Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
  • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
  • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
• • G—PHYSICS
  • G02—OPTICS
  • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
  • G02B5/00—Optical elements other than lenses
  • G02B5/20—Filters
• • G—PHYSICS
  • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
  • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
  • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
• • G—PHYSICS
  • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
  • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
  • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
  • G03F7/0005—Production of optical devices or components in so far as characterised by the lithographic processes or materials used therefor
  • G03F7/0007—Filters, e.g. additive colour filters; Components for display devices
• • G—PHYSICS
  • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
  • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
  • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
  • G03F7/004—Photosensitive materials
• • 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
  • G03F7/0045—Photosensitive materials with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors
• • 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

Definitions

• the present specification relates to a quinophthalone-based compound and a photosensitive resin composition including the same.
• the present specification relates to a photosensitive material manufactured using the photosensitive resin composition, a color filter, and a display device including the same.
• the performance of the color filter characterized by high brightness and high contrast ratio has been demanded.
• one of the main purposes of the display device development is to differentiate the display device performance through the improvement of color purity and to improve the productivity in the manufacturing process.
• the pigment type conventionally used as the color material of the color filter exists in the color photoresist in the state of particle dispersion, it is difficult to control the brightness and contrast ratio according to the pigment particle size and distribution control.
• the light particles are aggregated in the color filter, resulting in poor dissolution and dispersibility, and multiple scattering of light occurs due to the aggregation of large particles.
• the scattering of the polarized light has been pointed out as a main factor for lowering the contrast ratio.
• Efforts have been made to improve the luminance and contrast ratio through ultrafine atomization and dispersion stabilization of pigments, but the degree of freedom in selecting colorants to implement color coordinates for high color purity display devices is limited.
• the pigment dispersion method using the already developed color material especially pigment has reached the limit to improve the color purity, brightness and contrast ratio of the color filter using the same.
• the present inventors provide a quinophthalone compound having a novel structure, a photosensitive resin composition comprising the same, a photosensitive material prepared using the same, a color filter, and a display device including the same.
• An exemplary embodiment of the present specification provides a compound represented by the following formula (1).
• At least one of R1 and R3 is represented by the following formula (2) or formula (3),
• X is O; Or NH,
• L is a substituted or unsubstituted alkylene group; Substituted or unsubstituted heteroalkylene group; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
• M is a direct bond; Substituted or unsubstituted alkylene group; Substituted or unsubstituted heteroalkylene group; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group; Or a dianhydride group containing a substituted or unsubstituted divalent nitrogen atom,
• R1 and R3, which are not the above Formula 2 or 3, R4, R41 and R42 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxyl group; -COR; -COOR; Imide group; Amide group; Anionic group; Sulfonic acid groups; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted cycloalkenyl group; Substituted or unsubstituted sulfonate group; Substituted or unsubstituted amine group; Substituted or unsubstituted aryl group; Substituted or unsubstituted heteroaryl group; And it is selected from the group
• R is hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Or a substituted or unsubstituted aryl group,
• r1 and r3 are integers of 1 to 4, and when r1 and r2 are 2 or more, the structures in parentheses () are the same or different,
• r4 is an integer of 0 to 4, when r4 is 2 or more, R4 is the same or different,
• r2 is an integer from 0 to 2, when r2 is 2, R2 is the same or different,
• r41 and r42 are integers of 0-3, and when r41 and r42 are two or more, the structure in parentheses () is the same or different.
• the compound represented by Formula 1 is represented by Formula 1; Binder resins; Polyfunctional monomers; Photoinitiators; And it provides a photosensitive resin composition comprising a solvent.
• An exemplary embodiment of the present specification provides a photosensitive material manufactured using the photosensitive resin composition.
• An exemplary embodiment of the present specification provides a color filter including the photosensitive material.
• An exemplary embodiment of the present specification provides a display device including the color filter.
• the compound according to one embodiment of the present specification may be used as a colorant in the photosensitive resin composition, and may have a good solubility in organic solvents, thereby reducing the dispersing process.
• the compound can be used as colorant in an economical way.
• the quinophthalone-based compound represented by Formula 1 may be used as a color material to improve color reproduction, brightness, and contrast ratio.
• An exemplary embodiment of the present specification includes a compound represented by Chemical Formula 1, thereby having excellent solubility in organic solvents. Specifically, since Formula 1 includes a phthalimide linked with an ester group (-COOR), solubility is increased.
• Formula 1 includes a phthalimide linked with an ester group (-COOR), solubility is increased.
• the term "substituted or unsubstituted” is deuterium; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Carboxy group; Imide group; Amide group; Anionic group; An alkoxy group; An alkyl group; Cycloalkyl group; Alkenyl groups; Cycloalkenyl group; Sulfonate groups; Amine group; Aryl group; Heteroaryl group; Silyl groups; Alkyl sulfoxy groups; Aryl sulfoxy group; Boron group; Acryloyl group; Acrylate group; Ether group; It means that it is substituted with one or more substituents selected from the group comprising an anionic group and a heterocyclic group containing one or more of N, O, S or P atoms or have no substituents.
• adjacent means a substituent substituted on an atom directly connected to an atom to which the substituent is substituted, a substituent positioned closest to the substituent, or another substituent substituted on an atom to which the substituent is substituted.
• two substituents substituted at the ortho position in the benzene ring and two substituents substituted at the same carbon in the aliphatic ring may be interpreted as "adjacent" groups.
• the ring refers to an aromatic or aliphatic ring in that adjacent groups can combine to form a “ring”.
• the ring may be an aromatic ring, it may be an aryl group or a heteroaryl group. The following description may be applied to the aryl group and heteroaryl group.
• the ring may be an aliphatic ring, the aliphatic ring means a ring that is not an aromatic ring.
• examples of the halogen group include fluorine, chlorine, bromine or iodine.
• the carbonyl group may be represented by -COR ', wherein R' is hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Or a substituted or unsubstituted aryl group.
• R' is hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Or a substituted or unsubstituted aryl group.
• carbon number of the said carbonyl group is not specifically limited, It is preferable that it is C1-C30. Specifically, it may be a compound having a structure as follows, but is not limited thereto.
• the ester group may be represented by -COOR '', wherein R '' is hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Or a substituted or unsubstituted aryl group.
• the ester group may be substituted with oxygen of the ester group having 1 to 25 carbon atoms, a linear, branched or cyclic alkyl group or an aryl group having 6 to 30 carbon atoms. Specifically, it may be a compound of the following structural formula, but is not limited thereto.
• carbon number of an imide group is not specifically limited, It is preferable that it is C1-C30. Specifically, it may be a compound having a structure as follows, but is not limited thereto.
• the amide group may be substituted with nitrogen of the amide group is hydrogen, a linear, branched or cyclic alkyl group having 1 to 30 carbon atoms or an aryl group having 6 to 30 carbon atoms. Specifically, it may be a compound of the following structural formula, but is not limited thereto.
