WO2020106095A1 - 감광성 수지 조성물, 감광재, 컬러필터 및 디스플레이 장치 - Google Patents

감광성 수지 조성물, 감광재, 컬러필터 및 디스플레이 장치

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Publication number
WO2020106095A1
WO2020106095A1 PCT/KR2019/016119 KR2019016119W WO2020106095A1 WO 2020106095 A1 WO2020106095 A1 WO 2020106095A1 KR 2019016119 W KR2019016119 W KR 2019016119W WO 2020106095 A1 WO2020106095 A1 WO 2020106095A1
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WIPO (PCT)
Prior art keywords
group
substituted
present specification
unsubstituted
same
Prior art date
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PCT/KR2019/016119
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English (en)
French (fr)
Korean (ko)
Inventor
이다미
김한수
김혜진
백경림
양승진
이재용
김영웅
최상아
Original Assignee
주식회사 엘지화학
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
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Application filed by 주식회사 엘지화학 filed Critical 주식회사 엘지화학
Priority to CN201980036391.3A priority Critical patent/CN112204465B/zh
Publication of WO2020106095A1 publication Critical patent/WO2020106095A1/ko

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Classifications

    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03FPHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004Photosensitive materials
    • G03F7/027Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • G03F7/032Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09BORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B11/00Diaryl- or thriarylmethane dyes
    • C09B11/28Pyronines ; Xanthon, thioxanthon, selenoxanthan, telluroxanthon dyes
    • GPHYSICS
    • G02OPTICS
    • G02BOPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00Optical elements other than lenses
    • G02B5/20Filters
    • GPHYSICS
    • G02OPTICS
    • G02FOPTICAL 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
    • G02F1/00Devices 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
    • G02F1/01Devices 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 
    • G02F1/13Devices 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
    • G02F1/133Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
    • G02F1/1333Constructional arrangements; Manufacturing methods
    • G02F1/1335Structural association of cells with optical devices, e.g. polarisers or reflectors
    • GPHYSICS
    • G02OPTICS
    • G02FOPTICAL 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
    • G02F1/00Devices 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
    • G02F1/01Devices 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 
    • G02F1/13Devices 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
    • G02F1/133Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
    • G02F1/1333Constructional arrangements; Manufacturing methods
    • G02F1/1335Structural association of cells with optical devices, e.g. polarisers or reflectors
    • G02F1/133509Filters, e.g. light shielding masks
    • G02F1/133514Colour filters
    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03FPHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03FPHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/0005Production of optical devices or components in so far as characterised by the lithographic processes or materials used therefor
    • G03F7/0007Filters, e.g. additive colour filters; Components for display devices
    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03FPHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004Photosensitive materials
    • G03F7/09Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
    • G03F7/105Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers having substances, e.g. indicators, for forming visible images

Definitions

  • the present specification relates to a photosensitive resin composition, a photosensitive material, a color filter and a display device.
  • a pigment dispersion method using a pigment as a colorant is generally applied.
  • the pigment in the case of a pigment dispersion liquid, the pigment is present in a particle state, and not only scatters light, but also causes a sharp increase in the surface area of the pigment due to the miniaturization of the pigment, resulting in uneven pigment particles due to deterioration of dispersion stability. Therefore, in order to achieve high brightness, high contrast ratio and high resolution, which have been recently required, it has been considered to use dyes instead of pigments as colorants in recent years.
  • dyes have the advantage of high permeability compared to pigments.
  • the present specification provides a photosensitive resin composition, a photosensitive material, a color filter and a display device.
  • An exemplary embodiment of the present specification is a xanthene dye; A binder resin comprising a structure represented by Formula 1 below; Polyfunctional monomers; Photoinitiators; And it provides a photosensitive resin composition comprising a solvent.
  • L ' is a substituted or unsubstituted alkylene group
  • T1 to T3 are the same as or different from each other, and each independently hydrogen; Hydroxy group; Or a substituted or unsubstituted alkyl group,
  • t2 is an integer from 0 to 4, and when t2 is 2 or more, T2 is the same as or different from each other,
  • t3 is an integer from 0 to 5, and when t3 is 2 or more, T3 is the same or different from each other.
  • One embodiment of the present specification provides a photosensitive material prepared using the photosensitive resin composition.
  • An exemplary embodiment of the present specification provides a color filter including the photosensitive material.
  • One embodiment of the present specification provides a display device including the color filter.
  • the photosensitive resin composition according to an exemplary embodiment of the present specification includes a binder resin having a structure represented by Chemical Formula 2, it has an advantage of excellent chemical resistance properties of dilution and elution.
  • derived unit means a unit molecule or a repeating structure forming a polymer.
  • An exemplary embodiment of the present specification is a xanthene dye; A binder resin comprising a structure represented by Formula 1 below; Polyfunctional monomers; Photoinitiators; And it provides a photosensitive resin composition comprising a solvent.
