WO2020022670A1 - Résine liante, composition de résine photosensible, résine photosensible, filtre coloré et dispositif d'affichage - Google Patents

Résine liante, composition de résine photosensible, résine photosensible, filtre coloré et dispositif d'affichage Download PDF

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Publication number
WO2020022670A1
WO2020022670A1 PCT/KR2019/008469 KR2019008469W WO2020022670A1 WO 2020022670 A1 WO2020022670 A1 WO 2020022670A1 KR 2019008469 W KR2019008469 W KR 2019008469W WO 2020022670 A1 WO2020022670 A1 WO 2020022670A1
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Prior art keywords
group
formula
binder resin
present specification
mol
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PCT/KR2019/008469
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English (en)
Korean (ko)
Inventor
김한수
이다미
김혜진
양승진
Original Assignee
주식회사 엘지화학
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Priority to JP2020511188A priority Critical patent/JP6996050B2/ja
Priority to CN201980003990.5A priority patent/CN111032713B/zh
Publication of WO2020022670A1 publication Critical patent/WO2020022670A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F212/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
    • C08F212/02—Monomers containing only one unsaturated aliphatic radical
    • C08F212/04—Monomers containing only one unsaturated aliphatic radical containing one ring
    • C08F212/06—Hydrocarbons
    • C08F212/08—Styrene
    • 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
    • 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
    • C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
    • C08F220/30—Esters containing oxygen in addition to the carboxy oxygen containing aromatic rings in the alcohol moiety
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • G—PHYSICS
    • G02—OPTICS
    • G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
    • G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour 
    • G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on liquid crystals, e.g. single liquid crystal display cells
    • G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
    • G02F1/1333—Constructional arrangements; Manufacturing methods
    • G02F1/1335—Structural association of cells with optical devices, e.g. polarisers or reflectors
    • G—PHYSICS
    • G02—OPTICS
    • G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
    • G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour 
    • G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on liquid crystals, e.g. single liquid crystal display cells
    • G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
    • G02F1/1333—Constructional arrangements; Manufacturing methods
    • G02F1/1335—Structural association of cells with optical devices, e.g. polarisers or reflectors
    • G02F1/133509—Filters, e.g. light shielding masks
    • G02F1/133514—Colour 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
    • 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
    • G03F7/0005—Production of optical devices or components in so far as characterised by the lithographic processes or materials used therefor
    • G03F7/0007—Filters, e.g. additive colour filters; Components for display devices
    • 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

Definitions

  • the present specification relates to a binder resin, a photosensitive resin composition, a photosensitive material, a color filter, and a display device.
  • the dye has a higher solubility than the pigment, so that a dispersant, a dispersing aid, etc. may not be used, and a high molar absorptivity coefficient allows a desired color to be obtained with a small amount, which is advantageous in increasing luminance.
  • dyes are often washed off due to good solubility compared to pigments when developed with an alkaline developer after exposure to form a pattern, and decomposed and sublimed and patterned due to poor heat resistance during the post-heating process (generally 230 °C to 250 °C). There is a disadvantage that causes discoloration of pixels.
  • Chemical resistance also tends to be inferior to pigments.
  • Chemical resistance of the pigment type composition can generally be improved by introducing an unsaturated ethylenic reactor (crosslinking site) in the binder resin.However, in the case of the dye type composition, the alcohol group generated during the introduction of the reactor can cause the dye to disappear. Doubled.
  • the present specification provides a binder resin, a photosensitive resin composition, a photosensitive material, a color filter, and a display device.
  • An exemplary embodiment of the present specification has a structure represented by the formula (1); A structure represented by Formula 2 below; And it provides a binder resin comprising a structure represented by the formula (3).
  • R1 to R5 are the same as or different from each other, and each independently hydrogen; Or a substituted or unsubstituted alkyl group,
  • r3 is an integer of 0 to 4, when r3 is 2 or more, R3 is the same as or different from each other,
  • r4 is an integer of 0 to 5, and if r4 is 2 or more, R4 is the same or different,
  • L1 to L4 are the same as or different from each other, and each independently a substituted or unsubstituted alkylene group,
  • A is a thermosetting group.
  • One embodiment of the present specification is the binder resin; Dye compounds; Polyfunctional monomers; Photoinitiators; And it provides a photosensitive resin composition comprising a solvent.
  • An exemplary embodiment of the present specification provides a photosensitive material manufactured using the photosensitive resin composition.
  • An exemplary embodiment of the present specification provides a color filter including the photosensitive material.
  • An exemplary embodiment of the present specification provides a display device including the color filter.
  • binder resin of the present specification it is possible to improve the processability and reliability of the photosensitive resin composition by supplementing the heat resistance problem occurring during the post-heating process and also improving chemical resistance.
  • the cross-linked matrix is formed by the photocuring reaction during exposure in the color filter manufacturing process to prevent the elution of the exposure part dye during the development process, and then the cross-linked matrix is formed once more by the thermosetting reaction during the post-heating process.
  • the heat resistance and chemical resistance of the photosensitive resin composition can be improved.
