CN107743487B - Xanthene compound and photosensitive resin composition containing same - Google Patents

Xanthene compound and photosensitive resin composition containing same Download PDF

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CN107743487B
CN107743487B CN201680034516.5A CN201680034516A CN107743487B CN 107743487 B CN107743487 B CN 107743487B CN 201680034516 A CN201680034516 A CN 201680034516A CN 107743487 B CN107743487 B CN 107743487B
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CN107743487A (en
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朴钟镐
李多美
李在容
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LG Chem Ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
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    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B11/00—Diaryl- or thriarylmethane dyes
    • C09B11/04—Diaryl- or thriarylmethane dyes derived from triarylmethanes, i.e. central C-atom is substituted by amino, cyano, alkyl
    • C09B11/10—Amino derivatives of triarylmethanes
    • C09B11/24—Phthaleins containing amino groups ; Phthalanes; Fluoranes; Phthalides; Rhodamine dyes; Phthaleins having heterocyclic aryl rings; Lactone or lactame forms of triarylmethane dyes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/44—Iso-indoles; Hydrogenated iso-indoles
    • C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
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    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/78—Ring systems having three or more relevant rings
    • C07D311/80—Dibenzopyrans; Hydrogenated dibenzopyrans
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B11/00—Diaryl- or thriarylmethane dyes
    • C09B11/28—Pyronines ; Xanthon, thioxanthon, selenoxanthan, telluroxanthon dyes
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    • 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
    • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds

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Abstract

The present specification provides a xanthene compound having a novel structure, a photosensitive resin composition containing the same, and a photosensitive material, a color filter and a display element produced using the same.

Description

Xanthene compound and photosensitive resin composition containing same
Technical Field
The specification claims priority based on korean patent application No. 10-2015-0086200, filed on korean patent office on 17.6.2015, the entire contents of which are disclosed in the korean patent application are incorporated as part of the specification.
The present specification relates to a xanthene compound and a photosensitive resin composition containing the same. The present specification also relates to a color filter produced using the photosensitive resin composition, and a display device including the color filter.
Background
In recent years, color filters have been required to have high brightness and high contrast. In addition, one of the main purposes of development of display elements is to differentiate the display element performance by improving color purity and to improve productivity in the manufacturing process.
Since pigment types used as coloring materials for conventional color filters exist in a particle-dispersed state in a color resist, it is difficult to adjust brightness and contrast by adjusting the size and distribution of pigment particles. In the case of pigment particles, dissolution and dispersibility are reduced by agglomeration in the color filter, and multiple scattering (multiple scattering) of light occurs due to agglomerated large particles. Such scattering of polarized light is considered to be a main cause of lowering the contrast. Efforts are continuously made to improve brightness and contrast by ultrafine particle formation and dispersion stabilization of pigments, but there is a limit to the degree of freedom in selecting coloring materials for realizing color coordinates for high color purity display devices. In addition, the pigment dispersion method using color materials, particularly pigments, which has been developed, reaches a limit in improving color purity, brightness, and contrast of a color filter using the same.
Accordingly, development of a novel coloring material capable of improving color reproduction, brightness, and contrast by improving color purity has been demanded.
Disclosure of Invention
The present inventors have aimed to provide a xanthene compound having a novel structure, a photosensitive resin composition containing the same, a color filter produced using the same, and a display element containing the same.
One embodiment of the present specification provides a compound represented by the following chemical formula 1.
[ chemical formula 1]
Figure BDA0001505775360000021
In the chemical formula 1 described above,
R1to R6Each independently selected from hydrogen, deuterium, halogen atom, nitro group, substituted or unsubstituted C1-30 atomsA chain or branched alkyl group, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, and a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms,
R7to R11Each independently selected from hydrogen, deuterium, an anionic group, a hydroxyl group, a substituted or unsubstituted, linear or branched alkyl group of carbon number 1 to 30, a substituted or unsubstituted, monocyclic or polycyclic aryl group of carbon number 6 to 30, and a substituted or unsubstituted, monocyclic or polycyclic heteroaryl group of carbon number 2 to 30,
r is as defined above7To R11At least one of which is an anionic group,
R12to R14Each independently selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted monocyclic or polycyclic aryl group of 6 to 30 carbon atoms, a substituted or unsubstituted monocyclic or polycyclic heteroaryl group of 2 to 30 carbon atoms, and a dianhydride group containing a nitrogen atom,
R15and R16Each independently selected from hydrogen, deuterium, an anionic group, a hydroxyl group, a substituted or unsubstituted straight-chain or branched alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms, or combined with each other to form a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms, or a substituted or unsubstituted monocyclic or polycyclic heterocyclic ring having 2 to 30 carbon atoms,
L1and L2Each independently is a direct bond or a 2-valent linking group.
One embodiment of the present specification provides a colorant composition comprising the compound of chemical formula 1.
One embodiment of the present description can provide a resin composition including the compound represented by chemical formula 1, a binder resin, a polyfunctional monomer, a photoinitiator, and a solvent.
One embodiment of the present specification provides a photosensitive material produced using the resin composition.
One 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 xanthene compound according to one embodiment of the present specification can be used as a coloring material in a photosensitive resin composition, and color purity can be improved by coordinating the spectrum emitted from a light source with the absorption and transmission spectrum of a color filter, as compared with a conventional coloring material.
Further, the xanthene compound according to one embodiment of the present specification is used as a color material, and can improve color reproduction, brightness, and contrast.
Drawings
Fig. 1 is a graph showing transmittance of a compound according to an embodiment of the present specification.
Detailed Description
The present specification will be described in more detail below.
In the present specification, when a part is referred to as "including" a certain component, unless specifically stated to the contrary, it means that the other component may be further included, and the other component is not excluded.
According to one embodiment of the present disclosure, there is provided a compound represented by the above chemical formula 1.
Examples of the substituent of the compound represented by the above chemical formula 1 will be described below, but not limited thereto.
The term "substituted or unsubstituted" in this specification means that the compound is selected from deuterium; a halogen atom; an alkyl group; an alkenyl group; an alkoxy group; a cycloalkyl group; a silyl group; arylalkenyl group (
Figure BDA0001505775360000031
Figure BDA0001505775360000041
arylalkenyl); an aryl group; an aryloxy group; aralkyl group;aralkenyl radicals (
Figure BDA0001505775360000042
aralkenyl); alkylthio radicals (A), (B), (C), (D), (C), (D), (E), (D), (E) and (D)
Figure BDA0001505775360000043
Alkyl thio xy); alkyl sulfoxide group (C)
Figure BDA0001505775360000044
Alkyl sulfo xy); aryl sulfoxide group (A)
Figure BDA0001505775360000045
Aryl sulfoxy); a boron group; an alkylamino group; an aralkylamino group; an arylamine group; a heteroaryl group; a carbazolyl group; an acryloyl group; an acrylate group; an ether group; a nitrile group; a nitro group; a hydroxyl group; a cyano group; containing N, O, S or 1 or more heterocyclic groups among P atoms and 1 or more substituents among anionic groups, or having no substituent.
In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but may be 1 to 30. Specific examples thereof include, but are not limited to, methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, pentyl, hexyl, and heptyl.
In the present specification, the alkenyl group may be a straight chain or a branched chain, and the number of carbon atoms is not particularly limited, but may be 2 to 25. Specific examples thereof include aryl-substituted alkenyl groups such as stilbene (styryl) and styryl (styrenyl), but the present invention is not limited thereto.
