CN107743487A - Xanthene based compound and the photosensitive polymer combination for including it - Google Patents

Xanthene based compound and the photosensitive polymer combination for including it Download PDF

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CN107743487A
CN107743487A CN201680034516.5A CN201680034516A CN107743487A CN 107743487 A CN107743487 A CN 107743487A CN 201680034516 A CN201680034516 A CN 201680034516A CN 107743487 A CN107743487 A CN 107743487A
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CN107743487B (en
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朴钟镐
李多美
李在容
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LG Corp
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LG Chemical Co Ltd
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    • 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
    • C09B11/04—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
    • 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
    • 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
    • C07D—HETEROCYCLIC COMPOUNDS
    • 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
    • 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
    • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds

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  • General Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Materials For Photolithography (AREA)
  • Optical Filters (AREA)
  • Polymerisation Methods In General (AREA)

Abstract

This specification provides the xanthene based compound of new structure and the photosensitive polymer combination comprising it, photosensitive material, colour filter and display element using its manufacture.

Description

Xanthene based compound and the photosensitive polymer combination for including it
Technical field
The korean patent application 10-2015- that this specification requirement is submitted based on June 17th, 2015 to Koran Office The priority of No. 0086200, full content as part of this specification disclosed in the document of the korean patent application and Comprising.
This specification is related to a kind of xanthene based compound and includes its photosensitive polymer combination.In addition, this explanation Book is related to a kind of colour filter using the manufacture of above-mentioned photosensitive polymer combination and includes its display element.
Background technology
Colour filter is required the performance characterized by high brightness, high-contrast in recent years.In addition, the master of display element exploitation Want the first purpose be by improve colour purity make display element performance difference and improve manufacturing process on productivity ratio.
The pigment type used due to the colorant as conventional colour filter is present in colourama with particle dispersity In resist, therefore had difficulties in terms of brightness and contrast is adjusted by adjusting pigment particles size and distribution.In pigment In the case of particle, condensed in colour filter and dissolve and dispersiveness reduce, and due to condense (aggregation) big grain Son and the multiple scattering (multiple scattering) of light occurs.The scattering of this light by polarisation is considered as reducing contrast The main reason for spending.People's ongoing effort improves brightness and contrast by the ultra micro granulation and dispersion stability of pigment, But for realizing that high color purity display device is limited with the selected middle free degree of the colorant of chromaticity coordinates.In addition, using having developed Color material especially pigment pigment dispersion method improve using its colour filter excitation, brightness and contrast side Face has reached the limit.
Then, it is desirable to which exploitation can improve the new color of color reproduction, brightness and contrast by improving excitation Material.
The content of the invention
The present inventor aims to provide the xanthene based compound, the photosensitive polymer combination comprising it, utilization of new structure Its manufacture colour filter and include its display element.
One embodiment of this specification provides the compound represented by following chemical formula 1.
[chemical formula 1]
In above-mentioned chemical formula 1,
R1To R6It is each independently selected from hydrogen, deuterium, halogen atom, nitro, substituted or unsubstituted carbon number 1 to 30 The alkyl of straight or branched, the alkoxy of substituted or unsubstituted carbon number 1 to 30 and substituted or unsubstituted carbon atom The monocyclic or polycyclic aryl of number 6 to 30 and the monocyclic or polycyclic heteroaryl of substituted or unsubstituted carbon number 2 to 30 Base,
R7To R11Be each independently selected from hydrogen, deuterium, anionic property group, hydroxyl, substituted or unsubstituted carbon number 1 to The alkyl of 30 straight or branched, substituted or unsubstituted carbon number 6 to 30 monocyclic or polycyclic aryl and substitution or The monocyclic or polycyclic heteroaryl of unsubstituted carbon number 2 to 30,
Above-mentioned R7To R11In it is at least one be anionic property group,
R12To R14Be each independently selected from hydrogen, deuterium, substituted or unsubstituted carbon number 6 to 30 it is monocyclic or polycyclic Aryl, the monocyclic or polycyclic heteroaryl of substituted or unsubstituted carbon number 2 to 30 and two anhydride groups containing nitrogen-atoms,
R15And R16It is each independently selected from hydrogen, deuterium, anionic property group, hydroxyl, substituted or unsubstituted carbon number 1 The monocyclic or polycyclic aryl of alkyl, substituted or unsubstituted carbon number 6 to 30 to 30 straight or branched and substitution Or the monocyclic or polycyclic heteroaryl of unsubstituted carbon number 2 to 30, or be combined with each other and formed substituted or unsubstituted The monocyclic or polycyclic aromatic series hydrocarbon ring of carbon number 6 to 30 or the monocyclic of substituted or unsubstituted carbon number 2 to 30 or Polycyclic heterocycle,
L1And L2It is each independently Direct Bonding or divalent linking group.
One embodiment of this specification provides the colorant composition of the compound comprising above-mentioned chemical formula 1.
One embodiment of this specification can be provided comprising the compound represented by chemical formula 1, adhesive resin, more officials The resin combination of energy property monomer, light trigger and solvent.
One embodiment of this specification provides the photosensitive material manufactured using above-mentioned resin combination.
One embodiment of this specification provides the colour filter for including above-mentioned photosensitive material.
One embodiment of this specification provides the display device for including above-mentioned colour filter.
Xanthene based compound involved by one embodiment of this specification can the conduct in photosensitive polymer combination Colorant uses, and compared with conventional colorant, passes through the absorption of spectrum and colour filter sent from light source and the association of transmitted spectrum Adjust, so as to improve excitation.
In addition, the xanthene based compound involved by an embodiment of this specification uses as color material, so as to To improve color reproduction, brightness and contrast.
Brief description of the drawings
Fig. 1 is the figure for the transmissivity for representing the compound involved by an embodiment of this specification.
Embodiment
Below, this specification is illustrated in more detail.
In this specification, when pointing out a certain inscape of certain a part of "comprising", as long as no especially opposite record, Then mean further include other inscapes, rather than other inscapes are excluded.
According to an embodiment of this specification, there is provided the compound represented by above-mentioned chemical formula 1.
The example of the substituent of compound represented by above-mentioned chemical formula 1 will be described below, but not limit In this.
" substituted or unsubstituted " this term is meant by selected from deuterium in this manual；Halogen atom；Alkyl；Alkene Base；Alkoxy；Cycloalkyl；Silicyl；Aryl alkenyl ( arylalkenyl)；Aryl；Aryloxy group；Virtue Alkyl；Arylalkenyl (aralalkenyl)；Alkyl sulfenyl (Alkyl thioxy)； Alkyl sulfoxide base (Alkyl sulfoxy)；Aryl sulfoxid es base (Aryl sulfoxy)；Boryl；Alkyl amine group；Aralkyl amido；Arylamine group；Heteroaryl；Carbazyl；Acryloyl group；It is acrylate-based； Ether；Itrile group；Nitro；Hydroxyl；Cyano group；Include the heterocyclic radical of more than 1 and anionic property group in N, O, S or P atom In the substituent of more than 1 substitution or without any substituent.