  • a part "includes" a certain component this means that the component may further include other components, except for the case where there is no description to the contrary.
  • the structure represented by following formula (1); A structure represented by Formula 2 below; And a binder resin including a structure represented by the following Chemical Formula 3 may further include a structure represented by the following Chemical Formula 4.
  • the structure represented by the formula (1) A structure represented by Formula 2 below; And it provides a binder resin comprising a structure represented by the formula (3).
  • the binder resin according to an exemplary embodiment of the present specification has a structure represented by the formula (1) capable of thermosetting; A structure represented by the following Chemical Formula 2 capable of photocuring; And a structure represented by the following Chemical Formula 3 for imparting developability to an alkaline developer.
  • a crosslinked matrix is formed by a photocuring reaction during exposure in a color filter manufacturing process to prevent elution of the exposure part dye during a developing process, and then a crosslinked matrix is formed once again by a thermosetting reaction during a post-heating process. It is possible to improve the heat resistance and chemical resistance of the photosensitive resin composition according to one embodiment of the present specification.
  • the binder resin of the present invention is represented by the following general formula (2):
  • the introduction of a photocurable group does not generate an alcohol group, thereby improving the dye dissolution problem in the developing process.
  • photocuring is possible spontaneously without the addition of a separate photoinitiator for photocuring of unsaturated double bond groups.
  • the binder resin of the present invention is composed of a copolymer of three kinds of unsaturated double bond monomers according to the role of each of the thermosetting group, the photocuring group, and the alkali-soluble group.
  • the thermosetting group may be a direct bond or a binder resin, including a carboxylic acid group or a binder resin included in a dye or a dye polymer and a monomer having a hardenable group (for example, epoxy, aziridine, oxazoline, etc.). This improves the heat resistance and chemical resistance of the dye.
  • the photocuring group includes a monomer containing a benzophenone group to form a matrix that can more firmly hold dyes by exposure between binder resins or bonding between binder resins and unsaturated double-bonding crosslinking agents to improve heat resistance and chemical resistance. .
  • An alkali soluble group (for example, methacrylic acid, acrylic acid, etc.) is introduced to impart developability of the composition to the alkaline developer.
  • substituted or unsubstituted is deuterium; Halogen group; Nitrile group; Nitro group; -OH; -COOH; Alkyl groups; Cycloalkyl group; Alkenyl groups; Cycloalkenyl group; Aryl group; Heteroaryl group; Acryloyl group; Acrylate group; And one or more substituents selected from the group comprising a heterocyclic group including one or more of N, O, S or P atoms, or means having no substituent.
  • examples of the halogen group include fluorine, chlorine, bromine or iodine.
  • the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but the carbon number of the alkyl group may be 1 to 30. According to another exemplary embodiment, the alkyl group has 1 to 20 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 10 carbon atoms.
  • alkyl group examples include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, tert-butyl group, n-pentyl group, n-hexyl group, n-heptyl group and n-jade Although there exist a tilt group, it is not limited to these.
  • the cycloalkyl group is not particularly limited, but preferably has 3 to 30 carbon atoms, and particularly preferably a cyclopentyl group and a cyclohexyl group, but is not limited thereto.
  • the alkylene group means that there are two bonding positions in the alkanes.
  • the alkylene group may be straight, branched or cyclic.
  • carbon number of an alkylene group is not specifically limited, For example, it may be C1-C30. It may also be 1 to 20 carbon atoms, it may be 1 to 10 carbon atoms.
  • the cycloalkyl group is not particularly limited, but according to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group and the like, but is not limited thereto.
  • the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to an exemplary embodiment, the aryl group has 6 to 30 carbon atoms. According to an exemplary embodiment, the aryl group has 6 to 20 carbon atoms.
  • the aryl group may be a phenyl group, a biphenyl group, a terphenyl group, etc. as the monocyclic aryl group, but is not limited thereto.
  • the polycyclic aryl group may be naphthyl group, anthracenyl group, indenyl group, phenanthrenyl group, pyrenyl group, perrylenyl group, triphenyl group, chrysenyl group, fluorenyl group and the like, but is not limited thereto.
  • the heterocyclic group is a heterocyclic group containing O, N or S as a hetero atom, and the carbon number is not particularly limited, but is 2 to 30 carbon atoms, specifically 2 to 20 carbon atoms.
  • the heterocyclic group are thiophene group, furan group, pyrrole group, imidazole group, thiazole group, oxazole group, oxadiazole group, triazole group, pyridyl group, bipyridyl group, triazine group, acridil group, pyridazine group , Quinolinyl group, isoquinoline group, indole group, carbazole group, benzoxazole group, benzoimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuranyl group, dibenzofuran And the like, but are not limited thereto.
  • heterocyclic group may be applied except that the heteroaryl group is aromatic.
  • the alkoxy group may be linear or branched, and the number of carbon atoms is not particularly limited, but may be 1 to 30, specifically 1 to 20, and more specifically 1 to 10.