In the present specification, the alkoxy group may be linear or branched, and the number of carbon atoms is not particularly limited, but may be 1 to 30.
In the present specification, the cycloalkyl group is not particularly limited, but the number of carbon atoms may be 3 to 20, and may be a cyclopentyl group or a cyclohexyl group.
In the present specification, examples of the halogen atom include fluorine, chlorine, bromine, and iodine.
In the present specification, the phenoxy group is not particularly limited, but the number of carbon atoms may be 3 to 20.
In the present specification, the carboxyl group is not particularly limited, but the number of carbon atoms may be 1 to 30.
In the present specification, the carboxylic acid ester group is not particularly limited, but the number of carbon atoms may be 2 to 30. Specific examples thereof include methyl carboxylate, ethyl carboxylate, isopropyl carboxylate, benzyl carboxylate, and the like, but the present invention is not limited thereto.
In the present specification, carboxylate and sulfonate are salts formed with cations having a valence of 1, respectively, and the cations having a valence of 1 may be selected from Na+、K+And quaternary ammonium cations, but is not limited thereto. Specific examples of the quaternary ammonium cation include, but are not limited to, a tetraalkylammonium cation such as a tetramethylammonium cation, an ethyltrimethylammonium cation, and a tetrapropylammonium cation.
In the present specification, the alkoxycarbonyl group is not particularly limited, but the number of carbon atoms may be 1 to 30. In the alkoxycarbonyl group, as a specific example of the alkyl group, the same alkyl groups as described above with respect to the alkyl group can be applied. Specific examples thereof include, but are not limited to, alkoxycarbonyl groups having an alkyl group described in the specific examples of alkyl groups.
In the present specification, the sulfonic acid group is not particularly limited, but the number of carbon atoms may be 1 to 30.
Specific examples of the sulfonate group in the present specification include alkylsulfonyl groups having 1 to 4 carbon atoms such as methylsulfonyl group, ethylsulfonyl group, and hexylsulfonyl group, but are not limited thereto.
In the present specification, the above aralkyl group is specifically such that the number of carbon atoms of the aryl moiety is 6 to 49 and the number of carbon atoms of the alkyl moiety is 1 to 44. Specific examples thereof include, but are not limited to, benzyl, p-methylbenzyl, m-methylbenzyl, p-ethylbenzyl, m-ethylbenzyl, 3, 5-dimethylbenzyl, α -methylbenzyl, α -dimethylbenzyl, α -methylphenylbenzyl, 1-naphthylbenzyl, 2-naphthylbenzyl, p-fluorobenzyl, 3, 5-difluorobenzyl, α -bistrifluoromethylbenzyl, p-methoxybenzyl, m-methoxybenzyl, α -phenoxybenzyl, α -benzyloxybenzyl, naphthylmethyl, naphthylethyl, naphthylisopropyl, pyrrolylmethyl, pyrrolylethyl, aminobenzyl, nitrobenzyl, cyanobenzyl, 1-hydroxy-2-phenylisopropyl, and 1-chloro-2-phenylisopropyl.
In the present specification, the aryl portion of the aralkenyl group may be the aryl group described later, and the alkenyl portion may be the alkenyl group described above.
In the present specification, an aryl group may be a monocyclic aryl group or a polycyclic aryl group.
When the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but may be 6 to 40. Specifically, the monocyclic aryl group may be a phenyl group, a biphenyl group, a terphenyl group, or the like, but is not limited thereto.
When the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited, but may be 10 to 40. Specifically, the polycyclic aryl group may be a naphthyl group, an anthryl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a perylene group,
Figure BDA0001505775360000052
A fluorenyl group, etc., but is not limited thereto.
In the present specification, the fluorenyl group may have a substituent, and the substituents may be bonded to each other to form a spiro structure. Examples of the fluorenyl group are
Figure BDA0001505775360000051
And the like.
In the present specification, the heteroaryl group is a heterocyclic group containing O, N or S as a heteroatom, and the number of carbon atoms is not particularly limited, and may be 2 to 30. Examples of the heterocyclic group include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, and the like,
Figure BDA0001505775360000053
Azolyl group,
Figure BDA0001505775360000054
Oxadiazolyl, triazolyl, pyridylBipyridyl, triazinyl, acridinyl, pyridazinyl, quinolyl, isoquinolyl, indolyl, carbazolyl, benzo
Figure BDA0001505775360000055
Examples of the heterocyclic group include, but are not limited to, an oxazolyl group, a benzimidazolyl group, a benzothiazolyl group, a benzocarbazolyl group, a benzothienyl group, a dibenzothienyl group, a benzofuranyl group, and a dibenzofuranyl group.
In the present specification, alkylene means a group having two binding sites in paraffin (alkane). The alkylene group may be a straight chain, a branched chain or a cyclic chain. The number of carbon atoms of the alkylene group is not particularly limited, and the number of carbon atoms may be 2 to 25.
In the present specification, an aromatic hydrocarbon ring is not a 1-valent group, and an aryl group can be applied.
In this specification, the description of heteroaryl may be applied to heterocyclic rings other than 1-valent groups.
According to the above embodiment, R1To R6Each independently may be selected from the group consisting of hydrogen, deuterium, a halogen atom, a nitro group, a substituted or unsubstituted straight or branched alkyl group of carbon number 1 to 30, a substituted or unsubstituted alkoxy group of carbon number 1 to 30, and a substituted or unsubstituted monocyclic or polycyclic aryl group of carbon number 6 to 30, and a substituted or unsubstituted monocyclic or polycyclic heteroaryl group of carbon number 2 to 30.
According to another embodiment of the present specification, R is1To R6Each independently may be selected from hydrogen, deuterium, substituted or unsubstituted straight or branched alkyl of 1 to 20 carbon atoms, substituted or unsubstituted alkoxy of 1 to 20 carbon atoms, and substituted or unsubstituted monocyclic or polycyclic aryl of 6 to 20 carbon atoms, and substituted or unsubstituted monocyclic or polycyclic heteroaryl of 2 to 20 carbon atoms.
According to another embodiment of the present specification, R is1To R6Each independently selected from hydrogen, deuterium, substituted or unsubstituted C1-10 linear or branched alkyl, substituted or unsubstituted C6-10 monocyclic or polycyclic aromaticAnd a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 10 carbon atoms.
According to another embodiment of the present specification, R is1To R6May be hydrogen.
In addition, R7To R11Each independently selected from the group consisting of hydrogen, deuterium, an anionic group, a hydroxyl group, a substituted or unsubstituted, linear or branched alkyl group of carbon number 1 to 30, a substituted or unsubstituted, monocyclic or polycyclic aryl group of carbon number 6 to 30, and a substituted or unsubstituted, monocyclic or polycyclic heteroaryl group of carbon number 2 to 30, R7To R11At least one of which may be an anionic group.
According to another embodiment of the present description, R7To R11Each independently selected from the group consisting of hydrogen, deuterium, an anionic group, a substituted or unsubstituted, linear or branched alkyl group of carbon number 1 to 20, a substituted or unsubstituted, monocyclic or polycyclic aryl group of carbon number 6 to 20, and a substituted or unsubstituted, monocyclic or polycyclic heteroaryl group of carbon number 2 to 20, R7To R11At least one of which may be an anionic group.
According to another embodiment of the present description, R7To R11Each independently selected from the group consisting of hydrogen, deuterium, an anionic group, a substituted or unsubstituted, linear or branched alkyl group of carbon number 1 to 10, a substituted or unsubstituted, monocyclic or polycyclic aryl group of carbon number 6 to 10, and a substituted or unsubstituted, monocyclic or polycyclic heteroaryl group of carbon number 2 to 10, R7To R11At least one of which may be an anionic group.
