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WO2023008750A1 - Composition de résine et dispositif d'affichage l'utilisant - Google Patents

Composition de résine et dispositif d'affichage l'utilisant Download PDF

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Publication number
WO2023008750A1
WO2023008750A1 PCT/KR2022/009097 KR2022009097W WO2023008750A1 WO 2023008750 A1 WO2023008750 A1 WO 2023008750A1 KR 2022009097 W KR2022009097 W KR 2022009097W WO 2023008750 A1 WO2023008750 A1 WO 2023008750A1
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Prior art keywords
group
formula
resin composition
aliphatic
mol
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PCT/KR2022/009097
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English (en)
Korean (ko)
Inventor
배준
고윤종
이창민
전서정
김진현
서한욱
김남균
문성윤
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DukSan Neolux Co Ltd
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DukSan Neolux Co Ltd
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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
    • C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
    • 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
    • C08F2/00—Processes of polymerisation
    • C08F2/44—Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
    • 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
    • C08F2/00—Processes of polymerisation
    • C08F2/46—Polymerisation initiated by wave energy or particle radiation
    • C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
    • C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
    • 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
    • C08F220/26—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
    • 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
    • C08F220/34—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
    • C08J5/18—Manufacture of films or sheets
    • 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
    • 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
    • G03F7/0048—Photosensitive materials characterised by the solvents or agents facilitating spreading, e.g. tensio-active agents
    • 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
    • G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
    • 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
    • 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
    • G03F7/105—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers having substances, e.g. indicators, for forming visible images

Definitions

  • the present invention relates to a photosensitive resin composition, a pattern or film formed of the photosensitive composition, and an organic light emitting display device to which the pattern or film is applied.
  • a liquid crystal display device LCD
  • an organic light emitting display device OLED
  • the organic light emitting display device has advantages such as low power consumption, fast response speed, high color gamut, high luminance, and wide viewing angle.
  • the pigment dispersion composition must have a small dispersion particle diameter to form a fine pattern and must be composed of a composition that does not leave residue during development.
  • the primary particle size of the pigment used should be small, and the type and amount of the dispersant are also very important.
  • the primary particle diameter of pigments mainly produced for electronic materials is manufactured to be around 50 nm, and the dispersed particle diameter can be further reduced after dispersion.
  • a functional group capable of adhering to the surface of the pigment is introduced to maintain dispersion by controlling the distance between the particles of the pigment using the steric hindrance effect.
  • the resins capable of sufficiently imparting steric hindrance such as polyesters, acrylic resins, modified urethane resins, and polyethers, are used.
  • the pigment having such a small primary particle diameter can be finely dispersed using a dispersing agent that can adhere well to the pigment surface and disperse well between particles by the steric hindrance effect.
  • a pigment dispersion composition is prepared by using a dispersant capable of reducing residues during development, and the photosensitive resin composition for a color filter containing such a pigment dispersion composition can implement a fine pattern when manufacturing a color filter.
  • one embodiment of the present invention provides a photosensitive composition capable of finely dispersing a pigment, and provides a pattern or film formed of the photosensitive composition and having high resolution and stability, the pattern or It is to provide an organic light emitting display device in which a film is applied to at least one of a pixel separator, a color filter, a flat layer, and an insulating film of a touch panel.
  • the present invention is an alkali-soluble resin; reactive unsaturated compounds; photoinitiators; A pigment dispersion containing a dispersant comprising a structure represented by the following formula (1); And it provides a resin composition comprising a solvent.
  • Ar 21 is a C 3 ⁇ C 30 aliphatic ring group; C 6 ⁇ C 30 aryl group; A C 2 ⁇ C 30 heterocyclic group containing at least one heteroatom selected from O, N, S, Si, and P; A C 6 ⁇ C 30 fused ring group of aliphatic and aromatic rings; or a combination thereof;
  • R 21 is a C 5 ⁇ C 20 ethylene glycol chain group
  • R 22 and R 23 are each independently hydrogen; heavy hydrogen; C 6 ⁇ C 30 aryl group; A C 2 ⁇ C 30 heterocyclic group containing at least one heteroatom selected from O, N, S, Si, and P; A C 6 ⁇ C 30 fused ring group of aliphatic and aromatic rings; C 3 ⁇ C 30 aliphatic ring group; C 1 ⁇ C 20 Alkyl group; C 2 ⁇ C 20 alkenyl group; A C 2 ⁇ C 20 alkynyl group; A C 1 ⁇ C 20 alkoxy group; C 6 ⁇ C 30 aryloxy group; fluorenyl group; carbonyl group; ether group; C 1 ⁇ C 20 alkoxycarbonyl group; or a combination thereof;
  • R 24 to R 26 are each independently hydrogen; heavy hydrogen; halogen; C 6 ⁇ C 30 aryl group; A C 2 ⁇ C 30 heterocyclic group containing at least one heteroatom selected from O, N, S, Si, and P; A C 6 ⁇ C 30 fused ring group of aliphatic and aromatic rings; C 3 ⁇ C 30 aliphatic ring group; C 1 ⁇ C 20 Alkyl group; C 2 ⁇ C 20 alkenyl group; A C 2 ⁇ C 20 alkynyl group; A C 1 ⁇ C 20 alkoxy group; C 6 ⁇ C 30 aryloxy group; fluorenyl group; carbonyl group; ether group; C 1 ⁇ C 20 alkoxycarbonyl group; or a combination thereof;
  • L 21 , L 24 and L 25 may each independently be a single bond; Fluorenylene group; C 1 ⁇ C 30 alkylene; C 6 ⁇ C 30 arylene; C 2 ⁇ C 30 heterocycle; C 1 ⁇ C 30 Alkoxyrene; or a combination thereof;
  • d is an integer of 1 or 2;
  • a is 10 to 30 mol%
  • b is 40 to 60 mol%
  • c is 20 to 40 mol%
  • Each of Ar 21 , R 21 to R 26 , L 21 , L 24 and L 25 is deuterium; halogen; A silane group unsubstituted or substituted with a C 1 ⁇ C 30 alkyl group or a C 6 ⁇ C 30 aryl group; Siloxane group; boron group; Germanium group; cyano group; amino group; nitro group; C 1 ⁇ C 30 Alkylthio group; C 1 ⁇ C 30 alkoxy group; A C 6 ⁇ C 30 arylalkoxy group; C 1 ⁇ C 30 Alkyl group; A C 2 ⁇ C 30 alkenyl group; A C 2 ⁇ C 30 alkynyl group; C 6 ⁇ C 30 aryl group; C 6 ⁇ C 30 aryl group substituted with deuterium; fluorenyl group; A C 2 ⁇ C 30 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P; C 3 ⁇ C 30 aligon
  • the alkali-soluble resin preferably includes a resin containing a repeating unit represented by the following formula (2).