• the anionic group has a chemical bond with the structure of Chemical Formula 1, and the anionic group is not particularly limited, for example, US Patent No. 7,939,644, Japanese Patent Application Laid-Open No. 2006-003080, Japanese Patent Application Laid-Open No. 2006-001917, Japanese Patent Laid-Open No. 2005-159926, Japanese Patent Laid-Open No. 2007-7028897, Japanese Patent Laid-Open No. 2005-071680, Korean Patent Application Laid-Open No. 2007-7000693, Japanese Patent Laid-Open No. 2005-111696, Japanese Patent Laid-Open No. 2008-249663, Japan
• the anions described in JP 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 per se, or may exist in complex form with other cations. Therefore, the sum of the total charge of the compound molecules of the present invention may vary depending on the number of substituted anionic groups. Since the cation is contained in one of the amine groups of the compound of the present invention, the sum of the total charge of the molecules may have a value ranging from 0 to 0 by an amount minus 1 from the number of substituted anionic groups.
• the sulfonic acid group is -SO 3 H.
• the alkoxy group may be linear or branched, and the number of carbon atoms is not particularly limited, but may be 1 to 30, specifically 1 to 20, and more specifically 1 to 10.
• the alkyl group may be linear or branched chain, carbon number is not particularly limited, but is preferably 1 to 60. According to an exemplary embodiment, the alkyl group has 1 to 30 carbon atoms. 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.
• the alkyl group examples include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, tert-butyl group, n-pentyl group, n-hexyl group, n-heptyl group and n-jade And the like, but are not limited thereto.
• the cycloalkyl group is not particularly limited, but preferably has 3 to 30 carbon atoms, and particularly preferably cyclopentyl group and cyclohexyl group, but is not limited thereto. .
• the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and according to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group and the like, but is not limited thereto.
• the alkenyl group may be linear or branched chain, carbon number is not particularly limited, but is preferably 2 to 60. According to an exemplary embodiment, the alkyl group has 2 to 30 carbon atoms. According to another exemplary embodiment, the alkyl group has 2 to 20 carbon atoms. According to another exemplary embodiment, the alkyl group has 2 to 10 carbon atoms. Specific examples of the alkenyl group include, but are not limited to, alkenyl groups substituted with aryl groups such as stylbenyl and styrenyl groups.
• the cycloalkenyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and according to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 6 carbon atoms.
• Examples of the cycloalkenyl group include, but are not limited to, a cyclopentenylene group and a cyclohexenylene group.
• the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to an exemplary embodiment, the aryl group has 6 to 30 carbon atoms. According to an exemplary embodiment, the aryl group has 6 to 20 carbon atoms.
• the aryl group may be a monocyclic aryl group, but may be a phenyl group, a biphenyl group, a terphenyl group, etc., but is not limited thereto.
• the polycyclic aryl group may be naphthyl group, anthracenyl group, indenyl group, phenanthrenyl group, pyrenyl group, perrylenyl group, triphenyl group, chrysenyl group, fluorenyl group and the like, but is not limited thereto.
• the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure.
• Spirofluorenyl groups such as (9,9-dimethylfluorenyl group
• Substituted fluorenyl groups such as (9,9-diphenylfluorenyl group
• the present invention is not limited thereto.
• the heterocyclic group is a heterocyclic group containing O, N or S as a hetero atom, and the carbon number is not particularly limited, but is 2 to 30 carbon atoms, specifically 2 to 20 carbon atoms.
• the heterocyclic group include thiophene group, furan group, pyrrole group, imidazole group, thiazole group, oxazole group, oxadiazole group, triazole group, pyridyl group, bipyridyl group, triazine group, acridil group, pyridazine group , Quinolinyl group, isoquinoline group, indole group, carbazole group, benzoxazole group, benzoimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuranyl group, dibenzofuran And the like, but are not limited thereto.
• heterocyclic group may be applied except that the heteroaryl group is aromatic.
• the silyl group may be represented by a chemical formula of -SiY1Y2Y3, wherein Y1, Y2 and Y3 are each hydrogen; Substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group.
• Specific examples of the silyl group include trimethylsilyl group (TMS), triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, and phenylsilyl group. It is not limited to this.
• the alkyl sulfoxy group includes methyl sulfoxy group, ethyl sulfoxy group, propyl sulfoxy group, butyl sulfoxy group, and the like, but is not limited thereto.
• the alkyl group in the alkyl sulfoxy group may be applied to the description of the alkyl group described above.
• aryl sulfoxy groups include, but are not limited to, benzene sulfoxy groups, p-toluene sulfoxy groups, and the like.
• the aryl group in the aryl sulfoxy group may be described for the aforementioned aryl group.
• the boron group may be represented by a chemical formula of -BY 4 Y 5, wherein Y 4 and Y 5 are each hydrogen; Substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group.
• the boron group may include, but is not limited to, trimethylboron group, triethylboron group, t-butyldimethylboron group, triphenylboron group, and phenylboron group.
• the acryloyl group means a photopolymerizable unsaturated group, and for example, (meth) acryloyl group may be mentioned, but is not limited thereto.
• the acrylate group refers to a photopolymerizable unsaturated group, and examples thereof include (meth) acrylate groups, but are not limited thereto.
• (meth) acryloyl represents at least 1 sort (s) chosen from the group which consists of acryloyl and methacryloyl.
• the description of '(meth) acrylate' also has the same meaning.
• the ether group may be represented by -COR '' '.
• R '' ' is a substituted or unsubstituted alkyl group.
• the alkyl group may be applied to the description of the alkyl group described above.
• the sulfonate group may be an alkylsulfonate group, a cycloalkylsulfonate group or an arylsulfonate group.
• the description of the alkyl group described above may be applied to 'alkyl', the description of the cycloalkyl group described above may be applied to the 'alkyl', and the description of the aforementioned aryl group may be applied to the 'aryl'.
• the sulfonate group may be represented by the following Chemical Formula S, but is not limited thereto.
• A is a substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Or a substituted or unsubstituted aryl group.
• the amine group is -NH 2 ; Alkylamine group; N-alkylarylamine group; Arylamine group; N-aryl heteroaryl amine group; It may be selected from the group consisting of an N-alkylheteroarylamine group and a heteroarylamine group, and carbon number is not particularly limited, but is preferably 1 to 30.
• Specific examples of the amine group include methylamine group, dimethylamine group, ethylamine group, diethylamine group, phenylamine group, naphthylamine group, biphenylamine group, anthracenylamine group, and 9-methyl-anthracenylamine group.