According to another embodiment of the present description, R7To R11Each independently may be hydrogen, or an anionic group, R7To R11At least one of which may be an anionic group.
In addition, R12Can be selected from hydrogen, deuterium, substituted or unsubstituted monocyclic or polycyclic aryl of 6 to 30 carbon atoms, substituted or unsubstituted monocyclic or polycyclic heteroaryl of 2 to 30 carbon atoms, and nitrogen-containing compoundsA dianhydride group.
According to another embodiment of the present description, R12May be selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted monocyclic or polycyclic aryl groups of 6 to 20 carbon atoms, substituted or unsubstituted monocyclic or polycyclic heteroaryl groups of 2 to 20 carbon atoms, and dianhydride groups containing nitrogen atoms.
According to another embodiment of the present description, R12May be selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted monocyclic or polycyclic aryl groups of 6 to 10 carbon atoms, substituted or unsubstituted monocyclic or polycyclic heteroaryl groups of 2 to 10 carbon atoms, and dianhydride groups containing nitrogen atoms.
According to another embodiment of the present description, R12May be a dianhydride group containing a nitrogen atom.
And, R13And R14Each independently can be selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted monocyclic or polycyclic aryl of 6 to 30 carbon atoms, substituted or unsubstituted monocyclic or polycyclic heteroaryl of 2 to 30 carbon atoms, and dianhydrides containing nitrogen atoms.
According to another embodiment of the present description, R13And R14Each independently can be selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted monocyclic or polycyclic aryl of 6 to 20 carbon atoms, substituted or unsubstituted monocyclic or polycyclic heteroaryl of 2 to 20 carbon atoms, and dianhydrides containing nitrogen atoms.
According to another embodiment of the present description, R13And R14Each independently can be selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted monocyclic or polycyclic aryl of 6 to 10 carbon atoms, substituted or unsubstituted monocyclic or polycyclic heteroaryl of 2 to 10 carbon atoms, and dianhydrides containing nitrogen atoms.
According to another embodiment of the present description, R13And R14Each independently selected from hydrogen, substituted or unsubstituted phenyl, and dianhydrides containing nitrogen atoms.
According to another embodiment of the present description, R13And R14Each independently at least one member selected from the group consisting of hydrogen, methyl and anionic groupsA substituted phenyl group, and a dianhydride group containing a nitrogen atom.
In addition, R15And R16Each independently may be selected from hydrogen, deuterium, an anionic group, a hydroxyl group, a substituted or unsubstituted linear or branched alkyl group of carbon number 1 to 30, a substituted or unsubstituted monocyclic or polycyclic aryl group of carbon number 6 to 30, and a substituted or unsubstituted monocyclic or polycyclic heteroaryl group of carbon number 2 to 30, or may be combined with each other to form a substituted or unsubstituted monocyclic or polycyclic aryl group of carbon number 6 to 30, or a substituted or unsubstituted monocyclic or polycyclic heteroaryl group of carbon number 2 to 30.
According to another embodiment of the present description, R15And R16Each independently may be selected from hydrogen, deuterium, an anionic group, a hydroxyl group, a substituted or unsubstituted linear or branched alkyl group of carbon number 1 to 20, a substituted or unsubstituted monocyclic or polycyclic aryl group of carbon number 6 to 20, and a substituted or unsubstituted monocyclic or polycyclic heteroaryl group of carbon number 2 to 20, or may be combined with each other to form a substituted or unsubstituted monocyclic or polycyclic aryl group of carbon number 6 to 20, or a substituted or unsubstituted monocyclic or polycyclic heteroaryl group of carbon number 2 to 20.
According to another embodiment of the present description, R15And R16Each independently may be selected from hydrogen, deuterium, an anionic group, a hydroxyl group, a substituted or unsubstituted linear or branched alkyl group of carbon number 1 to 20, a substituted or unsubstituted monocyclic or polycyclic aryl group of carbon number 6 to 20, and a substituted or unsubstituted monocyclic or polycyclic heteroaryl group of carbon number 2 to 20, or may be combined with each other to form a substituted or unsubstituted monocyclic or polycyclic aryl group of carbon number 6 to 20, or a substituted or unsubstituted monocyclic or polycyclic heteroaryl group of carbon number 2 to 20.
According to another embodiment of the present description, R15And R16Each independently selected from hydrogen, deuterium, an anionic group, a hydroxyl group, a substituted or unsubstituted, linear or branched alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted, monocyclic or polycyclic aryl group having 6 to 10 carbon atoms, a substituted or unsubstituted, or a pharmaceutically acceptable salt thereof,And a substituted or unsubstituted monocyclic or polycyclic heteroaryl group of 2 to 10 carbon atoms, or may be combined with each other to form a substituted or unsubstituted monocyclic or polycyclic aryl group of 6 to 10 carbon atoms, or a substituted or unsubstituted monocyclic or polycyclic heteroaryl group of 2 to 10 carbon atoms.
According to another embodiment of the present description, R15And R16Each independently may be selected from hydrogen, deuterium, and anionic groups, or may combine with each other to form a substituted or unsubstituted benzene ring.
In addition, L1And L2Each independently may be a direct bond or a 2-valent linking group, more specifically, may be a direct bond or an alkylene group, and further specifically, may be an unsubstituted alkylene group having 1 to 6 carbon atoms.
In addition, according to another embodiment of the present specification, there may be provided a compound represented by the following chemical formula 2 in the above chemical formula 1.
[ chemical formula 2]
Figure BDA0001505775360000091
In the above chemical formula 2, R1To R11、R13To R16、L1And L2As defined in the above chemical formula 1, R17And R18Each independently as above R15And R16And (4) description.
In addition, according to another embodiment of the present specification, there may be provided a compound represented by the following chemical formula 3 in the above chemical formula 1.
[ chemical formula 3]
Figure BDA0001505775360000092
In the above chemical formula 3, R1To R14、L1And L2As defined in the above chemical formula 1, R19Can be selected from hydrogen, deuterium, and substituted or unsubstituted C1-20 linear or branched alkyl group, substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms, halogen atom, nitro group, phenoxy group, carboxyl group, carboxylate group, alkoxycarbonyl group, hydroxyl group, sulfonic acid group, sulfonate group, -SO2NHR21A group of and-SO2NR22R23R is as defined above21To R23Each independently may be an alkyl group having 1 to 30 carbon atoms, m may be an integer of 1 to 4, and when m is 2, R19May be the same as or different from each other.
According to another embodiment of the present description, R19Can be selected from hydrogen, deuterium, substituted or unsubstituted straight or branched alkyl group of 1 to 10 carbon atoms, substituted or unsubstituted alkoxy group of 1 to 10 carbon atoms, substituted or unsubstituted monocyclic or polycyclic aryl group of 6 to 20 carbon atoms, substituted or unsubstituted monocyclic or polycyclic heteroaryl group of 2 to 20 carbon atoms, sulfonic acid group, sulfonic ester group, -SO2NHR21A group of and-SO2NR22R23R is as defined above21To R23Each independently may be an alkyl group having 1 to 20 carbon atoms, m may be an integer of 1 to 4, and when m is 2 or more, R19May be the same as or different from each other.
According to another embodiment of the present description, R19Can be selected from hydrogen, deuterium, sulfonic acid group, sulfonate group, -SO2NHR21A group of and-SO2NR22R23R is as defined above21To R23Each independently may be an alkyl group having 1 to 10 carbon atoms, m may be an integer of 1 to 4, and when m is 2 or more, R19The same or different from each other.