  • n is an integer from 2 to 200,000;
  • R 1 and R 2 are each independently hydrogen; heavy hydrogen; halogen; C 6 ⁇ C 30 aryl group; A C 2 ⁇ C 30 heterocyclic group containing at least one heteroatom selected from O, N, S, Si, and P; A C 6 ⁇ C 30 fused ring group of aliphatic and aromatic rings; C 1 ⁇ C 20 Alkyl group; C 2 ⁇ C 20 alkenyl group; A C 2 ⁇ C 20 alkynyl group; A C 1 ⁇ C 20 alkoxy group; C 6 ⁇ C 30 aryloxy group; fluorenyl group; carbonyl group; ether group; C 1 ⁇ C 20 alkoxycarbonyl group; or a combination thereof;
  • R 1 and R 2 can form a ring with an adjacent group, respectively;
  • X 1 is a single bond, O, CO, SO 2 , CR'R", SiR'R", formula (A) or formula (B);
  • R' and R" are each independently hydrogen; heavy hydrogen; halogen; C 6 ⁇ C 30 aryl group; C 2 ⁇ C containing at least one hetero atom of O, N, S, Si and P; 30 -membered heterocyclic group; C 6 ⁇ C 30 fused ring group of aliphatic and aromatic rings; C 1 ⁇ C 20 alkyl group; C 2 ⁇ C 20 alkenyl group; C 2 ⁇ C 20 alkynyl group; C 1 ⁇ C 20 alkoxy group; C 6 ⁇ C 30 aryloxy group; fluorenyl group; carbonyl group; ether group; C 1 ⁇ C 20 alkoxycarbonyl group; or a combination thereof;
  • R' and R" can each form a ring with an adjacent group
  • X 3 is O, S, SO 2 or NR',
  • R' is hydrogen; heavy hydrogen; halogen; C 6 ⁇ C 30 aryl group; A C 2 ⁇ C 30 heterocyclic group containing at least one heteroatom selected from O, N, S, Si, and P; A C 6 ⁇ C 30 fused ring group of aliphatic and aromatic rings; C 1 ⁇ C 20 Alkyl group; C 2 ⁇ C 20 alkenyl group; A C 2 ⁇ C 20 alkynyl group; A C 1 ⁇ C 20 alkoxy group; C 6 ⁇ C 30 aryloxy group; fluorenyl group; carbonyl group; ether group; C 1 ⁇ C 20 alkoxycarbonyl group; or a combination thereof;
  • R 3 to R 6 are each independently hydrogen; heavy hydrogen; halogen; C 6 ⁇ C 30 aryl group; a C 2 ⁇ C 30 heterocyclic group containing at least one heteroatom selected from O, N, S, Si, and P; A C 6 ⁇ C 30 fused ring group of aliphatic and aromatic rings; C 1 ⁇ C 20 Alkyl group; C 2 ⁇ C 20 alkenyl group; A C 2 ⁇ C 20 alkynyl group; A C 1 ⁇ C 20 alkoxy group; C 6 ⁇ C 30 aryloxy group; fluorenyl group; carbonyl group; ether group; C 1 ⁇ C 20 alkoxycarbonyl group; or a combination thereof;
  • Each of R 3 to R 6 can form a ring with an adjacent group
  • c to f are independently integers from 0 to 4,
  • X 2 is a fluorenyl group; C 6 ⁇ C 30 aryl group; A C 2 ⁇ C 30 heterocyclic group containing at least one heteroatom selected from O, N, S, Si, and P; A C 6 ⁇ C 30 fused ring group of aliphatic and aromatic rings; C 1 ⁇ C 20 Alkyl group; C 2 ⁇ C 20 alkenyl group; A C 2 ⁇ C 20 alkynyl group; A C 1 ⁇ C 20 alkoxy group; C 6 ⁇ C 30 aryloxy group; or a combination thereof;
  • a 1 and A 2 are independently of each other Formula (C) or Formula (D);
  • R 7 to R 10 are each independently hydrogen; heavy hydrogen; halogen; C 6 ⁇ C 30 aryl group; A C 2 ⁇ C 30 heterocyclic group containing at least one heteroatom selected from O, N, S, Si, and P; A C 6 ⁇ C 30 fused ring group of aliphatic and aromatic rings; C 1 ⁇ C 20 Alkyl group; C 2 ⁇ C 20 alkenyl group; A C 2 ⁇ C 20 alkynyl group; A C 1 ⁇ C 20 alkoxy group; C 6 ⁇ C 30 aryloxy group; fluorenyl group; carbonyl group; ether group; C 1 ⁇ C 20 alkoxycarbonyl group; or a combination thereof;
  • Y 1 and Y 2 are independently of formula (E) or formula (F);
  • R 11 to R 15 are each independently hydrogen; heavy hydrogen; halogen; C 6 ⁇ C 30 aryl group; A C 2 ⁇ C 30 heterocyclic group containing at least one heteroatom selected from O, N, S, Si, and P; A C 6 ⁇ C 30 fused ring group of aliphatic and aromatic rings; C 1 ⁇ C 20 Alkyl group; C 2 ⁇ C 20 alkenyl group; A C 2 ⁇ C 20 alkynyl group; A C 1 ⁇ C 20 alkoxy group; C 6 ⁇ C 30 aryloxy group; fluorenyl group; carbonyl group; ether group; C 1 ⁇ C 20 alkoxycarbonyl group; or a combination thereof;
  • L 1 to L 3 are each independently a single bond; Fluorenylene group; C 1 ⁇ C 30 alkylene; C 6 ⁇ C 30 arylene; C 2 ⁇ C 30 heterocycle; C 1 ⁇ C 30 Alkoxyrene; or a combination thereof;
  • the rings formed by combining R 1 to R 15 , R', R", X 2 and L 1 to L 3 and neighboring groups are each deuterium; halogen; C 1 to C 30 alkyl group or C 6 Silane group unsubstituted or substituted with a ⁇ C 30 aryl group; Siloxane group; Boron group; Germanium group; Cyano group; Amino group; Nitro group; C 1 ⁇ C 30 alkylthio group; C 1 ⁇ C 30 alkoxy group; C 6 ⁇ C 30 arylalkoxy group; C 1 ⁇ C 30 alkyl group; C 2 ⁇ C 30 alkenyl group; C 2 ⁇ C 30 alkynyl group; C 6 ⁇ C 30 aryl group; deuterium-substituted C 6 ⁇ C 30 aryl group; Fluorenyl group; C 2 ⁇ C 30 heterocyclic group containing at least one hetero atom selected from the group consisting of O, N, S, Si and P; C 3
  • the weight average molecular weight of the dispersant including the structure represented by Formula (1) is preferably 3,000 to 30,000 g/mol.
  • the amine value of the dispersant containing the structure represented by the formula (1) is 30 to 150 mgKOH/g.
  • the pigment dispersion may include 1 to 30 parts by weight of a pigment based on 100 parts by weight of the pigment dispersion; 1 to 10 parts by weight of a dispersed binder resin; 1 to 10 parts by weight of a dispersant containing a structure represented by Formula (1); It is preferable to include; and 20 to 80 parts by weight of the solvent.
  • the pigment is preferably a pigment exhibiting one color selected from black, red, blue, green, yellow, purple, orange, and white.
  • the pigment particles in the photosensitive resin composition have an average particle size (D50) of 60 to 220 nm and a full width at half maximum of 70 to 180 nm.
  • the alkali-soluble resin preferably has a weight average molecular weight of 1,000 to 100,000 g/mol.
  • the total amount of the alkali-soluble resin is preferably 1 to 30% by weight based on the total amount of the resin composition.
  • the amount of the reactive unsaturated compound is preferably 1 to 50% by weight based on the total amount of the resin composition.
  • the photoinitiator is preferably 0.01 to 10% by weight based on the total amount of the resin composition.
  • the amount of the pigment dispersion is preferably 5 to 40% by weight based on the total amount of the resin composition.
  • the present invention provides a pattern or film formed of the resin composition.
  • the pattern or film is included in at least one of a flattening layer, an organic light emitting device layer, a sealing layer, a touch panel, and a color filter.
  • the present invention provides an electronic device including the display device and a control unit driving the display device.
  • the photosensitive resin composition comprising a dispersant and an alkali-soluble resin according to the present invention provides a pattern or film having high resolution and low outgas generation as well as stability in which generation of residue is suppressed, and the pattern or film is a pixel separator. , a color filter, a flat layer, and an organic light emitting display device applied to at least one of an insulating film of a touch panel.
  • FIG. 1 conceptually illustrates a display device for implementing the present invention.
  • Figure 2 shows the evaluation criteria for evaluating the residue level using an optical microscope (ECLIPSE LV100POL Model, Nikon Co.).
  • the present invention is an alkali-soluble resin; reactive unsaturated compounds; photoinitiators; A pigment dispersion containing a dispersant comprising a structure represented by the following formula (1); And it provides a resin composition comprising a solvent.
  • first, second, A, B, (a), and (b) may be used. These terms are only used to distinguish the component from other components, and the nature, sequence, order, or number of the corresponding component is not limited by the term.
  • a component such as a layer, film, region, or plate
  • this is not only when it is “directly on” the other component, but also when there is another component in between. It should be understood that the case may also be included. Conversely, when an element is said to be “directly on” another part, it should be understood that there is no intervening part.
  • halo or halogen includes fluorine (F), chlorine (Cl), bromine (Br), and iodine (I) unless otherwise specified.
  • alkyl or "alkyl group”, unless otherwise specified, has 1 to 60 carbon atoms connected by a single bond, and includes a straight-chain alkyl group, a branched-chain alkyl group, a cycloalkyl (alicyclic) group, an alkyl-substituted A radical of a saturated aliphatic functional group, including a cycloalkyl group, a cycloalkyl-substituted alkyl group.
  • haloalkyl group or halogenalkyl group refers to a halogen-substituted alkyl group unless otherwise specified.
  • alkenyl or “alkynyl” used in this application has a double bond or triple bond, includes a straight or branched chain group, and has a carbon number of 2 to 60, but is limited thereto. it is not going to be
  • cycloalkyl refers to, but is not limited to, a ring-forming alkyl having 3 to 60 carbon atoms, unless otherwise specified.
  • alkoxy group or "alkyloxy group” used in this application refers to an alkyl group to which an oxygen radical is bonded, and has 1 to 60 carbon atoms unless otherwise specified, but is not limited thereto.
  • alkenoxyl group refers to an alkenyl group to which an oxygen radical is attached, and unless otherwise specified, 2 to 60 It has a carbon number of, but is not limited thereto.
  • aryl group and arylene group used in this application have 6 to 60 carbon atoms, respectively, unless otherwise specified, but are not limited thereto.
  • the aryl group or arylene group includes a single ring type, a ring aggregate, and a conjugated multi-ring type compound.
  • the aryl group may include a phenyl group, a monovalent functional group of biphenyl, a monovalent functional group of naphthalene, a fluorenyl group, or a substituted fluorenyl group
  • the arylene group may include a fluorenyl group or a substituted fluorenyl group. group may be included.
  • ring assemblies means that two or more ring systems (single or fused ring systems) are directly connected to each other through a single bond or a double bond, and the means that the number of direct links is one less than the total number of ring systems in the compound.
  • identical or different ring systems may be directly linked to each other through single or double bonds.
  • the aryl group in the present application includes a ring assembly
  • the aryl group includes biphenyl and terphenyl in which benzene rings, which are single aromatic rings, are connected by a single bond.
  • the aryl group includes a compound in which an aromatic ring system conjugated with an aromatic ring system is connected by a single bond, for example, a compound in which a benzene ring conjugated with an aromatic ring system and fluorene conjugated aromatic ring system are connected by a single bond. do.
  • spiro compound has a 'spiro union', which means a connection formed by two rings sharing only one atom. At this time, the atoms shared by the two rings are called 'spiro atoms', and according to the number of spiro atoms in a compound, they are called 'monospiro-', 'dispiro-', and 'trispiro-', respectively. ' It's called a compound.