  • L ' is a substituted or unsubstituted alkylene group
  • T1 to T3 are the same as or different from each other, and each independently hydrogen; Hydroxy group; Or a substituted or unsubstituted alkyl group,
  • t2 is an integer from 0 to 4, and when t2 is 2 or more, T2 is the same as or different from each other,
  • t3 is an integer from 0 to 5, and when t3 is 2 or more, T3 is the same or different from each other.
  • the photosensitive resin composition according to an exemplary embodiment of the present specification includes a binder resin including a structure represented by Chemical Formula 1, so that a structure represented by Chemical Formula 1 promotes a radical reaction when an exposure process is performed.
  • the degree of polymerization of the binder resin and the polyfunctional monomers in the photosensitive resin composition may be increased to increase the curing degree of the film. As the degree of curing of the film increases, the color filter manufactured using the photosensitive resin composition according to the present specification improves heat resistance and chemical resistance.
  • substituted or unsubstituted refers to deuterium; Halogen group; Nitrile group; Nitro group; -OH; Carbonyl group; Ester groups; -COOH; Imide group; Amide group; Anionic groups; Alkoxy groups; Alkyl groups; Cycloalkyl group; Alkenyl group; Cycloalkenyl group; Arylalkyl groups; Phosphine group; Sulfonate groups; Amine group; Aryl group; Heteroaryl group; Silyl group; Boron group; (Meth) acryloyl group; (Meth) acrylate group; Ether group; It means that it is substituted with one or more substituents selected from the group containing heterocyclic groups and anionic groups containing one or more of N, O, S or P atoms, or does not have any substituents.
  • examples of the halogen group include fluorine, chlorine, bromine or iodine.
  • the alkyl group may be a straight chain or a branched chain, and the number of carbon atoms is not particularly limited, but the number of carbon atoms 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, n-ox Tilgi, and the like, but are not limited to these.
  • the cycloalkyl group is not particularly limited, but is preferably 3 to 30 carbon atoms, particularly preferably a cyclopentyl group or a cyclohexyl group, but is not limited thereto.
  • the alkylene group means that the alkane has two binding positions.
  • the alkylene group may be straight chain, branched chain or cyclic chain.
  • the number of carbon atoms of the alkylene group is not particularly limited, but may be, for example, 1 to 30 carbon atoms. In addition, it may be 1 to 20 carbon atoms, it may be 1 to 10 carbon atoms.
  • the alkylene group may be an alkanediyl group (alkanediyl), the alkanediyl group may be applied to the description of the alkylene group.
  • the cycloalkyl group is not particularly limited, but according to an exemplary 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, a 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 is preferably 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the carbon number of the aryl group is 6 to 30. According to one embodiment, the carbon number of the aryl group is 6 to 20.
  • the aryl group may be a phenyl group, a biphenyl group, a terphenyl group, etc., as a monocyclic aryl group, but is not limited thereto.
  • the polycyclic aryl group may be a naphthyl group, anthracenyl group, indenyl group, phenanthrenyl group, pyrenyl group, perylene group, triphenyl group, chrysenyl group, fluorenyl group, and the like, but is not limited thereto.
  • the heterocyclic group is a heteroatom, a heterocyclic group containing O, N or S, and may be aromatic or aliphatic.
  • the number of carbon atoms of the heterocyclic group is not particularly limited, but is 2 to 30 carbon atoms, and specifically 2 to 20 carbon atoms.
  • heterocyclic group examples include thiophene group, furan group, pyrrol 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 Flags, etc., but are not limited to these.
  • heterocyclic group may be applied, except that the heteroaryl group is aromatic.
  • the alkoxy group may be a straight chain or a branched chain, 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.
  • the anionic group has a chemical bond with the structure of Chemical Formula 1, and the chemical bond may mean an ionic bond.
  • the anionic group is not particularly limited, for example, US Patent No. 7,939,644, Japanese Patent No. 2006-003080, Japanese Patent No. 2006-001917, Japanese Patent No. 2005-159926, Japanese Patent No. 2007-7028897, Japan
  • the negative ions described in Japanese Patent Application Publication No. 2005-071680, Korean Application Publication No. 2007-7000693, Japanese Patent Application No. 2005-111696, Japanese Patent Application No. 2008-249663, and Japanese Patent Application No. 2014-199436 may be applied.
  • anionic group examples include trifluoromethanesulfonic acid anion, bis (trifluoromethylsulfonyl) amide anion, bistrifluoromethanesulfonimide anion, bisperfluoroethylsulfonimide anion, tetraphenylborate anion, tetrakis (4-fluorophenyl) borate, tetrakis (pentafluorophenyl) borate, tris trifluoromethane sulfonyl nilme suited to, SO 3 -, CO 2 - , SO 2 N - SO 2 CF 3, SO 2 N - SO 2 CF 2 CF 3, but include a halogen group such as fluorine group, an iodo group, a chlorine group, it is not limited thereto.
  • the anionic group may have an anion by itself, or may exist in the form of a complex with other cations. Therefore, the sum of the total charges of the compound molecules of the present invention may vary according to the number of substituted anionic groups. Since the compound of the present invention has a cation in one amine group, the sum of the total charges of the molecule may have an anion to 0 as many as the number of substituted anionic groups minus one.