• Diphenylamine group N-phenylnaphthylamine group, ditolylamine group, N-phenyltolylamine group, triphenylamine group, N-phenylbiphenylamine group; N-phenylnaphthylamine group; N-biphenyl naphthylamine group; N-naphthylfluorenylamine group; N-phenylphenanthrenylamine group; N-biphenylphenanthrenylamine group; N-phenyl fluorenyl amine group; N-phenylterphenylamine group; N-phenanthrenyl fluorenyl amine group; N-biphenyl fluorenyl amine group and the like, but is not limited thereto.
• the carbon number of the dianhydride group including the nitrogen atom is not particularly limited, but may be 4 to 30, specifically 4 to 20, and more specifically 4 to 15.
• the dianhydride group including the nitrogen atom may be represented by the following Chemical Formula N or Chemical Formula M, but is not limited thereto.
• Independently hydrogen; heavy hydrogen; N; Or S, or adjacent groups combine with each other to form a ring
• Z1 to Z3 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group, or adjacent groups may combine with each other to form a ring.
• the dianhydride group including the substituted or unsubstituted divalent nitrogen atom may be applied to the description of the aforementioned dianhydride group including the nitrogen atom, except that the dianhydride group is divalent.
• an alkylene group means that there are two bonding positions in an alkane.
• the alkylene group may be straight, branched or cyclic.
• carbon number of an alkylene group is not specifically limited, For example, it is C1-C30, Specifically, 1-20, More specifically, it is 1-10.
• the heteroalkylene group means that there are two bonding positions in an alkane including O, N or S as a hetero atom.
• the heteroalkylene group may be linear, branched or cyclic.
• carbon number of a heteroalkylene group is not specifically limited, For example, it is C2-C30, Specifically, it is C2-C20, More specifically, it is C2-C10.
• the arylene group refers to a divalent group having two bonding positions in the aryl group.
• the description of the aforementioned aryl group can be applied except that they are each divalent.
• the heteroarylene group means a divalent group having two bonding positions in the heteroaryl group.
• the description of the aforementioned heteroaryl group can be applied except that they are each divalent.
• X is O; Or NH.
• X is O.
• X is NH
• L in Chemical Formula 1 is a substituted or unsubstituted C 1-30 alkylene group; A substituted or unsubstituted heteroalkylene group having 2 to 30 carbon atoms; A substituted or unsubstituted arylene group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms.
• L in Chemical Formula 1 is a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms; Substituted or unsubstituted C2-C20 heteroalkylene group; A substituted or unsubstituted arylene group having 6 to 20 carbon atoms; Or a substituted or unsubstituted heteroarylene group having 2 to 20 carbon atoms.
• L in Chemical Formula 1 is a substituted or unsubstituted linear or branched alkylene group having 1 to 30 carbon atoms.
• L in Chemical Formula 1 is a substituted or unsubstituted linear or branched alkylene group having 1 to 20 carbon atoms.
• L in Chemical Formula 1 is a substituted or unsubstituted linear or branched alkylene group having 1 to 10 carbon atoms.
• L in Chemical Formula 1 is a substituted or unsubstituted alkylene group having 1 to 30 carbon atoms.
• L in Chemical Formula 1 is a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms.
• L in Chemical Formula 1 is a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms.
• L in Chemical Formula 1 is a substituted or unsubstituted propylene group.
• L in Chemical Formula 1 is a propylene group.
• M of Chemical Formula 1 is a direct bond; Substituted or unsubstituted alkylene group; Substituted or unsubstituted heteroalkylene group; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group; Or a dianhydride group containing a substituted or unsubstituted divalent nitrogen atom.
• M of Chemical Formula 1 is a direct bond; Or a dianhydride group containing a substituted or unsubstituted divalent nitrogen atom.
• M in Chemical Formula 1 is a direct bond.
• M in Formula 1 is a dianhydride group including a substituted or unsubstituted divalent nitrogen atom.
• M in Formula 1 is a dianhydride group containing a divalent nitrogen atom.
• M in Chemical Formula 1 may be represented by the following chemical formula.
• M in Chemical Formula 1 may be represented by the following chemical formula.
• At least one of R1 and R3 of Formula 1 is represented by Formula 2 or Formula 3.
• R1 of Chemical Formula 1 is represented by Chemical Formula 2 or Chemical Formula 3.
• R1 of Chemical Formula 1 is represented by Chemical Formula 2.
• R1 of Chemical Formula 1 is represented by Chemical Formula 2.
• R1 of the general formula (1) other than the general formula (2) or the general formula (3) is hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxyl group; -COR; -COOR; Imide group; Amide group; Anionic group; Sulfonic acid groups; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted cycloalkenyl group; Substituted or unsubstituted sulfonate group; Substituted or unsubstituted amine group; Substituted or unsubstituted aryl group; Substituted or unsubstituted heteroaryl group; And a dianhydride group including
• R1 of Chemical Formula 1 is not one of Chemical Formula 2 or Chemical Formula 3, which includes hydrogen; Halogen group; Nitro group; Hydroxyl group; -COOR; Or a substituted or unsubstituted alkyl group, or adjacent R1's may combine with each other to form a ring, wherein R is hydrogen; Or a substituted or unsubstituted alkyl group.
• R1 of Chemical Formula 1 is not one of Chemical Formula 2 or Chemical Formula 3, which includes hydrogen; Halogen group; Nitro group; Hydroxyl group; -COOR; Or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or adjacent R 1 may be bonded to each other to form an aromatic ring, wherein R is hydrogen; Or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.
• R1 of Chemical Formula 1 is not one of Chemical Formula 2 or Chemical Formula 3, which includes hydrogen; Halogen group; Nitro group; Hydroxyl group; -COOR; Or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or adjacent R1's may combine with each other to form an aromatic ring, wherein R is hydrogen; Or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.
• R1 of Chemical Formula 1 is not one of Chemical Formula 2 or Chemical Formula 3, which includes hydrogen; Halogen group; Nitro group; Hydroxyl group; -COOR; Or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or adjacent R1 may combine with each other to form an aromatic ring, wherein R is hydrogen; Or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.
• R1 of Chemical Formula 1 is not one of Chemical Formula 2 or Chemical Formula 3, which includes hydrogen; F; Cl; Br; Nitro group; Hydroxyl group; -COOR; Or a substituted or unsubstituted tert-butyl group, or adjacent R1's may combine with each other to form a substituted or unsubstituted benzene ring, wherein R is hydrogen; Or a substituted or unsubstituted methyl group.
• R1 of Chemical Formula 1 is not one of Chemical Formula 2 or Chemical Formula 3, which includes hydrogen; F; Cl; Br; Nitro group; Hydroxyl group; -COOR; Or a tert-butyl group, or adjacent R1's combine with each other to form a halogen group; Nitro group; Or a benzene ring unsubstituted or substituted with a sulfonic acid group, wherein R is hydrogen; Or methyl group.