According to another embodiment of the present description, R19May be hydrogen or deuterium.
In addition, according to another embodiment of the present specification, there may be provided a compound of the above chemical formula 1 represented by the following chemical formula 4.
[ chemical formula 4]
Figure BDA0001505775360000101
In the above chemical formula 4, R1To R11, R13、R14、L1And L2As defined in the above chemical formula 1, R19And R20Each independently of the above R19The same description applies.
However, further, in the above chemical formula 4, R13And R14Each independently may be selected from substituted or unsubstituted monocyclic or polycyclic aryl groups of 6 to 30 carbon atoms, and substituted or unsubstituted monocyclic or polycyclic heteroaryl groups of 2 to 30 carbon atoms.
In the above chemical formula 4, R13And R14Each independently may be a substituted or unsubstituted monocyclic or polycyclic aromatic group having 6 to 30 carbon atoms.
In the above chemical formula 4, R13And R14Each independently may be a substituted monocyclic aryl group having 6 to 30 carbon atoms.
In the above chemical formula 4, R13And R14Each independently may be a substituted phenyl group having 6 to 30 carbon atoms.
In the above chemical formula 4, R13And R14Each independently may be a phenyl group having 6 to 30 carbon atoms substituted with an alkyl group.
In the above chemical formula 4, R13And R14Each independently may be a phenyl group having 6 to 10 carbon atoms substituted with an alkyl group.
In the above chemical formula 4, R13And R14Each independently may be a phenyl group having 6 to 10 carbon atoms substituted with a methyl group.
In the above chemical formula 4, R13And R14Each independently may be 2, 6-dimethylphenyl.
When hydrogen (H) having a small size is substituted at the position 2 or 6, since there are a plurality of absorption bands due to the rotation of the substituent in the case of having the characteristic of a single bond, the region of absorption wavelength becomes wide and the transmittance at short wavelength becomes low.
When a substituent having 2 or more carbon atoms larger than methyl group is introduced into the 2-and 6-position, the substituent is sterically excluded from the other alkyl substituent of nitrogen atom and it is difficult to maintain planarity, and λ occursmaxBlue shift (hypochromo shift) and transmittance at short wavelengths becomes low.
When substituents different from each other are introduced into the positions 2 and 6, the different substituents can rotate as compared with the case where the substituents are the same, and thus, there are a plurality of absorption bands, so that a region absorbing a wavelength becomes wide and transmittance at a short wavelength becomes low. Thus, the same substituent can be introduced into nos. 2 and 6, and specifically, methyl group shows the most excellent color characteristics.
Further, the anionic group may be selected from-OH and-SO3-、-SO3H、-SO3-Z+、-CO2H、-CO2-Z+、-CO2Ra、-SO3Rb and-SO3At least one of NRcRd, Z+To represent+N(Re)4、Na+Or K+Each of Ra to Re independently may represent a substituted or unsubstituted straight-chain or branched alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.
According to another embodiment of the present disclosure, the anionic group may be selected from-OH and-SO3 -、-SO3H、-SO3 -Z+、-CO2H、-CO2 -Z+、-CO2Ra、-SO3Rb and-SO3At least one of NRcRd, Z+To represent+N(Re)4、Na+Or K+Ra to Re each independently may represent a substituted or unsubstituted straight-chain or branched alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, and a substituted or unsubstituted monocyclic or polycyclic hetero group having 2 to 20 carbon atomsAnd (4) an aryl group.
According to another embodiment of the present disclosure, the anionic group may be selected from-SO3-、-SO3H、-SO3 -Z+、-SO3Rb and-SO3At least one of NRcRd, Z+Represents Na+Or K+Each of Ra to Rd may independently represent a substituted or unsubstituted straight or branched alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 10 carbon atoms, and a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 10 carbon atoms.
According to another embodiment of the present disclosure, the anionic group may be-SO3 -or-SO3 -Na+。
The anionic group may have an anion itself or may be present in a complex form with another cation. Thus, the sum of the total charge of the molecules of the compounds of the invention may vary depending on the number of substituted anionic groups. Since one amine group of the compound of the present invention has a cation, the sum of all charges of the molecule may have a value of 0 to 0, which is equivalent to a value obtained by subtracting 1 from the number of substituted anionic groups.
When an alkylphthalimide is substituted with a nitrogen atom, the substituted alkylphthalimide group compound improves the dispersibility of the pigment, suppresses the crystal transformation of the pigment at high temperatures, and stabilizes the pigment at high temperatures.
Furthermore, xanthene substituted with phthalimide groups improves the dispersibility of the pigment used therewith, and thus more excellent CR characteristics can be expected, and the color change can be reduced by changing the crystal of the pigment and stabilizing the pigment at high temperatures. That is, by stabilization of the pigment, dispersibility and storage stability can be improved and color change can be reduced.
As a result, the xanthene compound having a methyl-substituted phenyl group and a phthalimide group introduced into the positions 2 and 6 not only exhibits excellent color characteristics, but also has the effect of improving dispersibility and storage stability and reducing color change by stabilizing the pigment.
The compound represented by chemical formula 1 may be represented by any one of the following chemical formulae, but is not limited thereto.
Figure BDA0001505775360000131
Figure BDA0001505775360000141
Figure BDA0001505775360000151
Figure BDA0001505775360000161
Figure BDA0001505775360000171
Figure BDA0001505775360000181
Figure BDA0001505775360000191
Figure BDA0001505775360000201
In addition, according to an embodiment of the present specification, a colorant composition containing the above compound can be provided.
The colorant composition may further include at least 1 of a dye and a pigment in addition to the compound of chemical formula 1. For example, the colorant composition may contain only the compound of the above chemical formula 1, but may contain the compound of the above chemical formula 1 and 1 or more kinds of dyes, or contain the compound of the above chemical formula 1 and 1 or more kinds of pigments, or contain the compound of the above chemical formula 1,1 or more kinds of dyes, and 1 or more kinds of pigments.
According to an embodiment of the present specification, a resin composition containing the colorant composition can be provided.
According to an embodiment of the present disclosure, the resin composition may further include a compound represented by the chemical formula 1, a binder resin, a polyfunctional monomer, a photoinitiator, and a solvent.
The binder resin is not particularly limited as long as it can exhibit physical properties such as strength and developability of a film produced from the resin composition.
The binder resin may be a copolymer resin of a polyfunctional monomer imparting mechanical strength and a monomer imparting alkali solubility, and may further contain a binder generally used in the art.
The polyfunctional monomer for imparting mechanical strength to the film may be at least one selected from the group consisting of unsaturated carboxylic acid esters, aromatic ethylenes, unsaturated ethers, unsaturated imides, and acid anhydrides.