In this specification, abovementioned alkyl can be straight or branched, and carbon number is not particularly limited, but carbon number can Think 1 to 30.As specific example, there are methyl, ethyl, propyl group, isopropyl, butyl, the tert-butyl group, amyl group, hexyl and heptyl Deng, but it is not limited to this.
In this specification, above-mentioned alkenyl can be straight or branched, and carbon number is not particularly limited, but carbon number can Think 2 to 25.Can be the virtue of stilbenyl (stylbenyl), styryl (styrenyl) etc. as specific example The substituted alkenyl of base, but it is not limited to this.
In this specification, above-mentioned alkoxy can be straight or branched, and carbon number is not particularly limited, but carbon number Can be 1 to 30.
In this specification, cycloalkyl is not particularly limited, but carbon number can be 3 to 20, particularly can be ring penta Base, cyclohexyl.
In this specification, as the example of halogen atom, there are fluorine, chlorine, bromine or iodine.
In this specification, phenoxy group is not particularly limited, but carbon number can be 3 to 20.
In this specification, carboxyl is not particularly limited, but carbon number can be 1 to 30.
In this specification, carboxylic acid ester groups is not particularly limited, but carbon number can be 2 to 30.As specific example, have Carboxylate methyl ester, carboxylic acid, ethyl ester, carboxylic acid isopropyl and benzyl carboxylate etc., but it is not limited to this.
In this specification, the salt of carboxylate group and sulphonate-base respectively with the cation formation of 1 valency, the cation of 1 valency Can be selected from Na+、K+And any one in quaternary ammonium cation, but it is not limited to this.Concrete example as quaternary ammonium cation Son, can be tetraalkylammonium cations such as tetramethylammonium cation, ethyl-trimethyl ammonium cation, tetrapropylammonium cation etc., But it is not limited to this.
In this specification, alkoxy carbonyl is not particularly limited, but carbon number can be 1 to 30.In alkoxy carbonyl, As the specific example of alkyl, the explanation identical alkyl with abovementioned alkyl can be applicable.As specific example, it can enumerate and provide There is the alkoxy carbonyl of described alkyl in the specific example of alkyl, but be not limited to this.
In this specification, sulfonic group is not particularly limited, but carbon number can be 1 to 30.
In this specification, as the specific example of sulfonate group, mesyl, ethylsulfonyl, hexane sulphonyl can be included The carbon numbers such as base are 1 to 4 alkyl sulphonyl, but are not limited to this.
In this specification, above-mentioned aralkyl is specially that the carbon number of aryl moiety is former for the carbon of 6 to 49 and moieties Subnumber is 1 to 44.As specific example, have benzyl, to methyl-benzyl, a methyl-benzyl, to Ethylbenzyl, an Ethylbenzyl, 3,5- dimethyl benzyls, α-methylbenzyl, bis (alpha, alpha-dimethylbenzyl) base, α, Alpha-Methyl phenylbenzyl, 1- naphthobenzyls, 2- naphthyl benzyls Base, to luorobenzyl, 3,5- difluorobenzyls, α, α-bistrifluoromethylbenzyl, to methoxy-benzyl, meta-methoxy benzyl, α-benzene oxygen Base benzyl, α-benzyloxy-benzyl, naphthyl methyl, naphtylethyl group, naphthylisopropyl, pyrrol ylmethyl, pyrrolylethyl, amino benzyl Base, nitrobenzyl, cyanobenzyls, 1- hydroxyls -2- propyloxy phenyls base and the chloro- 2- propyloxy phenyls bases of 1- etc., but be not limited to This.
In this specification, the aryl moiety of arylalkenyl can be applicable the explanation described later on aryl, and alkenyl part can be with It is applicable the above-mentioned explanation on alkenyl.
In this specification, aryl can be monocyclic aryl or polycycle aryl.
In the case that above-mentioned aryl is monocyclic aryl, carbon number is not particularly limited, but carbon number can be 6 To 40.Specifically, can be phenyl, xenyl or terphenyl etc., but be not limited to this as monocyclic aryl.
In the case that above-mentioned aryl is polycycle aryl, carbon number is not particularly limited, but carbon number can be 10 to 40.Specifically, as polycycle aryl, can be naphthyl, anthryl, phenanthryl, pyrenyl, base,Base or fluorenyl etc., but It is not limited to this.
In this specification, fluorenyl can have substituent, and substituent can be bonded to each other and form spiro structure.As fluorenyl Example, haveDeng.
In this specification, above-mentioned heteroaryl is that carbon number is without spy comprising the heterocyclic radical as heteroatomic O, N or S Do not limit, carbon number can be 2 to 30.As the example of heterocyclic radical, there are thienyl, furyl, pyrrole radicals, imidazole radicals, thiophene Oxazolyl,Oxazolyl,Di azoly, triazolyl, pyridine radicals, bipyridyl, triazine radical, acridinyl, pyridazinyl, quinolyl, isoquinoline Quinoline base, indyl, carbazyl, benzoOxazolyl, benzimidazolyl, benzothiazolyl, benzo carbazole base, benzothienyl, two Benzothienyl, benzofuranyl and dibenzofuran group etc., but it is not limited to this.
In this specification, alkylidene refers to the group for having two basic change position in alkane (alkane).Above-mentioned alkylidene Can be straight chain, side chain or loop chain.The carbon number of alkylidene is not particularly limited, and carbon number can be 2 to 25.
In this specification, aromatic series hydrocarbon ring can be applicable the explanation of aryl in addition to not being 1 valency group.
In this specification, heterocycle can be applicable the explanation of heteroaryl in addition to not being 1 valency group.
According to above-mentioned embodiment, R1To R6Hydrogen, deuterium, halogen atom, nitro, substitution or not are may be selected from independently of one another The alkyl of the straight or branched of substituted carbon number 1 to 30, substituted or unsubstituted carbon number 1 to 30 alkoxy, with And substituted or unsubstituted carbon number 6 to 30 monocyclic or polycyclic aryl and substituted or unsubstituted carbon number 2 to 30 monocyclic or polycyclic heteroaryl.
According to another embodiment of this specification, above-mentioned R1To R6Hydrogen, deuterium, substitution are may be selected from independently of one another or are not taken The alkyl of the straight or branched of the carbon number 1 to 20 in generation, substituted or unsubstituted carbon number 1 to 20 alkoxy and The monocyclic or polycyclic aryl and substituted or unsubstituted carbon number 2 to 20 of substituted or unsubstituted carbon number 6 to 20 Monocyclic or polycyclic heteroaryl.