  • fluorenyl group As used in this application, the terms “fluorenyl group”, “fluorenylene group”, and “fluorentriyl group” are all hydrogen in the following structure, respectively, unless otherwise specified. Means a monovalent, divalent or trivalent functional group, “substituted fluorenyl group”, “substituted fluorenyl group” or “substituted fluorentriyl group” refers to substituents R, R', R", R' It means that at least one of "is a substituent other than hydrogen, and includes the case where R and R' are bonded to each other to form a spyro compound together with the carbon to which they are bonded.
  • a fluorenyl group, a fluorenylene group, and a fluorentriyl group may all be referred to as a fluorene group regardless of valency such as monovalent, divalent, or trivalent.
  • R, R', R" and R'" are each independently an alkyl group having 1 to 20 carbon atoms, an alkenyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, and It may be a heterocyclic group having 30 carbon atoms, for example, the aryl group may be phenyl, biphenyl, naphthalene, anthracene, or phenanthrene, and the heterocyclic group may be pyrrole, furan, thiophene, pyrazole, imidazole, triazole, pyridine, pyrimidine, pyridazine, pyrazine, triazine, indole, benzofuran, quinazoline or quinoxaline.
  • substituted fluorenyl group and fluorenylene group are monovalent groups of 9,9-dimethylfluorene, 9,9-diphenylfluorene, and 9,9'-spirobi[9H-fluorene], respectively. It may be a functional group or a divalent functional group.
  • heterocyclic group includes not only aromatic rings such as “heteroaryl group” or “heteroarylene group” but also non-aromatic rings, and unless otherwise specified, the carbon number each containing at least one hetero atom It means a ring of 2 to 60, but is not limited thereto.
  • heteroatom refers to N, O, S, P, or Si, unless otherwise specified, and a heterocyclic group includes a heteroatom, a single ring, a ring aggregate, a fused multi-ring system, a spy means a compound, etc.
  • ring includes monocyclic and polycyclic rings, includes hydrocarbon rings as well as heterocycles containing at least one heteroatom, and includes aromatic and non-aromatic rings.
  • alicyclic group refers to cyclic hydrocarbons other than aromatic hydrocarbons, including monocyclics, ring aggregates, bonded multiple ring systems, spiro compounds, etc., unless otherwise specified, carbon atoms It means a ring of 3 to 60, but is not limited thereto. For example, even when benzene, which is an aromatic ring, and cyclohexane, which is a non-aromatic ring, are fused, it corresponds to an aliphatic ring.
  • an arylalkoxy group means an alkoxy group substituted with an aryl group
  • an alkoxycarbonyl group means a carbonyl group substituted with an alkoxy group
  • an arylcarbonylalkenyl group means an alkenyl group substituted with an arylcarbonyl group, where An arylcarbonyl group is a carbonyl group substituted with an aryl group.
  • substituted in the term “substituted or unsubstituted” as used herein means deuterium, halogen, amino group, nitrile group, nitro group, C 1 ⁇ C 30 alkyl group, C 1 ⁇ C 30 alkoxy group, C 1 ⁇ C 30 alkylamine group, C 1 ⁇ C 30 alkylthiophene group, C 6 ⁇ C 30 arylthiophene group, C 2 ⁇ C 30 alkenyl group, C 2 ⁇ C 30 alkynyl group, C 3 ⁇ C 30 cycloalkyl group, C 6 ⁇ C 30 aryl group, deuterium-substituted C 6 ⁇ C 30 aryl group, C 8 ⁇ C 30 arylalkenyl group, silane group, boron means substituted with one or more substituents selected from the group consisting of a C 2 ⁇ C 30 heterocyclic group containing at least one heteroatom selected from the group
  • the 'functional group name' corresponding to an aryl group, an arylene group, a heterocyclic group, etc. exemplified as examples of each symbol and its substituent may be described as a 'name of a functional group reflecting a valence', but described as a 'parent compound name' You may.
  • the name of the group is divided into valences such as 'phenanthryl (group)' for the monovalent 'group' and 'phenanthrylene (group)' for the divalent group. It can be described, but it can also be described as 'phenanthrene', which is the name of the parent compound, regardless of the valency.
  • pyrimidine it is described as 'pyrimidine' regardless of the valence, or the 'group of the corresponding valence, such as pyrimidinyl (group) in the case of monovalent, pyrimidinylene (group) in the case of divalent It can also be written as 'the name of'. Therefore, in the present application, when the type of substituent is described as a parent compound name, it may mean an n-valent 'group' formed by elimination of a hydrogen atom bonded to a carbon atom and/or a heteroatom of the parent compound.
  • numbers or alphabets indicating positions may be omitted when describing compound names or substituent names.
  • pyrido[4,3-d]pyrimidine to pyridopyrimidine benzofuro[2,3-d]pyrimidine to benzofuropyrimidine
  • 9,9-dimethyl-9H-flu Orenes can be described as dimethylfluorene and the like. Therefore, both benzo[g]quinoxaline and benzo[f]quinoxaline can be described as benzoquinoxaline.
  • substituent R 1 when a is an integer of 0, substituent R 1 means that it does not exist, that is, when a is 0, it means that hydrogen is bonded to all carbons forming the benzene ring. It may be omitted and the chemical formula or compound may be described.
  • substituent R 1 when a is an integer of 1, one substituent R 1 is bonded to any one of carbon atoms forming a benzene ring, and when a is an integer of 2 or 3, for example, it may be bonded as follows, and a is 4 to 6 Even if it is an integer of, it is bonded to the carbon of the benzene ring in a similar way, and when a is an integer of 2 or more, R 1 may be the same as or different from each other.
  • a number in 'number-condensed ring' indicates the number of condensed rings.
  • a form in which three rings are condensed with each other, such as anthracene, phenanthrene, and benzoquinazoline can be expressed as a 3-condensed ring.
  • bridged bicyclic compound refers to a compound in which two rings share three or more atoms to form a ring, unless otherwise specified.
  • the shared atom may include carbon or a heteroatom.
  • an organic electric element may mean a component (s) between an anode and a cathode, or an organic light emitting diode including an anode and a cathode, and a component (s) positioned therebetween.
  • the display device in this application may mean an organic electric element, an organic light emitting diode and a panel including the same, or may mean an electronic device including a panel and a circuit.
  • electronic devices include lighting devices, solar cells, portable or mobile terminals (eg, smart phones, tablets, PDAs, electronic dictionaries, PMPs, etc.), navigation terminals, game machines, various TVs, various computer monitors, and the like. It may include all, but is not limited thereto, and may be any type of device as long as it includes the above constituent(s).
  • the photosensitive resin composition according to one embodiment of the present invention may include an alkali-soluble resin, a reactive unsaturated compound, a photoinitiator, a pigment dispersion, and a solvent.
  • the photosensitive composition according to one embodiment of the present invention includes a resin including a repeating unit having a structure represented by Chemical Formula (2) below.
  • n is an integer from 2 to 200,000;
  • R 1 and R 2 are each independently hydrogen; heavy hydrogen; halogen; C 6 ⁇ C 30 aryl group; A C 2 ⁇ C 30 heterocyclic group containing at least one heteroatom selected from O, N, S, Si, and P; A C 6 ⁇ C 30 fused ring group of aliphatic and aromatic rings; C 1 ⁇ C 20 Alkyl group; C 2 ⁇ C 20 alkenyl group; A C 2 ⁇ C 20 alkynyl group; A C 1 ⁇ C 20 alkoxy group; C 6 ⁇ C 30 aryloxy group; fluorenyl group; carbonyl group; ether group; Or a C 1 ⁇ C 20 alkoxycarbonyl group,
  • R 1 and R 2 can form a ring with an adjacent group, respectively;
  • a and b are independently integers from 0 to 4,
  • X 1 is a single bond, O, CO, SO 2 , CR'R", SiR'R", the following formula (A) or formula (B),
  • R' and R" can each form a ring with an adjacent group, and an example in which R' and R" combine to form a ring is as follows.