  • '(meth) acrylic acid' refers to at least one selected from the group consisting of acrylic acid and methacrylic acid.
  • the notation '(meth) acrylic acid' has the same meaning.
  • the binder resin including the structure represented by Chemical Formula 1 further includes a unit derived from an unsaturated compound having a cyclic ether structure having 2 to 4 carbon atoms.
  • the unsaturated compound having a cyclic ether structure having 2 to 4 carbon atoms may be any one of the following structures, but is not limited thereto.
  • R is hydrogen; Or a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms,
  • X3 and X4 are the same as or different from each other, and each is a direct bond; -Rz-; -Rz-O-; -Rz-S-; Or -Rz-NH-, and Rz is a substituted or unsubstituted alkanediyl group having 1 to 6 carbon atoms.
  • R may be an alkyl group substituted with -OH having 1 to 4 carbon atoms.
  • the photosensitive resin composition may further include a binder resin containing a unit derived from an unsaturated compound having a cyclic ether structure having 2 to 4 carbon atoms.
  • the photosensitive resin composition may further include a binder resin generally used in the art in addition to the binder resin including the structure represented by Chemical Formula 1.
  • the xanthene dye is represented by Formula 2 below.
  • R1 to R6 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitro group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryl group; And it is selected from the group consisting of a substituted or unsubstituted heteroaryl group,
  • R7 to R11 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; -OH; -SO 3 -; -SO 3 H; -SO 3 - Z +; -COO -; -COOH; -COO - Z + ; -COORa; -SO 3 Rb; -SO 2 NRcRd; -CONRe; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; And it is selected from the group consisting of a substituted or unsubstituted heteroaryl group,
  • Z + represents + N (Rf) 4 , Na + or K + ,
  • Ra to Re are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; And it is selected from the group consisting of a substituted or unsubstituted heteroaryl group,
  • Rc and Rd may combine with each other to form a hetero ring containing a nitrogen atom
  • Rf may be the same or different
  • At least one of the R7 to R11 is -SO 3 -; -SO 3 H; -SO 3 - Z +; -COO -; -COO - Z + ; -COORa; -SO 3 Rb; Or -SO 2 NRcRd; ego,
  • R12 to R15 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; And it is selected from the group consisting of a substituted or unsubstituted heteroaryl group,
  • Q1 and Q2 are the same as or different from each other, and each independently a direct bond; Or a substituted or unsubstituted alkylene group,
  • Rx is an anionic group or an ammonium structure
  • a 0 or 1.
  • R1 to R6 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitro group; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; And it is selected from the group consisting of a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.
  • R1 to R6 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitro group; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms; A substituted or unsubstituted aryl group having 6 to 20 carbon atoms; And it is selected from the group consisting of a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms.
  • R1 to R6 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitro group; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms; A substituted or unsubstituted aryl group having 6 to 20 carbon atoms; And it is selected from the group consisting of a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms.
  • R1 to R6 are hydrogen; Or a substituted or unsubstituted methyl group.
  • R1 to R6 are hydrogen; Or a methyl group.
  • R7 to R11 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; -OH; -SO 3 -; -SO 3 H; -SO 3 - Z +; -COO -; -COOH; -COO - Z + ; -COORa; -SO 3 Rb; -SO 2 NRcRd; -CONRe; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; And a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.
  • R7 to R11 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; -OH; -SO 3 -; -SO 3 H; -SO 3 - Z +; -COO -; -COOH; -COO - Z + ; -COORa; -SO 3 Rb; -SO 2 NRcRd; -CONRe; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted aryl group having 6 to 20 carbon atoms; And it is selected from the group consisting of a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms.
  • R7 to R11 are the same as or different from each other, and each independently hydrogen; -SO 3 -; -SO 3 H; -SO 3 - Z +; -COO -; -COO - Z + ; -COORa; -SO 3 Rb; And -SO 2 NRcRd.
  • R7 to R11 are the same as or different from each other, and each independently hydrogen; -SO 3 -; -SO 3 H; -COO -; -COO - Z + ; And -COORa.
  • Z + is + N (Rf) 4 , Na + or K + .
  • Z + is Na + .
  • Ra to Re are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; And a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, Rc and Rd may combine with each other to form a hetero ring containing a nitrogen atom, and Rf may be the same or different.
  • Ra to Re are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted aryl group having 6 to 20 carbon atoms; And it is selected from the group consisting of a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms, Rc and Rd may be bonded to each other to form a hetero ring containing a nitrogen atom, Rf may be the same or different.
  • Ra to Re are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; A substituted or unsubstituted aryl group having 6 to 20 carbon atoms; And it is selected from the group consisting of a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms, Rc and Rd may be bonded to each other to form a hetero ring containing a nitrogen atom, Rf may be the same or different.
  • Ra is a substituted or unsubstituted methyl group.
  • Ra is a methyl group.
  • Rc and Rd 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.
  • Rc and Rd are the same as or different from each other, and each independently hydrogen; Or a substituted or unsubstituted alkyl group having 3 to 20 carbon atoms.