According to another embodiment of this specification, above-mentioned R1To R6Hydrogen, deuterium, substitution are may be selected from independently of one another or are not taken The alkyl of the straight or branched of the carbon number 1 to 10 in generation, substituted or unsubstituted carbon number 6 to 10 it is monocyclic or polycyclic The monocyclic or polycyclic heteroaryl of aryl and substituted or unsubstituted carbon number 2 to 10.
According to another embodiment of this specification, above-mentioned R1To R6Can be hydrogen.
In addition, R7To R11It is former that hydrogen, deuterium, anionic property group, hydroxyl, substituted or unsubstituted carbon are may be selected from independently of one another The alkyl of the straight or branched of subnumber 1 to 30, substituted or unsubstituted carbon number 6 to 30 monocyclic or polycyclic aryl, with And the monocyclic or polycyclic heteroaryl of substituted or unsubstituted carbon number 2 to 30, R7To R11In it is at least one can be the moon Ionic group.
According to another embodiment of this specification, R7To R11May be selected from independently of one another hydrogen, deuterium, anionic property group, The list of the alkyl of the straight or branched of substituted or unsubstituted carbon number 1 to 20, substituted or unsubstituted carbon number 6 to 20 The monocyclic or polycyclic heteroaryl of ring or polycyclic aryl and substituted or unsubstituted carbon number 2 to 20, R7To R11In At least one can be anionic property group.
According to another embodiment of this specification, R7To R11May be selected from independently of one another hydrogen, deuterium, anionic property group, The list of the alkyl of the straight or branched of substituted or unsubstituted carbon number 1 to 10, substituted or unsubstituted carbon number 6 to 10 The monocyclic or polycyclic heteroaryl of ring or polycyclic aryl and substituted or unsubstituted carbon number 2 to 10, R7To R11In At least one can be anionic property group.
According to another embodiment of this specification, R7To R11Can be hydrogen or anionic property group independently of one another, R7 To R11In it is at least one can be anionic property group.
In addition, R12It may be selected from hydrogen, deuterium, the monocyclic or polycyclic aryl of substituted or unsubstituted carbon number 6 to 30, substitution Or monocyclic or polycyclic heteroaryl and two anhydride groups comprising nitrogen-atoms of unsubstituted carbon number 2 to 30.
According to another embodiment of this specification, R12It may be selected from hydrogen, deuterium, substituted or unsubstituted carbon number 6 to 20 Monocyclic or polycyclic aryl, substituted or unsubstituted carbon number 2 to 20 monocyclic or polycyclic heteroaryl and include nitrogen Two anhydride groups of atom.
According to another embodiment of this specification, R12It may be selected from hydrogen, deuterium, substituted or unsubstituted carbon number 6 to 10 Monocyclic or polycyclic aryl, substituted or unsubstituted carbon number 2 to 10 monocyclic or polycyclic heteroaryl and include nitrogen Two anhydride groups of atom.
According to another embodiment of this specification, R12Can be two anhydride groups comprising nitrogen-atoms.
Also, R13And R14May be selected from independently of one another hydrogen, deuterium, substituted or unsubstituted carbon number 6 to 30 monocyclic or Polycyclic aryl, the monocyclic or polycyclic heteroaryl of substituted or unsubstituted carbon number 2 to 30 and comprising nitrogen-atoms two Anhydride group.
According to another embodiment of this specification, R13And R14Hydrogen, deuterium, substitution or unsubstituted are may be selected from independently of one another The monocyclic or polycyclic aryl of carbon number 6 to 20, substituted or unsubstituted carbon number 2 to 20 it is monocyclic or polycyclic miscellaneous Aryl and two anhydride groups comprising nitrogen-atoms.
According to another embodiment of this specification, R13And R14Hydrogen, deuterium, substitution or unsubstituted are may be selected from independently of one another The monocyclic or polycyclic aryl of carbon number 6 to 10, substituted or unsubstituted carbon number 2 to 10 it is monocyclic or polycyclic miscellaneous Aryl and two anhydride groups comprising nitrogen-atoms.
According to another embodiment of this specification, R13And R14Hydrogen, substituted or unsubstituted benzene are may be selected from independently of one another Base and two anhydride groups comprising nitrogen-atoms.
According to another embodiment of this specification, R13And R14May be selected from independently of one another hydrogen, by selected from methyl and it is cloudy from At least one substituted phenyl in sub- property group and two anhydride groups comprising nitrogen-atoms.
In addition, R15And R16Hydrogen, deuterium, anionic property group, hydroxyl, substituted or unsubstituted carbon are may be selected from independently of one another The alkyl of the straight or branched of atomicity 1 to 30, substituted or unsubstituted carbon number 6 to 30 monocyclic or polycyclic aryl, And the monocyclic or polycyclic heteroaryl of substituted or unsubstituted carbon number 2 to 30, or can be bonded to each other and be formed and taken The monocyclic or polycyclic aryl or substituted or unsubstituted carbon number 2 to 30 of generation or unsubstituted carbon number 6 to 30 Monocyclic or polycyclic heteroaryl.
According to another embodiment of this specification, R15And R16May be selected from independently of one another hydrogen, deuterium, anionic property group, Hydroxyl, the alkyl of straight or branched of substituted or unsubstituted carbon number 1 to 20, substituted or unsubstituted carbon number 6 to 20 monocyclic or polycyclic aryl and the monocyclic or polycyclic heteroaryl of substituted or unsubstituted carbon number 2 to 20, or It can be bonded to each other and form monocyclic or polycyclic aryl or the substitution or not of substituted or unsubstituted carbon number 6 to 20 The monocyclic or polycyclic heteroaryl of substituted carbon number 2 to 20.
According to another embodiment of this specification, R15And R16May be selected from independently of one another hydrogen, deuterium, anionic property group, Hydroxyl, the alkyl of straight or branched of substituted or unsubstituted carbon number 1 to 20, substituted or unsubstituted carbon number 6 to 20 monocyclic or polycyclic aryl and the monocyclic or polycyclic heteroaryl of substituted or unsubstituted carbon number 2 to 20, or It can be bonded to each other and form monocyclic or polycyclic aryl or the substitution or not of substituted or unsubstituted carbon number 6 to 20 The monocyclic or polycyclic heteroaryl of substituted carbon number 2 to 20.
According to another embodiment of this specification, R15And R16It is each independently selected from hydrogen, deuterium, anionic property group, hydroxyl Base, substituted or unsubstituted carbon number 1 to 10 straight or branched alkyl, substituted or unsubstituted carbon number 6 to 10 Monocyclic or polycyclic aryl and substituted or unsubstituted carbon number 2 to 10 monocyclic or polycyclic heteroaryl, Huo Zheke The monocyclic or polycyclic aryl of substituted or unsubstituted carbon number 6 to 10 is formed to be bonded to each other or substitution or is not taken The monocyclic or polycyclic heteroaryl of the carbon number 2 to 10 in generation.
