxyl group attached to a polymer having a hydroxyl group is also suitable.
  • benzyl (medium described in US Pat. No. 4,139,391) can be used.
  • the above-mentioned noinder polymer having a polar group may be used alone or in the form of a composition used in combination with a normal film-forming polymer.
  • the content of the alkali-soluble binder in the photosensitive resin composition is generally 20 to 50 mass%, preferably 25 to 45 mass%, based on the total solid content of the composition.
  • the monomer or oligomer is preferably a monomer or oligomer that has two or more ethylenically unsaturated double bonds and undergoes addition polymerization upon irradiation with light.
  • Examples of such monomers and oligomers include compounds having at least one addition-polymerizable ethylenically unsaturated group in the molecule and a boiling point of 100 ° C. or higher at normal pressure.
  • Examples include monofunctional acrylates and monofunctional methacrylates such as polyethylene glycol mono (meth) acrylate, polypropylene glycol mono (meth) acrylate and phenoxychetyl (meth) acrylate; polyethylene glycol di (meth) acrylate, poly Propylene glycol di (meth) acrylate, trimethylol ethane triacrylate, trimethylol propane tri (meth) acrylate, trimethylol propane diathalate, neopentyl tallicol di (meth) acrylate, pentaerythritol tetra (meth) Atalylate, Pentaerythritol Tri (meth) Atalylate, Dipentaerythritol Hexa (me
  • urethane acrylates described in JP-B-48-41708, JP-B-50-6034, and JP-A-51-37193; JP-A-48-64183, JP-B 4 9 43191 and polyester ter relates described in Japanese Patent Publication No. 52-30490; epoxy acrylates that are the reaction products of epoxy resin and (meth) acrylic acid, etc. Mention may be made of multifunctional ateliers and metatarylates.
  • trimethylolpropane tri (meth) acrylate pentaerythritol tetra (meth) acrylate, dipentaerythritol hex (meth) acrylate, dipentaerythritol penta (meth) acrylate are preferred. ,.
  • polymerizable compound B described in JP-A-11-133600 can also be mentioned as a preferable example.
  • the monomer or oligomer may be used alone or in combination of two or more.
  • the monomer or Z or oligomer content in the photosensitive resin composition may be the total solid content of the composition. On the other hand, 5-50 mass% is common, and 10-40 mass% is preferable.
  • Examples of the photopolymerization initiator or photopolymerization initiation system include vicinal polyketaldo duplex compounds described in U.S. Pat.No. 2,367,660, acyloin ether compounds described in U.S. Pat. Aromatic hydrocarbon substituted by ⁇ -hydrocarbon described in US Pat. No. 2722512, polynuclear quinone compound described in US Pat. Nos. 3046127 and 2951 758, US Pat. No. 3,549,367 A combination of a triarylimidazolnimer and a ⁇ -aminoketone described in the specification, a benzothiazole compound and a trihalomethyl monos-triazine compound described in Japanese Patent Publication No.
  • polymerization initiator C described in JP-A-11-133600 can also be mentioned as a preferable example, and further, paragraph numbers [0028] to [0042] of JP-A-2000-310707. ] Can also be used as a suitable thing.
  • the photopolymerization initiator and Z or the photopolymerization initiation system may be used singly or in combination of two or more, but it is particularly preferable to use two or more in combination. When at least two kinds of photopolymerization initiators are used, display characteristics, particularly display unevenness, can be reduced.
  • Content in photopolymerization initiator and photosensitive resin composition of Z or photopolymerization initiation system Is generally 0.5 to 20% by mass, preferably 1 to 15% by mass, based on the total solid content of the composition.
  • organic pigments, inorganic pigments, dyes and the like can be suitably used.
  • carbon black titanium oxide, iron tetroxide, etc.
  • a mixture of pigments such as red, blue, and green can be used.
  • carbon black is particularly preferred because of its excellent light shielding properties.
  • the amount of the colorant in the photosensitive resin composition can be appropriately selected as desired.
  • a solvent a surfactant, a thermal polymerization inhibitor, an ultraviolet absorber, and the like can be added to the photosensitive resin composition.
  • organic solvent may be further used for the preparation of the photosensitive resin composition.
  • organic solvents include methyl ethyl ketone, propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, cyclohexanone, cyclohexanol, methyl isobutyl ketone, lactic acid ethyl, methyl lactate, and strength prolatatum. be able to.
  • the photosensitive resin composition contains a thermal polymerization inhibitor.
  • thermal polymerization inhibitors include hydroquinone, hydroquinone monomethyl ether, p-methoxyphenol, di-tert-butyl-cresole, pyrogallol, tert-butinole strength Teconole, benzoquinone, 4,4'-thiobis (3-methyl-6 t- Butylphenol), 2,2′-methylenebis (4-methyl-6t-butylphenol), 2 mercaptobenzimidazole, phenothiazine and the like.
  • a known colorant can be further added as needed in addition to the colorant (pigment) for the purpose of obtaining higher light-shielding properties.
  • the pigment when a pigment is used, it is desirable that the pigment is uniformly dispersed in the photosensitive resin composition, so that the particle size is 0.1 ⁇ m or less, particularly 0.0 ⁇ m. m or less is preferable.
  • the coloring material described in [0040], the pigment described in JP-A-2005-361447, paragraph numbers [00 68] to [0072], and the paragraph number in JP-A-2005-17521 can be preferably used.
  • the photosensitive resin composition in the present invention can contain an ultraviolet absorber as necessary.
  • the ultraviolet absorber include compounds such as salicylates, benzophenones, benzotriazoles, cyanacrylates, nickel chelates, hindered amines and the like of the compounds described in JP-A-5-72724.
  • ferric salicylate 4 t-butyl ferric salicylate, 2,4-di-t-butyl ferulic acid 3 ', 5'-di-t-4'-hydroxybenzoate, 4-t-butyl Rufe-Rusalicylate, 2,4-dihydroxybenzophenone, 2 Hydroxy-4-methoxybenzophenone, 2 Hydroxy 4-n-Otoxybenzophenone, 2- (2'-Hydro 5'-methylphenyl) benzotriazole, 2- (2'-hydroxy 3 't-butyl-5, 1-methylphenol) 5 clonal benzotriazole, ethyl 2 cyano 3, 3—diphenyl acrylate, 2, 2 , Monohydroxy 1 4-methoxybenzophenone, nickel dibutyldithiocarbamate, bis (2, 2, 6, 6-tetramethyl-4-pyridine) sebacate, 4 t-butylphenol salicylate, salicylate phenol, 4 t-butylphenol sal
  • the photosensitive resin composition of the present invention may contain “adhesion aid” described in JP-A-11-133600, other additives, and the like.
  • the photosensitive resin composition of the present invention contains the fluorinated resin according to the present invention as described above, for example, (a) a phenol containing at least p-taresole is acidified.
  • a positive photoresist composition containing a non-high-ortho-type cresol novolac resin obtained by reacting with an aldehyde under a catalyst and (b) a quinonediazide group-containing compound may be used.
  • this positive photoresist yarn composition has a binuclear content of p-cresol in the component (a) of less than 2.0% in the GPC (gel “permeation” chromatography) method. Preferably there is.
  • Examples of the positive photoresist composition include those described in paragraph Nos. [0007] to [0026] of Japanese Patent No. 362 4718.
  • a positive photoresist composition When a positive photoresist composition is used, it is possible to form a resist pattern close to a rectangle with a high residual film ratio as well as excellent sensitivity and resolution that hardly generate sublimates even when subjected to high temperature beta. .
  • the photosensitive transfer material of the present invention includes at least a photosensitive resin layer and a surface treatment layer provided in contact with the surface of the photosensitive resin layer on the temporary support side, as necessary.
  • Other layers such as a thermoplastic resin layer can be provided.
  • the surface treatment layer according to the present invention should be in contact with the surface of the photosensitive resin layer on the temporary support side. It is a layer for forming and treating the surface of the photosensitive resin layer on the temporary support side. Specifically, as the surface treatment layer, for example,
  • thermoplastic resin layer is indicated.
  • thermosensitive transfer material in which a thermoplastic resin layer, an intermediate layer, another layer as a surface treatment layer, and a photosensitive resin layer are formed in this order on the temporary support, this other layer is indicated.
  • the photosensitive transfer material is pressure-bonded to a substrate for the purpose of forming a partition wall, etc., it is excellent in prevention of mixing of each layer, oxygen barrier property, adhesion at the time of pressure-bonding, and economical efficiency.
  • the photosensitive transfer material of the invention is particularly preferably the embodiment (1).
  • the coating solution for forming the surface treatment layer contains a fluorine compound containing a polymerizable group, which is a resin represented by the structural formula (1), and is temporarily supported by, for example, coating.