  • Rc and Rd are the same as or different from each other, and each independently hydrogen; Or it is a C3-C20 linear or branched alkyl group.
  • Rc and Rd are the same as or different from each other, and each independently hydrogen; Or a branched chain alkyl group having 3 to 20 carbon atoms.
  • Rc and Rd 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.
  • Rc and Rd are the same as or different from each other, and each independently hydrogen; Or it is a C1-C10 linear or branched alkyl group.
  • Rc and Rd are the same as or different from each other, and each independently hydrogen; Or it is a C1-C10 branched chain alkyl group.
  • Rc and Rd are the same as or different from each other, and each independently hydrogen; Or a substituted or unsubstituted 2-ethylhexyl group.
  • Rc and Rd are the same as or different from each other, and each independently hydrogen; Or 2-ethylhexyl group.
  • -SO 2 NRcRd may be represented by -SO 2 NY, and Y may be defined by Rc and Rd.
  • R12 to R15 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; And a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.
  • R12 to R15 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted aryl group having 6 to 20 carbon atoms; And a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms.
  • R12 to R15 are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; And it is selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 12 carbon atoms.
  • R12 and R14 are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted ethyl group; Or a substituted or unsubstituted propyl group.
  • R12 and R14 are the same as or different from each other, and each independently hydrogen; Ethyl group; n-propyl group; Or an isopropyl group.
  • R13 and R15 are the same as or different from each other, and each independently an substituted or unsubstituted ethyl group; Or a substituted or unsubstituted phenyl group.
  • R13 and R15 are the same as or different from each other, and each independently an ethyl group; Or a methyl group, -SO 2 NHY, -SO 3 - and -SO 3 H is a phenyl group substituted with one or more selected from the group consisting of, Y is as described above.
  • Q1 and Q2 are the same as or different from each other, and each independently a direct bond; Or a substituted or unsubstituted alkylene group having 1 to 30 carbon atoms.
  • Q1 and Q2 are the same as or different from each other, and each independently a direct bond; Or a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms.
  • Q1 and Q2 are the same as or different from each other, and each independently a direct bond; Or a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms.
  • Q1 and Q2 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted methylene group; A substituted or unsubstituted ethylene group; Or a substituted or unsubstituted propylene group.
  • Q1 and Q2 are the same as or different from each other, and each independently a direct bond; Methylene group; Ethylene group; Or a propylene group.
  • Rx is an anionic group or an ammonium structure.
  • Rx is an anionic group
  • the anionic group is a chlorine group (Cl ⁇ ).
  • Rx is an ammonium structure, and the ammonium structure may be represented by Formula A below.
  • A1 to A4 are the same as or different from each other, and each independently hydrogen; Or a substituted or unsubstituted alkyl group.
  • A1 to A4 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.
  • A1 to A4 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.
  • A1 to A4 are the same as or different from each other, and each independently hydrogen; Or a substituted or unsubstituted alkyl group having 1 to 12 carbon atoms.
  • a is 0 or 1.
  • a is 0.
  • a is 1.
  • Chemical Formula 2 may be any one of the following structures.
  • Y is a branched alkyl group having 3 to 20 carbon atoms. Specifically, Y is a 2-ethylhexyl group.
  • -SO 2 NHY can be substituted on any one of carbons except for the portion substituted with a methyl group among the carbons included in the phenyl group.
  • X ' is O.
  • X ' is NH
  • L1 is a direct bond
  • L1 is a substituted or unsubstituted methylene group; A substituted or unsubstituted ethylene group; Or a substituted or unsubstituted propylene group.
  • L1 is a methylene group; Ethylene group; Or a propylene group.
  • L2 is a direct bond
  • L ' is a substituted or unsubstituted alkylene group having 1 to 30 carbon atoms.
  • L ' is a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms.
  • L ' is a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms.
  • L ' is a substituted or unsubstituted methylene group.
  • L ' is a methylene group.
  • T1 to T3 are the same as or different from each other, and each independently hydrogen; Hydroxy group; It is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.
  • T1 to T3 are the same as or different from each other, and each independently hydrogen; Hydroxy group; It is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.
  • T1 to T3 are the same as or different from each other, and each independently hydrogen; Hydroxy group; It is a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.
  • T1 to T3 are the same as or different from each other, and each independently hydrogen; Hydroxy group; It is a substituted or unsubstituted methyl group.
  • T1 is hydrogen; Or a methyl group.
  • T2 is hydrogen
  • T3 is hydrogen; Hydroxy group; Or a methyl group substituted with an amine group.
  • the formula 1 may be represented by the formula (3).
  • X ', L1, L2, T1 to T3, t2 and t3 are as defined in Chemical Formula 1.
  • Chemical Formula 1 may be represented by any one of the following structures, but is not limited thereto.
  • Formula 1 is to form a polymerized portion from any one of the following structures.
  • the binder resin may further include one or more structures represented by any one of the following Chemical Formulas 4 to 7.