According to another embodiment of this specification, R15And R16Hydrogen, deuterium and anionic property base are may be selected from independently of one another Group, or can be bonded to each other and form substituted or unsubstituted phenyl ring.
In addition, L1And L2It can be Direct Bonding or divalent linking group independently of one another, can be direct key in more detail Conjunction or alkylidene, can be the unsubstituted alkylidene of carbon number 1 to 6 in further detail.
In addition, according to another embodiment of this specification, above-mentioned chemical formula 1 can be provided and represented by following chemical formula 2 Compound.
[chemical formula 2]
In above-mentioned chemical formula 2, R1To R11、R13To R16、L1And L2Such as the definition in above-mentioned chemical formula 1, R17And R18Each solely On the spot such as above-mentioned R15And R16Explanation.
In addition, according to another embodiment of this specification, above-mentioned chemical formula 1 can be provided and represented by following chemical formula 3 Compound.
[chemical formula 3]
In above-mentioned chemical formula 3, R1To R14、L1And L2Such as the definition in above-mentioned chemical formula 1, R19May be selected from hydrogen, deuterium, substitution or The straight or branched alkyl of unsubstituted carbon number 1 to 20, substituted or unsubstituted carbon number 1 to 20 alkoxy, take Generation or the monocyclic or polycyclic aryl of unsubstituted carbon number 6 to 30, substituted or unsubstituted carbon number 2 to 30 it is monocyclic Or polycyclic heteroaryl, halogen atom, nitro, phenoxy group, carboxyl, carboxylic acid ester groups, carboxylate group, alkoxy carbonyl, hydroxyl, sulphur Acidic group, sulfonate group, sulphonate-base ,-SO2NHR21Base and-SO2NR22R23, above-mentioned R21To R23Can be carbon independently of one another The alkyl of atomicity 1 to 30, m can be 1 to 4 integer, when m is 2, R19It can be same to each other or different to each other.
According to another embodiment of this specification, R19It may be selected from hydrogen, deuterium, substituted or unsubstituted carbon number 1 to 10 Straight or branched alkyl, alkoxy, the substituted or unsubstituted carbon number 6 of substituted or unsubstituted carbon number 1 to 10 Monocyclic or polycyclic heteroaryl, the sulfonic acid of monocyclic or polycyclic aryl, substituted or unsubstituted carbon number 2 to 20 to 20 Base, sulfonate group, sulphonate-base ,-SO2NHR21Base and-SO2NR22R23, above-mentioned R21To R23Can be that carbon is former independently of one another The alkyl of subnumber 1 to 20, m can be 1 to 4 integer, when m is more than 2, R19It can be same to each other or different to each other.
According to another embodiment of this specification, R19May be selected from hydrogen, deuterium, sulfonic group, sulfonate group, sulphonate-base ,- SO2NHR21Base and-SO2NR22R23, above-mentioned R21To R23Can be the alkyl of carbon number 1 to 10 independently of one another, m can be with For 1 to 4 integer, when m is more than 2, R19It is same to each other or different to each other.
According to another embodiment of this specification, R19Can be hydrogen or deuterium.
In addition, according to another embodiment of this specification, above-mentioned chemical formula 1 can be provided and represented by following chemical formula 4 Compound.
[chemical formula 4]
In above-mentioned chemical formula 4, R1To R11, R13、R14、L1And L2Such as the definition in above-mentioned chemical formula 1, R19And R20Each solely On the spot with above-mentioned R19Explanation it is identical.
But further, in above-mentioned chemical formula 4, R13And R14It is former that substituted or unsubstituted carbon is may be selected from independently of one another The monocyclic or polycyclic aryl of subnumber 6 to 30, the monocyclic or polycyclic heteroaryl of substituted or unsubstituted carbon number 2 to 30.
In addition, in above-mentioned chemical formula 4, R13And R14Can be substituted or unsubstituted carbon number 6 to 30 independently of one another Monocyclic or polycyclic aryl.
In addition, in above-mentioned chemical formula 4, R13And R14Can be the monocyclic of the carbon number 6 to 30 of substitution independently of one another Aryl.
In addition, in above-mentioned chemical formula 4, R13And R14Can be the phenyl of the carbon number 6 to 30 of substitution independently of one another.
In addition, in above-mentioned chemical formula 4, R13And R14Can be by alkyl-substituted carbon number 6 to 30 independently of one another Phenyl.
In addition, in above-mentioned chemical formula 4, R13And R14Can be by alkyl-substituted carbon number 6 to 10 independently of one another Phenyl.
In addition, in above-mentioned chemical formula 4, R13And R14Can be by methyl substituted carbon number 6 to 10 independently of one another Phenyl.
In addition, in above-mentioned chemical formula 4, R13And R14Can be 2,6- 3,5-dimethylphenyls independently of one another.
In 2, No. 6 small hydrogen (H) of position substitution size, in the case of the characteristic with singly-bound, exist by substituent Rotation caused by a variety of absorption bands, therefore the region of absorbing wavelength broadens, the transmissivity step-down of short wavelength.
In addition, when the substituent of the carbon number bigger than methyl more than 2 is imported 2, No. 6 positions, it is another with nitrogen-atoms One alkyl substituent occurs steric repulsion and is difficult to keep flatness, so as to which λ occurmaxBlue shift (hypsochromic Shift) and short wavelength transmissivity step-down.
When importing substituent different from each other 2, No. 6 positions, compared with substituent identical situation, different substituents It is rotatable, a variety of absorption bands thus be present, broadened so as to the region of absorbing wavelength, the transmissivity step-down of short wavelength.Thus, 2, Identical substituent can be imported in No. 6, specifically, methyl shows classic color characteristics.
Moreover, anionic property group can be selected from-OH ,-SO3-、-SO3H、-SO3-Z+、-CO2H、-CO2-Z+、- CO2Ra、-SO3Rb and-SO3It is at least one in NRcRd, Z+Represent+N(Re)4、Na+Or K+, Ra to Re independently of one another can table Show straight or branched alkyl, the list of substituted or unsubstituted carbon number 6 to 30 of substituted or unsubstituted carbon number 1 to 20 The monocyclic or polycyclic heteroaryl of ring or polycyclic aryl and substituted or unsubstituted carbon number 2 to 30.
According to another embodiment of this specification, above-mentioned anionic property group can be selected from-OH ,-SO3 -、-SO3H、- SO3 -Z+、-CO2H、-CO2 -Z+、-CO2Ra、-SO3Rb and-SO3It is at least one in NRcRd, Z+Represent+N(Re)4、Na+Or K+, Ra to Re can represent the straight or branched alkyl of substituted or unsubstituted carbon number 1 to 10, substitute or do not take independently of one another The monocyclic or polycyclic aryl of the carbon number 6 to 20 in generation and substituted or unsubstituted carbon number 2 to 20 it is monocyclic or more The heteroaryl of ring.