  • the polymerizable group-containing fluorine compound is concentrated on the air interface side (the side not in contact with the temporary support) of the film.
  • the fluorine compound containing a polymerizable group is concentrated on the interface on the photosensitive resin layer side in the surface treatment layer.
  • the photosensitive resin layer is pressure-bonded to a desired transfer target, and exposed after pressure bonding (preferably from the surface treatment layer side).
  • the fluorine compound containing a polymerizable group in the surface treatment layer causes an interaction such as chemical bonding or physical adsorption with the photosensitive resin layer, and is fixed to the surface treatment layer side interface. .
  • ink repellency can be imparted only to the exposed surface treatment layer side interface of the photosensitive resin layer.
  • the surface treatment layer is removed in a development step (c) for developing the photosensitive resin layer, which will be described later. Only the upper surface of the photosensitive resin layer on the body) A partition wall having ink repellency can be formed. It is also possible to provide a step of heating the surface treatment layer and the photosensitive resin layer before (a) the crimping step or between (a) the crimping step and (b) the exposure step. It is preferable in that it can be performed.
  • the surface treatment layer is formed using the resin represented by the structural formula (1), the liquid contact of the pattern formed by the transferred photosensitive resin layer is performed.
  • the corners can be kept high, and a liquid for forming a photosensitive resin layer (hereinafter, referred to as “photosensitive resin layer forming liquid” may be superimposed on the surface of the surface treatment layer on the temporary support.
  • photosensitive resin layer forming liquid it is possible to prevent occurrence of repelling when applying (for example, applying) a coating solution for forming a photosensitive resin layer, and to perform uniform application.
  • ink repellency can be obtained, and ink is applied to an area surrounded by a partition wall composed of a photosensitive resin layer by ink jetting to form a colored area. It is possible to effectively prevent protrusion and color mixing.
  • the surface treatment layer can achieve its purpose if it has a film thickness of about one molecule. Therefore, the layer thickness of the surface treatment layer is not particularly limited. However, from the viewpoint of economy and developability, the thickness of the surface treatment layer is preferably 15.0 m or less, and more preferably 3.0 m or less.
  • a polymerizable group-containing fluorine compound having a thickness of 0.1 ⁇ m or more exists on the surface of the photosensitive resin layer after exposure and development.
  • the polymerizable group-containing fluorinated compound forms a layer, there is a possibility that the surface of the photosensitive resin layer that is not completely removed from the surface treatment layer remains unfixed by interaction. Is expensive.
  • the fluorine compound may cry into the liquid crystal, which may hinder the drive of the liquid crystal.
  • the thickness of the partition wall may be larger than the desired thickness, and the cell gap may not be a desired value, causing problems such as display unevenness.
  • the upper surface of the partition wall on the transferred body (opposite to the side in contact with the transferred body). Only the exposed surface on the side) has ink repellency, and no side surface has ink repellency. For this reason, there is an advantage that white-out failures are unlikely to occur. Further, the thickness of the partition wall can be made the same as the thickness of the photosensitive resin layer, and there is an advantage that no problem due to the variation of the film thickness occurs.
  • the surface-treated layer does not necessarily need to have photosensitivity in terms of imparting ink repellency, and it may be non-photosensitive not including a photopolymerization initiator and a photopolymerization initiator system. preferable.
  • “does not contain” means that a photopolymerization initiator or a photopolymerization initiator system is not added when preparing a liquid for forming a surface treatment layer (for example, a coating liquid used for coating). .
  • the content of the photopolymerization initiator and the photopolymerization initiator system in the layer is preferably 10% by mass or less of the total mass of the layer.
  • the surface treatment layer contains a photopolymerization initiator or a photopolymerization initiator system
  • the surface treatment layer also hardens during exposure, and the thickness of the partition wall becomes thicker than desired.
  • the cell gap may not be a desired value, and problems such as display unevenness may occur.
  • the surface-treated layer according to the present invention may be provided between the temporary support and the photosensitive resin layer as long as it is provided adjacent to the photosensitive resin layer!
  • Other layers such as an undercoat layer for the temporary support may be provided between the treatment layer and the temporary support.
  • the surface treatment layer may be composed of a single layer or may be composed of two or more layers.
  • the surface treatment layer is a layer containing at least one kind of the resin represented by the structural formula (1) described above (fluorine-based resin according to the present invention), and if necessary, further It can be constructed using other components.
  • the content of the surface treatment layer of the fluorine-based ⁇ according to the present invention preferably is 0. 01 ⁇ 5g / m 2 instrument 0. 05 ⁇ 4g / m 2 and more preferably tool 0. l ⁇ 4 g / m 2 is particularly preferred. If the content of the fluorine-based resin is within the above range, the liquid contact angle of the cured pattern composed of the transferred photosensitive resin layer (for example, on a light-shielding film such as a black matrix when producing a color filter) The photosensitive resin layer forming liquid was applied to the surface of the surface treatment layer on the temporary support while ensuring the ink repellency (for example, application of a coating liquid for forming the photosensitive resin layer). It can effectively prevent the repelling of mushrooms.
  • the intermediate layer as the surface treatment layer contains at least one fluorine-based resin according to the present invention.
  • the intermediate layer is preferably an aqueous layer (a layer formed using a liquid in which 25% by mass or more of the solvent is water) from the viewpoint of coating with the photosensitive resin layer.
  • the intermediate layer may be an intermediate layer having an oxygen blocking function, which is described as “separation layer” in paragraphs [0014] to [0015] of JP-A-5-72724.
  • an oxygen blocking function As the oxygen-blocking membrane, a known medium force that exhibits low oxygen permeability and is preferably dispersed or dissolved in water or an aqueous alkali solution can be appropriately selected.
  • the oxygen barrier layer is preferably polybulal alcohol, and particularly preferably a combination of polybulal alcohol and polybulphine redidone.
  • the thickness of the intermediate layer is generally 0.2 to 5 ⁇ m in terms of dry thickness, and 1 to 2 is particularly preferably 0.5 to 3 ⁇ m.
  • thermoplastic resin layer may be formed as necessary.
  • the thermoplastic resin layer as the surface treatment layer contains at least one fluorine-based resin according to the present invention.
  • the thermoplastic resin layer is an alkali-soluble layer composed of at least a resin component.
  • the resin component preferably has a substantial soft point of 80 ° C or lower.
  • a thermoplastic resin layer When a thermoplastic resin layer is provided, it can be satisfactorily adhered to a permanent support (substrate) during transfer (for example, when forming a partition such as black matrix constituting a color filter).
  • alkali-soluble thermoplastic resins having a substantially soft softness point of 80 ° C or lower examples include saponified products of ethylene and acrylate copolymers, styrene and (meth) acrylic acid. Saponified with ester copolymer, butyltoluene and (meth) acrylic acid ester copolymer And saponified products of poly (meth) acrylic acid esters, and (meth) acrylic acid ester copolymers such as butyl (meth) acrylate and butyl acetate.
  • thermoplastic resin layer at least one of the above-mentioned thermoplastic resins can be appropriately selected and used.
  • thermoplastic resins can be appropriately selected and used.
  • “Plastic Performance Handbook” Japan Plastic Industry Federation, All Japan Plastic Molding Industry Federation) Edited by the Industrial Research Council, published on October 25, 1968
  • organic polymers that are soluble in an alkaline solution among organic polymers with a soft spot of about 80 ° C or less.
  • an organic polymer substance having a soft spot of 80 ° C or higher can be substantially added by adding various plasticizers compatible with the polymer substance to the organic polymer substance.
  • the softening point can be lowered to 80 ° C or lower.
  • these organic polymer substances have various polymers, supercooled substances, and adhesion improvements as long as the actual soft spot does not exceed 80 ° C in order to adjust the adhesive strength with the temporary support.
  • An agent, a surfactant, a release agent or the like can also be added.
  • plasticizers include polypropylene glycol, polyethylene glycol, dioctyl phthalate, diheptyl phthalate, dibutyl phthalate, tricresyl phosphate, cresyl diphenyl phosphate biphenyl diphosphate. Can do.
  • At least one photosensitive resin layer is provided on the surface of the surface treatment layer on the temporary support constituting the photosensitive transfer material of the present invention.
  • This photosensitive resin layer is a layer for forming a pattern by performing pattern exposure and development after transfer to a transfer target, and the surface treatment according to the present invention described above provided on a temporary support. Since the layer is formed directly on the surface of the layer, formation of the photosensitive resin layer (for example, coating formation) is performed while maintaining a high liquid contact angle (for example, ink repellency) on the cured pattern of the photosensitive resin layer. It is performed with the repelling of liquid (repellency) suppressed.