  • (meth) acrylic acid represents at least 1 sort (s) chosen from the group which consists of acrylic acid and methacrylic acid.
  • the description of "(meth) acrylic acid” also has the same meaning.
  • An exemplary embodiment of the present specification has a structure represented by the formula (1); A structure represented by Formula 2 below; And it provides a binder resin comprising a structure represented by the formula (3).
  • R1 to R5 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group,
  • r3 is an integer of 0 to 4, when r3 is 2 or more, R3 is the same as or different from each other,
  • r4 is an integer of 0 to 5, and if r4 is 2 or more, R4 is the same or different,
  • L1 to L4 are the same as or different from each other, and each independently a substituted or unsubstituted alkylene group,
  • A is a thermosetting group.
  • the photocurable group including the structure represented by Formula 2 of the present specification contributes to the improvement of heat resistance by giving a photoinitiator effect to the binder resin during the exposure process to cause a crosslinking reaction.
  • R3 or R4 when R3 or R4 is a hydroxyl group (-OH), like the photocurable group of the present specification does not function as a photocuring, as a ultraviolet absorber. That is, in the structure represented by the formula (2), when R3 or R4 is a hydroxyl group (-OH) is used for the purpose of absorbing the ultraviolet rays reflected back when the color filter is formed, to improve the pattern defects.
  • R 3 or R 4 is a hydroxy group (-OH) may correspond to Comparative Example 2 to be described later.
  • R3 or R4 is a hydroxy group (-OH)
  • R3 or R4 is a hydroxy group (-OH)
  • the hydroxy group serves only as a ultraviolet absorber, which may lower the exposure sensitivity.
  • thermosetting group is a binder resin having any of the following structures.
  • R11 to R18 are the same as or different from each other, and each independently hydrogen; Or a substituted or unsubstituted alkyl group.
  • R1 to R5 are the same as or different from each other, and each independently hydrogen; Or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.
  • R1 to R5 are the same as or different from each other, and each independently hydrogen; Or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.
  • R1 to R5 are the same as or different from each other, and each independently hydrogen; Or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.
  • R1 to R5 are the same as or different from each other, and each independently hydrogen; Or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.
  • R1 to R5 are the same as or different from each other, and each independently hydrogen; Or a substituted or unsubstituted methyl group.
  • L1 to L4 are the same as or different from each other, and each independently a substituted or unsubstituted alkylene group having 1 to 30 carbon atoms.
  • L1 to L4 are the same as or different from each other, and each independently a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms.
  • L1 to L4 are the same as or different from each other, and each independently a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms.
  • L1 to L4 are the same as or different from each other, and are each independently a substituted or unsubstituted methylene group.
  • L1 to L4 are methylene groups.
  • R11 to R18 are the same as or different from each other, and each independently hydrogen; Or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.
  • R11 to R18 are the same as or different from each other, and each independently hydrogen; Or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.
  • R11 to R18 are the same as or different from each other, and each independently hydrogen; Or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.
  • R11 to R18 are hydrogen.
  • Formula 1 may be represented by the following Formula 1-1, but is not limited thereto.
  • Chemical Formula 2 may be represented by the following Chemical Formula 2-1.
  • R2 to R4, L3, r3, and r4 are as defined in Chemical Formula 2.
  • Chemical Formula 2 may be represented by the following Chemical Formula 2-2, but is not limited thereto.
  • Chemical Formula 3 may be represented by the following Chemical Formula 3-1, but is not limited thereto.
  • the binder resin further includes at least one of structures represented by the following Chemical Formula 4 or 5.
  • L5 and L6 are the same as or different from each other, and each independently a substituted or unsubstituted alkylene group,
  • R41, R42, R51 and R52 are the same as or different from each other, and each independently hydrogen; Or a substituted or unsubstituted alkyl group,
  • r42 is an integer of 0 to 5, when r42 is 2 or more, R42 is the same as or different from each other,
  • r52 is an integer of 0-11, and when r52 is two or more, R52 is same or different from each other.
  • L5 and L6 are the same as or different from each other, and each independently a substituted or unsubstituted alkylene group having 1 to 30 carbon atoms.
  • L5 and L6 are the same as or different from each other, and each independently a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms.
  • L5 and L6 are the same as or different from each other, and each independently a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms.
  • L5 and L6 are the same as or different from each other, and are each independently a substituted or unsubstituted methylene group.
  • L5 is a methylene group.
  • L6 is a methylene group.
  • R41, R42, R51 and R52 are the same as or different from each other, and each independently hydrogen; Or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, r42 is an integer of 0 to 5, when r42 is 2 or more, R42 is the same as or different from each other, r52 is an integer of 0 to 11, and r52 is 2 or more R52 is the same as or different from each other.
  • R41, R42, R51 and R52 are the same as or different from each other, and each independently hydrogen; Or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, r42 is an integer of 0 to 5, when r42 is 2 or more, R42 is the same as or different from each other, r52 is an integer of 0 to 11, and r52 is 2 or more R52 is the same as or different from each other.