Specific examples of the unsaturated carboxylic acid ester include benzyl (meth) acrylate, methyl (meth) acrylate, ethyl (meth) acrylate, butyl (meth) acrylate, dimethylaminoethyl (meth) acrylate, isobutyl (meth) acrylate, t-butyl (meth) acrylate, cyclohexyl (meth) acrylate, isobornyl (meth) acrylate, ethylhexyl (meth) acrylate, 2-phenoxyethyl (meth) acrylate, tetrahydrofurfuryl (meth) acrylate, hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 2-hydroxy-3-chloropropyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, acyloctyloxy-2-hydroxypropyl (meth) acrylate, and mixtures thereof, Glycerol (meth) acrylate, 2-methoxyethyl (meth) acrylate, 3-methoxybutyl (meth) acrylate, ethoxyethyleneglycol (meth) acrylate, methoxytriethyleneglycol (meth) acrylate, methoxytripropyleneglycol (meth) acrylate, poly (ethyleneglycol) methyl ether (meth) acrylate, phenoxydiethyleneglycol (meth) acrylate, p-nonylphenoxypolyethyleneglycol (meth) acrylate, p-nonylphenoxypolypropyleneglycol (meth) acrylate, glycidyl (meth) acrylate, tetrafluoropropyl (meth) acrylate, 1,1,1,3,3, 3-hexafluoroisopropyl (meth) acrylate, octafluoropentyl (meth) acrylate, heptadecafluorodecyl (meth) acrylate, tribromophenyl (meth) acrylate, methyl alpha-hydroxymethacrylate, heptadecafluorodecyl (meth) acrylate, n-butyl (meth) acrylate, n-butyl (meth) acrylate, n-butyl acrylate, n-butyl acrylate, n-butyl acrylate, n-acrylate, n-butyl acrylate, n-acrylate, n-butyl acrylate, n-butyl acrylate, n-acrylate, But are not limited to, ethyl α -hydroxymethylmethacrylate, propyl α -hydroxymethylmethacrylate, and butyl α -hydroxymethylacrylate.
Specific examples of the aromatic vinyl monomers include, but are not limited to, styrene, α -methylstyrene, (o, m, p) -vinyltoluenes, (o, m, p) -methoxystyrenes, and (o, m, p) -chlorostyrenes.
Specific examples of the unsaturated ethers include, but are not limited to, vinyl methyl ether, vinyl ethyl ether, and allyl glycidyl ether.
Specific examples of the unsaturated imides include, but are not limited to, N-phenylmaleimide, N- (4-chlorophenyl) maleimide, N- (4-hydroxyphenyl) maleimide, and N-cyclohexylmaleimide.
Examples of the acid anhydride include, but are not limited to, maleic anhydride, methylmaleic anhydride, and tetrahydrophthalic anhydride.
The monomer for imparting alkali solubility is not particularly limited as long as it contains an acid group, and for example, one or more selected from (meth) acrylic acid, crotonic acid, itaconic acid, maleic acid, fumaric acid, monomethyl maleate, 5-norbornene-2-carboxylic acid, mono (2- ((meth) acryloyloxy) ethyl phthalate, mono-2- ((meth) acryloyloxy) ethyl succinate, and ω -carboxy polycaprolactone mono (meth) acrylate are preferably used, but not limited thereto.
According to one embodiment of the present disclosure, the binder resin has an acid value of 50 to 130KOHmg and a weight average molecular weight of 1000 to 50000.
The polyfunctional monomer is a monomer that functions to form a photoresist phase by light, and specifically may be one or a mixture of two or more selected from the group consisting of propylene glycol methacrylate, dipentaerythritol hexaacrylate, dipentaerythritol acrylate, neopentyl glycol diacrylate, 6-hexanediol diacrylate, 1, 6-hexanediol acrylate tetraethylene glycol methacrylate, bisphenoxyethanol diacrylate, tris (hydroxyethyl) isocyanurate trimethacrylate, trimethylpropane trimethacrylate, diphenyl pentaerythritol hexaacrylate, pentaerythritol trimethacrylate, pentaerythritol tetramethacrylate, and dipentaerythritol hexamethacrylate.
The photoinitiator is not particularly limited as long as it is an initiator that initiates crosslinking by generating radicals by light, and may be, for example, one or more of an acetophenone-based compound, a biimidazole-based compound, a triazine-based compound, and an oxime-based compound.
Examples of the acetophenone-based compound include 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) one, 1-hydroxycyclohexyl phenyl ketone, benzoin methyl ether, benzoin ethyl ether, benzoin isobutyl ether, benzoin butyl ether, 2-dimethoxy-2-phenylacetophenone, 2-methyl- (4-methylthio) phenyl-2-morpholino-1-propan-1-one, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -propan-1-one 2- (4-bromo-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butan-1-one or 2-methyl-1- [4- (methylthio) phenyl ] -2-morpholinopropan-1-one, but is not limited thereto.
Examples of the biimidazole compound include, but are not limited to, 2-bis (2-chlorophenyl) -4,4',5,5' -tetraphenylbiimidazole, 2 '-bis (o-chlorophenyl) -4,4',5,5 '-tetrakis (3,4, 5-trimethoxyphenyl) -1,2' -biimidazole, 2 '-bis (2, 3-dichlorophenyl) -4,4',5,5 '-tetraphenylbiimidazole, and 2,2' -bis (o-chlorophenyl) -4,4,5,5 '-tetraphenyl-1, 2' -biimidazole.
The triazine compound includes 3- {4- [2,4-bis (trichloromethyl) -s-triazin-6-yl ] phenylthio } propanoic acid, 1,1,1,3,3, 3-hexafluoroisopropyl-3- {4- [2,4-bis (trichloromethyl) -s-triazin-6-yl ] phenylthio } propanoic acid ester, ethyl 2- {4- [2,4-bis (trichloromethyl) -s-triazin-6-yl ] phenylthio } propanoic acid ester, 2-oxiranyl-2- {4- [2,4-bis (trichloromethyl) -s-triazin-6-yl ] phenylthio } ethanoic acid ester, cyclohexyl-2- {4- [2,4-bis (trichloromethyl) -s-triazin-6-yl ] phenylthio } ethanoic acid ester, Benzyl-2- {4- [2,4-bis (trichloromethyl) -s-triazin-6-yl ] phenylthio } acetate, 3- { chloro-4- [2,4-bis (trichloromethyl) -s-triazin-6-yl ] phenylthio } propanoic acid, 3- {4- [2,4-bis (trichloromethyl) -s-triazin-6-yl ] phenylthio } propanamide, 2,4-bis (trichloromethyl) -6-p-methoxystyryl-s-triazine, 2,4-bis (trichloromethyl) -6- (1-p-dimethylaminophenyl) -1, 3-butadiene-s-triazine, 2-trichloromethyl-4-amino-6-p-methoxystyryl-s-triazine, and the like, but is not limited thereto.
Examples of the oxime compounds include, but are not limited to, 1- (4-phenylthio) phenyl-1, 2-octanedione 2- (O-benzoyloxime) (CI BA-GEIGY Corp., CGI 124), 1- (9-ethyl) -6- (2-methylbenzoyl-3-yl) -ethanone 1- (O-acetyloxime) (CGI 242), and N-1919 (ADEKA).
The solvent can be acetone, methyl ethyl ketone, methyl isobutyl ketone, methyl cellosolve, ethyl cellosolve, tetrahydrofuran, 1, 4-di-ethanol
Figure BDA0001505775360000231
Alkane, 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-trichloroethylene, hexane, heptane, octane, cyclohexane, benzene, toluene, xylene, methanol, ethanol, isopropanol, propanol, butanol, tert-butanol, 2-ethoxypropanol, 2-methoxypropanol, 3-methoxybutanol, cyclohexanone, cyclopentanone, propylene glycol methyl ether acetate, propylene glycol ethyl ether acetate, 3-methoxybutyl acetate, ethyl 3-ethoxypropionate, ethyl cellosolve acetate, methyl cellosolve acetate, butyl acetate, methyl cellosolve acetate, ethyl cellosolve, ethyl acetate, ethyl, Propylene glycol monoOne or more of methyl ether and dipropylene glycol monomethyl ether, but not limited thereto.