• R1 of Chemical Formula 1 is not one of Chemical Formula 2 or Chemical Formula 3, which includes hydrogen; F; Cl; Br; Nitro group; Hydroxyl group; -COOR; Or a tert-butyl group, or adjacent R1 are bonded to each other to Br; Nitro group; Or a benzene ring unsubstituted or substituted with a sulfonic acid group, wherein R is hydrogen; Or methyl group.
• R2 is hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxyl group; -COR; -COOR; Imide group; Amide group; Anionic group; Sulfonic acid groups; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted cycloalkenyl group; Substituted or unsubstituted sulfonate group; Substituted or unsubstituted amine group; Substituted or unsubstituted aryl group; Substituted or unsubstituted heteroaryl group; And a dianhydride group including a substituted or unsubstituted nitrogen atom, adjacent R
• R2 is hydrogen; Or deuterium.
• R2 is hydrogen
• R3 of Chemical Formula 1 is represented by Chemical Formula 2 or Chemical Formula 3.
• R3 of Chemical Formula 1 is represented by Chemical Formula 2.
• R3 of Chemical Formula 1 is represented by Chemical Formula 3.
• R3 of Chemical Formula 1 which is not the Chemical Formula 2 or the Chemical Formula 3, is hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxyl group; -COR; -COOR; Imide group; Amide group; Anionic group; Sulfonic acid groups; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted cycloalkenyl group; Substituted or unsubstituted sulfonate group; Substituted or unsubstituted amine group; Substituted or unsubstituted aryl group; Substituted or unsubstituted heteroaryl group; And it is selected from the group consist
• R is hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Or a substituted or unsubstituted aryl group.
• R3 of Chemical Formula 1, which is not Chemical Formula 2 or Chemical Formula 3, is hydrogen; Substituted or unsubstituted sulfonate group; Substituted or unsubstituted aryl group; Dianhydride groups containing nitrogen atoms; Or adjacent R 3 may combine with each other to form a ring.
• R3 of Chemical Formula 1, which is not Chemical Formula 2 or Chemical Formula 3, is hydrogen; Substituted or unsubstituted sulfonate group; Substituted or unsubstituted aryl group; Dianhydride groups containing nitrogen atoms; Or adjacent R 3 may combine with each other to form a ring.
• R3 of Chemical Formula 1, which is not Chemical Formula 2 or Chemical Formula 3, is hydrogen; Substituted or unsubstituted arylsulfonate group having 6 to 30 carbon atoms; Substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a dianhydride group containing a nitrogen atom, or adjacent R3 may combine with each other to form an aromatic ring.
• R3 of Chemical Formula 1, which is not Chemical Formula 2 or Chemical Formula 3, is hydrogen; Substituted or unsubstituted arylsulfonate group having 6 to 20 carbon atoms; Substituted or unsubstituted aryl group having 6 to 20 carbon atoms; Or a dianhydride group containing a nitrogen atom, or adjacent R3 may combine with each other to form an aromatic ring.
• R3 of Chemical Formula 1, which is not Chemical Formula 2 or Chemical Formula 3, is hydrogen; Substituted or unsubstituted arylsulfonate group having 6 to 10 carbon atoms; Phenyl group; Or a dianhydride group containing a nitrogen atom, or adjacent R3 are bonded to each other to form a benzene ring; Or a pyridine ring.
• one of R3 of Chemical Formula 1 that is not Chemical Formula 2 or Chemical Formula 3 is hydrogen.
• R3 of Chemical Formula 1, which is not the Chemical Formula 2 or the Chemical Formula 3, is a substituted or unsubstituted arylsulfonate group, and the substituted or unsubstituted arylsulfonate group is represented by the following Chemical Formula S: Can be displayed.
• A is a substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Or a substituted or unsubstituted aryl group.
• a of Formula S is a substituted or unsubstituted aryl group.
• a of Formula S is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
• a of Formula S is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.
• a of Formula S is a substituted or unsubstituted phenyl group; Or a substituted or unsubstituted naphthyl group.
• a of Formula S is a phenyl group; Or a naphthyl group.
• Chemical Formula S may be represented by any one of the following Chemical Formulas.
• R3 of Chemical Formula 1, which is not Chemical Formula 2 or Chemical Formula 3, is a phenyl group.
• R3 of Chemical Formula 1, which is not Chemical Formula 2 or Chemical Formula 3, is a dianhydride group including a nitrogen atom, and the dianhydride group including the nitrogen atom is represented by Formula N or Formula M below It may be indicated by.
• Independently hydrogen; heavy hydrogen; N; Or S, or adjacent groups combine with each other to form a ring
• Z1 to Z3 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group, or adjacent groups may combine with each other to form a ring.
• Z1 to Z3 of the formula M are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or adjacent groups may be bonded to each other to form an aromatic ring.
• Z1 to Z3 of the formula M are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or adjacent groups may be bonded to each other to form an aromatic ring.
• Z1 to Z3 of the general formula M may each independently combine with an adjacent group to form an aromatic ring.
• Z1 and Z2 of Formula M may be bonded to each other to form an aromatic ring, and Z2 and Z3 may be bonded to each other to form an aromatic ring.
• Z1 and Z2 of Formula M may be combined with each other to form a substituted or unsubstituted benzene ring, and Z2 and Z3 may be combined with each other to form a substituted or unsubstituted benzene ring.
• Z1 and Z2 of Formula M may be bonded to each other to form a benzene ring, and Z2 and Z3 may be bonded to each other to form a benzene ring.
• Chemical Formula N may be represented by any one of the following Chemical Formulas.
• N1 to N18 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxyl group; -COR; -COOR; Imide group; Amide group; Anionic group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted cycloalkenyl group; Substituted or unsubstituted sulfonate group; Substituted or unsubstituted amine group; Substituted or unsubstituted aryl group; Substituted or unsubstituted heteroaryl group; And it is selected from the group consisting of a dianhydride group containing a substituted or unsub
• R is hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Or a substituted or unsubstituted aryl group,
• n1 is an integer from 0 to 4
• n2 is an integer from 0 to 2
• n3 is an integer from 0 to 4
• n8 is an integer from 0 to 8
• n9 is an integer from 0 to 4
• n10 is an integer from 0 to 4
• n11 is N12 is an integer of 0 to 2
• n12 is an integer of 0 to 5
• n13 is an integer of 0 to 2
• n14 is an integer of 0 to 2
• n15 is an integer of 0 to 4
• n16 is an integer of 0 to 4
• n17 is 0 to An integer of 3
• n18 is an integer of 0 to 3
• n1-n18 is two or more, the structure in parentheses () is the same or different.
• N1 to N18 are hydrogen.
• Chemical Formula M may be represented by the following Chemical Formula M-1.
• N19 and N20 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxyl group; -COR; -COOR; Imide group; Amide group; Anionic group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted cycloalkenyl group; Substituted or unsubstituted sulfonate group; Substituted or unsubstituted amine group; Substituted or unsubstituted aryl group; Substituted or unsubstituted heteroaryl group; And it is selected from the group consisting of a dianhydride group containing a substituted or unsub
• R is hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Or a substituted or unsubstituted aryl group,
• n19 and n20 are the same as or different from each other, each independently represent an integer of 0 to 3, and when n19 and n20 are 2 or more, the structures in parentheses () are the same or different.