  • the photosensitive resin layer comprises at least (1) an alkali-soluble binder, (2) a monomer and Z or oligomer, and ( 3 ) a photopolymerization initiator and Z or a photopolymerization initiation system. It can be formed by applying (preferably coating) the composition in layers. From the viewpoint of imparting light-shielding properties, this resin composition preferably further comprises (4) a colorant. It is preferable that the photosensitive resin layer has a light shielding property because it can have a function as a partition that separates each colored region (colored pixel) of a pixel group constituting a color filter such as a black matrix! /.
  • the content of the alkali-soluble binder in the photosensitive resin layer is generally 20 to 50% by mass, preferably 25 to 45% by mass, based on the total solid content of the layer.
  • content in the photosensitive resin layer of the said monomer, Z, or an oligomer 5-50 mass% is common with respect to the total solid of a layer, and 10-40 mass% is preferable.
  • the content of the photopolymerization initiator and Z or the photopolymerization initiation system in the photosensitive resin layer is generally 0.5 to 20% by mass with respect to the total solid content of the layer, and 1 to 15% by mass. % Is preferred.
  • the amount of the colorant in the photosensitive resin layer can be appropriately selected as desired.
  • the photosensitive resin layer in the present invention can be formed using a photosensitive resin composition, and preferably formed using the photosensitive resin composition of the present invention described above. You can also. Furthermore, for example, (a) a non-no-ortho-type cresol novolac resin obtained by reacting phenols containing at least p-taresol with an aldehyde under an acid catalyst, and (b) a quinone diazide group-containing compound. It may be a positive photoresist composition containing Further, the positive photoresist composition has a dinuclear content of p-taresol in the component (a) of less than 2.0% in the GP C (gel “permeation” chromatography) method. It is preferable. Examples of the positive photoresist composition include those described in paragraph Nos. [0 007] to [0026] of Japanese Patent No. 3624718.
  • a positive photoresist composition it is possible to form a resist pattern close to a rectangle with a high residual film ratio as well as excellent sensitivity and resolution that hardly generate sublimates even when subjected to high-temperature beta. .
  • the photosensitive resin composition of the present invention and the photosensitive resin layer of the present invention have a mass reduction rate of 2% by mass or less when heated at 230 ° C for 1 hour.
  • this resin is used, the color characteristics of optical elements (color filters, etc.) caused by discoloration due to deterioration of the resin even in heating processes exceeding 200 ° C, such as the production of ITO films and the production of alignment films
  • a display device for example, a liquid crystal display
  • Examples of the resin include those described in paragraphs [0013] to [0016] of JP-A-11-194214.
  • inorganic fine particles having an average particle diameter smaller than the exposure wavelength may be added.
  • the organic fine particles have a functional group (for example, a photosensitive group) and may be composed of colloidal silica or the like.
  • the photosensitive resin composition and the photosensitive resin layer may be either a negative type or a positive type, and may be water or alkali developable.
  • oxygen plasma resistance, heat resistance, dry etching resistance, sensitivity and resolution can be greatly improved.
  • examples of the inorganic fine particles include those described in paragraph numbers [003 6] to [0047] of JP-A-11-327125.
  • the photosensitive resin composition of the present invention and the photosensitive resin layer according to the present invention may contain retardation-reducing particles.
  • the retardation-reducing particles By including the retardation-reducing particles, the absolute value of the retardation can be reduced to 15 nm or less, and the color filter formed thereby has excellent viewing angle dependence, and a high-quality image can be obtained by using the color filter.
  • Liquid crystal display device can be provided. Specific examples of the retardation-reducing particles include those described in paragraph numbers [0014] to [0035] of JP-A-2000-187114.
  • the photosensitive resin composition of the present invention and the photosensitive resin layer of the present invention may contain a light stabilizer.
  • a light stabilizer for example, at least one compound selected from phosphite-based, benzotriazole-based, benzophenone-based, hindered amine-based, salicylic acid ester-based, triazine-based, hindered technol-based power, and thioether-based power is preferable.
  • Specific examples of the light stabilizer include those described in paragraphs [0007] to [0014] of JP-A No. 2000-214580.
  • a green organic pigment is used for the photosensitive resin composition and the photosensitive resin layer
  • the amounts of tetrachlorophthalic acid, tetrachlorophthalic anhydride and tetrachlorophthalic phthalimide in the green organic pigment are analyzed.
  • the total of them is preferably 500 ppm or less.
  • Preferred range Examples of the method for obtaining the pigment include those described in paragraphs [0005] to [0020] of JP-A No. 2000-321417.
  • impurities of pigments other than green can be reduced.
  • the organic pigment When the organic pigment is used, the pattern during development is not missing or peeled off, and display defects such as image sticking do not occur when the display panel is used, and the mechanical strength after film formation is increased. It is possible to obtain a color filter that is excellent in adhesion, non-turn substrate adhesion, and good pattern shape.
  • the pigment is preferably a pigment that has been selected and processed so that the voltage holding ratio is 80% or more.
  • Preferred examples of the pigment include pigments described in paragraphs [0005] to [0026] of JP-A No. 2000-329929.
  • the photosensitive resin composition of the present invention and the photosensitive resin layer according to the present invention have a glass transition temperature Tg of 60 to 120 ° C and a weight average molecular weight of 10,000 to 100,000.
  • Tg glass transition temperature
  • An embodiment using a polymer, a polyfunctional monomer having a viscosity of 10 to 8000 mPa's at 25 ° C., and a colorant is preferable.
  • preferred examples of the resin composition include combinations described in paragraphs [0016] to [0033] of JP-A-10-115917.
  • the photosensitive resin layer has an appropriate viscosity in the range of 20 to 30 ° C, so that it is excellent in material use efficiency and does not include a wet development process and a washing process, and the manufacturing process is simple. Can be provided.
  • the content of free copper contained in the pigment is 200 ppm or less. It is preferable that Examples of the pigment include those described in paragraph numbers [0011] to [0020] of JP-A-2004-189852.
  • the pigment is effective for enhancing the storage stability of the photosensitive resin composition.
  • the primary particle size is 20 to 30 nm
  • the DBP absorption is 140 mlZl00 g or less
  • pH 2 pH 2.
  • Carbon black of 5-4 is preferred. Examples of the carbon black include those described in paragraph numbers [0010] to [0014] of JP-A No. 2004-292672.
  • the carbon black is effective in forming partition walls (black matrix, colored layer, etc.) excellent in developability and OD value.
  • the specific gravity of the photosensitive resin composition for forming the photosensitive resin layer is 2 It is preferably 5 or more.
  • this resin composition those described in JP-A 2004-352890, paragraphs [0007] to [0013] are preferable.
  • a pattern eg, a partition such as a black matrix
  • a better black pattern than before can be formed.
  • the photosensitive resin composition of the present invention and the photosensitive resin layer according to the present invention have a pencil pattern hardness of 3H or more and 9H or less after curing, such as a partition such as a black matrix.
  • the resin layer obtained after exposure is immersed in an alkaline aqueous solution at 25 ° C under stirring at lOOr.pm, and the transmittance of the part where the unexposed area of the photosensitive resin layer is dissolved after 120 seconds has elapsed.
  • a composition having an (average of 400 to 780 nm) of 98% or more and 100% or less is preferable.
  • the resin composition described in paragraph Nos. [0007] to [0075] of JP-A-2005-10763 can be mentioned. When a pattern is formed using this resin composition, both high surface hardness and good developability can be achieved.
  • the residual ratio mass ratio of the total nitrogen amount after heating to the total nitrogen amount before heating
  • examples of the dispersant include those described in JP-A-2004-325968, paragraph numbers [0043] to [0047].
  • a color filter (including a partition wall and colored pixels) using the dispersant has a very small influence on the voltage holding ratio of the liquid crystal, and therefore a display device of extremely high quality that hardly causes display defects such as display unevenness and image sticking. Can be made.
  • a cured film (a partition wall such as a black matrix) formed by using the photosensitive resin composition of the present invention or by transferring the photosensitive resin layer of the photosensitive transfer material of the present invention is formed.
  • the composition for this purpose include the resin composition described in paragraphs [0008] to [0061] of JP-A-10-293397.
  • the indentation hardness of the overcoat is preferably within the range of the following formula (1).
  • the indentation hardness of the power filter is within the range of the following formula (2).
  • display unevenness of the liquid crystal display device due to non-uniform cell gap is unlikely to occur. Examples of means for achieving the preferred hardness range include the methods described in JP-A-11-271525, step numbers [0012] to [0061].
  • the color filter is preferably formed of a colored layer having an average refractive index of 1.60 or more and 1.90 or less and an absolute value of birefringence of 0.01 or less. Since the retardation of the color filter using the colored layer (including the partition wall) within the preferable range is reduced, a liquid crystal display device having excellent display characteristics can be provided. Examples of means for producing a color filter within the preferred range include the methods described in paragraph numbers [0007] to [004 2] of JP-A No. 2000-136253.