  • X 3 is O, S, SO 2 or NR',
  • R' is hydrogen; heavy hydrogen; halogen; C 6 ⁇ C 30 aryl group; A C 2 ⁇ C 30 heterocyclic group containing at least one heteroatom selected from O, N, S, Si, and P; A C 6 ⁇ C 30 fused ring group of aliphatic and aromatic rings; C 1 ⁇ C 20 Alkyl group; C 2 ⁇ C 20 alkenyl group; A C 2 ⁇ C 20 alkynyl group; A C 1 ⁇ C 20 alkoxy group; C 6 ⁇ C 30 aryloxy group; fluorenyl group; carbonyl group; ether group; Or a C 1 ⁇ C 20 alkoxycarbonyl group,
  • R 3 to R 6 are each independently hydrogen; heavy hydrogen; halogen; C 6 ⁇ C 30 aryl group; A C 2 ⁇ C 30 heterocyclic group containing at least one heteroatom selected from O, N, S, Si, and P; A C 6 ⁇ C 30 fused ring group of aliphatic and aromatic rings; C 1 ⁇ C 20 Alkyl group; C 2 ⁇ C 20 alkenyl group; A C 2 ⁇ C 20 alkynyl group; A C 1 ⁇ C 20 alkoxy group; C 6 ⁇ C 30 aryloxy group; fluorenyl group; carbonyl group; ether group; Or a C 1 ⁇ C 20 alkoxycarbonyl group,
  • c to f are independently integers from 0 to 4,
  • a 1 and A 2 are each independently the following formula (C) or formula (D);
  • R 7 to R 10 are each independently hydrogen; heavy hydrogen; halogen; C 6 ⁇ C 30 aryl group; A C 2 ⁇ C 30 heterocyclic group containing at least one heteroatom selected from O, N, S, Si, and P; A C 6 ⁇ C 30 fused ring group of aliphatic and aromatic rings; C 1 ⁇ C 20 Alkyl group; C 2 ⁇ C 20 alkenyl group; A C 2 ⁇ C 20 alkynyl group; A C 1 ⁇ C 20 alkoxy group; C 6 ⁇ C 30 aryloxy group; fluorenyl group; carbonyl group; ether group; Or a C 1 ⁇ C 20 alkoxycarbonyl group,
  • Y 1 and Y 2 are independently of formula (E) or formula (F);
  • R 11 to R 15 are each independently hydrogen; heavy hydrogen; halogen; C 6 ⁇ C 30 aryl group; A C 2 ⁇ C 30 heterocyclic group containing at least one heteroatom selected from O, N, S, Si, and P; A C 6 ⁇ C 30 fused ring group of aliphatic and aromatic rings; C 1 ⁇ C 20 Alkyl group; C 2 ⁇ C 20 alkenyl group; A C 2 ⁇ C 20 alkynyl group; A C 1 ⁇ C 20 alkoxy group; C 6 ⁇ C 30 aryloxy group; fluorenyl group; carbonyl group; ether group; Or a C 1 ⁇ C 20 alkoxycarbonyl group,
  • L 1 ⁇ L 3 are each independently a single bond, a fluorenylene group, a C 1 ⁇ C 30 alkylene, a C 6 ⁇ C 30 arylene, a C 2 ⁇ C 30 heterocyclic ring, or A C 1 ⁇ C 30 alkoxyrene,
  • the rings formed by combining R 1 to R 15 , R', R", X 2 and L 1 to L 3 and neighboring groups are each deuterium; halogen; C 1 to C 30 alkyl group or C 6 Silane group unsubstituted or substituted with a ⁇ C 30 aryl group; Siloxane group; Boron group; Germanium group; Cyano group; Amino group; Nitro group; C 1 ⁇ C 30 alkylthio group; C 1 ⁇ C 30 alkoxy group; C 6 ⁇ C 30 arylalkoxy group; C 1 ⁇ C 30 alkyl group; C 2 ⁇ C 30 alkenyl group; C 2 ⁇ C 30 alkynyl group; C 6 ⁇ C 30 aryl group; deuterium-substituted C 6 ⁇ C 30 aryl group; Fluorenyl group; C 2 ⁇ C 30 heterocyclic group containing at least one hetero atom selected from the group consisting of O, N, S, Si and P; C 3
  • R 1 to R 15 , R', R" and X 2 are aryl groups, preferably C 6 to C 30 aryl groups, more preferably C 6 to C 18 aryl groups such as phenyl and biphenyl , naphthyl, terphenyl, and the like.
  • R 1 to R 15 , R', R" and X 2 are fluorenyl groups, preferably 9,9-dimethyl-9H-fluorene, 9,9-diphenyl-9H-fluorenyl groups, 9,9'-spirobifluorene and the like.
  • L 1 to L 3 is an arylene group, preferably a C 6 to C 30 arylene group, more preferably a C 6 to C 18 arylene group, such as phenyl, biphenyl, naphthyl, terphenyl, etc. there is.
  • R 1 to R 15 , R′ and R′′ are alkyl groups, they may preferably be C 1 to C 10 alkyl groups, such as methyl and t-butyl.
  • R 1 to R 15 , R' and R" are alkoxyl groups, preferably C 1 to C 20 alkoxyl groups, more preferably C 1 to C 10 alkoxyl groups such as methoxy, t-part It may be toxy, etc.
  • a ring formed by bonding adjacent groups of R 1 to R 15 , R', R", X 2 and L 1 to L 3 to each other is a C 6 to C 60 aromatic ring group; a fluorenyl group; O, N, It may be a C 2 ⁇ C 60 heterocyclic group containing at least one heteroatom selected from S, Si and P; or a C 3 ⁇ C 60 aliphatic ring group, for example, by combining adjacent groups to form an aromatic ring.
  • a C 6 ⁇ C 20 aromatic ring more preferably a C 6 ⁇ C 14 aromatic ring, such as benzene, naphthalene, phenanthrene, and the like may be formed.
  • the ratio of Formula (E) to Formula (F) in the polymer chain of the resin including the repeating unit represented by Formula (2) is preferably 2:0 to 1:1, most preferably 1.5:0.5. is the ratio When the ratio of formula (F) is higher than that of formula (E), residue may be generated due to excessively increased adhesion, and the amount of outgas generation may also increase significantly, and the ratio of formula (E) to formula (F) is 1.5 When :0.5, the resolution of the pattern is the best and the amount of outgas can be satisfied.
  • the resin containing the repeating unit represented by Formula (2) may have a weight average molecular weight of 1,000 to 100,000 g/mol, preferably 1,000 to 50,000 g/mol, and more preferably 1,000 to 30,000 g/mol. .
  • a weight average molecular weight of the resin is within the above range, a pattern can be formed well without residue during the preparation of the pattern layer, there is no loss of film thickness during development, and a good pattern can be obtained.
  • the resin containing the repeating unit represented by Formula (2) may be included in an amount of 1 to 30% by weight, more preferably 3 to 20% by weight, based on the total amount of the photosensitive resin composition.
  • excellent sensitivity, developability and adhesiveness (adhesion) can be obtained.
  • the photosensitive resin composition may further include an acrylic resin in addition to the resin including the repeating unit represented by Formula (2).
  • the acrylic resin is a copolymer of a first ethylenically unsaturated monomer and a second ethylenically unsaturated monomer copolymerizable therewith, and includes one or more acrylic repeating units.
  • the acrylic resin may be a copolymer of ethylenically unsaturated monomers including 2 to 10 types of acrylates and methacrylates, and may have a weight average molecular weight of 5,000 to 30,000 g/mol.
  • the photosensitive resin composition according to one embodiment of the present invention includes a reactive unsaturated compound that can be crosslinked by a radical in an exposure step.
  • the reactive unsaturated compound has an ethylenically unsaturated double bond, sufficient polymerization occurs during exposure in the pattern forming process to form a pattern having excellent heat resistance, light resistance, and chemical resistance.
  • the reactive unsaturated compound examples include ethylene glycol diacrylate, ethylene glycol dimethacrylate, diethylene glycol diacrylate, triethylene glycol diacrylate, triethylene glycol dimethacrylate, and 1,6-hexanediol.
  • Examples of the bifunctional ester of (meth)acrylic acid include Aronix M-210, M-240, and M-6200 from Toagosei Chemical Industry Co., Ltd.; Nippon Kayaku Co., Ltd.'s KAYARAD HDDA, HX-220, R-604, etc.; Examples include V-260, V-312, and V-335 HP manufactured by Osaka Yuki Kagaku Kogyo Co., Ltd.
  • Examples of the trifunctional ester of (meth)acrylic acid include Aronix M-309, M-400, M-405, M-450, M-7100, M-8030, M from Toagosei Chemical Industry Co., Ltd. -8060, etc.; Nippon Kayaku Co., Ltd.'s KAYARAD TMPTA, DPCA-20, DPCA-60, DPCA-120, etc.; Examples include V-295, V-300, and V-360 from Osaka Yuki Kayaku Kogyo Co., Ltd.
  • the reactive unsaturated compound may be used after being treated with an acid anhydride to impart better developability.
  • the reactive unsaturated compound may be included in an amount of 1 to 50% by weight, for example, 5 to 30% by weight based on the total amount of the photosensitive resin composition. When the reactive unsaturated compound is included within the above range, sufficient curing occurs during exposure in the pattern forming process, resulting in excellent reliability, excellent heat resistance, light resistance and chemical resistance of the pattern, and excellent resolution and adhesion.
  • the photoinitiator that can be used in combination with the oxime ester-based compound is a photoinitiator used in the photosensitive resin composition, for example, an acetophenone-based compound, a benzophenone-based compound, a thioxanthone-based compound, a benzoin-based compound, a triazine-based compound, etc. can be used
  • Examples of the oxime-based compound include 2-(o-benzoyloxime)-1-[4-(phenylthio)phenyl]-1,2-octanedione, 1-(o-acetyloxime)-1-[9- Ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]ethanone, O-ethoxycarbonyl- ⁇ -oxyamino-1-phenylpropan-1-one, 2-dimethylamino-2 -(4-methylbenzyl)-1-(4-morpholin-4-yl-phenyl)-butan-1-one, 1-(4-phenylsulfanylphenyl)-butane-1,2-dione 2-oxime -O-benzoate, 1-(4-phenylsulfanylphenyl)-octane-1,2-dione 2-oxime-O-benzoate, 1-(4-phenylsulfanylphenyl)-oct
  • acetophenone-based compound examples include 2,2'-diethoxy acetophenone, 2,2'-dibutoxy acetophenone, 2-hydroxy-2-methylpropiophenone, p-t-butyltrichloro acetophenone, p-t-butyldichloroacetophenone, 4-chloroacetophenone, 2,2'-dichloro-4-phenoxyacetophenone, 2-methyl-1-(4-(methylthio)phenyl)-2-morpholinopropane- 1-one, 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-butan-1-one, etc. are mentioned.