  • R41, R42, R51 and R52 are the same as or different from each other, and each independently hydrogen; Or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, r42 is an integer of 0 to 5, and when r42 is 2 or more, R42 is the same as or different from each other, r52 is an integer of 0 to 11, and r52 is 2 or more R52 is the same as or different from each other.
  • R41, R42 and R52 are hydrogen.
  • R51 is a substituted or unsubstituted methyl group.
  • R51 is a methyl group.
  • Chemical Formula 4 may be represented by the following Chemical Formula 4-1.
  • Chemical Formula 5 may be represented by the following Chemical Formula 5-1.
  • the structure represented by Formula 1 10 mol% to 90 mol%; 1 mol% to 20 mol% of a structure represented by Formula 2; And it provides a binder resin comprising 5 mol% to 40 mol% of the structure represented by the formula (3).
  • 100 mol% which is a standard of mol% of each structure, means to include all monomers included in the binder resin.
  • the structure represented by Formula 1 10 mol% to 80 mol%; 1 mol% to 20 mol% of a structure represented by Formula 2; 5 mol% to 40 mol% of a structure represented by Formula 3; And it provides a binder resin comprising 10 mol% to 50 mol% of the structure represented by the formula (4).
  • the structure represented by Formula 1 10 mol% to 80 mol%; 1 mol% to 20 mol% of a structure represented by Formula 2; 5 mol% to 40 mol% of a structure represented by Formula 3; And it provides a binder resin comprising 10 mol% to 50 mol% of the structure represented by the formula (5).
  • thermosetting, photo-curable and alkali-soluble of the binder resin according to one embodiment of the present specification may be excellent.
  • the weight average molecular weight of the binder resin is 3,000 g / mol to 50,000 g / mol. Preferably 5,000 g / mol to 20,000 g / mol.
  • the said weight average molecular weight is one of the average molecular weights whose molecular weight is not uniform and the molecular weight of a certain polymeric material is used as a reference, and is a value obtained by averaging the molecular weight of the component molecular species of the polymeric compound with molecular weight distribution in a weight fraction.
  • the weight average molecular weight can be measured through Gel Permeation Chromatography (GPC) analysis.
  • the acid value of the binder resin is 20 KOH mg / g to 200 KOH mg / g.
  • the developability can be prevented from being lowered, and overdevelopment can prevent the pattern from falling off.
  • the acid value of the binder resin can be measured by titration with 0.1 N potassium hydroxide (KOH) methanol solution.
  • One embodiment of the present specification is the binder resin; Dye compounds; Polyfunctional monomers; Photoinitiators; And it provides a photosensitive resin composition comprising a solvent.
  • the photosensitive resin composition may further include at least one kind of pigment compound in addition to the dye compound.
  • the photosensitive resin composition may include only the dye compound, but may include the dye compound and one or more pigment compounds.
  • the dye compound and the pigment compound may be a metal-complex based compound; Azo-based compounds; Metal azo-based compounds; Quinophthalone family compounds; Isoindoine family compounds; Methine family compounds; Phthalocyanine series compounds; Metal phthalocyanine-based compounds; Porphyrin family compounds; Metal porphyrin-based compounds; Tetra aza porphyrin-based compounds; Metal tetra aza porphyrin-based compounds; Cyanine-based compounds; Xanthene series compounds; Metal dipyrromethane-based compounds; Boron dipyrromethane-based compounds; Metal dipyrromethane-based compounds; Anthraquinone family compounds; Diketopyrrolopyrrole compounds; Triarylmethane-based compounds; And it may be selected from the group consisting of perylene-based compounds.
  • the dye compound may be a triarylmethane-based blue dye.
  • the polyfunctional monomer is a monomer that forms a photoresist image by light, specifically, propylene glycol methacrylate, dipentaerythritol hexaacrylate, dipentaerythritol acrylate, neopentyl glycol di Acrylate, 6-hexanediol diacrylate, 1,6-hexanediol acrylate tetraethyleneglycol methacrylate, bisphenoxy ethylalcohol diacrylate, trishydroxyethylisocyanurate trimethacrylate, trimethyl 1 selected from the group consisting of propane trimethacrylate, diphenylpentaerythritol hexaacrylate, pentaerythritol trimethacrylate, pentaerythritol tetramethacrylate and dipentaerythritol hexamethacrylate Species or a mixture of two or more thereof.
  • the photoinitiator is not particularly limited as long as it is an initiator that generates radicals by light to trigger crosslinking, but is selected from the group consisting of, for example, acetophenone compounds, biimidazole compounds, triazine compounds, and oxime compounds. It may be one or more kinds.