  • a specific surface area of preferred are intended to be within the scope of 35 to 120,111 2 1,.
  • means for obtaining a pigment having a specific surface area that is preferred include the methods described in paragraphs [0015] to [0022] of JP-A-2001-42117.
  • the temporary support constituting the photosensitive transfer material of the present invention can be appropriately selected from those that are chemically and thermally stable and composed of a flexible substance.
  • Specific examples include thin sheets such as Teflon (registered trademark), polyethylene terephthalate, polycarbonate, polyethylene, and polypropylene, films, and laminates thereof.
  • Teflon registered trademark
  • polyethylene terephthalate polycarbonate
  • polyethylene polyethylene
  • polypropylene films
  • a biaxially stretched polyethylene terephthalate film is particularly preferable.
  • the thickness of the temporary support is suitably 5 to 300 ⁇ m, preferably 20 to 150 ⁇ m.
  • the protective film may be made of the same or similar material as the temporary support, but it must be easily separated from the photosensitive resin layer! /.
  • Suitable materials for the protective film include, for example, silicone paper, polyolefin, or polytetrafluoroethylene sheet.
  • the photosensitive transfer material of the present invention has a surface treatment layer and a photosensitive resin layer on a temporary support, and has a laminated structure in which the surface treatment layer and the photosensitive resin layer are formed adjacent to each other.
  • the thermoplastic resin layer, the intermediate layer, and the photosensitive resin layer can be suitably configured on the temporary support so that they are in contact with each other in this order.
  • the fluorinated resin according to the present invention can be contained at least in the intermediate layer and optionally further contained in a thermoplastic resin layer or a photosensitive resin layer.
  • thermoplastic resin layer coating solution in which the components of the thermoplastic resin layer were dissolved was applied on the temporary support and dried to form a thermoplastic resin layer.
  • An application liquid (intermediate layer application liquid) containing a constituent component of the intermediate layer (including the fluororesin according to the present invention) using a solvent that does not dissolve the thermoplastic resin layer on the thermoplastic resin layer.
  • the intermediate layer is formed by coating and drying, and then the intermediate layer is formed on the formed intermediate layer. Do not dissolve! It can be prepared by applying a coating solution containing a component of a photosensitive resin layer using a solvent (a coating solution for a photosensitive resin layer) and drying to provide a photosensitive resin layer.
  • the layer thickness of the photosensitive resin layer is preferably 1.0 to 5.
  • O / zm force more preferably 1.0 to 4.
  • O / zm force 1. 0 ⁇ 3.0 m force ⁇
  • the preferable film thickness of each of the other layers is as follows: Temporary support body 15 ⁇ : LOO / zm ⁇ ma 0.5 ⁇ 3. O ⁇ m, and the protective film is generally 4 ⁇ 40 ⁇ m.
  • the application can be performed by a known application apparatus or the like.
  • application is preferably performed by a slit-like nozzle having a slit-like hole at a portion where the liquid is discharged.
  • the slit-shaped nozzle and slit coater described in Japanese Patent No. 79163, Japanese Patent Application Laid-Open No. 2001-310147, etc. are preferably used.
  • the partition wall of the present invention uses at least (a) the above-described photosensitive transfer material of the present invention, and the photosensitive transfer material is pressure-bonded to the transferred object so that the photosensitive resin layer is in contact with the transferred object.
  • a pressure bonding step ; and (b) an exposure step of exposing the photosensitive resin layer of the photosensitive transfer material pressure-bonded to the transfer object in a pattern (at least with or without a surface treatment layer); (C) a development step of developing the exposed photosensitive resin layer, and preferably a partition wall obtained by (d) development after (c) the development step.
  • a beta process is in place to beta process the pattern.
  • the partition wall of the present invention is formed using a photosensitive transfer material in which the surface treatment layer containing the fluorine-based resin according to the present invention is provided in contact with the photosensitive resin layer. Therefore, the upper surface of the partition formed through exposure, development, etc. after transfer (the side opposite to the side of the partition that contacts the transfer target) The opposite surface; the top surface 4) of the partition wall in FIG. 4 is selectively imparted with ink repellency (including oil repellency and water repellency), and the exposed substrate surface or side surface of the partition wall that becomes a colored region (pixel) (The side wall 5 in Fig. 4) is not fluorinated and does not have ink repellency.
  • ink repellency including oil repellency and water repellency
  • a transparent substrate is used, and a soda glass plate having a surface of an oxide film on its surface, a low expansion glass
  • a known glass plate such as a non-alkali glass or a quartz glass plate, or a plastic film can be used.
  • the thickness of the substrate is not particularly limited, but generally 700 to 1200 / ⁇ ⁇ is preferable.
  • the above-described photosensitive transfer material of the present invention is pressure-bonded to the surface of the transferred body so that the surface of the photosensitive resin layer is in contact with the transferred body.
  • the pressure bonding is, for example, contacting by applying pressure like a laminate, and using the photosensitive transfer material of the present invention, the photosensitive resin layer formed in a film shape is heated and wrinkled or pressed.
  • a laminate in which a photosensitive transfer material is attached onto a transfer target can be obtained.
  • JP-A-7-110575 Specific examples include a method using a laminator and a lamination method described in JP-A-7-110575, JP-A-11 77942, JP-A 2000-334836, and JP-A 2002-148794. From the viewpoint of low foreign matter, it is preferable to use the method described in JP-A-7-110575.
  • a laminator capable of supplying a plurality of transfer materials in parallel may be used.
  • the multi-cutter laminator include those described in step numbers [0007] to [0039] of JP-A-2004-333616.
  • the photosensitive resin layer of the photosensitive transfer material pressure-bonded to the transfer target in the pressure-bonding step is exposed in a pattern via at least the surface treatment layer.
  • a predetermined mask is disposed further above the photosensitive resin layer transferred onto the transfer material, and a light source is disposed further above the mask, with the mask and the surface treatment layer interposed therebetween. This can be done by irradiating from above the mask.
  • any light source capable of irradiating light in a wavelength region capable of curing the photosensitive resin layer (for example, 365 nm, 405 nm, etc.) can be appropriately selected and used.
  • Specific examples include ultra high pressure mercury lamps, high pressure mercury lamps, metal halide lamps, and the like.
  • the exposure amount is usually 5 to 300 miZcm 2 , preferably 10 to 200 miZcm 2 .
  • Pattern exposure can also be performed by exposure using a laser light source described in paragraphs [0061] to [0205] of JP-A No. 2004-240216, in addition to the exposure method performed using the mask.
  • the exposed surface of the photosensitive resin layer provided on the transfer medium that does not contact the transfer medium is fluorinated.
  • the fluorine-based resin according to the present invention in the surface treatment layer causes an interaction such as a chemical bond or physical adsorption with the photosensitive resin layer, and is photosensitive. Since it is fixed to the surface treatment layer side interface of the resin layer, ink repellency can be imparted to the surface treatment layer side interface of the photosensitive resin layer.
  • the photosensitive resin layer exposed in the exposure step is developed using a developer, and the photosensitive resin layer in the unexposed area is developed and removed.
  • the latent image formed by exposure can be made visible and obtained as a partition wall.
  • the surface treatment layer can be removed by development.
  • the surface treatment layer on the photosensitive resin layer is removed, but the fluorine-based resin according to the present invention fixed on the surface of the photosensitive resin layer remains, so that the photosensitive resin layer is covered.
  • the partition wall is selectively provided with ink repellency only on the surface opposite to the side in contact with the transfer body (the upper surface of the photosensitive resin layer on the transferred body). be able to.
  • the developer known developers such as those described in JP-A-5-72724, which are not particularly limited, can be used.
  • the developer has a developing behavior in which the photosensitive resin layer has a dissolution type.
  • a developer containing a compound having a pKa of 7 to 13 at a concentration of 0.05 to 5 molZL is preferable.
  • examples of the “organic solvent miscible with water” include, for example, methanol, ethanol, 2-propanol, 1 propanol, butanol, diacetone alcohol, ethylene glycol monomethinoatenole, ethylene glyconolemonoethino.
  • Rietenole ethylene glycol mono-n-butyl ether, benzyl alcohol, acetone, methyl ethyl ketone, cyclohexanone, ⁇ -force prolatatone, ⁇ -butarate ratataton, dimethylformamide, dimethylacetamide, hexamethylphosphoramide , Ethyl lactate, methyl lactate, epsilon ratatatam, ⁇ ⁇ ⁇ -methylpyrrolidone, and the like.
  • the concentration of the organic solvent is preferably 0.1 to 30% by mass.
  • a known surfactant may be further added to the developer.
  • the concentration of the surfactant is preferably from 0.01 to L0% by mass.
  • a development method a known method such as paddle development, shower development, shower & spin development, dip image, or the like can be used.
  • shower development will be described.