According to one embodiment of the present disclosure, the content of the compound represented by chemical formula 1 is 5 to 60% by weight, the content of the binder resin is 1 to 60% by weight, the content of the photoinitiator is 0.1 to 20% by weight, and the content of the polyfunctional monomer is 0.1 to 50% by weight, based on the total amount of solid components in the resin composition.
The total weight of the solid components is the sum of the total weight of the components excluding the solvent in the resin composition. The amount of the solid content and the weight% of the solid content of each component can be measured by a general analytical method used in the art, such as liquid chromatography or gas chromatography.
According to an embodiment of the present disclosure, the resin composition may further include an antioxidant.
According to one embodiment of the present disclosure, the antioxidant is contained in an amount of 0.1 to 20 wt% based on the total weight of solid components in the resin composition.
According to an embodiment of the present disclosure, the resin composition further includes one or more additives selected from a photo-crosslinking sensitizer, a curing accelerator, an adhesion accelerator, a surfactant, a thermal polymerization inhibitor, an ultraviolet absorber, a dispersant, and a leveling agent.
According to one embodiment of the present disclosure, the additive is contained in an amount of 0.1 to 20 wt% based on the total weight of solid components in the resin composition.
As the photo-crosslinking sensitizer, benzophenone-based compounds such as benzophenone, 4, 4-bis (dimethylamino) benzophenone, 4, 4-bis (diethylamino) benzophenone, 2,4, 6-trimethylaminobenzophenone, methylphthaloyl benzoate, 3-dimethyl-4-methoxybenzophenone, and 3,3,4, 4-tetrakis (t-butylperoxycarbonyl) benzophenone; fluorenone compounds such as 9-fluorenone, 2-chloro-9-fluorenone, and 2-methyl-9-fluorenone; thioxanthone compounds such as thioxanthone, 2, 4-diethylthioxanthone, 2-chlorothioxanthone, 1-chloro-4-propyloxythioxanthone, isopropylthioxanthone and diisopropylthioxanthone; xanthone-based compounds such as xanthone and 2-methylxanthone; anthraquinone compounds such as anthraquinone, 2-methylanthraquinone, 2-ethylanthraquinone, tert-butylanthraquinone, and 2, 6-dichloro-9, 10-anthraquinone; acridine compounds such as 9-phenylacridine, 1, 7-bis (9-acridinyl) heptane, 1, 5-bis (9-acridinylpentane), 1, 3-bis (9-acridinyl) propane and the like; dicarbonyl compounds such as benzil, 1,7, 7-trimethyl-bicyclo [2,2,1] heptane-2, 3-dione, and 9, 10-phenanthrenequinone; phosphine oxide compounds such as 2,4, 6-trimethylbenzoyldiphenylphosphine oxide and bis (2, 6-dimethoxybenzoyl) -2,4, 4-trimethylpentylphosphine oxide; benzoate-based compounds such as methyl-4- (dimethylamino) benzoate, ethyl-4- (dimethylamino) benzoate, and 2-n-butoxyethyl-4- (dimethylamino) benzoate; amino synergists such as 2, 5-bis (4-diethylaminobenzylidene) cyclopentanone, 2, 6-bis (4-diethylaminobenzylidene) cyclohexanone, and 2, 6-bis (4-diethylaminobenzylidene) -4-methyl-cyclopentanone; coumarin-based compounds such as 3, 3-carbonylvinyl-7- (diethylamino) coumarin, 3- (2-benzothiazolyl) -7- (diethylamino) coumarin, 3-benzoyl-7-methoxy-coumarin, and 10, 10-carbonylbis [1,1,7, 7-tetramethyl-2, 3,6, 7-tetrahydro-1H, 5H,11H-C1] -benzopyran [6,7,8-ij ] -quinolizin-11-one; chalcone compounds such as 4-diethylaminochalcone and 4-azidobenzalacetophenone; more than one of 2-benzoyl methylene and 3-methyl-b-naphthothiazoline.
The above-mentioned curing accelerator is used for curing and improving mechanical strength, and specifically, it is possible to use a curing accelerator selected from the group consisting of 2-mercaptobenzimidazole, 2-mercaptobenzothiazole, and 2-mercaptobenzothiazole
Figure BDA0001505775360000241
Oxazole, 2, 5-dimercapto-1, 3, 4-thiadiazole, 2-mercapto-4, 6-dimethylaminopyridine, pentaerythritol-tetrakis (3-mercaptopropionate), pentaerythritol-tris (3-mercaptopropionate), pentaerythritol-tetrakis (2-mercaptoacetate), pentaerythritol-tris (2-mercaptoacetate), trimethylolpropane-tris (2-mercaptoacetate), and trimethylolpropaneMore than one of alkane-tri (3-mercaptopropionate).
As the adhesion promoter used in the present specification, one or more species selected from methacryloxysilane coupling agents such as methacryloxypropyltrimethoxysilane, methacryloxypropyldimethoxysilane, methacryloxypropyltriethoxysilane, and methacryloxypropyldimethoxysilane can be used, and as the alkyltrimethoxysilane, one or more species selected from octyltrimethoxysilane, dodecyltrimethoxysilane, and octadecyltrimethoxysilane can be used.
The surfactant is a silicon surfactant or a fluorine surfactant, and specifically, 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-375, BYK-380, BYK-390, etc. of BYK-Chemicals, BYK-354, BYK-355, BYK-356, BYK-358, BYK-361, BYK-177, BYK-390, etc. of BYK-Chemicals, etc. of BYK-177, etc. can be used as the fluorine surfactant, DIC (DaiNippon & Chemicals) can be used, 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-1116-1121, TF-1132, TF1027SF, TF-1441, TF-1442, and the like, but not limited thereto.
The antioxidant may be at least one selected from Hindered phenol (Hindered phenol) antioxidants, amine antioxidants, sulfur antioxidants, and phosphine antioxidants, but is not limited thereto.
Specific examples of the antioxidant include phosphoric acid-based heat stabilizers such as phosphoric acid, trimethyl phosphate and triethyl phosphate; such as 2, 6-di-tert-butyl-p-cresol, octadecyl-3- (4-hydroxy-3, 5-di-tert-butylphenyl) propionate, tetrakis [ methylene-3- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionate ] methane, 1,3, 5-trimethyl-2, 4, 6-tris (3, 5-di-tert-butyl-4-hydroxybenzyl) benzene, diethyl 3, 5-di-tert-butyl-4-hydroxybenzylphosphite, 2-thiobis (4-methyl-6-tert-butylphenol), 2,6-g, t-butylphenol 4,4 '-butylidene-bis (3-methyl-6-tert-butylphenol), 4' -thiobis (3-methyl-6-tert-butylphenol) or bis [3 ", hindered phenol (Hindered phenol) primary antioxidants such as 3-Bis- (4'-hydroxy-3' -t-butylphenyl) butanoic acid ethylene glycol ester (Bis [3,3-Bis- (4'-hydroxy-3' -tert-butyl-phenyl) butanoic acid ] glycol ester); amine-based secondary antioxidants such as phenyl- α -naphthylamine, phenyl- β -naphthylamine, N '-diphenyl-p-phenylenediamine or N, N' -di- β -naphthyl-p-phenylenediamine; a sulfur-based secondary antioxidant such as dilauryl disulfide, dilauryl thiopropionate, distearyl thiopropionate, mercaptobenzothiazole, or tetramethylthiuram disulfide tetrakis [ methylene-3- (laurylthio) propionate ] methane; or phosphite-based secondary antioxidants such as triphenyl phosphite, tris (nonylphenyl) phosphite, triisodecyl phosphite, Bis (2, 4-dibutylphenyl) Pentaerythritol diphosphite (Bis (2, 4-dittouylphenyl) Pentaerythritol diphophite) or tetrakis [2,4-Bis (1, 1-dimethylethyl) phenyl ] 1,1' -diphosphonate ((1,1' -biphenoxy) -4,4' -diphosphonate acid tetrakis [2,4-Bis (1, 1-dimethylethyl) phenyl ] ester).