  • the acetophenone-based compound is 2-hydroxy-2-methyl-1-phenylpropan-1-one, 1- (4-isopropylphenyl) -2-hydroxy-2-methylpropan-1-one, 4- (2-hydroxyethoxy) -phenyl- (2-hydroxy-2-propyl) ketone, 1-hydroxycyclohexylphenylketone, benzoin methyl ether, benzoin ethyl ether, benzoin isobutyl ether, benzoin Butyl ether, 2,2-dimethoxy-2-phenylacetophenone, 2-methyl- (4-methylthio) phenyl-2-morpholino-1-propan-1-one, 2-benzyl-2-dimethylamino -1- (4-morpholinophenyl) -butan-1-one, 2- (4-bromo-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butan-1-one or 2-methyl-1- [4- (methylthio)
  • biimidazole-based compound 2,2-bis (2-chlorophenyl) -4,4 ', 5,5'-tetraphenyl biimidazole, 2,2'-bis (o-chlorophenyl) -4 , 4 ', 5,5'-tetrakis (3,4,5-trimethoxyphenyl) -1,2'-biimidazole, 2,2'-bis (2,3-dichlorophenyl) -4, 4 ', 5,5'-tetraphenyl biimidazole, 2,2'-bis (o-chlorophenyl) -4,4,5,5'-tetraphenyl-1,2'-biimidazole, It is not limited to this.
  • the triazine compound is 3- ⁇ 4- [2,4-bis (trichloromethyl) -s-triazin-6-yl] phenylthio ⁇ propionic acid, 1,1,1,3,3,3- Hexafluoroisopropyl-3- ⁇ 4- [2,4-bis (trichloromethyl) -s-triazin-6-yl] phenylthio ⁇ propionate, ethyl-2- ⁇ 4- [2,4 -Bis (trichloromethyl) -s-triazin-6-yl] phenylthio ⁇ acetate, 2-epoxyethyl-2- ⁇ 4- [2,4-bis (trichloromethyl) -s-triazine-6 -Yl] phenylthio ⁇ acetate, cyclohexyl-2- ⁇ 4- [2,4-bis (trichloromethyl) -s-triazin-6-yl] phenylthio ⁇ acetate,
  • the oxime compound is 1,2-octadione-1- (4-phenylthio) phenyl-2- (o-benzoyloxime) (Shibagai Co., Shijiai 124), ethanone-1- (9-ethyl) -6- (2-methylbenzoyl-3-yl) -1- (O-acetyloxime) (CGII242), N-1919 (Adecasa), and the like, but are not limited thereto.
  • the solvent is acetone, methyl ethyl ketone, methyl isobutyl ketone, methyl cellosolve, ethyl cellosolve, tetrahydrofuran, 1,4-dioxane, ethylene glycol dimethyl ether, ethylene glycol diethyl ether, propylene glycol dimethyl ether , Propylene glycol diethyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol methyl ethyl ether, chloroform, methylene chloride, 1,2-dichloroethane, 1,1,1-trichloroethane, 1 , 1,2-trichloroethane, 1,1,2-trichloroethene, hexane, heptane, octane, cyclohexane, benzene, toluene, xylene, methanol, ethanol, isopropano
  • the content of the binder resin is 3% by weight to 10% by weight
  • the content of the dye compound is 1% by weight to 5% by weight
  • the polyfunctional monomer is 3 wt% to 10 wt%
  • the photoinitiator is 0.1 wt% to 10 wt%
  • the solvent is 65 wt% to 90 wt%.
  • the content of the dye compound is 4% by weight to 20% by weight
  • the content of the binder resin is 20% by weight to 50% by weight
  • the content of the multifunctional monomer is 20% to 50% by weight
  • the content of the photoinitiator is 1% to 5% by weight.
  • the content of the dye compound is within the above range, it is possible to prevent the coloring power from being lowered, and the lack of transparent materials constituting the matrix may prevent the pattern dropout phenomenon.
  • the content of the binder resin is within the above range, it is possible to prevent a phenomenon in which developability is insufficient, and to prevent the viscosity of the photosensitive resin composition from becoming too high.
  • the degree of crosslinking may be reduced to prevent a pattern dropout phenomenon, and the degree of crosslinking may be too high to prevent a pattern residue from being left during development on a non-exposed part.
  • the content of the photoinitiator is within the above range, it is possible to prevent the exposure sensitivity from being lowered and cause a pattern dropout phenomenon, and as a result of excessive surface hardening during exposure, the pattern shape is trapezoidal (a trapezoidal pattern is generally). Can be prevented.
  • the total weight of the solid content means the sum of the total weight of the components excluding the solvent in the resin composition.
  • the weight percentages based on solids and solids of each component can be measured by common analytical means used in the art, such as liquid chromatography or gas chromatography.
  • the photosensitive resin composition may further include an antioxidant.
  • the content of the antioxidant is 0.1% to 20% by weight based on the total weight of solids in the photosensitive resin composition.
  • the photosensitive resin composition may include one or two or more additives selected from the group consisting of photocrosslinking sensitizers, curing accelerators, adhesion promoters, surfactants, thermal polymerization inhibitors, ultraviolet absorbers, dispersants, and leveling agents. Additionally included.
  • the content of the additive is 0.1% by weight to 20% by weight based on the total weight of solids in the photosensitive resin composition.