  • an uncured portion can be removed by spraying a developer onto the photosensitive resin layer after exposure.
  • it is preferable to remove the development residue by spraying a cleaning agent or the like with a shower and rubbing with a brush or the like.
  • the developer temperature is preferably 20-40 ° C, and the developer pH is preferably 8-13.
  • Beta processing is an image (partition pattern) formed by pattern exposure and development. It is cured by heating.
  • a method of the beta treatment various conventionally known methods can be used. That is, for example, a method of storing a plurality of substrates in a cassette and processing them in a competition oven, a method of processing one by one with a hot plate, or a method of processing with an infrared heater.
  • the beta temperature (heating temperature) is usually 150 to 280 ° C, preferably 180 to 250 ° C.
  • the heating time varies depending on the beta temperature, but when the beta temperature is 220 ° C, it is preferably 5 to 30 minutes for the intermediate beta treatment and 60 to 200 minutes for the final beta treatment.
  • the partition pattern formed by the exposure and development steps is included in the photosensitive resin layer to prevent uneven film reduction.
  • post-exposure may be performed before the beta treatment. If post-exposure is performed before the beta treatment is performed, it is possible to effectively prevent the minute foreign matter swollen during lamination from causing defects.
  • any light source capable of irradiating light in a wavelength region capable of curing the photosensitive resin layer (for example, 365 nm, 405 nm) can be appropriately selected and used.
  • an ultrahigh pressure mercury lamp, a high pressure mercury lamp, a metal halide lamp, etc. are mentioned.
  • Energy of exposure generally Yogu if exposure to compensate for the exposure is 50 ⁇ 5000MjZcm 2, preferably 200 ⁇ 2000MjZcm 2, more preferably Ru 500 ⁇ 1000MjZcm 2 der.
  • glass substrate When using an alkali-free glass substrate (hereinafter sometimes simply referred to as “glass substrate”), cleaning is performed to remove contamination on the substrate surface. For example, glass cleaning adjusted to 25 ° C Clean with a rotating brush with nylon bristles while spraying chemical solution (trade names: T-SD1, T-SD2, Fuji Photo Film Co., Ltd.) for 20 seconds with a shower, and then wash with pure water. .
  • chemical solution trade names: T-SD1, T-SD2, Fuji Photo Film Co., Ltd.
  • silane coupling agent those having a functional group that interacts with the photosensitive resin are preferable.
  • a silane coupling solution N- ⁇ (aminoethyl) ⁇ -aminopropyltrimethoxysilane 0.3 mass% aqueous solution, trade name: ⁇ 603, manufactured by Shin-Etsu Chemical Co., Ltd.
  • the reaction is carried out by heating.
  • a heating tank may be used, the reaction can be advanced even by preliminary substrate heat from a laminator.
  • the glass substrate is heated at 100 ° C. for 2 minutes by a substrate preheating device, and then sent to a laminator in the next step. Thereby, lamination can be performed uniformly.
  • a rubber roller temperature of 130 ° C., linear pressure of 100 N / cm, conveyance speed is applied to the surface of a glass substrate heated to 100 ° C. using a laminator. 2. Laminate under the condition of 2mZ.
  • the temperature of the rubber roller is preferably from 100 ° C to 150 ° C.
  • the temporary support may be peeled off by performing exposure (in this case, the photosensitive resin layer is exposed through the temporary support and the surface treatment layer), or the temporary support is peeled off before exposure. (In this case, the photosensitive resin layer is exposed through the surface treatment layer).
  • the surface treatment layer is in close contact with the photosensitive resin layer at the time of exposure, and when the temporary support is peeled off, it may or may not be peeled off at the same time as the surface treatment layer. It is preferable to leave only the temporary support while leaving the oil layer in close contact.
  • the size of the transfer object is 50 centimeters or more, it is preferable to expose the substrate and mask (quartz exposure mask with image pattern) vertically.
  • the distance between the mask surface and the surface of the photosensitive resin layer on the substrate side is short, and the resolution is better. However, foreign matter is likely to adhere, so 100 to 300 / ⁇ ⁇ ⁇ is set.
  • the exposure amount is preferably in the range of 10 to 300 miZcm 2 .
  • the pattern is exposed as described above.
  • a triethanolamine developer for example, 2.5% triethanolamine, a nonionic surfactant, and a polypropylene-based antifoaming agent (product) Name: T-PD1, manufactured by Fuji Photo Film Co., Ltd., etc.
  • T-PD1 manufactured by Fuji Photo Film Co., Ltd., etc.
  • it is supplied in a shower at a flat nozzle pressure of 0.04 MPa for 50 seconds at 30 ° C.
  • thermoplastic resin layer or intermediate layer may be removed together with the temporary support when the temporary support is peeled off.
  • the photosensitive resin layer is developed with an alkali to form a pattern.
  • a sodium carbonate developer e.g., 0.06 mol Z liters of sodium bicarbonate, sodium carbonate of the same concentration, 1% by weight of sodium dibutylnaphthalene sulfonate, a-on surfactant, antifoaming agent, and A stabilizer-containing (trade name: TCD1, manufactured by Fuji Photo Film Co., Ltd.) is used.
  • shower development is performed at 35 ° C. for 35 seconds at a cone type nozzle pressure of 0.15 MPa.
  • KOH or TMAH may be used as the developer.
  • detergents for example, phosphates, silicates, nonionic surfactants, antifoaming agents, and stabilizers (trade name: TSD1, manufactured by Fuji Photo Film Co., Ltd. or sodium carbonate and (Product name: T-SD2, manufactured by Fuji Photo Film Co., Ltd.) containing an enoxypolyoxyethylene surfactant is used.
  • detergents for example, phosphates, silicates, nonionic surfactants, antifoaming agents, and stabilizers (trade name: TSD1, manufactured by Fuji Photo Film Co., Ltd. or sodium carbonate and (Product name: T-SD2, manufactured by Fuji Photo Film Co., Ltd.) containing an enoxypolyoxyethylene surfactant is used.
  • the conditions are: 33 ° C for 20 seconds, cone type nozzle pressure 0.02 MPa, shower and nylon hair Residue removal is performed with a rotating brush. As described above, the remaining components of the photosensitive resin layer in the unexposed area are removed.
  • the glass substrate is post-exposed for about 500 mjZcm 2 from the pattern forming surface side with an ultra-high pressure mercury lamp.
  • Post-exposure may be carried out on both sides, and can be selected in the range of 100 to 800 mJ / cm 2 .
  • the reaction of the monomer or oligomer can be promoted to form a hard film.
  • the beta treatment is preferably performed by heat treatment at 200 to 240 ° C for 30 to 180 minutes. These temperature and time are more preferably set to a high temperature and a short time so as not to drop the production tact.
  • the partition wall of the present invention can be formed.
  • the photosensitive transfer material of the present invention is constituted by containing the fluorinated resin according to the present invention in the surface treatment layer provided in contact with the photosensitive resin layer. At least the fluorine-based resin according to the present invention is present on the partition such as a black matrix formed by transferring the photosensitive resin layer to the transfer object, that is, the partition on the transfer object.
  • the surface of the photosensitive resin layer constituting the surface opposite to the side in contact with the transfer object (the upper surface of the photosensitive resin layer on the transfer object) is fluorinated by the surface treatment layer, and the fluorinated surface is In forming each colored region (such as a colored pixel of an optical element such as a color filter) in an exposed state and separated by a partition provided on the transfer medium, an area between the colored regions is formed.
  • Ink repellency selectively applied to the upper surface of partition walls As a result, it is possible to prevent color mixing and protrusion of the ink applied to the ink jet, and to prevent the applied ink from flowing into or bleeding into other colored areas.
  • FIG. 4 is a cross-sectional view schematically showing the color filter.
  • the concave portion 3 at the right end is shown in a state in which no colored pixels are formed in order to facilitate the explanation.
  • the partition wall 1 is provided on the glass substrate 6 so that the recesses 3 are formed at a predetermined interval, and is surrounded by the partition wall. Colored pixels 2 are formed by adding ink to the recesses 3.
  • partition walls 1 and four recesses 3 are shown for ease of component force, but the partition walls and recesses can be provided as necessary.
  • the number of pixels is 640 in the case of a striped color filter, 3 colored areas of RGB per pixel are required, so 1921 partition walls 1 and 1920 recesses 3 I need it.
  • the precision of the gap between the substrates is not displayed, and a color filter pattern may be formed up to the periphery of the display pixel, and in this case, it further increases.
  • the partition wall 1 may not be formed in the longitudinal direction, but the periphery of the colored pixel 2 may be completely surrounded by the partition wall 1 in some cases. In particular, in the case of a mosaic color filter, the periphery of the colored pixel 2 is surrounded by a partition wall 1.