According to another embodiment of this specification, above-mentioned anionic property group can be selected from-SO3-、-SO3H、-SO3 - Z+、-SO3Rb and-SO3It is at least one in NRcRd, Z+Represent Na+Or K+, Ra to Rd can represent independently of one another substitution or The straight or branched alkyl of unsubstituted carbon number 1 to 10, substituted or unsubstituted carbon number 6 to 10 it is monocyclic or polycyclic Aryl and substituted or unsubstituted carbon number 2 to 10 monocyclic or polycyclic heteroaryl.
According to another embodiment of this specification, above-mentioned anionic property group can be-SO3 -Or-SO3 -Na+。
Above-mentioned anionic property group itself can have anion, or can be with other cations in the form of complex compound In the presence of.Therefore, according to the number of substituted anionic property group, compound molecule whole electric charge sum alterable of the invention. Because an amido of the compound of the present invention has a cation, therefore molecule whole electric charge sum can have equivalent to from taking The value for the anion to 0 being worth obtained from 1 is subtracted in the number of the anionic property group in generation.
In addition, when substitution has alkyl phthalimide in nitrogen-atoms, the compound for being substituted alkyl phthalimide group improves The dispersiveness of pigment, suppress crystalline pigment conversion in high temperature and make pigment stabilizer in high temperature.
In addition, the xanthene that substitution has phthalimide group improves the dispersiveness with this pigment being used together, so as to expect More excellent CR characteristics, make the crystal transformation of pigment and make pigment stabilizer in high temperature, so as to reduce color change. That is, by the stabilisation of pigment, so as to improve dispersiveness and storage stability and reduce color change.
As a result, substitution has been imported 2, No. 6 positions has the phenyl of methyl and the xanthene compound of phthalimide group not only to show Excellent color characteristics are shown, also by the stabilisation of pigment, so as to improving dispersiveness and storage stability and reduce The effect of color change.
In addition, the compound represented by above-mentioned chemical formula 1 can be represented by any one in following chemical formula, but not It is defined in this.
In addition, according to an embodiment of this specification, the colorant composition comprising above-claimed cpd can be provided.
Above-mentioned colorant composition can also be included in dyestuff and pigment extremely in addition to the compound of above-mentioned chemical formula 1 It is few a kind.For example, above-mentioned colorant composition only can include the compound of above-mentioned chemical formula 1, but above-mentioned chemical formula can also be included 1 compound and more than a kind of dyestuff, compound and more than a kind of pigment either comprising above-mentioned chemical formula 1 or comprising Compound, more than a kind of dyestuff and more than a kind of the pigment of above-mentioned chemical formula 1.
According to an embodiment of this specification, the resin combination for including above-mentioned colorant composition can be provided.
According to an embodiment of this specification, above-mentioned resin combination can also be included represented by above-mentioned chemical formula 1 Compound, adhesive resin, multi-functional monomer, light trigger and solvent.
As long as above-mentioned adhesive resin can show that the physical property such as the film strength manufactured by resin combination, developability, It is not particularly limited.
Above-mentioned adhesive resin can utilize the multi-functional monomer for assigning mechanical strength and the monomer for assigning alkali-solubility Copolymer resins, the usually used adhesive of the technical field can also be included.
The multi-functional monomer for assigning the mechanical strength of above-mentioned film can be selected from unsaturated carboxylate type, aromatic vinyl It is more than any one in class, unsaturated ether, unsaturated acyl imines and acid anhydrides.
As the specific example of above-mentioned unsaturated carboxylate type, (methyl) benzyl acrylate, (methyl) acrylic acid may be selected from Methyl esters, (methyl) ethyl acrylate, (methyl) butyl acrylate, (methyl) acrylate, (methyl) propylene Sour isobutyl ester, (methyl) tert-butyl acrylate, (methyl) cyclohexyl acrylate, (methyl) isobornyl acrylate, (methyl) third Olefin(e) acid ethylhexyl, (methyl) acrylic acid 2- phenoxy ethyls, (methyl) acrylic acid tetrahydro furfuryl ester, (methyl) dihydroxypropyl Ethyl ester, (methyl) 2-hydroxypropyl acrylate, (methyl) acrylic acid 2- hydroxyl -3- chlorine propyl ester, (methyl) acrylic acid 4- hydroxyl fourths Ester, (methyl) acrylic acid acyl group octyloxy -2- hydroxy propyl esters, (methyl) glycerol acrylate, (methyl) acrylic acid 2- methoxyl groups Ethyl ester, (methyl) acrylic acid 3- methoxybutyls, ethoxy ethyl glycol (methyl) acrylate, methoxy triethylene (methyl) Acrylate, methoxyl group tripropylene glycol (methyl) acrylate, PEG methyl ether (methyl) acrylate, phenoxy group diethyl Glycol (methyl) acrylate, to Nonylphenoxy polyethylene glycol (methyl) acrylate, to Nonylphenoxy polypropylene glycol (first Base) acrylate, (methyl) glycidyl acrylate, (methyl) acrylic acid tetrafluoro propyl ester, (methyl) acrylic acid 1,1,1,3, 3,3- hexafluoros isopropyl ester, (methyl) acrylic acid octafluoro pentyl ester, the fluorine last of the ten Heavenly stems ester of (methyl) acrylic acid 17, (methyl) acrylic acid tribromo-benzene Base ester, Alpha-hydroxy methyl methacrylate, Alpha-hydroxy EMA, Alpha-hydroxy propyl methacrylate and Alpha-hydroxy Butyl methacrylate, but it is not limited to this.
As the specific example of above-mentioned aromatic vinyl monomer class, may be selected from styrene, α-methylstyrene, (it is adjacent, Between, to)-vinyltoluene, (o-, m-, to)-methoxy styrene and (o-, m-, to)-chlorostyrene, but do not limit In this.
As the specific example of above-mentioned unsaturated ether, methoxy ethylene, vinyl ethyl ether and pi-allyl contracting may be selected from Water glycerin ether, but it is not limited to this.
As the specific example of above-mentioned unsaturated acyl imines, N-phenylmaleimide, N- (4- chlorphenyls) may be selected from Maleimide, N- (4- hydroxy phenyls) maleimides and N- N-cyclohexylmaleimides, but it is not limited to this.
As above-mentioned acid anhydrides, there are maleic anhydride, methyl maleic anhydride, tetrahydrophthalic anhydride etc., but do not limit In this.