  • L41, L51, L52 and L61 are the same as or different from each other, and each independently a substituted or unsubstituted alkylene group,
  • X1, X2, Y1, Y2, Z1 and Z2 are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Or a substituted or unsubstituted aryl group,
  • x2 is an integer from 0 to 5, and when x2 is 2 or more, X2 is the same as or different from each other.
  • L41, L51, L52, and L61 are the same as or different from each other, and each independently a substituted or unsubstituted alkylene group having 1 to 30 carbon atoms.
  • L41, L51, L52, and L61 are the same as or different from each other, and each independently a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms.
  • L41, L51, L52, and L61 are the same as or different from each other, and each independently a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms.
  • L41, L51, L52, and L61 are the same as or different from each other, and each independently a substituted or unsubstituted methylene group.
  • L41, L51, L52, and L61 are the same as or different from each other, and each independently a methylene group.
  • X1, X2, Y1, Y2, Z1, and Z2 are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
  • X1, X2, Y1, Y2, Z1, and Z2 are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.
  • X1, X2, Y1, Y2, Z1, and Z2 are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms.
  • X1 and Y1 are a substituted or unsubstituted methyl group.
  • X1 and Y1 are methyl groups.
  • X2 is hydrogen
  • Y2 is a substituted or unsubstituted cyclohexyl group; Or a substituted or unsubstituted phenyl group.
  • Y2 is a cyclohexyl group; Or a phenyl group.
  • Z1 is a substituted or unsubstituted phenyl group.
  • Z1 is a phenyl group.
  • Z2 is a substituted or unsubstituted methyl group.
  • Z2 is a methyl group.
  • Chemical Formula 4 may be represented by the following structure, but is not limited thereto.
  • Chemical Formula 5 may be represented by the following structure, but is not limited thereto.
  • Formula 6 may be represented by the following structure, but is not limited thereto.
  • Chemical Formula 7 may be represented by the following structure, but is not limited thereto.
  • the binder resin may be a copolymer including a structure selected from one or more of the structures represented by Chemical Formula 1 and Chemical Formulas 4 to 7.
  • the xanthene dye 0.1% to 30% by weight; 1 to 40% by weight of a binder resin comprising a structure represented by Formula 1; 1 to 40% by weight of the polyfunctional monomer; 0.1 to 10% by weight of the photoinitiator; And it provides a photosensitive resin composition comprising a residual solvent.
  • the weight average molecular weight of the binder resin is 5,000 to 30,000 g / mol. Preferably 5,000 to 20,000 g / mol.
  • the weight average molecular weight is a value obtained by averaging the molecular weights of the molecular weights of the component molecular species of the polymer compound having a molecular weight distribution as one of the average molecular weights in which the molecular weight is not uniform and the molecular weight of a certain polymer material is used as a standard.
  • the weight average molecular weight can be measured through Gel Permeation Chromatography (GPC) analysis.
  • the photosensitive resin composition may further include one selected from the group consisting of pigments and dyes.
  • the photosensitive resin composition may further include at least one of dyes and pigments in addition to the compound of Formula 1 above.
  • the photosensitive resin composition may include only the compound of Formula 1, but may include the compound of Formula 1 and one or more dyes, the compound of Formula 1 and one or more pigments, or of Formula 1 Compounds, one or more dyes, and one or more pigments.
  • the dye may be, but is not limited to, anthraquinone, azapophyrin, azo, triarylmethine, phthalocyanine or dipyrrolopyrrole.
  • the pigment may be a copper phthalocyanine-based blue pigment, or a purple pigment (Pigment violet 23), but is not limited thereto. Specifically, the pigment may be C.I Pigment Blue 15: 6.
  • the binder resin may use a copolymer resin of a polyfunctional monomer that imparts mechanical strength of the membrane and a monomer that imparts alkali solubility, and may further include a binder generally used in the art.
  • Polyfunctional monomers that impart the mechanical strength of the membrane include unsaturated carboxylic acid esters; Aromatic vinyls; Unsaturated ethers; Unsaturated imides; And acid anhydride.
  • unsaturated carboxylic acid esters include benzyl (meth) acrylate, methyl (meth) acrylate, ethyl (meth) acrylate, butyl (meth) acrylate, dimethylaminoethyl (meth) acrylate, and isobutyl ( Meth) acrylate, t-butyl (meth) acrylate, cyclohexyl (meth) acrylate, isobornyl (meth) acrylate, ethylhexyl (meth) acrylate, 2-phenoxyethyl (meth) acrylate, tetra Hydrofuryl (meth) acrylate, hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 2-hydroxy-3-chloropropyl (meth) acrylate, 4-hydroxybutyl ( Meth) acrylate, acyloctyloxy-2-hydroxypropyl (meth) acryl
  • aromatic vinyl monomers include styrene, ⁇ -methylstyrene, (o, m, p) -vinyl toluene, (o, m, p) -methoxy styrene, and (o, m, p) -chloro It may be selected from the group consisting of styrene, but is not limited to these.
  • unsaturated ethers may be selected from the group consisting of vinyl methyl ether, vinyl ethyl ether, and allyl glycidyl ether, but are not limited thereto.