  • benzophenone-based compound examples include benzophenone, benzoyl benzoic acid, methyl benzoyl benzoate, 4-phenyl benzophenone, hydroxy benzophenone, acrylated benzophenone, 4,4'-bis(dimethylamino)benzophenone, 4,4 '-bis(diethylamino)benzophenone, 4,4'-dimethylaminobenzophenone, 4,4'-dichlorobenzophenone, 3,3'-dimethyl-2-methoxybenzophenone, and the like.
  • benzoin-based compound examples include benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl ether, and benzyldimethylketal.
  • triazine-based compound examples include 2,4,6-trichloro-s-triazine, 2-phenyl 4,6-bis(trichloromethyl)-s-triazine, 2-(3', 4'- Dimethoxystyryl) -4,6-bis (trichloromethyl) -s-triazine, 2- (4'-methoxynaphthyl) -4,6-bis (trichloromethyl) -s-triazine, 2-(p-methoxyphenyl)-4,6-bis(trichloromethyl)-s-triazine, 2-(p-tolyl)-4,6-bis(trichloromethyl)-s-triazine, 2-biphenyl 4,6-bis(trichloromethyl)-s-triazine, bis(trichloromethyl)-6-styryl-s-triazine, 2-(naphtho1-yl)-4,6 -bis(trichlor
  • a peroxide-based compound, an azobis-based compound, or the like may be used as a radical polymerization initiator.
  • photoperoxide-based compound examples include ketone peroxides such as methyl ethyl ketone peroxide, methyl isobutyl ketone peroxide, cyclohexanone peroxide, methylcyclohexanone peroxide, and acetylacetone peroxide; diacyl peroxides such as isobutyryl peroxide, 2,4-dichlorobenzoyl peroxide, o-methylbenzoyl peroxide, and bis-3,5,5-trimethylhexanoyl peroxide; hydroperoxides such as 2,4,4-trimethylpentyl-2-hydroperoxide, diisopropylbenzene hydroperoxide, cumene hydroperoxide, and t-butyl hydroperoxide; Dicumyl peroxide, 2,5-dimethyl-2,5-di(t-butylperoxy)hexane, 1,3-bis(t-butyloxyisopropyl
  • azobis-based compound examples include 1,1'-azobiscyclohexane-1-carbonitrile, 2,2'-azobis(2,4-dimethylvaleronitrile), 2,2,-azobis( methylisobutyrate), 2,2'-azobis (4-methoxy-2,4-dimethylvaleronitrile), ⁇ , ⁇ '-azobis (isobutylnitrile) and 4,4'-azobis (4 -Cyanobalic acid) and the like.
  • the photoinitiator may be used together with a photosensitizer that causes a chemical reaction by absorbing light, becoming excited, and then transferring the energy thereto.
  • a photosensitizer that causes a chemical reaction by absorbing light, becoming excited, and then transferring the energy thereto.
  • the photosensitizer include tetraethylene glycol bis-3-mercapto propionate, pentaerythritol tetrakis-3-mercapto propionate, dipentaerythritol tetrakis-3-mercapto propionate, and the like. can be heard
  • the photoinitiator may be included in an amount of 0.01 to 10% by weight, for example, 0.1 to 5% by weight based on the total amount of the photosensitive resin composition.
  • excellent reliability can be obtained due to sufficient curing during exposure in the pattern forming process, excellent heat resistance, light resistance and chemical resistance of the pattern, excellent resolution and adhesion, and due to the unreacted initiator A decrease in transmittance can be prevented.
  • the photosensitive composition according to one embodiment of the present invention may include a pigment dispersion including a pigment, a dispersant, and a dispersion binder resin.
  • pigment both organic pigments and inorganic pigments may be used.
  • the pigment includes a red pigment, a green pigment, a blue pigment, a yellow pigment, a black pigment, and the like.
  • the pigments may be used alone or in combination of two or more, but are not limited to these examples.
  • red pigment examples include C.I. Red Pigment 254, C.I. Red Pigment 255, C.I. Red Pigment 264, C.I. Red Pigment 270, C.I. Red Pigment 272, C.I. Red Pigment 177, C.I. Red pigment 89 etc. are mentioned.
  • green pigment examples include C.I. Green Pigment 36, C.I. and halogen-substituted copper phthalocyanine pigments such as Green Pigment 7 and the like.
  • blue pigment examples include C.I. blue pigment 15:6, C.I. Blue Pigment 15, C.I. blue pigment 15:1, C.I. blue pigment 15:2, C.I. blue pigment 15:3, C.I. blue pigment 15:4, C.I. blue pigment 15:5, C.I. and copper phthalocyanine pigments such as blue pigment 16 and the like.
  • black pigment examples include benzofuranone black, lactam black, aniline black, perylene black, titanium black, and carbon black.
  • the pigment may be used after pretreatment with a water-soluble inorganic salt and a wetting agent.
  • the primary particle size of the pigment can be refined.
  • the pretreatment may be performed by kneading the pigment with a water-soluble inorganic salt and a wetting agent, and filtering and washing the pigment obtained in the kneading step.
  • the kneading may be performed at a temperature of 40° C. to 100° C., and the filtration and washing may be performed by washing the inorganic salt with water and then filtering.
  • water-soluble inorganic salt examples include, but are not limited to, sodium chloride and potassium chloride.
  • the pigment subjected to the kneading step may have an average particle diameter of 20 nm to 110 nm.
  • the average particle diameter of the pigment is within the above range, it is possible to effectively form a fine pattern while having excellent heat resistance and light resistance.
  • the pigment that has undergone the kneading step may be introduced to the surface of the pigment through acid treatment to bind the dispersant.
  • the dispersant interacts with the pigment and the dispersion binder in the pigment dispersion solution to serve to connect the pigment and the dispersion binder resin, and maintains stable dispersion of the pigment.
  • the dispersant is preferably a nonionic dispersant, and when a composition pattern including the nonionic dispersant is formed in contact with an electrode of an organic light emitting display device, defects of the electrode can be suppressed.
  • the nonionic dispersant there is an advantage in that the stability of the pattern is excellent because the outgassing amount is small.
  • the said dispersing agent is a dispersing agent containing the structure represented by the following formula (1).
  • Ar 21 is a C 3 ⁇ C 30 aliphatic ring group; C 6 ⁇ C 30 aryl group; A C 2 ⁇ C 30 heterocyclic group containing at least one heteroatom selected from O, N, S, Si, and P; A C 6 ⁇ C 30 fused ring group of aliphatic and aromatic rings; or a combination thereof;
  • R 21 is a C 5 ⁇ C 20 ethylene glycol chain group
  • R 22 and R 23 are each independently hydrogen; heavy hydrogen; C 6 ⁇ C 30 aryl group; A C 2 ⁇ C 30 heterocyclic group containing at least one heteroatom selected from O, N, S, Si, and P; A C 6 ⁇ C 30 fused ring group of aliphatic and aromatic rings; C 3 ⁇ C 30 aliphatic ring group; C 1 ⁇ C 20 Alkyl group; C 2 ⁇ C 20 alkenyl group; A C 2 ⁇ C 20 alkynyl group; A C 1 ⁇ C 20 alkoxy group; C 6 ⁇ C 30 aryloxy group; fluorenyl group; carbonyl group; ether group; C 1 ⁇ C 20 alkoxycarbonyl group; or a combination thereof;
  • R 24 to R 26 are each independently hydrogen; heavy hydrogen; halogen; C 6 ⁇ C 30 aryl group; A C 2 ⁇ C 30 heterocyclic group containing at least one heteroatom selected from O, N, S, Si, and P; A C 6 ⁇ C 30 fused ring group of aliphatic and aromatic rings; C 3 ⁇ C 30 aliphatic ring group; C 1 ⁇ C 20 Alkyl group; C 2 ⁇ C 20 alkenyl group; A C 2 ⁇ C 20 alkynyl group; A C 1 ⁇ C 20 alkoxy group; C 6 ⁇ C 30 aryloxy group; fluorenyl group; carbonyl group; ether group; C 1 ⁇ C 20 alkoxycarbonyl group; or a combination thereof;
  • L 21 , L 24 and L 25 may each independently be a single bond; Fluorenylene group; C 1 ⁇ C 30 alkylene; C 6 ⁇ C 30 arylene; C 2 ⁇ C 30 heterocycle; C 1 ⁇ C 30 Alkoxyrene; or a combination thereof;
  • d is an integer of 1 or 2;
  • a is 10 to 30 mol%
  • b is 40 to 60 mol%
  • c is 20 to 40 mol%
  • Each of Ar 21 , R 21 to R 26 , L 21 , L 24 and L 25 is deuterium; halogen; A silane group unsubstituted or substituted with a C 1 ⁇ C 30 alkyl group or a C 6 ⁇ C 30 aryl group; Siloxane group; boron group; Germanium group; cyano group; amino group; nitro group; C 1 ⁇ C 30 Alkylthio group; C 1 ⁇ C 30 alkoxy group; A C 6 ⁇ C 30 arylalkoxy group; C 1 ⁇ C 30 Alkyl group; A C 2 ⁇ C 30 alkenyl group; A C 2 ⁇ C 30 alkynyl group; C 6 ⁇ C 30 aryl group; C 6 ⁇ C 30 aryl group substituted with deuterium; fluorenyl group; A C 2 ⁇ C 30 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P; C 3 ⁇ C 30 aligon
  • the dispersant represented by the above formula (1) is preferably represented by the following formula (3) or formula (4), more preferably formula (4).