As long as the monomer of above-mentioned imparting alkali-solubility includes acidic group, it is not particularly limited, such as preferably uses and be selected from (first Base) acrylic acid, crotonic acid, itaconic acid, maleic acid, fumaric acid, monomethyl maleate, 5- ENB -2- carboxylic acids, single (2- ((methyl) acryloxy) ethyl phthalate, list -2- ((methyl) acryloxy) ethyl succinate, ω-carboxylic One or more of base polycaprolactone list (methyl) acrylate, but it is not limited to this.
According to an embodiment of this specification, the acid number of above-mentioned adhesive resin is 50 to 130KOHmg/g, is divided equally again Son amount is 1000 to 50000.
Above-mentioned multi-functional monomer is the monomer for playing a part of being formed photoresist phase by light, specifically, Ke Yiwei Selected from propylene glycol methyl acrylate, dipentaerythritol acrylate, dipentaerythritol acrylate, the propylene of neopentyl glycol two Acid esters, 6- hexanediyl esters, 1,6-HD acrylate tetraethylene glycol methacrylate, double phenoxetols two Acrylate, trihydroxyethyl isocyanuric ester trimethyl acrylic ester, trimethyl propane trimethyl acrylic ester, diphenyl season penta The acrylate of tetrol six, pentaerythritol acrylate trimethyl, pentaerythritol tetramethylacrylate and dipentaerythritol six Mixture more than one or both of methacrylate.
As long as above-mentioned light trigger excites the initiator of crosslinking by photogenerated free radical, it is not particularly limited, Such as can be in acetophenone based compound, bisglyoxaline based compound, triazine based compound and oxime compound it is a kind of with On.
Above-mentioned acetophenone based compound has 2- hydroxy-2-methyl -1- phenyl-propane -1- ketone, 1- (4- isopropyl phenyls) -2- Hydroxy-2-methyl propane -1- ketone, 4- (2- hydroxyl-oxethyls)-phenyl-(2- hydroxyl -2- propyl group) ketone, 1- hydroxycyclohexylphenyls Ketone, benzoin methylether, benzoin ethyl ether, benzoin isobutyl ether, benzoin butyl ether, 2,2- dimethoxy -2- phenyl acetophenones, 2- Methyl-(4- methyl mercaptos) phenyl -2- morpholino -1- propane -1- ketone, 2- benzyl -2- dimethylaminos -1- (4- morpholino benzene Base)-propane -1- ketone, 2- (the bromo- benzyl -2- dimethylaminos -1- of 4- (4- morphlinophenyls)-butane -1- ketone or 2- methyl isophthalic acids - [4- (methyl mercapto) phenyl] -2- morpholino propane -1- ketone, but it is not limited to this.
As above-mentioned bisglyoxaline based compound, there are 2,2- double (2- chlorphenyls) -4,4', 5,5'- tetraphenyl bisglyoxaline, 2, Double (Chloro-O-Phenyl) -4,4', 5,5'- tetra- (3,4,5- the trimethoxyphenyls) -1,2'- bisglyoxalines of 2'-, double (the 2,3- dichloros of 2,2'- Phenyl) -4,4', 5,5'- tetraphenyl bisglyoxalines, double (Chloro-O-Phenyl) -4,4,5,5'- tetraphenyl -1,2'- bisglyoxalines etc. of 2,2'-, But it is not limited to this.
Above-mentioned triazine based compound has 3- { 4- [double (trichloromethyl)-s-triazine -6- bases of 2,4-] thiophenyl } propionic acid, 1,1, 1,3,3,3- hexafluoro isopropyls -3- { 4- [double (trichloromethyl)-s-triazine -6- bases of 2,4-] thiophenyl } propionic ester, ethyl 2- { 4- [2,4- double (trichloromethyl)-s-triazine -6- bases] thiophenyl } acetic acid esters, 2- epoxy ethyls -2- { 4- [double (three chloromethanes of 2,4- Base)-s-triazine -6- bases] thiophenyl acetic acid esters, cyclohexyl -2- { 4- [2,4- double (trichloromethyl)-s-triazine -6- bases] benzene sulphur Base } acetic acid esters, benzyl -2- { 4- [2,4- double (trichloromethyl)-s-triazine -6- bases] thiophenyl } acetic acid esters, 3- { chloro- 4- [2,4- Double (trichloromethyl)-s-triazine -6- bases] thiophenyl propionic acid, 3- { 4- [2,4- double (trichloromethyl)-s-triazine -6- bases] benzene sulphur Base } propionamide, double (the trichloromethyl) -6- of 2,4- are to methoxyl-styrene-s-triazine, double (1- couples of (the trichloromethyl) -6- of 2,4- Dimethylaminophenyl) -1,3,-butadiene-s-triazine, 2- trichloromethyl -4- amino -6- are to methoxyl-styrene-equal three Piperazine etc., but it is not limited to this.
Above-mentioned oxime compound has 1- (4- thiophenyls) phenyl -1,2- acetyl caproyls 2- (o- benzoyl oximes) (CI BA- GEIGY Corp., CGI 124), 1- (9- ethyls) -6- (2- methyl benzoyl -3- bases)-ethyl ketone 1- (O- acetyl oxime) (CGI 242), N-1919 (ADEKA companies) etc., but it is not limited to this.
Above-mentioned solvent can be acetone, methyl ethyl ketone, methyl iso-butyl ketone (MIBK), methyl cellosolve, ethyl cellosolve, tetrahydrochysene Furans, 1,4- bis-Alkane, glycol dimethyl ether, ethylene glycol diethyl ether, Propylene Glycol Dimethyl Ether, propane diols diethyl ether, diethylene glycol Dimethyl ether, diethylene glycol diethyl ether, diethylene glycol methyl ethyl ether, chloroform, dichloromethane, 1,2- dichloroethanes, 1,1,1- tri- Chloroethanes, 1,1,2- trichloroethanes, 1,1,2- trichloro ethylenes, hexane, heptane, octane, hexamethylene, benzene,toluene,xylene, first Alcohol, ethanol, isopropanol, propyl alcohol, butanol, the tert-butyl alcohol, 2- ethyoxyls propyl alcohol, 2- methoxypropanols, 3- methoxybutanols, hexamethylene Ketone, cyclopentanone, propylene glycol methyl ether acetate, propylene-glycol ethyl ether acetic acid esters, 3- methoxybutyls acetic acid esters, 3- ethoxy-propionic acid second Ester, ethyl cellosolve acetate, methyl glycol acetate, butyl acetate, propylene glycol monomethyl ether and dipropylene glycol monomethyl ether One or more of, but it is not limited to this.
According to an embodiment of this specification, on the basis of the total amount of the solid constituent in above-mentioned resin combination, on The content for stating the compound represented by chemical formula 1 is 5 weight % to 60 weight %, and the content of above-mentioned adhesive resin is 1 weight % to 60 weight % is measured, the content of above-mentioned light trigger is 0.1 weight % to 20 weight %, the content of above-mentioned multi-functional monomer For 0.1 weight % to 50 weight %.