  • unsaturated imides include N-phenyl maleimide, N- (4-chlorophenyl) maleimide, N- (4-hydroxyphenyl) maleimide, and N-cyclohexyl maleimide. It can be, but is not limited to these.
  • Examples of the acid anhydride include maleic anhydride, methyl maleic anhydride, and tetrahydro phthalic anhydride, but are not limited thereto.
  • the monomer that gives the alkali solubility is not particularly limited as long as it contains an acid group, for example, (meth) acrylic acid, crotonic acid, itaconic acid, maleic acid, fumaric acid, monomethyl maleic acid, 5-norbornene-2-carboxylic acid, mono -2-((meth) acryloyloxy) ethyl phthalate, mono-2-((meth) acryloyloxy) ethyl succinate, ⁇ -carboxy polycaprolactone mono (meth) acrylate It is preferable to use one or more, but is not limited to these.
  • an acid group for example, (meth) acrylic acid, crotonic acid, itaconic acid, maleic acid, fumaric acid, monomethyl maleic acid, 5-norbornene-2-carboxylic acid, mono -2-((meth) acryloyloxy) ethyl phthalate, mono-2-((meth) acryloyl
  • the multifunctional monomer may be dipentaerythritol pentaacrylate.
  • the acid value of the binder resin may be 70 to 120 KOH mg / g.
  • the acid value of the binder resin can be measured by titration with a 0.1 N concentration of potassium hydroxide (KOH) methanol solution.
  • 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-based compounds, biimidazole-based compounds, triazine-based compounds, and oxime-based compounds. It may be one or more.
  • the acetophenone-based compounds are 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, benzoinmethyl ether, benzoinethyl ether, benzoinisobutyl 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) phenyl
  • the biimidazole-based compound is 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, etc. , But is not limited to this.
  • the triazine-based compound is 3- ⁇ 4- [2,4-bis (trichloromethyl) -s-triazine-6-yl] phenylthio ⁇ propionic acid, 1,1,1,3,3,3- Hexafluoroisopropyl-3- ⁇ 4- [2,4-bis (trichloromethyl) -s-triazine-6-yl] phenylthio ⁇ propionate, ethyl-2- ⁇ 4- [2,4 -Bis (trichloromethyl) -s-triazine-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-triazine-6-yl] phenylthio
  • the oxime-based compound is 1,2-octadione, -1- (4-phenylthio) phenyl, -2- (o-benzoyloxime) (Shibagai, Shijii124), ethanone, -1- (9 -Ethyl) -6- (2-methylbenzoyl-3-yl)-, 1- (O-acetyloxime) (CG 242), N-1919 (Adeka), and the like.
  • the photoinitiator may be SPI-03 from Samyang.
  • 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 solvent may be propylene glycol monomethyl ether acetate and / or 3-methoxybutyl acetate.
  • the content of the xanthene dye is 0.1 to 30% by weight
  • the content of the binder resin comprising the structure represented by Formula 1 Silver is 1 to 40% by weight
  • the content of the photoinitiator is 0.1 to 10% by weight.
  • the total weight of the solid content means the sum of the total weight of the components excluding the solvent in the photosensitive resin composition.
  • the basis of the solid content and the weight percent based on the solid content of each component can be measured by general analytical means used in the art, such as liquid chromatography or gas chromatography.
  • the photosensitive resin composition is a group consisting of an antioxidant, an adhesion aid, a photocrosslinking agent, a curing accelerator, an adhesion promoter, a surfactant, a thermal polymerization inhibitor, an ultraviolet absorber, an adhesion aid, a dispersant, and a leveling agent It further comprises one or two additives selected from.
  • the additive may be specifically selected from the group consisting of antioxidants, surfactants, and adhesion aids.
  • the photosensitive resin composition may further include a multi-thiol agent.
  • the content of the additive is 0.1% to 20% by weight based on the total weight of solids in the photosensitive resin composition.
  • the photocrosslinking agent 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, 3,3,4,4-tetra (t-butylperoxycarbonyl) benzophenone; Florenone-based compounds, such as 9-Florenone, 2-Croro-9-Prorenone, and 2-methyl-9-Florenone; Thioxanthone series such as thioxanthone, 2,4-diethyl thioxanthone, 2-chloro thioxanthone, 1-chloro-4-propyloxy thioxanthone, isopropyl thioxanthone, and diisopropyl thioxanthone compound; Xanthone compounds
  • the curing accelerator is used to increase 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-mercaptopropionate), penta Erythritol-tetrakis (2-mercaptoacetate), pentaerythritol-tris (2-mercaptoacetate), trimethylolpropane-tris (2-mercaptoacetate), and trimethylolpropane-tris (3-mercaptopropio) Nate) can be used one or more selected from the group consisting of.
  • the adhesive aids may be those commonly used in the art, and in one embodiment, the adhesive aids may be KBM-503.
  • the multi-thiol agent may be used generally used in the art, and in one embodiment, the multi-thiol agent may be PE-01.