  • the partition wall 1 for partitioning the colored pixel 2 is formed on the glass substrate 6 in a line shape or a lattice shape.
  • the shape of the partition wall 1 may be such that the recess 3 partitioned by the partition wall corresponds to the colored pixel 2 to be formed.
  • the recess 3 partitioned by the partition wall corresponds to the colored pixel 2 to be formed.
  • it is formed in a linear shape, and in order to correspond to the square colored pixel 2, it is formed in a lattice shape. Since this is appropriately determined depending on the shape of the colored pixel 2, various shapes such as a radial shape and a circumferential shape are also conceivable.
  • the partition wall 1 When the partition wall 1 is configured as a liquid crystal display element or the like, it is advantageous that the partition wall 1 also functions as a black matrix.
  • the partition wall 1 also serves as a black matrix will be described.
  • the partition wall 1 when the partition wall 1 is not formed as a black matrix, it may be configured not to include a black material or the like.
  • the partition wall 1 has a role of preventing ink that has been ejected from flowing into or bleeding into other recessed portions or existing colored pixels when the recessed portion 3 is colored by an inkjet method. It is. Therefore, it is preferable that the height of the partition wall 1 is high to some extent, but considering that the flatness of the entire color filter is also required, the height should be close to the required color pixel thickness. Is preferred. Specifically, the force that varies depending on the amount of ink deposited to obtain a desired colored pixel is usually about 0.1 to 3 / ⁇ ⁇ .
  • the partition wall 1 When ink is applied to the recess 3 on the glass substrate 6 by ink jetting, the upper surface of the partition wall 1 (upper surface 4 shown in Fig. 4), if the ink remains, flatness, thickness between colored pixels, and uniformity of coloring
  • the partition wall of the present invention is ink-repellent, uneven thickness and coloration can be effectively suppressed.
  • the partition wall of the present invention is not subjected to ink repellent treatment on its side surface (side surface 5 shown in FIG. 4). That is, the upper surface 4 of the partition wall 1 has a property of repelling ink, and the side surface has a property of hardly repelling ink.
  • the exposed surface of the concave portion 3 has a property that it is difficult to repel the ink.
  • the degree of ink repellency imparted to the upper surface 4 of the partition wall 1 constituting the color filter is preferably 85 to 140 ° in water contact angle. If the contact angle force is less than 85 °, the ink tends to remain on the upper surface of the partition wall, and if it exceeds 140 °, the coloring of the recesses between the partition walls tends to be hindered or the smoothness of the upper surface of the partition wall may be lost. In particular, a range of 100 to 125 ° is more preferable.
  • the degree of ink repellency (range of contact angle of water) is controlled by the content of the fluorine-based resin according to the present invention in the surface treatment layer described above, the pattern exposure amount to the photosensitive resin layer, and the like. Can do.
  • the contact angle of water can be measured with a contact angle meter DM300 manufactured by Kyowa Interface Science Co., Ltd., and the contact angle of ink can be determined in the same manner.
  • the black matrix is, for example, formed in a linear shape when forming a striped color filter, and formed in a lattice shape so as to correspond to a square pixel. It is a partition provided between the colored pixels which have.
  • the black matrix is appropriately determined depending on the shape of the colored pixel, and can be configured in various shapes such as a radial shape and a circumferential shape. Togashi.
  • the black matrix can be produced by using a colorant that can impart light shielding properties to the photosensitive resin layer.
  • a colored region (for example, a colored pixel) is formed by applying a liquid suitability by an inkjet method to a recess defined by a partition formed on a transfer target by transferring the photosensitive resin layer of the photosensitive transfer material of the present invention.
  • the optical element of the present invention can be manufactured.
  • the optical element of the present invention includes an optical element formed by coloring a concave region surrounded by a partition wall formed in advance by liquid application using an ink jet method, such as a color filter or an electoluminescence element. It is.
  • an example of the color filter rectangular images colored in red, green, blue, etc. are arranged in a matrix on a substrate such as glass, and the boundary between the images is defined by black bear tritus or the like. Examples include a configuration in which a partition wall is provided.
  • An example of an electroluminescent element is a structure in which a thin film containing a fluorescent inorganic or organic compound is sandwiched between a cathode and an anode, and electrons and holes are injected into the thin film. Examples include an element in which an exciton is generated by bonding and light is emitted using emission of fluorescence or phosphorescence when the exciton is deactivated.
  • an element can be configured by forming a light emitting layer by applying a fluorescent material onto a substrate on which an element such as a TFT is formed by an ink jet method.
  • the method of applying droplets such as the inkjet method can simplify the manufacturing process and reduce the cost, so it can be applied to the manufacture of color filters and electoluminescence elements! Has been.
  • the ink jet method includes a method in which charged ink is continuously ejected and controlled by an electric field, a method in which ink is intermittently ejected using a piezoelectric element, and an ink is heated and intermittently utilized by using its foaming.
  • Various methods such as a spraying method can be adopted.
  • the ink can be used both oil-based and water-based.
  • the colorant contained in the ink can be used for both dyes and pigments, and a pigment is preferable from the viewpoint of durability.
  • oil-based colored ink (colored resin composition) used for producing a known color filter can also be used.
  • the ink may be added with a component that is cured by heating or is cured by energy rays such as ultraviolet rays.
  • Various thermosetting resin is widely used as the component that cures by heating, and as the component that cures by energy rays, for example, an attalylate derivative or a metatalylate derivative to which a photoinitiator is added can be used. .
  • those having a plurality of alitaroyl groups and methacryloyl groups in the molecule are more preferable.
  • These attalylate derivatives and metatalylate derivatives can be used by emulsifying them, even if they are water-soluble and are hardly soluble in water.
  • a photosensitive resin composition containing a colorant such as a pigment listed in the above-mentioned “photosensitive resin layer” can be preferably used.
  • T are 0.5 m or less, preferably 0.2 m or less.
  • the color filter composed of colored pixels suppresses the occurrence of display defects such as a decrease in contrast and an afterimage due to light leakage, and can display an image with excellent image quality.
  • Examples of a method for adjusting the in-pixel step to a preferable range include the methods described in paragraph numbers [0038] to [0042] of JP-A-11-218607.
  • the color filter (colored pixel) that also includes at least three color powers has white display coordinates (u ', V) calculated based on the tristimulus values "X, Y, ZJ" of each film and Black display coordinates (u white white
  • coordinates S (0.15, 0.42) and coordinates S (0.15, 0.42) are preferably within the range of a straight line connecting the four coordinates.
  • Examples of the color filter include those described in paragraph numbers [0008] to [0 047] of JP-A-2005-25175.
  • a display device using a color filter can appropriately balance the pixels, and the display color can be easily adjusted. In particular, it can be preferably used as a color filter for television.
  • the ink (photosensitive resin composition) for forming the colored region is placed horizontally! One drop is dropped on a clean glass substrate, and the horizontal force of the glass substrate is also inclined by 45 °. In the spreading part of the photosensitive resin composition after the dripping material was allowed to flow down and beta-treated at 100 ° C for 3 minutes, A photosensitive resin composition having a haze value of 2 or less when the film thickness of the spread portion is converted to 1 ⁇ m is preferable.
  • Examples of the photosensitive resin composition include the compositions described in JP-A 2003-330174, paragraphs [0006] to [0059]. By using this composition, it is possible to form a color filter with good in-plane uniformity of film thickness and without unevenness.
  • the contrast of the colored pixels formed with the ink is preferably 2000 or more.
  • the method described in paragraph [0025] of JP-A-2005-25206 can be mentioned.
  • a display device using a color filter with high contrast can be used as an EBU standard TV liquid crystal display device with excellent color reproducibility.
  • color filters are usually formed by ejecting ink of RGB three colors by an ink jet method.
  • This color filter is used as a display element in combination with a liquid crystal display element, an electrophoretic display element, an electochromic display element, PLZT, or the like. It can also be used for applications using color cameras and other color filters.
  • optical element of the present invention including a color filter, defects such as bleeding of each color ink, protrusion, and color mixture with adjacent pixels are effectively suppressed.
  • the optical element of the present invention is used in various display devices as described above, and is also suitable as a liquid crystal display element in which a liquid crystal material is sealed between a pair of opposed substrates.
  • the optical element force color filter of the present invention is configured, for example, it is formed on a counter substrate of a liquid crystal display device to be described later (a substrate on the side without an active element such as TFT), or COA method to form on the TFT substrate side, BOA method to form only black on the TFT substrate side
  • An overcoat film or a transparent conductive film can be further formed on the color filter as necessary.
  • the display device of the present invention includes the above-described display element of the present invention (including a color filter).
  • a liquid crystal display device for example, a liquid crystal display device, a plasma display device, an EL display device And display devices such as CRT display devices.