  • the dispersing agent of the present invention containing a diamine side chain is preferable because it can more effectively finely disperse the pigment by forming a strong ⁇ -orbital stacking or hydrogen bond with the acid group of the dispersion binder resin and the acid group of the acid-treated pigment.
  • Ar 21 , R 21 to R 26 , L 21 , L 24 , L 25 and a to c are the same as defined in Formula (1) above;
  • R 27 and R 28 are each independently hydrogen; heavy hydrogen; halogen; C 6 ⁇ C 30 aryl group; A C 2 ⁇ C 30 heterocyclic group containing at least one heteroatom selected from O, N, S, Si, and P; A C 6 ⁇ C 30 fused ring group of aliphatic and aromatic rings; C 3 ⁇ C 30 aliphatic ring group; C 1 ⁇ C 20 Alkyl group; C 2 ⁇ C 20 alkenyl group; A C 2 ⁇ C 20 alkynyl group; A C 1 ⁇ C 20 alkoxy group; C 6 ⁇ C 30 aryloxy group; fluorenyl group; carbonyl group; ether group; C 1 ⁇ C 20 alkoxycarbonyl group; or a combination thereof.
  • the amine side chain preferably includes a urea moiety linking group.
  • the amine side chain of the dispersant having the structure represented by Formula (1) includes a urea moiety, the dispersibility of the pigment is improved due to the structural characteristics of the urea moiety.
  • the group connected by the urea moiety does not break during the post-heat treatment process, and accordingly, less outgas is generated, thereby increasing the stability of the pattern.
  • a is 10 to 30 mol%
  • b is 40 to 60 mol%
  • c is preferably 20 to 40 mol% do.
  • Ar 21 is preferably a phenyl group, and 40 to 60 mol% of repeating units containing a phenyl group with respect to 100 mol% of all repeating units included in the compound represented by Formula (1) In this case, it is possible to secure high heat resistance and Tg, and it is possible to prevent the pigment dispersion from exhibiting sticky characteristics like an adhesive due to a low Tg.
  • R 21 is preferably an ethylene glycol chain group, and the ethylene glycol chain group means a chain-like substituent extending from an ethylene glycol moiety.
  • An ethylene glycol chain group having less than 5 carbon atoms has a problem of deterioration in developability, and an ethylene glycol chain group having more than 20 carbon atoms is vulnerable to outgas generation, so an ethylene glycol chain group having 5 to 20 carbon atoms is more preferable.
  • the repeating unit containing a urea moiety and an amine group can increase pigment dispersibility as the content increases, but the heat resistance decreases due to the low Tg and the amount of outgas generated in the post-heat treatment process increases. there is. Therefore, in the case of the repeating unit containing the urea moiety and the amine group, as described above, 20 to 40 mol% of the total repeating unit included in the compound represented by Formula (1) is 100 mol%. desirable.
  • the amine value of the dispersant containing the structure represented by the formula (1) is 30 to 150 mgKOH/g.
  • the dispersant of the present invention represented by the formula (1) can effectively disperse the pigment in the range of 90 nm to 110 nm in average particle size (D50), and is very preferable because the amount of outgas generated compared to the amount of the dispersant used is small.
  • the dispersant of the present invention represented by the formula (1) is strongly bonded to the acid group of the dispersing binder and developed together with the dispersing binder resin in the development process, and has the advantage of being able to implement a pattern with high resolution due to less residue generation than conventional dispersants. there is.
  • the dispersing binder resin connected to the pigment through the dispersing agent causes a steric hindrance effect between the pigment particles and allows the pigment particles to be dispersed at regular intervals.
  • An acrylic resin containing a carboxyl group may be used as the dispersion binder resin, which is preferable because it can improve the stability of the pigment dispersion and also improve the developability and resolution of the pattern.
  • the pigment dispersion may be included in an amount of 5 to 40% by weight, more specifically 8 to 30% by weight, based on the total amount of the photosensitive resin composition.
  • the pigment dispersion is included within the above range, the curability and adhesion of the pattern are excellent, and the color according to the purpose can be sufficiently expressed.
  • the average particle size range (D50) of the pigment particles in the photosensitive resin composition is 80 nm to 220 nm, preferably 90 nm to 110 nm.
  • D50 The average particle size range of the pigment particles in the photosensitive resin composition is in the range of 90 nm to 110 nm, the resolution of the pattern is excellent and the generation of residue is preferably suppressed.
  • the half width of the pigment particle represents the width of n/2 points from the highest point (n) of the particle size distribution graph, and the smaller the value, the more even the pigment size, and is advantageous for pattern formation.
  • the full width at half maximum ranges from 70 nm to 170 nm, preferably from 75 nm to 95 nm.
  • the solvent examples include alcohols such as methanol and ethanol; ethers such as dichloroethyl ether, n-butyl ether, diisoamyl ether, methylphenyl ether, and tetrahydrofuran; glycol ethers such as ethylene glycol monomethyl ether and ethylene glycol monoethyl ether; Cellosolve acetates, such as methyl cellosolve acetate, ethyl cellosolve acetate, and diethyl cellosolve acetate; carbitols such as methyl ethyl carbitol, diethyl carbitol, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol dimethyl ether, diethylene glycol methyl ethyl ether, and diethylene glycol diethyl ether; propylene glycol alkyl ether acetates such as propylene glycol methyl ether acetate and
  • glycol ethers such as ethylene glycol monoethyl ether; ethylene glycol alkyl ether acetates such as ethyl cellosolve acetate; esters such as 2-hydroxy ethyl propionate; carbitols such as diethylene glycol monomethyl ether; Propylene glycol alkyl ether acetates such as propylene glycol methyl ether acetate and propylene glycol propyl ether acetate may be preferably used.
  • the solvent may be included in the remaining amount with respect to the total amount of the photosensitive resin composition, and specifically, may be included in 50 to 90% by weight.
  • the photosensitive resin composition has an appropriate viscosity, and thus processability in manufacturing the pattern layer is excellent.
  • Another embodiment of the present invention may provide an organic light emitting display device.
  • an organic light emitting display device includes a substrate 1, a TFT layer 2 on the substrate, a flat layer 3 on the TFT layer, An organic light emitting device layer on the flattening layer, a sealing layer 8 disposed on the organic light emitting device layer, a touch panel 9 disposed on the sealing layer, and a color filter disposed on the touch panel, wherein the At least one of the flattening layer, the organic light emitting element layer, the sealing layer, the touch panel, and the color filter is an organic light emitting display device characterized in that it includes a pattern or film formed of the photosensitive resin composition of the present invention.
  • the pattern or film is formed of a photosensitive composition containing, as an essential component, a pigment dispersion containing a resin containing a repeating unit represented by Chemical Formula (2) as a main component and a dispersant represented by a structure represented by Chemical Formula (1).
  • the substrate 1 may be a flexible substrate.
  • the substrate is polyimide (PI; polyimide), polyethylene terephthalate (PET; polyethylene naphtalate), polyethylene naphtalate (PEN), polycarbonate (PC; polycarbonate), polyarylate (PAR; polyarylate), polyetherimide (PEI; polyetherimide), polyether sulfone (PES; polyethersulphone), etc. can be made of plastics with excellent heat resistance and durability.
  • the present invention is not limited thereto, and various flexible materials such as metal foil or thin glass may be used.
  • the substrate may be a rigid substrate, and in this case, the substrate may be made of a glass material containing SiO 2 as a main component.
  • the substrate In the case of a bottom emission type in which an image is implemented in a direction of the substrate, the substrate must be formed of a transparent material. However, in the case of a top emission type in which an image is implemented in a direction opposite to that of the substrate, the substrate does not necessarily need to be formed of a transparent material.
  • the substrate may be formed of metal.
  • the substrate may include at least one selected from the group consisting of carbon, iron, chromium, manganese, nickel, titanium, molybdenum, and stainless steel (SUS), but is not limited thereto.
  • a TFT layer 2 may be disposed on the substrate.
  • the term TFT layer referred to in this specification collectively refers to a thin film transistor (TFT) array for driving an organic light emitting device, and refers to a driving part for displaying an image.
  • TFT thin film transistor
  • FIG. 1 only an organic light emitting element and a driving thin film transistor for driving the organic light emitting element are shown, which is only for convenience of explanation, and the present invention is not limited to what is shown, and a plurality of thin film transistors, storage capacitors, and various wirings. It is obvious to those skilled in the art that may be further included.
  • the TFT layer may be covered and protected with a planarization layer (3).
  • the planarization layer may include an inorganic insulating layer and/or an organic insulating layer.
  • inorganic insulating films that can be used for the planarization layer include silicon oxide (SiO 2 ), silicon nitride (SiN x ), silicon oxynitride (SiON), aluminum oxide (Al 2 O 3 ), titanium oxide (TiO 2 ), tantalum It may include oxide (Ta 2 O 5 ), hafnium oxide (HfO 2 ), zirconium oxide (ZrO 2 ), barium strontium titanate (BST), lead zirconate-titanate (PZT), and the like.
  • organic insulating films examples include general purpose polymers (PMMA, PS), polymer derivatives having phenolic groups, acrylic polymers, imide polymers, arylether polymers, amide polymers, fluorine polymers, p -Can include xylene-based polymers, vinyl alcohol-based polymers, and blends thereof.
  • the planarization layer may have a composite stack structure of an inorganic insulating film and an organic insulating film.
  • the flattening layer may include the photosensitive composition of the present invention. Details of the photosensitive composition of the present invention are the same as those according to one embodiment of the present invention, and thus will be omitted.