• N19 and N20 of Formula M-1 are hydrogen.
• R4 is hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxyl group; -COR; -COOR; Imide group; Amide group; Anionic group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted cycloalkenyl group; Substituted or unsubstituted sulfonate group; Substituted or unsubstituted amine group; Substituted or unsubstituted aryl group; Substituted or unsubstituted heteroaryl group; And it is selected from the group consisting of a dianhydride group containing a substituted or unsubstituted nitrogen atom
• R is hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Or a substituted or unsubstituted aryl group.
• R4 is hydrogen, or adjacent groups may combine with each other to form a ring.
• R4 is hydrogen, or adjacent groups may combine with each other to form an aromatic ring.
• R4 is hydrogen, or adjacent groups may combine with each other to form a substituted or unsubstituted benzene ring.
• R4 is hydrogen, or adjacent groups may combine with each other to form a benzene ring.
• the R41 and R42 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxyl group; -COR; -COOR; Imide group; Amide group; Anionic group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted cycloalkenyl group; Substituted or unsubstituted sulfonate group; Substituted or unsubstituted amine group; Substituted or unsubstituted aryl group; Substituted or unsubstituted heteroaryl group; And it is selected from the group consisting of a dianhydride group
• R is hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Or a substituted or unsubstituted aryl group.
• R41 and R42 are hydrogen.
• r1 is an integer of 1 to 4.
• r2 is an integer of 0 to 2.
• r3 is an integer of 1 to 4.
• r4 is an integer of 0 to 4.
• Chemical Formula 1 may be represented by the following structures, the following structures represent an isomer of Formula 1, wherein Formula 1 represents a representative structure.
• Isomers refer to molecules having the same molecular formula but different physical / chemical properties.
• R1 to R3 and r1 to r3 are as described above.
• Chemical Formula 1 may be represented by the following Chemical Formula 4 or Chemical Formula 5.
• R2 to R4, R41, R42, L, M, r2 to r4, r41 and r42 are the same as defined in Formula 1,
• R 5 is hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxyl group; -COR; -COOR; Imide group; Amide group; Anionic group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted cycloalkenyl group; Substituted or unsubstituted sulfonate group; Substituted or unsubstituted amine group; Substituted or unsubstituted aryl group; And it is selected from the group consisting of a substituted or unsubstituted heteroaryl group,
• R is hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Or a substituted or unsubstituted aryl group,
• r5 is an integer of 0-3, and when r5 is two or more, R5 is same or different from each other.
• R5 is hydrogen; Or deuterium.
• R5 is hydrogen
• Chemical Formula 1 may be represented by the following Chemical Formula 6 or Chemical Formula 7.
• R1, R2, R4, R41, R42 L, M, r1, r2, r4, r41 and r42 are the same as defined in Formula 1,
• R6 is hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxyl group; -COR; -COOR; Imide group; Amide group; Anionic group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted cycloalkenyl group; Substituted or unsubstituted sulfonate group; Substituted or unsubstituted amine group; Substituted or unsubstituted aryl group; And it is selected from the group consisting of a substituted or unsubstituted heteroaryl group,
• R is hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Or a substituted or unsubstituted aryl group,
• r6 is an integer of 0 to 3, and when r6 is 2 or more, R6 is the same as or different from each other.
• R6 is hydrogen; Or deuterium.
• R6 is hydrogen
• Chemical Formula 1 may be represented by the following Chemical Formula 4-1 or Chemical Formula 5-1.
• R2 to R5, R41, R42 L, M, r2 to r5, r41 and r42 are the same as defined in Chemical Formulas 4 and 5.
• Chemical Formula 1 may be represented by the following Chemical Formula 6-1 or Chemical Formula 7-1.
• R1, R2, R4, R6, R41, R42 L, M, r1, r2, r4, r6, r41 and r42 are the same as defined in Chemical Formulas 6 and 7.
• Chemical Formula 1 may be represented by the following Chemical Formula 1-1.
• R1 to R3, r1, and r2 are as defined in Formula 1,
• R31 is hydrogen; heavy hydrogen; Substituted or unsubstituted sulfonate group; Or a dianhydride group containing a substituted or unsubstituted nitrogen atom,
• r3-1 is an integer of 0-3, and when r3-1 is two or more, R3 is the same or different.
• a dianhydride group including a substituted or unsubstituted sulfonate group and a substituted or unsubstituted nitrogen atom is as described above.
• At least one of R3 is hydrogen; It may be represented by the formula (S), (N) or (M).
• Chemical Formula S Chemical Formula N and Chemical Formula M, Represents a site linked to the formula (1)
• A is a substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Or a substituted or unsubstituted aryl group,
• R 11 and R 12 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; N; Or S, or adjacent groups combine with each other to form a ring,
• Z1 to Z3 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group, or adjacent groups may combine with each other to form a ring.
• Chemical Formula 1 may be represented by any one of the following Chemical Formulas, but is not necessarily limited thereto.
• an exemplary embodiment of the present specification provides a color material composition including the compound represented by Chemical Formula 1.
• the color material composition may further include at least one of dyes and pigments in addition to the compound of Formula 1.
• the colorant composition may include only the compound of Formula 1, but may include the compound of Formula 1 and one or more dyes, or may include the compound of Formula 1 and one or more pigments, or the compound of Formula 1 And at least one dye and at least one pigment.
• One embodiment of the present specification provides a photosensitive resin composition comprising the color material composition.
• An exemplary embodiment of the present specification is a compound represented by Formula 1; Binder resins; Polyfunctional monomers; Photoinitiators; And it provides a photosensitive resin composition comprising a solvent.
• the binder resin is not particularly limited as long as it can exhibit physical properties such as strength, developability, and the like of the film made of the photosensitive resin composition.
• the binder resin may use a copolymer resin of a polyfunctional monomer imparting mechanical strength and a monomer imparting alkali solubility, and may further include a binder generally used in the art.
• Polyfunctional monomers to impart the mechanical strength of the membrane include unsaturated carboxylic acid esters; Aromatic vinyls; Unsaturated ethers; Unsaturated imides; And acid anhydrides.