  • a color filter that is an optical element of the present invention and a counter substrate prepared separately from the color filter are aligned with a predetermined gap, and liquid crystal is sealed between the color filter and the counter substrate.
  • a liquid crystal display device is manufactured.
  • the liquid crystal display method is not particularly limited and may be appropriately selected depending on the intended purpose.
  • ECB Electrically Controlled Birefringence
  • TN Transmission Nematic
  • O CB Optically Compensatory Bend
  • VA Very Aligned
  • HAN Hy brid Aligned Nematic
  • STN Supper Twisted Nematic
  • IPS In-Plane Switching
  • GH Guest Host
  • FLC ferroelectric liquid crystal
  • AFLC antiferroelectric liquid crystal
  • PDLC polymer dispersion type liquid crystal
  • thermoplastic resin coating solution of the following formulation C on a 75 ⁇ m-thick polyethylene terephthalate film temporary support using a slit-shaped nozzle, and dry the thermoplastic resin layer. Formed.
  • a coating solution for the surface treatment layer having the following formulation P1 is applied to the surface of the thermoplastic resin layer, dried to form a surface treatment layer, and further on the surface of the formed surface treatment layer, the following:
  • the photosensitive resin composition K1 shown in Table 1 was applied and dried to form a photosensitive resin layer K.
  • Black (K) photosensitive resin layer K, and a protective film (12 m thick polypropylene film) is pressure-bonded onto the photosensitive resin layer, and the temporary support Z thermoplastic resin layer Z
  • a photosensitive transfer material K1 having a laminated structure of a surface treatment layer (oxygen barrier film) / photosensitive resin layer K and a protective film was prepared.
  • the applicability of the photosensitive resin composition K1 was evaluated according to the following evaluation criteria.
  • the degree of unevenness and noise level A rank, B rank, and C rank are practically acceptable ranges.
  • the evaluation results are shown in Table 2 below.
  • Photosensitive resin composition K1 was prepared by removing the pigment dispersion 1 and propylene glycol monomethyl ether acetate in the amounts shown in Table 1 and mixing at a temperature of 24 ° C ( ⁇ 2 ° C). Stir at .pm for 10 minutes, then the amount of methylethylketone, binder 1, DPHA solution, 2, 4 bis (trichloromethyl) 6- [4,1 (N, N bisethoxycarbonyl) listed in Table 1 above Methylamino) 3'-bromophenyl]-s Triazine, hydroquinone monomethyl ether, and surfactant 1 are weighed and added in this order at a temperature of 25 ° C ( ⁇ 2 ° C), and the temperature is 40 ° C. It was obtained by stirring at 150 rpm for 30 minutes at C ( ⁇ 2 ° C)
  • composition of pigment dispersion 1, binder 1, DPHA liquid, and surfactant 1 in photosensitive resin composition K1 is as follows. * Pigment dispersion 1
  • a non-alkali glass substrate is cleaned with a rotating brush with nylon bristles while spraying a glass detergent solution adjusted to 25 ° C for 20 seconds with a shower.
  • the silane coupling solution N- ⁇ (aminoethinore ) ⁇ - Aminopropyltrimethoxysilane 0.3% aqueous solution, trade name: ⁇ 603, manufactured by Shin-Etsu Chemical Co., Ltd.
  • This glass substrate was heated at 100 ° C. for 2 minutes with a substrate preheating apparatus.
  • the exposed surface of the photosensitive resin layer K is a rubber roller using a laminator (manufactured by Hitachi Industries (Lamidl type)) at a temperature of 130 °. C, linear pressure 100NZcm, transport speed 2. Laminate on glass substrate after heating at 100 ° C for 2 minutes under the condition of 2mZ.
  • a laminator manufactured by Hitachi Industries (Lamidl type)
  • the black matrix forming surface side force is also post-exposed with an ultra-high pressure mercury lamp at lOOOmjZcm 2 and the force on the opposite side of the glass substrate on the black matrix forming surface side
  • heat treatment was performed at 220 ° C for 30 minutes.
  • R ink Among the components in the composition below, first, a pigment, a polymer dispersant, and a solvent were mixed, and a pigment dispersion was obtained using a three-roll and a bead mill. Then, while sufficiently stirring this pigment dispersion with a day solver or the like, the remaining components were added little by little to prepare an R (red) pixel colored ink (R ink).
  • an inkjet recording apparatus equipped with a piezo method and a nozzle resolution of 180 dpi was prepared, and R ink, G ink, and B ink prepared as described above were loaded into this, and black formed on a glass substrate. Droplets were applied to the recesses (exposed portions of the glass substrate) surrounded by the matrix (partitions) by the inkjet method so that each of the R, G, and B inks had a desired concentration.
  • a color filter comprising a color matrix (pixel) of R, G, and B colors and a black matrix (partition) that separates each color area is cured by heat treatment for 1 hour at ° C. Produced.
  • Ink protrusion and color mixing refer to the phenomenon shown in Fig. 1. In the case of the following A rank, B rank, or C rank, it is a practically acceptable range.
  • the evaluation results are shown in Table 2 below.
  • the flatness within the pixel of the color filter was performed as follows.
  • the surface shape of an arbitrary pixel was measured with a surface roughness meter P-10 manufactured by Tencor, and the height difference ⁇ between the most prominent part in the pixel and the lowest part in the pixel was determined.
  • the allowable step is 0.1 ⁇ m or less.
  • the black matrix and the colored area (pixel) of the color filter produced as described above An overcoat layer was not provided on the formation surface, and an ITO film was formed by sputtering directly on a color filter on which RGB pixels were formed to provide a transparent electrode.
  • the formulation of the photosensitive resin composition K1 was replaced with the following formulation S of the photosensitive resin layer coating solution, and the coating solution for the surface treatment layer was used.
  • a photosensitive transfer material K2 was prepared and a spacer was formed in the same manner as in [Formation of partition walls] except that the formulation P1 was changed to the following formulation PC1.
  • exposure, development, and heat treatment were performed by the following methods.
  • a liquid crystal display device using the substrate for a liquid crystal display device obtained above in the same manner as the method described in the first embodiment ([0079] to [0082]) of JP-A-11-242243 was made.
  • Example 1 the evaluation was carried out in the same manner as in Example 1 except that the amount of the exemplified rosin a used for the preparation of the coating solution P1 for the surface treatment layer was changed to 4.66 parts. It was.
  • Example 1 the evaluation was carried out in the same manner as in Example 1, except that the amount of the exemplified resin a used in the preparation of the coating solution P1 for the surface treatment layer was changed to 10.3 parts. It was.
  • Example 1 the evaluation was carried out in the same manner as in Example 1 except that the amount of the exemplified resin a used in the preparation of the coating solution P1 for the surface treatment layer was changed to 15.6 parts. It was.
  • Example 1 In the same manner as in Example 1 except that 59 parts of the exemplified resin aO. Used in the preparation of the coating solution P1 for the surface treatment layer was replaced by 3 parts of the exemplified resin blO. Evaluated
  • Example 1 In the same manner as in Example 1 except that 59 parts of the exemplified resin aO. Used in the preparation of the coating solution P1 for the surface treatment layer was replaced with 3 parts of the exemplified resin clO. Evaluated [0260] (Example 7)
  • Example 1 In the same manner as in Example 1, except that 59 parts of the exemplified resin aO. Used in the preparation of the coating solution P1 for the surface treatment layer was replaced with 3 parts of the exemplified resin dlO. Evaluated
  • Example 1 In the same manner as in Example 1, except that 59 parts of the exemplified resin aO. Used in the preparation of the coating solution P1 for the surface treatment layer was replaced with 3 parts of the exemplified resin elO. Evaluated
  • Example 1 In the same manner as in Example 1 except that 59 parts of the exemplified resin aO. Used in the preparation of the coating solution P1 for the surface treatment layer was replaced with 3 parts of the exemplified resin flO. Evaluated
  • Example 1 In the same manner as in Example 1 except that 59 parts of the exemplified resin aO. Used in the preparation of the coating solution P1 for the surface treatment layer was replaced with 3 parts of the exemplified resin glO. Evaluated
  • Example 1 In the same manner as in Example 1 except that 59 parts of the exemplified resin aO. Used in the preparation of the coating solution P1 for the surface treatment layer was replaced with 3 parts of the exemplified resin hlO. Evaluated
  • Example 1 In the same manner as in Example 1, except that 59 parts of the exemplified resin aO. Used in the preparation of the coating solution P1 for the surface treatment layer was replaced with 3 parts of the exemplified resin ilO. Was evaluated.
  • Example 1 Same as Example 1 except that 59 parts of the exemplified resin aO. Used in the preparation of the coating solution P1 for the surface treatment layer was replaced with 10.3 parts of the exemplified resin j 10.3 parts Evaluation was performed.