The gross weight of above-mentioned solid constituent refers to, the ingredient weight sum in resin combination in addition to solvent.With The benchmark of weight % on the basis of the solid constituent of solid constituent and each composition can use liquid chromatogram or gas-chromatography etc. should The general analysis method used in field is measured.
According to an embodiment of this specification, above-mentioned resin combination can also include antioxidant.
According to an embodiment of this specification, on the basis of the gross weight of the solid constituent in above-mentioned resin combination, The content of above-mentioned antioxidant is 0.1 weight % to 20 weight %.
According to an embodiment of this specification, above-mentioned resin combination also comprising photo-crosslinking sensitizer, curing accelerator, One kind in closely sealed accelerator, surfactant, thermal polymerization inhibitor, ultra-violet absorber, dispersant and levelling agent or two The additive of the kind above.
According to an embodiment of this specification, on the basis of the gross weight of the solid constituent in above-mentioned resin combination, The content of above-mentioned additive is 0.1 weight % to 20 weight %.
Above-mentioned photo-crosslinking sensitizer can use double (dimethylamino) benzophenone of benzophenone, 4,4-, 4,4- double (two Ethylamino) benzophenone, 2,4,6- trimethylaminos benzophenone, methyl o-benzoyl yl benzoic acid ester, 3,3- dimethyl- The benzophenone based compounds such as 4- methoxy benzophenones, 3,3,4,4- tetra- (tert-butyl hydroperoxide carbonyl) benzophenone；9- fluorenes The Fluorenone based compounds such as the chloro- 9-Fluorenone of ketone, 2-, 2- methyl -9-Fluorenone；Thioxanthones, 2,4- diethyl thioxanthones, 2- diuril tons The thioxanthones based compounds such as the chloro- 4- propyl group epoxide thioxanthones of ketone, 1-, isopropyl thioxanthone, diisopropylthioxanthone；Xanthone, The xanthone based compounds such as 2- methyl xanthones；Anthraquinone, 2-methylanthraquinone, 2- EAQs, tert-butyl group anthraquinone, 2,6- bis- are chloro- The anthraquinone based compound such as 9,10- anthraquinones；Double (9- acridinyls) heptane of 9- phenylacridines, 1,7-, 1,5- double (9- acridinyls pentanes), The acridine based compounds such as double (9- acridinyls) propane of 1,3-；Benzil, the ring of 1,7,7- trimethyls-two [2,2,1] heptane -2,3- two The dicarbonyl compounds such as ketone, 9,10- phenanthrenequione；2,4,6- trimethyl benzoyl diphenyl bases phosphine oxide, double (2,6- dimethoxy benzenes Formoxyl) the phosphine oxide based compound such as -2,4,4- trimethylpentylphosphine oxides；Methyl -4- (dimethylamino) benzoic ether, second The benzoic ether systems such as base -4- (dimethylamino) benzoic ether, 2- n-butoxyethyls -4- (dimethylamino) benzoic ether Compound；Double (the 4- diethylaminos benzal) cyclopentanone of 2,5-, double (the 4- diethylaminos benzal) cyclohexanone of 2,6-, 2,6- are double The amine synergists such as (4- diethylaminos benzal) -4- methyl-cyclopentanones；3,3- carbonyl ethenyls -7- (diethylamino) Cumarin, 3- (2-[4-morpholinodithio base) -7- (diethylamino) cumarin, 3- benzoyls -7- (diethylamino) cumarin, 3- benzoyls -7- methoxyl groups-cumarin, 10,10- carbonyls it is double [1,1,7,7- tetramethyl -2,3,6,7- tetrahydrochysene -1H, 5H, 11H-C1] coumarin series compounds such as-chromene [6,7,8-ij]-quinolizine -11- ketone；4- diethylaminos chalcone, 4- are folded The chalcone compounds such as nitrogen benzylidene acetophenone；In 2- benzoyls methylene, 3- methyl-b- aphthothiazoles quinolines it is a kind of with On.
Above-mentioned curing accelerator is used to solidify and improve mechanical strength, specifically, can use and be selected from 2- sulfydryl benzos Imidazoles, 2-mercaptobenzothiazole, 2- sulfydryl benzosAzoles, 2,5- dimercapto -1,3,4- thiadiazoles, 2- sulfydryl -4,6- dimethyl Aminopyridine, pentaerythrite-four (3-thiopropionate), pentaerythrite-three (3-thiopropionate), (the 2- mercaptos of pentaerythrite-four Yl acetate), pentaerythrite-three (2- mercaptoacetates), trihydroxymethyl propane-three (2- mercaptoacetates) and three methanol third One or more of alkane-three (3-thiopropionate).
As closely sealed accelerator as used in this specification, it can use and be selected from methacryloxypropyl trimethoxy Base silane, methacryloxypropyl dimethoxysilane, methacryloxypropyl, metering system One or more of methylacryloyl silane coupler such as acryloxypropylethoxysilane dimethoxysilane, as alkyl trimethoxy silicon Alkane, it can use in octyl group trimethoxy silane, dodecyltrimethoxysilane, octadecyl trimethoxysilane More than one.
Above-mentioned surfactant is silicon systems surfactant or fluorine system surfactant, specifically, silicon systems surface-active Agent can use BYK-077, BYK-085 of BYK-Chemie companies, BYK-300, BYK-301, BYK-302, BYK-306, BYK-307、BYK-310、BYK-320、BYK-322、BYK-323、BYK-325、BYK-330、BYK-331、BYK-333、BYK- 335、BYK-341v344、BYK-345v346、BYK-348、BYK-354、BYK-355、BYK-356、BYK-358、BYK-361、 BYK-370, BYK-371, BYK-375, BYK-380, BYK-390 etc., as fluorine system surfactant, DIC can be used F-114, F-177, F-410, F-411, F-450, F-493, F-494, F- of (DaiNippon Ink＆Chemicals) company 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., but it is not limited to this.
As above-mentioned antioxidant, it selected from hindered phenol (Hindered phenol) is antioxidant, amine system antioxygen that can be One or more of agent, sulphur system antioxidant and phosphine system antioxidant, but it is not limited to this.