• unsaturated carboxylic acid esters include benzyl (meth) acrylate, methyl (meth) acrylate, ethyl (meth) acrylate, butyl (meth) acrylate, dimethylaminoethyl (meth) acrylate, and isobutyl ( Meta) acrylate, t-butyl (meth) acrylate, cyclohexyl (meth) acrylate, isobornyl (meth) acrylate, ethylhexyl (meth) acrylate, 2-phenoxyethyl (meth) acrylate, tetra Hydroperpril (meth) acrylate, hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 2-hydroxy-3-chloropropyl (meth) acrylate, 4-hydroxybutyl ( Meth) acrylate, acyloctyloxy-2-hydroxypropyl (meth) acrylate
• aromatic vinyls include styrene, ⁇ -methylstyrene, (o, m, p) -vinyl toluene, (o, m, p) -methoxy styrene, and (o, m, p) -chloro styrene. It may be selected from the group consisting of, 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 are selected from the group consisting of N-phenyl maleimide, N- (4-chlorophenyl) maleimide, N- (4-hydroxyphenyl) maleimide, and N-cyclohexyl maleimide It may be, but is not limited to these.
• acid anhydride examples include maleic anhydride, methyl maleic anhydride, tetrahydro phthalic anhydride, and the like, but are not limited thereto.
• the monomer which imparts the alkali solubility is not particularly limited as long as it contains an acid group.
• the acid value of the binder resin is 50 to 130 KOH mg / g
• the weight average molecular weight is 1,000 to 50,000 g / mol.
• the acid value of the binder resin can be measured by titration with 0.1 N potassium hydroxide (KOH) methanol solution.
• the binder resin may be a copolymer of benzyl methacrylate and methacrylic acid (molar ratio 70:30).
• the polyfunctional monomer is a monomer that forms a photoresist image by light, specifically, propylene glycol methacrylate, dipentaerythritol hexaacrylate, dipentaerythritol acrylate, neopentyl glycol di Acrylate, 6-hexanediol diacrylate, 1,6-hexanediol acrylate tetraethyleneglycol methacrylate, bisphenoxy ethylalcohol diacrylate, trishydroxyethylisocyanurate trimethacrylate, trimethyl 1 selected from the group consisting of propane trimethacrylate, diphenylpentaerythritol hexaacrylate, pentaerythritol trimethacrylate, pentaerythritol tetramethacrylate and dipentaerythritol hexamethacrylate Species or a mixture of two or more thereof.
• the multifunctional monomer may be Dipentaerythritol hexacrylate (DPHA).
• DPHA Dipentaerythritol hexacrylate
• the photoinitiator is not particularly limited as long as it is an initiator that generates radicals by light to trigger crosslinking. It may be one or more kinds.
• the acetophenone-based compound is 2-hydroxy-2-methyl-1-phenylpropan-1-one, 1- (4-isopropylphenyl) -2-hydroxy-2-methylpropan-1-one, 4- (2-hydroxyethoxy) -phenyl- (2-hydroxy-2-propyl) ketone, 1-hydroxycyclohexylphenylketone, benzoin methyl ether, benzoin ethyl ether, benzoin isobutyl ether, benzoin Butyl ether, 2,2-dimethoxy-2-phenylacetophenone, 2-methyl- (4-methylthio) phenyl-2-morpholino-1-propan-1-one, 2-benzyl-2-dimethylamino -1- (4-morpholinophenyl) -butan-1-one, 2- (4-bromo-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butan-1-one or 2-methyl-1- [4- (methylthio)
• biimidazole-based compound 2,2-bis (2-chlorophenyl) -4,4 ', 5,5'-tetraphenyl biimidazole, 2,2'-bis (o-chlorophenyl) -4 , 4 ', 5,5'-tetrakis (3,4,5-trimethoxyphenyl) -1,2'-biimidazole, 2,2'-bis (2,3-dichlorophenyl) -4, 4 ', 5,5'-tetraphenyl biimidazole, 2,2'-bis (o-chlorophenyl) -4,4,5,5'-tetraphenyl-1,2'-biimidazole, It is not limited to this.
• the triazine compound is 3- ⁇ 4- [2,4-bis (trichloromethyl) -s-triazin-6-yl] phenylthio ⁇ propionic acid, 1,1,1,3,3,3- Hexafluoroisopropyl-3- ⁇ 4- [2,4-bis (trichloromethyl) -s-triazin-6-yl] phenylthio ⁇ propionate, ethyl-2- ⁇ 4- [2,4 -Bis (trichloromethyl) -s-triazin-6-yl] phenylthio ⁇ acetate, 2-epoxyethyl-2- ⁇ 4- [2,4-bis (trichloromethyl) -s-triazine-6 -Yl] phenylthio ⁇ acetate, cyclohexyl-2- ⁇ 4- [2,4-bis (trichloromethyl) -s-triazin-6-yl] phenylthio ⁇ acetate,
• the oxime-based compound is 1,2-octadione, -1- (4-phenylthio) phenyl, -2- (o-benzoyloxime) (Shibagai Co., Shijiai 124), ethanone, -1- (9 -Ethyl) -6- (2-methylbenzoyl-3-yl)-, 1- (O-acetyloxime) (CGII242), N-1919 (Adeca Co.), and the like.
• the photoinitiator may be I-369 (BASF Corporation).
• 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.
• An exemplary embodiment of the present specification is the content of the compound represented by Formula 1 based on the total weight of the photosensitive resin composition is 5% by weight to 60% by weight, the content of the binder resin is 1% by weight to 60% by weight, The content of the photoinitiator is 0.1% to 20% by weight, the content of the multifunctional monomer is 0.1% to 50% by weight, the content of the additive is 0.1% to 10% by weight, and the content of the solvent is 10 It provides a photosensitive resin composition which is by weight to 80% by weight.
• the content of the compound represented by Formula 1 is 5% by weight to 60% by weight
• the content of the binder resin is 1% by weight
• the content of the photoinitiator is 0.1% to 20% by weight
• the content of the multifunctional monomer is 0.1% to 50% 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 weight percentages based on solids and solids of each component can be measured by common analytical means used in the art, such as liquid chromatography or gas chromatography.
• the photosensitive resin composition may further include an additive.
• the photosensitive resin composition may include one or two or more additives selected from the group consisting of photocrosslinking sensitizers, curing accelerators, adhesion promoters, surfactants, thermal polymerization inhibitors, ultraviolet absorbers, dispersants, and leveling agents. It may further comprise.
• the content of the additive is 0.1% by weight to 20% by weight based on the total weight of solids in the photosensitive resin composition.
• the additive may be a surfactant.
• the content of the surfactant is 0.1% by weight to 10% by weight based on the total weight of the photosensitive resin composition.
• the content of the surfactant is 0.1% by weight to 10% by weight based on the total weight of solids in the photosensitive resin composition.