  • the amount of outgas generated is significantly reduced compared to the conventional flattening layer forming composition, resulting in stability of the flattening layer pattern. It is preferable because it has the effect of improving this, and it has the effect of preventing defects occurring in the electrodes in contact with the flattening layer.
  • An organic light emitting diode layer may be formed on the planarization layer.
  • the organic light emitting device layer may include a pixel electrode 4 formed on a flat layer, a counter electrode 7 disposed to face the pixel electrode 4, and an organic material layer 6 interposed therebetween. When a voltage is applied between the pixel electrode and the opposite electrode, the organic material layer may emit light.
  • the organic material layer may emit red light, green light, blue light, or white light.
  • the organic light emitting diode display may further include blue, green, and red color filters to express a color image when the organic layer emits white light or to increase color purity and light efficiency when the organic layer emits red, green, or blue light. there is.
  • the organic light emitting display device may be classified into a bottom emission type, a top emission type, and a dual emission type according to an emission direction.
  • a pixel electrode is provided as a light-transmitting electrode and a counter electrode is provided as a reflective electrode.
  • a pixel electrode is provided as a reflective electrode and a counter electrode is provided as a transflective electrode.
  • a top emission type in which an organic light emitting element emits light in a direction of an encapsulation layer will be described as a standard.
  • the pixel electrode may be a reflective electrode.
  • the pixel electrode may include a stacked structure of a reflective layer and a transparent or translucent electrode layer having a high work function.
  • the reflective layer may include Ag, Mg, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, or an alloy thereof.
  • the transparent or translucent electrode layer may be indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), indium oxide (In 2 O 3 ; indium oxide), or indium gallium. It may include at least one material selected from transparent conductive oxide materials such as indium gallium oxide (IGO) and aluminum zinc oxide (AZO).
  • the pixel electrode may be patterned and formed in an island shape corresponding to each pixel.
  • the pixel defining layer may include the photosensitive composition of the present invention. Details of the photosensitive composition of the present invention are the same as those according to one embodiment of the present invention, and thus will be omitted.
  • the resolution of the pixel defining layer pattern is improved and outgassing is reduced.
  • the photosensitive composition of the present invention may include a black pigment dispersion, and when a pixel defining layer is formed with the photosensitive composition of the present invention including the black pigment dispersion, the visibility of the organic light emitting display device is improved by absorbing light incident from the outside. has the effect of
  • the counter electrode may be formed of a transmissive electrode.
  • the counter electrode may be a semi-permeable film formed of a thin metal such as Li, Ca, LiF/Ca, LiF/Al, Al, Mg, or Ag having a low work function.
  • a transparent conductive layer made of a transparent conductive oxide may be stacked on the metal semi-transmissive layer.
  • the counter electrode may be formed over the entire surface of the substrate in the form of a common electrode.
  • Such a counter electrode may function as a cathode electrode.
  • Polarities of the pixel electrode and the opposite electrode may be opposite to each other.
  • the organic material layer includes an organic light emitting layer that emits light, and the organic light emitting layer may use a low molecular weight organic material or a high molecular weight organic material.
  • the organic light emitting layer is a low molecular weight organic layer formed of a low molecular weight organic material
  • a hole transport layer (HTL) and a hole injection layer (HIL) are disposed in the direction of the pixel electrode centering on the organic light emitting layer, and the opposite electrode
  • An electron transport layer (ETL) and an electron injection layer (EIL) may be disposed in the direction of .
  • a sealing layer 8 may be disposed on the organic light emitting diode layer to cover the organic light emitting diode layer.
  • the organic light emitting element included in the organic light emitting element layer is composed of organic materials and can be easily deteriorated by external moisture or oxygen. Therefore, in order to protect the organic light emitting element, the organic light emitting element layer must be sealed.
  • the sealing layer is a means for sealing the organic light emitting device layer and may have a structure in which a plurality of inorganic layers and a plurality of organic layers are alternately stacked.
  • the sealing layer may include a plurality of inorganic layers and a plurality of organic layers. Inorganic layers and organic layers may be alternately stacked with each other.
  • the inorganic layers may be formed of metal oxide, metal nitride, metal carbide, or a combination thereof.
  • the inorganic layers may be made of aluminum oxide, silicon oxide or silicon nitride.
  • the inorganic layers may include a stacked structure of a plurality of inorganic insulating layers. The inorganic layers may perform a function of suppressing penetration of external moisture and/or oxygen into the organic light emitting device layer.
  • the organic layers may be polymeric organic compounds.
  • organic layers may include any one of epoxy, acrylate, or urethane acrylate.
  • the organic layers may perform a function of relieving internal stress of the inorganic layers or compensating for and planarizing defects of the inorganic layers.
  • the stacking order of the inorganic layers and organic layers constituting the sealing layer is not limited, and an organic layer or an inorganic layer may be stacked on the organic light emitting device layer, and an uppermost layer of the sealing layer may also be an organic layer or an inorganic layer.
  • a touch panel 9 may be formed on the sealing layer.
  • the touch panel may include a first touch electrode formed on the sealing layer, a second touch electrode disposed to face the first touch electrode, and an insulating layer interposed therebetween.
  • the first touch electrode and the second touch electrode may be formed in a lattice pattern or a specific pattern.
  • the first touch electrode may be formed in contact with an upper portion of the sealing layer, and an inorganic layer may be further provided between the sealing layer and the first touch electrode.
  • the first touch electrode and the second touch electrode may be formed of ITO or metal mesh, and are preferably formed of metal mesh.
  • the metal mesh is an electrode manufactured by printing an opaque metal (copper, silver, gold, aluminum, etc.) in the form of a lattice with a thickness of 1 to 7 ⁇ m. Since a metal with high conductivity is used, the resistance value is very low, resulting in a touch response speed. It has the advantages of being fast, easy to implement on a large screen, and cheaper than ITO film. In addition, the metal mesh electrode has excellent durability against repeated bending compared to the ITO electrode and is suitable for use as a touch panel electrode for a foldable display.
  • the touch panel is a capacitive type touch panel that recognizes a portion where the amount of current is changed using capacitance of a person's body when a user touches it, calculates the size, and detects the location.
  • the organic light emitting display device of the present invention is not limited to what is shown, and converts an analog signal transmitted from a touch panel into a digital signal and controls a coordinate value necessary to determine the coordinates of a touch area. It is obvious to those skilled in the art that a flexible printed circuit board (FPCB) in which conductive and signal line patterns are formed to transmit various signals to electronic components, other various electronic components, and various wires may be further included.
  • FPCB flexible printed circuit board
  • a color filter may be formed on the touch panel.
  • the color filter is located on the touch panel, and a color part 10 aligned vertically with the light emitting area of the organic light emitting device layer and a color separating part vertically aligned with the non-light emitting area and separating the colored part ( 11) may be included.
  • the photosensitive composition of the present invention is included in the color part and narrows the wavelength range of light emitted from the light emitting region, thereby improving the color purity of the organic light emitting display device.
  • the photosensitive composition of the present invention is included in the color separation unit to absorb and block external light incident on the organic light emitting display device, thereby improving outdoor visibility.
  • the photosensitive composition of the present invention may include a red pigment or a red dye to form a red color portion aligned in a vertical direction with a red light emitting region.
  • the photosensitive composition of the present invention may include a green pigment or a green dye to form a green color portion aligned in a vertical direction with a green light emitting region.
  • the photosensitive composition of the present invention may include a blue pigment or blue dye to form a blue color portion aligned in a vertical direction with a blue light emitting region.
  • the photosensitive composition of the present invention may include a black pigment or a black dye to form a color separation part vertically aligned with the pixel defining layer.
  • the color part or the color separation part of the color filter When the color part or the color separation part of the color filter is formed using the photosensitive composition of the present invention, it has a low outgassing amount and can form a fine-sized pattern, so that a color filter with high resolution can be manufactured.
  • reaction solution was recovered to obtain polymers 1-1 to 1-7 in which the repeating units of the monomers 1-1, 1-2 and 1-3 were mixed in the form of a solution with a solid content of 45%.
  • the synthesized polymers were analyzed for molecular weight using gel permeation chromatography (Agilent Co.).
  • 6-Chlorohexyltrimethoxysilane 24g (0.1mol) and sodium methoxide 8g (0.15mol, Aldrich Co.), hydrogen sulfide THF solution (0.8M concentration) 187ml (0.15mol) and methanol 100ml were put in an autoclave and kept at 100°C for 2 hours. while the reaction proceeds. After cooling the reaction solution, 100 ml of hydrogen chloride in methanol (concentration of 1.25M) was added dropwise at room temperature for 30 minutes, and the resulting salt was removed by filtration, followed by distillation under reduced pressure to obtain 23 g of compound 2-1.
  • Synthesis Example 1-16 the silane group was substituted in the same manner as in Synthesis Example 1-16, except that Polymer 1-2 to Polymer 1-7 described in Table 2 were used instead of the solution of Polymer 1-1. Cardo-based binder resin Binder 1-2 to Binder 1-7 were prepared.
  • Polymer 2-2 (solid content 30.87%, weight An average molecular weight of 20,310 g/mol) was obtained.
  • a, b, and c represent each repeating unit, and when the total is assumed to be 100 mol%, a is 15.3 mol%; b is 50.4 mol%; c is 34.3 mol%.
  • Polymer 2-3 (solid content 30.86%, weight An average molecular weight of 20,220 g/mol) was obtained.