  • the photocrosslinking sensitizer is benzophenone, 4,4-bis (dimethylamino) benzophenone, 4,4-bis (diethylamino) benzophenone, 2,4,6-trimethylaminobenzophenone, methyl-o-benzoyl Benzophenone compounds such as benzoate, 3,3-dimethyl-4-methoxybenzophenone and 3,3,4,4-tetra (t-butylperoxycarbonyl) benzophenone; Fluorenone compounds such as 9-florenone, 2-chloro-9-prorenone, and 2-methyl-9-florenone; Thioxanthones such as thioxanthone, 2,4-diethyl thioxanthone, 2-chloro thioxanthone, 1-chloro-4-propyloxy thioxanthone, isopropyl thioxanthone and diisopropyl thioxanthone compound; Xanthone compounds such as
  • the curing accelerator is used to increase the curing and mechanical strength, specifically 2-mercaptobenzoimidazole, 2-mercaptobenzothiazole, 2-mercaptobenzoxazole, 2,5-dimercapto-1,3 , 4-thiadiazole, 2-mercapto-4,6-dimethylaminopyridine, pentaerythritol-tetrakis (3-mercaptopropionate), pentaerythritol-tris (3-mercaptopropio Nate), pentaerythritol-tetrakis (2-mercaptoacetate), pentaerythritol-tris (2-mercaptoacetate), trimethylolpropane-tris (2-mercaptoacetate), and trimethylolpropane- One or more types selected from the group consisting of tris (3-mercaptopropionate) can be used.
  • methacryloyl silane coupling agents such as these, can be selected and used, and at least 1 type can be selected from an octyl trimethoxy silane, a dodecyl trimethoxy silane, an octadecyl trimethoxy silane, etc. as an alkyl trimethoxy silane. You can choose to use it.
  • the surfactant is a silicone-based surfactant or a fluorine-based surfactant, specifically, the silicone-based surfactant is BYK-Chemie's BYK-077, BYK-085, BYK-300, BYK-301, BYK-302, BYK-306, BYK-307 , BYK-310, BYK-320, BYK-322, BYK-323, BYK-325, BYK-330, BYK-331, BYK-333, BYK-335, BYK-341v344, BYK-345v346, BYK-348, BYK -354, BYK-355, BYK-356, BYK-358, BYK-361, BYK-370, BYK-371, BYK-375, BYK-380, BYK-390, and the like.
  • F-114, F-177, F-410, F-411, F-450, F-493, F-494, F-443, F-444, F-445, F-446 , F-470, F-471, F-472SF, F-474, F-475, F-477, F-478, F-479, F-480SF, F-482, F-483, F-484, F -486, F-487, F-172D, MCF-350SF, TF-1025SF, TF-1117SF, TF-1026SF, TF-1128, TF-1127, TF-1129, TF-1126, TF-1130, TF-1116SF , TF-1131, TF1132, TF1027SF, TF-1441, TF-1442, etc. may be used, but is not limited thereto.
  • the antioxidant may be one or more selected from the group consisting of hindered phenol antioxidants, amine antioxidants, thio antioxidants, and phosphine antioxidants, but is not limited thereto.
  • antioxidants include phosphoric acid thermal stabilizers such as phosphoric acid, trimethyl phosphate or triethyl phosphate; 2,6-di-t-butyl-p-cresol, octadecyl-3- (4-hydroxy-3,5-di-t-butylphenyl) propionate, tetrabis [methylene-3- (3, 5-di-t-butyl-4-hydroxyphenyl) propionate] methane, 1,3,5-trimethyl-2,4,6-tris (3,5-di-t-butyl-4-hydroxy Benzyl) benzene, 3,5-di-t-butyl-4-hydroxybenzylphosphite diethyl ester, 2,2-thiobis (4-methyl-6-t-butylphenol), 2,6-g, t-butylphenol 4,4'-butylidene-bis (3-methyl-6-t-butylphenol), 4,4'-thiobis (3-methyl-6-t-t-
  • UV absorber 2- (3-t-butyl-5-methyl-2-hydroxyphenyl) -5-chloro-benzotriazole, alkoxy benzophenone, and the like may be used, but are not limited thereto. All commonly used ones can be used.
  • thermal polymerization inhibitor examples include p-anisole, hydroquinone, pyrocatechol, t-butyl catechol, N-nitrosophenylhydroxyamine ammonium salt and N-nitrosophenylhydroxy Amine aluminum salt, p-methoxyphenol, di-t-butyl-p-cresol, pyroggarol, benzoquinone, 4,4-thiobis (3-methyl-6-t-butylphenol), 2,2- It may include one or more selected from the group consisting of methylenebis (4-methyl-6-t-butylphenol), 2-mercaptoimidazole and phenothiazine, but is not limited thereto. It may include those generally known in the art.
  • the dispersant may be used as a method of internally adding to the pigment in the form of surface treatment of the pigment in advance, or a method of externally adding to the pigment.
  • a compound type, nonionic, anionic or cationic dispersant may be used, and examples thereof include fluorine, ester, cationic, anionic, nonionic and amphoteric surfactants. These can be used individually or in combination of 2 or more types.