  • Example 14 Example 1! In the same manner as in Example 1 except that 59 parts of the exemplified resin aO. Used in the preparation of the surface treatment layer coating liquid PI were replaced with 3 parts of the exemplified resin klO. Evaluated
  • Example 3 Evaluation was performed in the same manner as in Example 3 except that the amount of pattern exposure performed by the proximity type exposure machine was changed to 300 mjZcm 2 in [Formation of partition walls] in Example 3.
  • Example 3 the exposure amount of the pattern exposure performed by the proximity type exposure machine was set to 300 mjZcm 2, and the development time was obtained by diluting the KOH-based developer 100 times with pure water. Evaluation was performed in the same manner as in Example 3 except that the time was 40 seconds.
  • Evaluation was performed in the same manner as in Example 3 except that R ink, G ink, and B ink were replaced with the following R ink, G ink, and B ink in Example 3.
  • thermosetting component Using an acrylic copolymer having the following compositional power as a thermosetting component, inks of R ink, G ink, and B ink having the following composition were prepared.
  • Example 3 the evaluation was performed in the same manner as in Example 3 except that the wrinkle pattern was formed after the overcoat layer was formed.
  • Example 2 After removing the residue and foreign matter by cleaning the surface of the color filter produced in the same manner as in Example 1 where the black matrix and colored areas (pixels) are formed using a low-pressure mercury lamp UV cleaning device (manufactured by Cleantech). Then, a transparent overcoat agent was applied over the entire surface so that the film thickness was 1. Then, beta was conducted at 230 ° C for 40 minutes to provide a transparent overcoat layer. At this time, in order to form an overcoat layer, a polyamic acid represented by the following structural formula (A) and an epoxy compound represented by the following structural formula (B) were mixed at a mass ratio of 3: 1.
  • ITO indium stannate
  • Example 1 59 parts of the exemplified rosin aO. Used in the preparation of the coating solution P1 for the surface treatment layer was added to EF-123A (EF-123A (bisphosphate [2— (N-propylperfluorooctylsulfo-lumino) ethyl] ester) 10. Except for substituting 3 parts Evaluation was carried out in the same manner as in Example 1.
  • EF-123A bisphosphate [2— (N-propylperfluorooctylsulfo-lumino) ethyl] ester
  • Example 1 the coating solution for the surface treatment layer of Formulation P1 is replaced with the coating solution for the surface treatment layer of Formulation PC1 used for forming the spacer in Example 1, and R, G, and B inks are changed. Evaluation was performed in the same manner as in Example 1 except that the R ink, the G ink, and the B ink in Example 18 were used.
  • a partition wall was formed in the same manner as in Comparative Example 1, and the formed partition wall was subjected to a hydrophilic plasma treatment by the following method, and then the upper surface of the partition wall was subjected to an ink-repellent plasma treatment. Evaluation was performed in the same manner.
  • Plasma processing was performed under the following conditions using a plasma processing apparatus (apparatus described in FIG. 12 of JP-A-2003-344640).
  • plasma processing was further performed under the following conditions: o
  • the photosensitive transfer material K1 of Example 1 was replaced with the following transfer film consisting of a first layer and a second layer. Further, except that the exposure and development methods were changed as described below, a black matrix was formed, a color filter and the like were produced and evaluated in the same manner as in Example 1.
  • the first layer had a thickness of 0.5 / ⁇ ⁇
  • the second layer had a thickness of 1.5 m.
  • a first layer and a second layer having the following composition were provided to form a transfer film.
  • the applicability of the photosensitive resin composition was poor, and neither the protrusion of ink nor the occurrence of color mixing during ink ejection could be suppressed. Therefore, the display characteristics of the manufactured liquid crystal display device were inferior!

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  • Chemical & Material Sciences (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Polymers & Plastics (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Organic Chemistry (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Optics & Photonics (AREA)
  • Engineering & Computer Science (AREA)
  • Architecture (AREA)
  • Structural Engineering (AREA)
  • Materials For Photolithography (AREA)
  • Optical Filters (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Macromonomer-Based Addition Polymer (AREA)

Abstract

L'invention concerne une composition de résine photosensible contenant au moins une résine, représentée par la formule structurale suivante (1), dans laquelle [R1-R5 représente H ou un groupe alkyle comportant au total de 1 à 5 atomes de carbone; L1-L3 représente un groupe de liaison divalent; X1 représente un groupe ester, un groupe amide ou un groupe arylène; X2 représente un groupe éther, un groupe ester, un groupe amide, un groupe arylène ou un résidu hétérocyclique; Rf représente un substituant contenant du fluor; n=2-20, a=0-40, b=1-40, c=20-98 (rapport molaire)].
PCT/JP2007/056735 2006-03-28 2007-03-28 Composition de résine photosensible, matière de transfert photosensible, paroi de séparation et procédé de formation de celle-ci, dispositif optique et procédé de fabrication de celui-ci et affichage Ceased WO2007111356A1 (fr)

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CN200780010889XA CN101410758B (zh) 2006-03-28 2007-03-28 感光性树脂组合物、感光性转印材料、间壁墙及其形成方法、光学元件及其制造方法以及显示装置
JP2008507522A JP5159608B2 (ja) 2006-03-28 2007-03-28 感光性樹脂組成物、感光性転写材料、隔壁及びその形成方法、光学素子及びその製造方法、並びに表示装置

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JP2008287251A (ja) * 2007-04-18 2008-11-27 Daikin Ind Ltd 撥液レジスト組成物
JP2009139568A (ja) * 2007-12-05 2009-06-25 Tokyo Electron Ltd 塗布装置
JP2009280801A (ja) * 2008-04-25 2009-12-03 Hitachi Chem Co Ltd 樹脂組成物及びその硬化物を用いた光学部材
JP5590046B2 (ja) * 2009-12-28 2014-09-17 旭硝子株式会社 感光性組成物、隔壁、カラーフィルタおよび有機ｅｌ素子
WO2019163505A1 (fr) * 2018-02-21 2019-08-29 富士フイルム株式会社 Composition durcissable, objet durci, filtre de couleur, procédé de production d'un filtre de couleur, élément d'imagerie à semi-conducteurs et dispositif d'affichage d'image

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KR102567855B1 (ko) * 2017-05-31 2023-08-16 니폰 제온 가부시키가이샤 터치 센서 기재 및 그 제조 방법, 터치 센서 부재 및 그 제조 방법, 그리고, 표시 장치
KR20230168224A (ko) * 2022-06-03 2023-12-13 주식회사 동진쎄미켐 표시 소자 및 이를 위한 감광성 수지 조성물

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KR20080003389A (ko) * 2005-05-02 2008-01-07 후지필름 가부시키가이샤 그래프트 패턴 형성 방법, 그것에 의해 얻어진 그래프트패턴 재료 및 그것을 이용한 리소그래피 방법

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JPS62227140A (ja) * 1986-03-28 1987-10-06 Fuji Photo Film Co Ltd 画像形成材料
JP2002025432A (ja) * 2000-07-04 2002-01-25 Hitachi Chem Co Ltd 誘電体層及び障壁形成用樹脂組成物エレメント及びこれを用いたプラズマディスプレイパネル用基板の製造法
JP2002207114A (ja) * 2001-01-10 2002-07-26 Canon Inc 光学素子とその製造方法、該光学素子を用いた液晶素子
WO2003050620A1 (fr) * 2001-12-13 2003-06-19 Fuji Photo Film Co., Ltd. Materiau de formation d'image

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2008287251A (ja) * 2007-04-18 2008-11-27 Daikin Ind Ltd 撥液レジスト組成物
JP2009139568A (ja) * 2007-12-05 2009-06-25 Tokyo Electron Ltd 塗布装置
JP2009280801A (ja) * 2008-04-25 2009-12-03 Hitachi Chem Co Ltd 樹脂組成物及びその硬化物を用いた光学部材
JP5590046B2 (ja) * 2009-12-28 2014-09-17 旭硝子株式会社 感光性組成物、隔壁、カラーフィルタおよび有機ｅｌ素子
WO2019163505A1 (fr) * 2018-02-21 2019-08-29 富士フイルム株式会社 Composition durcissable, objet durci, filtre de couleur, procédé de production d'un filtre de couleur, élément d'imagerie à semi-conducteurs et dispositif d'affichage d'image
JPWO2019163505A1 (ja) * 2018-02-21 2020-12-03 富士フイルム株式会社 硬化性組成物、硬化物、カラーフィルタ、カラーフィルタの製造方法、固体撮像素子及び画像表示装置
US11718695B2 (en) 2018-02-21 2023-08-08 Fujifilm Corporation Curable composition, cured product, color filter, method for producing color filter, solid imaging element, and image display device

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CN101410758A (zh) 2009-04-15
CN101410758B (zh) 2012-06-13
KR20080105046A (ko) 2008-12-03

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