Examples of the ultraviolet absorber include 2- (3-tert-butyl-5-methyl-2-hydroxyphenyl) -5-chloro-benzotriazole and alkoxybenzophenone, but the ultraviolet absorber is not limited thereto and any ultraviolet absorber generally used in this field can be used.
The thermal polymerization inhibitor may include, for example, at least one selected from the group consisting of p-anisole, hydroquinone, catechol (pyrocatechol), t-butylcatechol (t-butyl catechol), N-nitrosophenylhydroxylamine ammonium salt, N-nitrosophenylhydroxylamine aluminum salt, p-methoxyphenol, di-t-butyl-p-cresol, pyrogallol, benzoquinone, 4-thiobis (3-methyl-6-t-butylphenol), 2-methylenebis (4-methyl-6-t-butylphenol), 2-mercaptoimidazole, and phenothiazine (phenothiazine), but is not limited thereto, and may include a thermal polymerization inhibitor generally known in the art.
The dispersant may be used by a method of internally adding the dispersant to the pigment in a form in which the pigment is surface-treated in advance, or a method of externally adding the dispersant to the pigment. The dispersant may be a compound type, nonionic, anionic or cationic dispersant, and examples thereof include fluorine type, ester type, cationic type, anionic type, nonionic type, amphoteric type surfactants, and the like. These may be used individually or in combination of two or more.
Specifically, the dispersant is at least one selected from the group consisting of polyalkylene glycols and esters thereof, polyoxyalkylene polyols, ester alkylene oxide adducts, alcohol alkylene oxide adducts, sulfonic acid esters, sulfonic acid salts, carboxylic acid esters, carboxylic acid salts, alkylamide alkylene oxide adducts, and alkylamines, but is not limited thereto.
The leveling agent may be a polymerizable leveling agent or a non-polymerizable leveling agent. Specific examples of the polymerizable leveling agent include polyethyleneimine, polyamidoamine, and a reaction product of an amine and an epoxide, and specific examples of the non-polymerizable leveling agent include a non-polymeric sulfur-containing compound and a non-polymeric nitrogen-containing compound, but the non-polymerizable leveling agent is not limited thereto, and leveling agents generally used in this field can be used.
According to an embodiment of the present specification, there is provided a photosensitive material produced from the above resin composition.
More specifically, the resin composition of the present specification is applied to a substrate by an appropriate method to form a photosensitive material in the form of a film or a pattern.
The coating method is not particularly limited, and a spray coating method, a roll coating method, a spin coating method, and the like can be used, and a spin coating method is generally widely used. After the coating film is formed, the residual solvent may be partially removed under reduced pressure according to circumstances.
Examples of the light source for curing the resin composition according to the present specification include, but are not limited to, mercury vapor arc (arc), carbon arc, and Xe arc, which emit light having a wavelength of 250 to 450 nm.
The resin composition according to the present specification can be used for a pigment dispersion type photosensitive material for manufacturing a color filter of a thin film transistor liquid crystal display device (TFT LCD), a photosensitive material for forming a black matrix of a thin film transistor liquid crystal display device (TFT LCD) or an organic light emitting diode, a photosensitive material for forming an overcoat layer, a photosensitive material for a column spacer, a photocurable coating material, a photocurable ink, a photocurable adhesive, a printing plate, a photosensitive material for a printed wiring board, a photosensitive material for a Plasma Display Panel (PDP), and the like, but the use thereof is not particularly limited.
According to one embodiment of the present specification, a color filter including the photosensitive material is provided.
The color filter may be manufactured using a resin composition including the compound represented by chemical formula 1. The color filter can be formed by applying the resin composition on a substrate to form a coating film, and exposing, developing and curing the coating film.
The resin composition according to one embodiment of the present specification is excellent in heat resistance and is less likely to undergo color change due to heat treatment, and therefore, a color filter having high color reproducibility even after a curing process in the production of a color filter, and high brightness and contrast can be provided.
The substrate may be a glass plate, a silicon wafer, a plastic-based plate such as Polyethersulfone (PES) or Polycarbonate (PC), and the like, and the type thereof is not particularly limited.
The color filter may include a red pattern, a green pattern, a blue pattern, and a black matrix.
According to another embodiment, the color filter may further include an overcoat layer.
For the purpose of improving contrast, a lattice-like black pattern called a black matrix may be arranged between the color pixels of the color filter. As a material of the black matrix, chromium may be used. In this case, a method of forming a pattern by performing vapor deposition of chromium on the entire glass substrate and etching treatment may be used. However, in consideration of high process costs, high reflectance of chromium, and environmental pollution caused by chromium waste liquid, a resin black matrix obtained by a pigment dispersion method capable of microfabrication may be used.
In the black matrix according to an embodiment of the present specification, a black pigment or a black dye may be used as a coloring material. For example, carbon black may be used alone or carbon black and a coloring pigment may be used in combination, and in this case, since the coloring pigment having insufficient light-shielding property is mixed, there is an advantage that even if the amount of the coloring material is relatively increased, the strength of the film and the adhesion to the substrate are not decreased.
Provided is a display device including a color filter according to the present specification.
The Display device may be any one of 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-Liquid Crystal Display (LCD-TFT), and a Cathode Ray Tube (CRT).
Hereinafter, examples will be described in detail to specifically describe the present specification. However, the embodiments described in the present specification may be modified into other various forms, and the scope of the present specification should not be construed as being limited to the embodiments described below. The embodiments of the present description are provided to more fully describe the present description to those skilled in the art.
[ Experimental example 1]
Synthesis of Compounds
Compound 1 is produced by the reaction of the following reaction formula 1.
Reaction scheme 1
Figure BDA0001505775360000281
5g (8.710mmol) of A-1, 8.233g (34.838mmol) of B-1, 4.815g (34.5838mmol) of K2CO3Added to 100ml of NMP and stirred at 95 ℃ for 12 hours. Then, the solvent was removed under reduced pressure, and 200ml of water was added to the precipitate and stirred for 1 hour. The precipitate was filtered under reduced pressure and dried at 80 ℃ for 12 hours. Then, the dried precipitate was separated by column chromatography. (eluent-MC: MeOH)
As a result, 6g (3.322mmol) of Compound 1 was obtained in a yield of 72%.
The results are as follows.
APCI + 949M + H + 948 with accurate Mass (Exact Mass):948
Of the above Compound 11The measurement results of H-NMR were as follows.
1H NMR(500MHz,DMSO,ppm):8.03(m,11H),7.69～7.18(m,10H),6.99～6.95(t,1H),6.80～6.01(dd,1H),5.93～5.85(dd,1H),4.06～3.79(m,4H),3.72～3.60(m,4H),2.17～1.70(m,16H)
Further, compound 2 is produced by the following reaction formula 2.