  • adhesion promoter examples include metaacryloyloxy propyl trimethoxy silane, methacryloyloxy propyl dimethoxy silane, methacryloyloxy propyl triethoxy silane, and methacryloyloxy propyl dimethoxysilane.
  • silane silane coupling agents can be selected and used, and as the alkyl trimethoxy silane, one or more of octyl trimethoxy silane, dodecyl trimethoxy silane, and octadecyl trimethoxy silane can be used. have.
  • the surfactant is a silicone-based surfactant or a fluorine-based surfactant.
  • the silicone-based surfactant is 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, etc.
  • DIC is a fluorine-based surfactant (DaiNippon Ink & Chemicals) 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-554, 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 surfactant may be a fluorine-based surfactant, specifically, F-554 of DIC Corporation.
  • the antioxidant may be at least one selected from the group consisting of hindered phenol antioxidants, amine antioxidants, thio antioxidants, and phosphine antioxidants, but is not limited thereto.
  • Specific examples of the antioxidant include phosphoric acid-based thermal stabilizers such as phosphoric acid, trimethylphosphate or triethylphosphate; 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-buty
  • the antioxidant may be a hindered phenol-based antioxidant, and specifically, Songnox-1010 of Songwon Industry.
  • UV absorber 2- (3-t-butyl-5-methyl-2-hydroxyphenyl) -5-chloro-benzotriazole, alkoxy benzophenone, etc. may be used, but is not limited thereto, and in the art Anything commonly used 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, pyrogarol, benzoquinone, 4,4-thiobis (3-methyl-6-t-butylphenol), 2,2- Methylene bis (4-methyl-6-t-butylphenol), 2-mercaptoimidazole, and phenothiazine (phenothiazine) may include one or more selected from the group consisting of, but are not limited to these, and the sugar technology These may include those commonly known in the art.
  • the dispersant may be used as a method of internally adding the pigment to the pigment in the form of surface treatment 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-based, ester-based, cationic-based, anionic-based, nonionic-based, and amphoteric surfactants. These may be used individually or in combination of two or more.
  • the dispersant is polyalkylene glycol and esters thereof, polyoxyalkylene polyhydric alcohols, ester alkylene oxide adducts, alcohol alkylene oxide adducts, sulfonic acid esters, sulfonic acid salts, carboxylic acid esters, carboxylic acid salts, There is at least one selected from the group consisting of alkylamide alkylene oxide adducts and alkylamines, but is not limited thereto.
  • the leveling agent may be polymeric or non-polymeric.
  • Specific examples of the leveling agent of the polymer include polyethyleneimine, polyamideamine, amine and epoxide reaction products, and specific examples of the non-polymeric leveling agent include non-polymer sulfur-containing and non-polymer nitrogen-containing Compounds include, but are not limited to, any of those commonly used in the art may be used.
  • One embodiment of the present specification provides a photosensitive material prepared using the photosensitive resin composition.
  • the photosensitive resin composition of the present specification is coated on a substrate by an appropriate method and cured to provide a thin film or patterned photosensitive material.
  • the coating method is not particularly limited, a spray method, a roll coating method, a spin coating method, or the like can be used, and the spin coating method is generally widely used.
  • the residual solvent may be partially removed under reduced pressure.
  • a light source for curing the photosensitive resin composition according to the present specification for example, there is a mercury vapor arc (arc), carbon arc, Xe arc, etc. that emits light having a wavelength of 250 nm to 450 nm, but is not limited thereto.
  • arc mercury vapor arc
  • carbon arc carbon arc
  • Xe arc etc. that emits light having a wavelength of 250 nm to 450 nm, but is not limited thereto.
  • the photosensitive resin composition according to the present specification is a pigment dispersion type photosensitive material for manufacturing a thin film transistor liquid crystal display (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
  • TFT LCD thin film transistor liquid crystal display device
  • PDP photosensitive material for plasma display panel
  • a color filter including the photosensitive material is provided.
  • the color filter may be manufactured by using a photosensitive resin composition including a binder resin including a structure represented by Chemical Formula 1.
  • a 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 substrate may be a glass plate, a silicon wafer, and a plastic-based plate such as polyethersulfone (PES) or polycarbonate (PC), and the type is not particularly limited.
  • PES polyethersulfone
  • PC polycarbonate
  • 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 on a grid called a black matrix can be arranged between color pixels of a color filter for the purpose of improving contrast.
  • Chrome can be used as the material of the black matrix.
  • a method of depositing chromium on the entire glass substrate and forming a pattern by etching may be used.
  • a resin black matrix by a pigment dispersion method capable of fine processing can be used.
  • the black matrix may be a black pigment or black dye as a color material.
  • carbon black may be used alone, or a mixture of carbon black and a coloring pigment may be used.
  • the coloring pigment having insufficient light-shielding property is mixed, the strength of the film or the adhesion to the substrate decreases even when the amount of the coloring material is relatively increased. It has the advantage of not being.
  • One embodiment of the present specification provides a display device including the color filter.
  • the display device includes 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 It may be any one of a liquid crystal display (Thin FIlm Transistor-Liquid Crystal Display, LCD-TFT) and a cathode ray tube (CRT).