• the photocrosslinking sensitizer is benzophenone, 4,4-bis (dimethylamino) benzophenone, 4,4-bis (diethylamino) benzophenone, 2,4,6-trimethylaminobenzophenone, methyl-o-benzoyl Benzophenone compounds such as benzoate, 3,3-dimethyl-4-methoxybenzophenone, 3,3,4,4-tetra (t-butylperoxycarbonyl) benzophenone; Fluorenone compounds such as 9-florenone, 2-chloro-9-prorenone, and 2-methyl-9-florenone; Thioxanthones such as thioxanthone, 2,4-diethyl thioxanthone, 2-chloro thioxanthone, 1-chloro-4-propyloxy thioxanthone, isopropyl thioxanthone and diisopropyl thioxanthone compound; Xanthone compounds such as
• the curing accelerator is used to increase the curing and mechanical strength, specifically 2-mercaptobenzoimidazole, 2-mercaptobenzothiazole, 2-mercaptobenzoxazole, 2,5-dimercapto-1,3 , 4-thiadiazole, 2-mercapto-4,6-dimethylaminopyridine, pentaerythritol-tetrakis (3-mercaptopropionate), pentaerythritol-tris (3-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.
• methacryloyloxy propyltrimethoxy silane methacryloyloxy propyldimethoxy silane
• methacryloyloxy propyltriethoxy silane methacryloyloxy propyldimethoxysilane
• methacryloyl silane coupling agents such as these, can be selected and used, and at least 1 type can be selected from octyl trimethoxy silane, dodecyl trimethoxy silane, and octadecyl trimethoxy silane as an alkyl trimethoxy silane. You can choose to use it.
• the surfactant is a silicone-based surfactant or a fluorine-based surfactant, specifically, the silicone-based surfactant is BYK-Chemie's BYK-077, BYK-085, BYK-300, BYK-301, BYK-302, BYK-306, BYK-307 , BYK-310, BYK-320, BYK-322, BYK-323, BYK-325, BYK-330, BYK-331, BYK-333, BYK-335, BYK-341v344, BYK-345v346, BYK-348, BYK -354, BYK-355, BYK-356, BYK-358, BYK-361, BYK-370, BYK-371, BYK-375, BYK-380, BYK-390, and the like.
• F-114, F-177, F-410, F-411, F-450, F-493, F-494, F-443, F-444, F-445, F-446 , F-470, F-471, F-472SF, F-474, F-475, F-477, F-478, F-479, F-480SF, F-482, F-483, F-484, F -486, F-487, F-172D, MCF-350SF, TF-1025SF, TF-1117SF, TF-1026SF, TF-1128, TF-1127, TF-1129, TF-1126, TF-1130, TF-1116SF , TF-1131, TF1132, TF1027SF, TF-1441, TF-1442, etc. may be used, but is not limited thereto.
• the surfactant may be F-475 of DIC Corporation.
• the antioxidant may be one or more selected from the group consisting of hindered phenol antioxidants, amine antioxidants, thio antioxidants, and phosphine antioxidants, but is not limited thereto.
• antioxidants include phosphoric acid thermal stabilizers such as phosphoric acid, trimethyl phosphate or triethyl phosphate; 2,6-di-t-butyl-p-cresol, octadecyl-3- (4-hydroxy-3,5-di-t-butylphenyl) propionate, tetrabis [methylene-3- (3, 5-di-t-butyl-4-hydroxyphenyl) propionate] methane, 1,3,5-trimethyl-2,4,6-tris (3,5-di-t-butyl-4-hydroxy Benzyl) benzene, 3,5-di-t-butyl-4-hydroxybenzylphosphite diethyl ester, 2,2-thiobis (4-methyl-6-t-butylphenol), 2,6-g, t-butylphenol 4,4'-butylidene-bis (3-methyl-6-t-butylphenol), 4,4'-thiobis (3-methyl-6-t-t-
• UV absorber 2- (3-t-butyl-5-methyl-2-hydroxyphenyl) -5-chloro-benzotriazole, alkoxy benzophenone, etc. may be used, but is not limited thereto. All commonly used ones can be used.
• thermal polymerization inhibitor examples include p-anisole, hydroquinone, pyrocatechol, t-butyl catechol, N-nitrosophenylhydroxyamine ammonium salt and N-nitrosophenylhydroxy Amine aluminum salt, p-methoxyphenol, di-t-butyl-p-cresol, pyroggarol, benzoquinone, 4,4-thiobis (3-methyl-6-t-butylphenol), 2,2- It may include one or more selected from the group consisting of methylenebis (4-methyl-6-t-butylphenol), 2-mercaptoimidazole and phenothiazine, but is not limited thereto. It may include those generally known in the art.
• the dispersant may be used as a method of internally adding to the pigment in the form of surface treatment of the pigment in advance or externally adding to the pigment.
• a compound type, nonionic, anionic or cationic dispersant may be used, and examples thereof include fluorine, ester, cationic, anionic, nonionic and amphoteric surfactants. These can be used individually or in combination of 2 or more types.
• the dispersant may be polyalkylene glycol and esters thereof, polyoxyalkylene polyhydric alcohols, ester alkylene oxide adducts, alcohol alkylene oxide adducts, sulfonic acid esters, sulfonate salts, carboxylic acid esters, carboxylate salts, At least one selected from the group consisting of alkylamide alkylene oxide adducts and alkylamines is not limited thereto.
• the leveling agent may be polymeric or nonpolymeric.
• polymeric leveling agents include polyethyleneimine, polyamideamine, reaction products of amines and epoxides
• nonpolymeric leveling agents include non-polymeric sulfur-containing and non-polymeric nitrogen-containing. Including but not limited to the compounds, all generally used in the art can be used.
• An exemplary embodiment of the present specification provides a photosensitive material manufactured using the photosensitive resin composition.
• the photosensitive resin composition of the present disclosure may be applied and cured on a substrate by an appropriate method to prepare a photosensitive material in the form of a thin film or a pattern.
• a spray method, a roll coating method, a spin coating method, etc. can be used, Generally, a spin coating method is used widely.
• some residual solvent can be removed in some cases under reduced pressure.
• Light sources for curing the photosensitive resin composition according to the present specification include, but are not limited to, mercury vapor arcs, carbon arcs, Xe arcs, etc., which emit light having a wavelength of 250 nm to 450 nm.
• the photosensitive resin composition according to the present disclosure is a pigment-dispersed photosensitive material for manufacturing a thin film transistor liquid crystal display device (TFT LCD) color filter, a thin film transistor liquid crystal display device (TFT LCD) or a photosensitive material for forming a black matrix of an organic light emitting diode.
• TFT LCD thin film transistor liquid crystal display device
• TFT LCD thin film transistor liquid crystal display device
• photosensitive material for forming a black matrix of an organic light emitting diode.
• PDP plasma display panel
• An exemplary embodiment of the present specification provides a color filter including the photosensitive material.
• the color filter may be prepared using the photosensitive resin composition including the compound represented by Chemical Formula 1.
• the photosensitive resin composition may be coated on a substrate to form a coating film, and the coating film may be exposed, developed, and cured to produce a photosensitive material and provide a color filter including the same.
• the photosensitive resin composition according to the exemplary embodiment of the present specification is excellent in heat resistance, so that there is little change in color by heat treatment, thereby providing a color filter having high color reproducibility and high luminance and contrast ratio even during the curing process during the manufacture of the color filter. Can be.