Reaction formula 2
Figure BDA0001505775360000291
5g (7.388mmol) of acid Red 289 and 4.09g (29.554mmol) of K2CO3Added to 100ml of NMP and stirred at 95 ℃ for 12 hours. Then, the solvent was removed under reduced pressure, and 100 g of Brine (Brine) was added to the precipitate, followed by stirring for 1 hour. Then, the precipitate was filtered under reduced pressure and dried at 80 ℃ for 12 hours.
As a result, 7.3g (6.945mmol) of a coloring material containing Compound 2 as a main product was obtained, and the yield thereof was 94%.
Further, compound 3 is produced by the following reaction formula 3.
Reaction formula 3
Figure BDA0001505775360000292
CHCl was added at 0 deg.C37.4g of DMF was added, followed by stirring. 2.479g (20.835mmol) of SOCl were added2Further stirring was carried out at 0 ℃ for 30 minutes. Slowly dropwise adding 73g (6.945mmol) of a coloring material containing Compound 2 as a main product. Then, the temperature was raised to 35 ℃ and stirred for 1 hour and 30 minutes. Then, it was cooled to 0 ℃ and 2.693g (20.835mmol) of 2-ethylhexylamine was added dropwise, and 7.028g (69.45mmol) of Et was added dropwise3N, stirred at ambient temperature for 16 hours. The solvent was removed under reduced pressure, and water and MC were added to conduct extraction. The organic layer was passed over MgSO4Thereafter, the solvent was removed under reduced pressure, and the mixture was dried at 80 ℃ for 12 hours.
As a result, 2.772g (2.431mmol) of a coloring material containing compound 3 as a main product was obtained, and the yield was 35%.
Further, compound 4 is produced by the following reaction formula 4.
Reaction formula 4
Figure BDA0001505775360000301
1.43g (2.732mmol) of D-1, 2.99g (9.490mmol) of B-1, 1.31g (9.490mmol) of K2CO3Added to 20ml of NMP and stirred at 95 ℃ for 12 hours. Then, the solvent was removed under reduced pressure, and 200ml of water was added to the precipitate, followed by stirring for 1 hour. The precipitate was filtered under reduced pressure and dried at 80 ℃ for 12 hours. Then, the dried precipitate was separated by column chromatography. (eluent-MC: MeOH)
As a result, 1.622g (1.912mmol) of compound 4 was obtained, and the yield was 70%.
APCI + M/z 977M + H + with precise mass 976
Then, compound 5 is produced by the following reaction formula 5.
Reaction formula 5
Figure BDA0001505775360000302
1.608g (2.732mmol) of E-1, 2.99g (9.490mmol) of B-1, 1.31g (9.490mmol) of K2CO3Added to 20ml of NMP and stirred at 95 ℃ for 12 hours. Then, under reduced pressureThe solvent was removed, and 200ml of water was added to the precipitate, followed by stirring for 1 hour. The precipitate was filtered under reduced pressure and dried at 80 ℃ for 12 hours. Then, the dried precipitate was separated by column chromatography. (eluent-MC: MeOH)
As a result, 1.526g (1.622mmol) of compound 5 was obtained, and the yield was 59%.
Ionization mode APCI + M/z 963M + H + accurate mass 962
The compounds used as comparative subjects were as follows.
Comparative Compound 1
Figure BDA0001505775360000311
Comparative Compound 2
Figure BDA0001505775360000312
The above comparative example 1 is basic blue 7, and comparative example 2 is rhodamine 6G.
Examples and comparative examples were manufactured at the ratios as shown in table 1 below. The unit of compound input is grams (g).
[ Table 1]
Figure BDA0001505775360000321
Substrate fabrication
The compound produced by the above synthesis was spin-coated (spinning) on glass (5 × 5cm), and prebaked (prebake) at 100 ℃ for 100 seconds to form a film. The distance between the substrate on which the film was formed and a photomask (photo mask) was set to 250 μm, and the entire surface of the substrate was exposed to 40mJ/cm by an exposure machine2The exposure amount of (2) is used for irradiation.
Then, the exposed substrate was developed in a developing solution (KOH, 0.05%) for 60 seconds and post-baked (post bake) at 230 ℃ for 20 minutes to fabricate a substrate.
Evaluation of Heat resistance
The prebaked (prebake) substrate produced under the above conditions was used to obtain a transmittance spectrum in the visible light region in the range of 380nm to 780nm by a spectrometer (MCPD-Otsuka). In addition, the prebaked (prebake) substrate was further subjected to post-baking (post-bake) at 230 ℃ for 20 minutes, and a transmittance spectrum was obtained in the same apparatus and measurement range.
Using the obtained transmittance spectrum and the C light source backlight, Δ Eab was calculated from the obtained values E (L, a, b) and shown in table 2 below.
ΔE(L*,a*,b*)＝{(ΔL*)2+(Δa*)2+(Δb*)2}/2
A small value of Δ E means excellent color heat resistance.
The heat resistance was measured for the compounds of the experimental examples and comparative examples 1 and 2, and the results are shown in table 1. As shown in table 2, it was confirmed that the compound showed a smaller color change (Δ Eab) than comparative examples 1 and 2.
[ Table 2]
ΔEab(PB-PrB)
Example 1 2.02
Example 2 1.98
Example 3 2.15
Example 4 2.30
Comparative example 1 26.52
Comparative example 2 23.95
FIG. 1 is a view showing R in chemical formula 1 according to one embodiment of the present application13And R14The transmittance is shown in the graphs for the case of a phenyl group substituted with a methyl group, the case of a phenyl group substituted with an isopropyl group, and the case of a phenyl group substituted with an ethyl group. As can be seen from fig. 1, a desired transmittance can be obtained by using the compound according to an embodiment of the present application.

Claims (11)

1. A compound represented by the following chemical formula 4:
chemical formula 4
Figure FDA0003009539490000011
In the chemical formula 4, the first and second organic solvents,
R1to R6Is a hydrogen atom, and is,
R7to R11Each independently selected from hydrogen and-SO3 -，
The R is7To R11One of them is-SO3 -，
R13 and R14 are each independently selected from phenyl substituted with an alkyl group having 1 to 30 carbon atoms or an anionic group, wherein the anionic group is-SO3NRcRd, Rc and Rd each independently represent an unsubstituted straight or branched alkyl group having 1 to 10 carbon atoms,
L1and L2Each independently being a direct bond or an alkylene group of 1 to 6 carbon atoms,
R19and R20Is a hydrogen atom, and is,
m is 4, and
n is 4.
2. The compound according to claim 1, wherein the compound represented by chemical formula 4 is a compound represented by any one of the following chemical formulae:
Figure FDA0003009539490000021
Figure FDA0003009539490000031
3. the compound of claim 1, wherein R13And R14Each independently is 2, 6-dimethylphenyl.
4. A colorant composition comprising the compound according to any one of claims 1 to 3.
5. The colorant composition according to claim 4, further comprising at least one of a dye and a pigment.
6. A resin composition comprising the compound of chemical formula 4 according to any one of claims 1 to 3, a binder resin, a polyfunctional monomer, a photoinitiator, and a solvent.
7. The resin composition according to claim 6, wherein the compound represented by chemical formula 4 is contained in an amount of 5 to 60 wt%, the binder resin is contained in an amount of 1 to 60 wt%, the photoinitiator is contained in an amount of 0.1 to 20 wt%, and the polyfunctional monomer is contained in an amount of 0.1 to 50 wt%, based on the total weight of solid components in the resin composition.
8. The resin composition according to claim 6, further comprising an antioxidant.
9. A photosensitive material produced by using the resin composition according to claim 6.
10. A color filter comprising the photosensitive material according to claim 9.
11. A display device comprising the color filter according to claim 10.
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