  • a, b, and c represent each repeating unit, and when the total is assumed to be 100 mol%, a is 18.2 mol%; b is 48.7 mol%; c is 33.1 mol%.
  • Dispersant 1-1 a, b, and c represent each repeating unit, and when the total is assumed to be 100 mol%, a is 13.1 mol%; b is 51.7 mol%; c is 35.2 mol%.
  • Dispersant 1-2 a, b, and c represent each repeating unit, and when the total is assumed to be 100 mol%, a is 13.1 mol%; b is 51.7 mol%; c is 35.2 mol%.
  • Dispersants 1-4 a, b, and c represent each repeating unit, and when the total is assumed to be 100 mol%, a is 13.1 mol%; b is 51.7 mol%; c is 35.2 mol%.
  • Dispersants 1-5 a, b, and c represent each repeating unit, and when the total is assumed to be 100 mol%, a is 15.3 mol%; b is 50.4 mol%; c is 34.3 mol%.
  • Dispersants 1-6 a, b, and c represent each repeating unit, and when the total is assumed to be 100 mol%, a is 18.2 mol%; b is 48.7 mol%; c is 33.1 mol%.
  • Irgaphor Black S0100 CF black pigment/BASF 17g
  • dispersant 1-1 3.05g
  • SR-3613 SMS
  • Pigment dispersion 7 was prepared in the same manner as in Preparation Example 1-1, except that 3.05 g of comparative dispersant 1 was used instead of dispersant 1-1.
  • Pigment dispersion 8 was prepared in the same manner as in Preparation Example 1-1, except that 3.05 g of Disperbyk 2001 (BYK Co.) was used instead of the dispersant 1-1.
  • compositions 1-1 to 1-9 containing the pigment dispersion of the present invention and the alkali-soluble resin of the present invention were prepared according to the composition (wt%) shown in Table 5 below.
  • Preparation Example 4-1 it was prepared with the same composition except that Binder 1-6 was used instead of Binder 1-1 in Preparation Example 3-1.
  • Preparation Example 4-5 it was prepared with the same composition except that Pigment Dispersion 7 was used instead of Pigment Dispersion 1 in Preparation Example 3-7.
  • Preparation Example 4-6 it was prepared with the same composition except that Pigment Dispersion 8 was used instead of Pigment Dispersion 1 in Preparation Example 3-7.
  • compositions in Tables 5 and 6 were applied to a washed 5 cm * 5 cm stainless steel substrate to a thickness of 3 ⁇ m using a spin coater, and then heated at a temperature of 100 ° C. for 1 minute to remove the solvent to form a coating film. .
  • the pattern of the composition 1-1 obtained through the photolithography step was measured for the minimum pattern size on the substrate using an optical microscope (ECLIPSE LV100POL Model, Nikon Co.).
  • a pattern of the composition 1-1 was formed on a glass substrate through the photolithography step.
  • a total of six specimens were prepared by cutting the patterned glass substrate into a size of 1 cm x 3 cm.
  • the outgassing of the specimens was collected at 250 °C for 30 minutes using JAI's JTD-5052.
  • a calibration curve was prepared, and the outgassing amount of the collected samples was measured.
  • Composition 1-1 was diluted 1000 times in propylene glycol methyl ether acetate (PGMEA) (sample 0.02 g, PGMEA 20 g) and stirred in a stirrer for 30 minutes to completely dissolve.
  • a particle size analyzer SZ-100, Horiba Co.
  • D50 was calculated as an average value by measuring three times, and the width (half-maximum width) of the x-axis corresponding to the 1/2 point of the highest peak in the graph was measured and listed in Table 7.
  • Example 1 a pattern was formed in the same manner as in Example 1 using Compositions 1-2 to 1-9 instead of Composition 1-1. After evaluating the resolution of the formed pattern, the presence of residue and the amount of outgas generated in the same manner as in Example 1, the results are shown in Table 7 below.
  • Patterns were formed in the same manner as in Example 1 using Compositions 2-1 to 2-7 instead of Composition 1-1 in Example 1. After evaluating the resolution of the formed pattern, the presence of residue and the amount of outgas generated in the same manner as in Example 1, the results are shown in Table 7 below.
  • Example 1 Composition 1-1 4.1 O 2.9 97.4 76.3
  • Example 2 Composition 1-2 4.0 O 3.0 96.9 77.3
  • Example 3 Compositions 1-3 3.9 O 3.3 95.7 79.5
  • Example 4 Compositions 1-4 3.4 O 2.8 92.5 74.6
  • Example 5 Compositions 1-5 3.6 O 2.5 93.8 75.1
  • Example 6 Compositions 1-6 3.7 O 2.2 94.2 75.9
  • Example 7 Compositions 1-7 4.2 O 2.8 96.9 76.8
  • Example 8 Compositions 1-8 3.4 O 2.9 93.1 74.9
  • Example 9 Compositions 1-9 3.8 O 2.3 94.8 76.2 Comparative Example 1 Composition 2-1 6.8 ⁇ 6.5 106.6 92.4 Comparative Example 2 Composition 2-2 6.3 ⁇ 7.3 105.8 91.7 Comparative Example 3 Composition 2-3 7.0 ⁇ 6.1 10
  • Binder 1-1 and Binder 2-3 used in Examples 1, 2 and 7, they were polymerized into three types of monomers having different structures, compared to Binder 1-6 and Binder 2-7. It has a relatively reticular structure. Therefore, Binder 1-1 and Binder 2-3 are structures more suitable for the photolithography process by effectively intermolecular bonding with surrounding compounds due to their structural characteristics, and accordingly, Examples 1, 2, and 7 are comparative examples. It is determined that the pattern resolution is higher than that of Comparative Examples 1 to 3, the amount of outgas generated is small, and the generation of residue is suppressed.
  • Example 7 and Example 8 show excellent results in terms of resolution, amount of outgassing, and residue evaluation.
  • Comparative Example 5 using the tertiary amine dispersant containing a carbamate moiety linking group in the pigment dispersion and Example 7 using the tertiary amine dispersant of the present invention containing a urea moiety linking group in the pigment dispersion were compared.
  • Comparative Example 5 and Example 7 both used the same alkali-soluble resin 2-3 of the present invention, but Example 7 containing both the tertiary amine dispersant and the alkali-soluble resin of the present invention has a resolution compared to Comparative Example 5 , outgas generation amount, and residue evaluation were all excellent.
  • Comparative Example 4 using the tertiary amine dispersant of the present invention and the acrylic binder, it shows a very low resolution and high outgassing amount compared to Example 2 using the same tertiary amine dispersant and the alkali-soluble resin of the present invention, residue It was also found that there was a significant difference in evaluation.
  • the present invention is not limited to the above embodiments, but can be manufactured in a variety of different shapes.
  • substrate 2 TFT layer
  • planarization layer 4 pixel electrode
  • the present invention relates to a photosensitive resin composition, a pattern or film formed of the photosensitive composition, and an organic light emitting display device to which the pattern or film is applied.

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Abstract

Un mode de réalisation de la présente invention concerne une composition photosensible et un dispositif d'affichage électroluminescent organique l'utilisant, la composition photosensible étant préparée à l'aide de particules de silice ayant des groupes fonctionnels réactifs introduits sur la surface de celle-ci de manière à avoir une photosensibilité élevée, et un motif durci hautement fiable est obtenu même à partir d'un traitement post-thermique effectué à basse température.
PCT/KR2022/009097 2021-07-27 2022-06-27 Composition de résine et dispositif d'affichage l'utilisant Ceased WO2023008750A1 (fr)

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KR101321380B1 (ko) * 2008-09-29 2013-10-23 후지필름 가부시키가이샤 착색 경화성 조성물, 컬러필터, 및 컬러필터의 제조방법
KR20150095827A (ko) * 2012-12-11 2015-08-21 다이니치 세이카 고교 가부시키가이샤 안료 분산제, 안료 분산제의 제조 방법 및 안료 분산액
WO2016208258A1 (fr) * 2015-06-24 2016-12-29 富士フイルム株式会社 Composition absorbant l'infrarouge proche, filtre bloquant l'infrarouge proche, procédé permettant de produire un filtre bloquant l'infrarouge proche, appareil, procédé permettant de produire un polymère contenant du cuivre et polymère contenant du cuivre
WO2021132247A1 (fr) * 2019-12-24 2021-07-01 東洋インキＳｃホールディングス株式会社 Composition de résine et article moulé

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KR101321380B1 (ko) * 2008-09-29 2013-10-23 후지필름 가부시키가이샤 착색 경화성 조성물, 컬러필터, 및 컬러필터의 제조방법
KR20100093481A (ko) * 2009-02-16 2010-08-25 후지필름 가부시키가이샤 안료 분산 조성물, 착색 경화성 조성물, 컬러필터, 액정 표시 장치, 및 고체 촬상 소자
KR20150095827A (ko) * 2012-12-11 2015-08-21 다이니치 세이카 고교 가부시키가이샤 안료 분산제, 안료 분산제의 제조 방법 및 안료 분산액
WO2016208258A1 (fr) * 2015-06-24 2016-12-29 富士フイルム株式会社 Composition absorbant l'infrarouge proche, filtre bloquant l'infrarouge proche, procédé permettant de produire un filtre bloquant l'infrarouge proche, appareil, procédé permettant de produire un polymère contenant du cuivre et polymère contenant du cuivre
WO2021132247A1 (fr) * 2019-12-24 2021-07-01 東洋インキＳｃホールディングス株式会社 Composition de résine et article moulé

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