  • PDP plasma display panel
  • LED light emitting diode
  • OLED organic light emitting diode
  • LCD liquid crystal display
  • LCD liquid crystal display
  • CRT cathode ray tube
  • benzyl methacrylate 51.75 mol%, N-phenylmaleimide 8.63 mol%, styrene 10.35 mol%, methacrylic acid 29.28 mol% was added, mixed with a solvent, mixed in a nitrogen atmosphere, and heated to 60 ° C.
  • 10 parts by weight of the thermal polymerization initiator V65 (2,2-Azobis (2,4-dimethylvaleronitrile) was added based on the total weight of the solid content of the binder resin to react for 16 hours to prepare a binder resin A.
  • the acid value of the prepared binder resin A was 125 mgKOH / g, and the weight average molecular weight was 8,200.
  • the prepared binder resin A has a structural unit shown below.
  • Binder resin B was prepared in the same manner as in Synthesis Example 2.
  • the acid value of the prepared binder resin B was 85 mgKOH / g, and the weight average molecular weight was 10,700.
  • the produced binder resin B has a structural unit shown below.
  • Binder resin C was prepared by adding 36.49 mol% of styrene, 39.62 mol% of glycidyl methacrylate, 18.80 mol% of methacrylate, and 5.10 mol% of benzophenone methacrylate in the same manner as in Synthesis Example 2.
  • the acid value of the prepared binder resin C was 88 mgKOH / g, and the weight average molecular weight was 8,300.
  • the prepared binder resin C has a structural unit shown below.
  • Binder resin D was prepared by adding 29.87 mol% of styrene, 40.00 mol% of glycidyl methacrylate, 20.02 mol% of methacrylate, and 10.12 mol% of benzophenone methacrylate in the same manner as in Synthesis Example 2.
  • the acid value of the prepared binder resin D was 88 mgKOH / g, and the weight average molecular weight was 9,200.
  • the prepared binder resin D has the same structural unit as the binder resin C.
  • Binder resin E was prepared by adding 36.49 mol% of styrene, 36.92 mol% of glycidyl methacrylate, 18.80 mol% of methacrylate, and 5.10 mol% of N- (4-benzoylphenyl) methacrylamide and preparing in the same manner as in Synthesis Example 2. It was prepared.
  • the acid value of the prepared binder resin E was 78 mgKOH / g, and the weight average molecular weight was 7,900.
  • the prepared binder resin E has a structural unit shown below.
  • Binder resin F was prepared by adding 36.49 mol% of styrene, 36.92 mol% of cyclohexyl methacrylate, 18.80 mol% of methacrylate, and 5.10 mol% of benzophenone methacrylate in the same manner as in Synthesis Example 2.
  • the acid value of the prepared binder resin F was 82 mgKOH / g, and the weight average molecular weight was 8,500.
  • the produced binder resin F has a structural unit shown below.
  • Photosensitive resin compositions of Comparative Examples 2 to 4 and Examples 1 to 4 were prepared with the same components and contents as those described in Table 1 above, except that the types and contents of the binder resin and the photoinitiator were applied as described in Table 2 below.
  • Binder resin Photoinitiator (% by weight) Comparative Example 2 B SPI-03 (1.30) - Comparative Example 3 A SPI-03 (1.00) Benzophenone methacrylate (0.30) Comparative Example 4 A SPI-03 (1.00) N- (4-benzoylphenyl) methacrylamide (0.30) Example 1 C SPI-03 (1.30) - Example 2 D SPI-03 (1.30) - Example 3 E SPI-03 (1.30) - Example 4 F SPI-03 (1.30) -
  • the photosensitive resin compositions prepared by Examples 1 to 4 and Comparative Examples 1 to 4 were spin coated on glass (5 cm X 5 cm) and preheated at 110 ° C. for 70 seconds to form a film. After exposing the film to an energy of 40 mJ / cm 2 under a high pressure mercury lamp using a photomask, the pattern was developed using an aqueous solution of KOH alkali and washed with distilled water. After distilled water was removed, a post-heat treatment was performed at 230 ° C for 20 minutes to obtain a color pattern.
  • the post-heat-treated substrate was further treated at 230 ° C for 120 minutes to obtain a transmittance spectrum in the same measuring range as the same equipment.
  • ⁇ Eab heat resistance
  • a small ⁇ Eab value means little color change, indicating excellent heat resistance.
  • the substrate which had been subjected to one post-heat treatment, was cut to 1 cm X 5 cm, and absorption spectra of a wavelength range of 380 to 780 nm were measured using a spectrometer (MCPD, Otsuka Co.).
  • ⁇ Eab (chemical resistance) is shown in Table 3 below by calculating the above [Calculation Formula 1] as a spectrum before and after immersion.
  • a small ⁇ Eab value means that there is little color change, indicating excellent chemical resistance.

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PCT/KR2019/016119 2018-11-23 2019-11-22 감광성 수지 조성물, 감광재, 컬러필터 및 디스플레이 장치 WO2020106095A1 (ko)

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