  • the dispersant may be polyalkylene glycol and esters thereof, polyoxyalkylene polyhydric alcohols, ester alkylene oxide adducts, alcohol alkylene oxide adducts, sulfonic acid esters, sulfonate salts, carboxylic acid esters, carboxylate salts, At least one selected from the group consisting of alkylamide alkylene oxide adducts and alkylamines is not limited thereto.
  • the leveling agent may be polymeric or nonpolymeric.
  • polymeric leveling agents include polyethyleneimine, polyamideamine, reaction products of amines and epoxides
  • nonpolymeric leveling agents include non-polymeric sulfur-containing and non-polymeric nitrogen-containing. Including but not limited to compounds, all those commonly used in the art may be used.
  • An exemplary embodiment of the present specification provides a photosensitive material manufactured using the photosensitive resin composition.
  • the photosensitive resin composition of the present specification is applied and cured on a substrate by an appropriate method to form a photosensitive material in the form of a thin film or a pattern.
  • a spray method, a roll coating method, a spin coating method, etc. can be used, Generally, a spin coating method is used widely.
  • some residual solvent can be removed in some cases under reduced pressure.
  • a light source for curing the photosensitive resin composition according to the present specification for example, mercury vapor arc (arc), carbon arc, Xe arc, etc., which emit light having a wavelength of 250 nm to 450 nm, but is not limited thereto. .
  • the photosensitive resin composition according to the present disclosure is a pigment dispersion type photosensitive material for manufacturing a thin film transistor liquid crystal display device (TFT LCD) color filter, a thin film transistor liquid crystal display device (TFT LCD) or a photosensitive material for forming a black matrix of an organic light emitting diode.
  • TFT LCD thin film transistor liquid crystal display device
  • TFT LCD thin film transistor liquid crystal display device
  • photosensitive material for forming a black matrix of an organic light emitting diode.
  • PDP plasma display panel
  • a color filter including the photosensitive material is provided.
  • the color filter may include a thermosetting group including a structure represented by Chemical Formula 1; A photocurable group including the structure represented by Formula 2; And it can be prepared using a photosensitive resin composition comprising a binder resin comprising a structure represented by the formula (3).
  • the color filter may be formed by applying the photosensitive resin composition on a substrate to form a coating film and exposing, developing and curing the coating film.
  • the photosensitive resin composition according to the exemplary embodiment of the present specification is excellent in heat resistance and chemical resistance, and does not have a problem in developability, thereby providing a color filter having high color reproducibility and high luminance and contrast ratio by a curing process at the time of manufacturing the color filter. Can be.
  • the substrate may be a glass plate, a silicon wafer, a plate of a plastic substrate such as polyethersulfone (PES), polycarbonate (PC), or the like, and the type thereof is not particularly limited.
  • a plastic substrate such as polyethersulfone (PES), polycarbonate (PC), or the like, and the type thereof is not particularly limited.
  • the color filter may include a red pattern, a green pattern, a blue pattern, and a black matrix.
  • the color filter may further include an overcoat layer.
  • a black pattern of a lattice called a black matrix may be disposed between color pixels of the color filter in order to improve contrast.
  • Chromium can be used as the material of the black matrix.
  • a method of depositing chromium over the entire glass substrate and forming a pattern by etching may be used.
  • a resin black matrix by pigment dispersion method capable of fine processing can be used.
  • the black matrix according to one embodiment of the present specification may use black pigment or black dye as a colorant.
  • black pigment or black dye may be used alone, or carbon black and coloring pigments may be used.
  • coloring pigments lacking light shielding properties are mixed, even if the amount of colorant is relatively increased, the strength of the film or the adhesion to the substrate are reduced. There is no advantage.
  • a display device including a color filter according to the present specification.
  • the display device may be a plasma display panel (PDP), a light emitting diode (LED), an organic light emitting diode (OLED), a liquid crystal display (LCD), a thin film transistor.
  • the liquid crystal display device may be any one of a liquid crystal display (LCD-TFT) and a cathode ray tube (CRT).
  • Methacrylic acid is added to 11, 31, 45, 13% by weight based on the total weight of the binder resin solids, and then mixed with a solvent (propylene glycol monomethyl ether acetate, Cas No. 108-65-6) nitrogen It heated up at 60 degreeC in atmosphere.
  • a solvent propylene glycol monomethyl ether acetate, Cas No. 108-65-6
  • thermal polymerization initiator v-65 (2,2'-Azobis (2,4-dimethylvaleronitrile) was added to 10 parts by weight based on the total weight of the binder resin solids, and reacted for 16 hours to prepare a binder resin.
  • the acid value of the prepared binder resin was 85 KOH mg / g, the weight average molecular weight was 9,000 g / mol.
  • the thermal polymerization initiator v-65 (2,2'-Azobis (2,4-dimethylvaleronitrile) was added to 10 parts by weight based on the total weight of the binder resin solids, and reacted for 16 hours to prepare a binder resin.
  • the acid value of the prepared binder resin was 87 KOH mg / g, the weight average molecular weight was 9,500 g / mol.