• the substrate may be a glass plate, a silicon wafer, a plate of a plastic substrate such as polyethersulfone (PES), polycarbonate (PC), or the like, and the type thereof is not particularly limited.
• a plastic substrate such as polyethersulfone (PES), polycarbonate (PC), or the like, and the type thereof is not particularly limited.
• the photosensitive resin composition according to an exemplary embodiment of the present specification may be spincoated on glass (5 ⁇ 5 cm 2 ), and subjected to prebake at 100 ° C. for 100 seconds to form a film. .
• the distance between the substrate on which the film is formed and the photo mask is set to 250 um, and 40 mJ / cm 2 exposure dose is irradiated to the entire surface of the substrate using an exposure machine.
• the exposed substrate may be developed in a developer (potassium hydroxide (KOH), 0.05%) for 60 seconds, and postbake at 230 ° C. for 20 minutes to prepare a substrate.
• KOH potassium hydroxide
• the heat resistance evaluation can be measured by the method described below.
• the substrate manufactured according to the exemplary embodiment of the present invention obtains a transmittance spectrum of a visible light region in the range of 380 nm to 780 nm.
• the prebake substrate is further postbake at 230 ° C. for 20 minutes to obtain transmittance spectra in the same equipment and measurement range.
• the spectrometer may be that of MCPD-Otsuka, but is not limited thereto.
• the color change (hereinafter, ⁇ Eab) is calculated using the obtained values E (L *, a *, b *).
• ⁇ Eab ⁇ 3
• E L *, a *, b *
• 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 lattice called a black matrix can be disposed between the color pixels of the color filter for the purpose of improving contrast.
• Chromium can be used as the material of the black matrix.
• a method of depositing chromium over the entire glass substrate and forming a pattern by etching may be used.
• a resin black matrix by a pigment dispersion method capable of fine processing can be used.
• the black matrix may use a black pigment or a black dye as a colorant.
• a black pigment or a black dye for example, carbon black may be used alone, or carbon black and coloring pigments may be used.
• coloring pigments lacking light shielding properties may be mixed, even if the amount of colorant is increased, the strength of the film or the adhesion to the substrate may be reduced. There is no advantage.
• An exemplary embodiment of the present specification provides a display device including the color filter.
• the display device may be a plasma display panel (PDP), a light emitting diode (LED), an organic light emitting diode (OLED), a liquid crystal display (LCD), a thin film transistor.
• the liquid crystal display device may be any one of a liquid crystal display (LCD-TFT) and a cathode ray tube (CRT).
• DMF dimethylformamide
• RBF 2-neck round bottom flask
• intermediate 1 5 g (10.813 mmol) and sodium hydrogen carbonate (NaHCO 3 ) 2.725 g (30.439 mmol) were added.
• the mixture was heated to 50 ° C. and stirred to prepare a reaction solution.
• reaction solution 2 was prepared by reacting at 180 ° C. for 12 hours.
• reaction solution 2 was cooled to room temperature, and precipitated in 250 g of MeOH.
• the mixture was stirred for 30 minutes and the precipitate was filtered under reduced pressure and dried in a vacuum oven at 80 ° C. to obtain intermediate 2, which proceeded without further separation.
• reaction solution 1 was prepared by reacting at 180 ° C. for 12 hours.
• reaction solution 1 was cooled to room temperature, and precipitated in 250 g of methanol (MeOH). The mixture was stirred for 30 minutes and the precipitate was filtered under reduced pressure and dried in a vacuum oven at 80 ° C. to obtain intermediate 2, which proceeded without further separation.
• MeOH methanol
• reaction was cooled to room temperature and precipitated in 250 g of methanol (MeOH). Stir for 30 minutes The precipitate was filtered under reduced pressure and dried in a vacuum oven at 80 degrees to give compound 4, the reaction was carried out without further separation.
• MeOH methanol
• the coloring agent (PY 138) of the following structural formula was obtained from BASF, and used as a comparative compound.
• the photosensitive resin composition of Examples 2 to 24 was prepared in the same composition as the photosensitive resin composition of Example 1.
• Comparative example Compound PY 138 5.554 g a copolymer of benzyl methacrylate and methacrylic acid with a binder resin (molar ratio 70:30, acid value 113 KOH mg / g, weight average molecular weight 20,000 measured by gel permeation chromatography (GPC)) g / mol), molecular weight distribution (PDI) 2.0 g, solids (SC) 25%, solvent propylene glycol monomethyl ether acetate (PGMEA) 10.376 g, photoinitiator I-369 (BASF Corporation) ) 2.018 g, a photopolymerizable compound that is a multifunctional monomer, 12.443 g of DPHA (polypropylene glycol), 68.593 g of a solvent PGMEA (polypropylene glycol monomethyl ether acetate), and DIC F-475, 1.016 g of an additive, were mixed.
• the photosensitive resin composition was prepared.
• pigments do not dissolve in organic solvents, so dispersion is necessary through derivatives and dispersants.
• a derivative or a dispersant is not required, or the amount of use thereof can be reduced, and thus it can be easily applied commercially.
• the photosensitive resin composition of Examples 1-24 was used for board
• the distance between the substrate on which the film was formed and the photo mask was set at 250 um, and the exposure amount of 40 mJ / cm 2 was irradiated on the entire surface of the substrate using an exposure machine.
• the exposed substrate was developed for 60 seconds in a developer (KOH, 0.05%), and postbake at 230 ° C. for 20 minutes to prepare a substrate.
• the substrate produced according to the substrate manufacturing method was obtained using a spectrometer (MCPD-Otsuka Co., Ltd.) to obtain a transmittance spectrum of the visible light range of 380nm to 780nm.
• the prebake substrate was further postbake at 230 ° C. for 20 minutes to obtain transmittance spectra in the same equipment and measurement range.
• a small ⁇ Eab value indicates excellent color heat resistance.
• ⁇ Eab ⁇ 3 When ⁇ Eab ⁇ 3, it can be used as a color filter dye, and it can be said that it is a color material having excellent heat resistance.
• Example 1 0.85 Example 13 0.92
• Example 2 1.37
• Example 14 1.02
• Example 3 0.76
• Example 15 1.25
• Example 4 0.70
• Example 16 0.92
• Example 5 0.51
• Example 17 0.64
• Example 6 1.79
• Example 18 1.47
• Example 7 1.07
• Example 19 0.94
• Example 8 1.21
• Example 20 1.07
• Example 9 1.33
• Example 21 1.13
• Example 10 0.47
• Example 22 0.59 Example 11 2.53
• Example 23 2.01
• Example 12 2.13
• Example 24 2.37
• the difference in transmittance spectrum ( ⁇ Eab) after the post-heat treatment and post-heat treatment is less than 3
• the color stability It was confirmed that the heat resistance was very high because it is very small.

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