  • Benzophenone methacrylate represented by the formula (2-2) in the reaction vessel / cyclohexyl methacrylate represented by the following formula (5-1) / glycidyl methacrylate represented by the formula (1-1) / formula Methacrylic acid represented by 3-1 was added to 10, 41, 38, 13% by weight based on the total weight of the binder resin solid content, and then mixed with the solvent and heated to 60 °C in a nitrogen atmosphere. Thereafter, a thermal polymerization initiator v-65 (2,2'-Azobis (2,4-dimethylvaleronitrile) was added to 10 parts by weight based on the total weight of the binder resin solids and reacted for 16 hours to prepare a binder resin.
  • v-65 2,2'-Azobis (2,4-dimethylvaleronitrile
  • the acid value of the prepared binder resin was 84 KOH mg / g, the weight average molecular weight was 9,200 g / mol.
  • a photosensitive resin composition was prepared in the same manner as in Example 1, except that 6 g of the binder resin prepared in Synthesis Example 2 was used instead of the binder resin prepared in Synthesis Example 1.
  • a photosensitive resin composition was prepared in the same manner as in Example 1, except that 6 g of the binder resin prepared in Synthesis Example 3 was used instead of the binder resin prepared in Synthesis Example 1.
  • the styrene represented by Chemical Formula 4-1 / glycidyl methacrylate represented by Chemical Formula 1-1 / methacrylic acid represented by Chemical Formula 3-1 in the reaction vessel based on the total weight of binder resin solids, respectively 42, 45 and 13 wt% of the mixture was mixed with a solvent and heated to 60 °C in a nitrogen atmosphere. Thereafter, a thermal polymerization initiator v-65 (2,2'-Azobis (2,4-dimethylvaleronitrile) was added to 10 parts by weight based on the total weight of the binder resin solids and reacted for 16 hours to prepare a binder resin.
  • the acid value of the prepared binder resin was 88 KOH mg / g, the weight average molecular weight was 9,300 g / mol.
  • a benzophenone monomer comprising a structure wherein R 3 in Formula 2 is a hydroxyl group (—OH), r 3 is 1, R 4 is hydrogen, r 4 is 0, L 3 is a methylene group, and R 2 is a methyl group; Styrene represented by the formula (4-1) / glycidyl methacrylate represented by the formula (1-1) / methacrylic acid represented by the formula (3-1) based on the total weight of the binder resin solids, respectively, 11, 31, 45, 13 wt% of the mixture was mixed with a solvent and heated to 60 ° C. in a nitrogen atmosphere.
  • a thermal polymerization initiator v-65 (2,2'-Azobis (2,4-dimethylvaleronitrile) was added to 10 parts by weight based on the total weight of the binder resin solids and reacted for 16 hours to prepare a binder resin.
  • the acid value of is 85 KOH mg / g, the weight average molecular weight is 9,000 g / mol.
  • a photosensitive resin composition was manufactured in the same manner as in Example 1, except that 6 g of the binder resin prepared in Comparative Synthesis Example 1 was used instead of the binder resin prepared in Synthesis Example 1.
  • a photosensitive resin composition was prepared in the same manner as in Example 1, except that 6 g of the binder resin prepared in Comparative Synthesis Example 2 was used instead of the binder resin prepared in Synthesis Example 1.
  • the photosensitive resin composition was spin coated on glass and subjected to a heat transfer treatment at about 100 ° C. for 2 minutes ( prebake) to form a film.
  • the pattern was developed using aqueous KOH aqueous solution and washed with deionized water.
  • the patterned glass substrate was immersed in methylpyrrolidone (NMP) and then visually observed at 40 ° C. at 40 ° C. with the naked eye.
  • NMP methylpyrrolidone
  • Examples 1 to 3 showed excellent properties in dye dissolution and chemical resistance, whereas Comparative Examples 1 and 2 showed poor results in dye dissolution and chemical resistance.

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Abstract

La présente invention concerne : une résine liante comprenant une structure représentée par la formule chimique 1, une structure représentée par la formule chimique 2, et une structure représentée par la formule chimique 3 ; une composition de résine photosensible ; une résine photosensible ; un filtre coloré ; et un dispositif d'affichage.
PCT/KR2019/008469 2018-07-27 2019-07-10 Résine liante, composition de résine photosensible, résine photosensible, filtre coloré et dispositif d'affichage WO2020022670A1 (fr)

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KR20100073674A (ko) * 2008-12-23 2010-07-01 제일모직주식회사 컬러필터용 감광성 수지 조성물 및 이를 이용하여 제조된 컬러필터
JP2017167399A (ja) * 2016-03-17 2017-09-21 株式会社Ｄｎｐファインケミカル カラーフィルタ用感光性着色樹脂組成物、カラーフィルタ、表示装置

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Publication number Priority date Publication date Assignee Title
WO2020106095A1 (fr) * 2018-11-23 2020-05-28 주식회사 엘지화학 Composition de résine photosensible, résine photosensible, filtre coloré et dispositif d'affichage

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KR102247290B1 (ko) 2021-04-30
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