As the specific example of above-mentioned antioxidant, such as phosphoric acid, trimethyl phosphate or triethyl phosphate phosphorus can be included Acid system heat stabilizer；As DBPC 2,6 ditertiary butyl p cresol, octadecyl -3- (4- hydroxyl -3,5- di-tert-butyl-phenyls) propionic ester, Four couples of [methylene -3- (3,5- di-tert-butyl-hydroxy phenyls) propionic ester] methane, (3,5- of 1,3,5- trimethyls -2,4,6- three Di-tert-butyl-4-hydroxyl benzyl) benzene, 3,5- di-tert-butyl-4-hydroxyl benzyls diethyl phosphite, the double (4- methyl -6- of 2,2- sulphur Tert-butyl phenol), 2,6-g, the double (3- of t- butylphenol 4,4'- butylidenes-bis- (3 methy 6 tert butyl phenols), 4,4'- sulphur Methyl-6-tert-butylphenol) or double [3,3- couples-(4'- hydroxyl -3'- tert-butyl-phenyls) butyric acid] glycol ester (Bis [3,3- Bis- (4'-hydroxy-3'-tert-butylphenyl) butanoicacid] glycol ester) etc. hindered phenol (Hindered phenol) owner's antioxidant；Such as phenyl-α-naphthylamine, phenyl-β-naphthylamine, N, N'- diphenyl-p-phenylenediamines Or the amine system secondary antioxidant such as bis--betanaphthyl of N, N'--p-phenylenediamine；Dilauryl disulphide, the bay of propane thioic acid two Ester, propane thioic acid distearyl alcohol ester, mercaptobenzothiazoler or the [methylene -3- (lauryls of tetramethyl thiuram disulfide four pairs It is thio) propionic ester] the sulphur system secondary antioxidant such as methane；Or such as triphenyl phosphite, phosphorous acid three (nonyl phenyl) ester, phosphorous Sour three isodecyl esters, double (2,4- dibutylphenyls) pentaerythritol diphosphites (Bis (2,4-ditbutylphenyl) Pentaerythritol Diph osphite) or [double (1,1- bis- of 2,4- of (1,1'- xenyls) -4,4'- diyls di 2 ethylhexyl phosphonic acid four Methylethyl) phenyl] ester ((1,1'-Biphenyl) -4,4'-Diylbisphosphonous acid tetrakis [2,4- Bis (1,1-dimethyl ethyl) phenyl] ester) etc. phosphite ester system secondary antioxidant.
As above-mentioned ultra-violet absorber, 2- (the 3- tert-butyl group -5- methyl -2- hydroxy phenyls) chloro- benzos of -5- can be used Triazole, alkoxy benzophenone etc., but this is not limited to, all ultraviolet radiation absorptions that the field can be used typically to use Agent.
As above-mentioned thermal polymerization inhibitor, such as it can include and be selected to methyl phenyl ethers anisole, hydroquinones, catechol (pyrocatechol), tert-butyl catechol (t-butyl catechol), N- nitroso phenylhydroxylamines ammonium salt, N- nitrosos Double (the 3- methyl-6-terts of phenylhydroxylamine aluminium salt, p methoxy phenol, BHT, 1,2,3,-thrihydroxy-benzene, benzoquinones, 4,4- sulphur Butylphenol), 2,2- di-2-ethylhexylphosphine oxides (4- methyl-6-tert-butylphenols), 2- mercaptoimidazoles and phenthazine One or more of (phenothiazine), but this is not limited to, generally known hot polymerization in the technical field can be included Close inhibitor.
Above-mentioned dispersant can be by carrying out internal addition in the form of being surface-treated in advance to pigment to pigment Method carries out the method for outside addition to use to pigment.Compound type, nonionic can be used as above-mentioned dispersant Property, anionic property or cationic dispersant, can enumerate fluorine system, ester system, cation system, anion system, nonionic system, both sexes table Face activating agent etc..These can respectively using or be used in combination of two or more.
Specifically, above-mentioned dispersant has adds selected from PAG and its ester, polyoxyalkylene polyol, ester alkylene oxide Into thing, alcohol alkylene oxide adduct, sulphonic acid ester, sulfonate, carboxylate, carboxylate, alkylamide alkylene oxide adduct and alkyl One or more of amine, but it is not limited to this.
Can be the levelling agent of polymerism or the levelling agent of non-polymerization as above-mentioned levelling agent.Levelling as polymerism The specific example of agent, the reaction product of polyethyleneimine, polyamide-amide, amine and epoxides can be included, as non-polymeric The specific example of the levelling agent of property, comprising non-polymeric sulfur-containing compound and non-polymeric nitrogen-containing compound, but is not limited to this, The levelling agent typically used in the field can be used.
According to an embodiment of this specification, there is provided the photosensitive material manufactured by above-mentioned resin combination.
More specifically, by suitable method, the resin combination of this specification is applied on base material, so as to be formed The photosensitive material of film or pattern.
As above-mentioned coating method, it is not particularly limited, spraying process, rolling method, spin-coating method etc. can be used, it is general extensive Use spin-coating method.In addition, after coated film is formed, can according to circumstances, part removes residual solvent under reduced pressure.
As for making the light source of the resin composition involved by this specification, such as have and project wavelength in 250nm To the mercury vapour arc (arc) of 450nm light, carbon arc, Xe arcs etc., but it is not limited to this.
Resin combination involved by this specification can be used for thin-film transistor LCD device (TFT LCD) colour filter Device is manufactured with pigment-dispersing type photosensitive material, thin-film transistor LCD device (TFT LCD) or Organic Light Emitting Diode Black matrix" formed with photosensitive material, external coating formed with photosensitive material, column spacer photosensitive material, Photocurable coating material, Light curable type ink, light-cured type bonding agent, printed panel, printed substrate photosensitive material, Plasmia indicating panel (PDP) are used Photosensitive material etc., but its purposes is not particularly limited.
According to an embodiment of this specification, there is provided include the colour filter of above-mentioned photosensitive material.
Above-mentioned colour filter can utilize the resin combination comprising the compound represented by above-mentioned chemical formula 1 to manufacture. Above-mentioned resin combination is coated with substrate and forms coated film, and makes above-mentioned coated film exposure, development and solidification, so as to Form colour filter.
The excellent heat resistance of resin combination involved by one embodiment of this specification, the color as caused by heat treatment It is with low uncertainty, therefore the also high colorrendering quality after solidification process can be provided when colour filter is manufactured and brightness and right The colour filter higher than degree.
Aforesaid substrate can be glass plate, silicon chip and polyether sulfone (Polyethersulfone, PES), makrolon Plate of plastic basis materials such as (Polycarbonate, PC) etc., its species are not particularly limited.
Above-mentioned colour filter can include red pattern, green pattern, blue color patterns, black matrix".
According to another embodiment, above-mentioned colour filter can also include external coating.
For the purpose for improving contrast, the lattice for being referred to as black matrix" can be configured between the colour element of colour filter The black pattern of sub- shape.As the material of black matrix", chromium can be used.At this moment, can utilize chromium is overall in glass substrate On be deposited, and the method for pattern is formed by etching process.But, it is contemplated that the height of high cost, chromium in process Reflectivity, the environmental pollution as caused by chromium waste liquid, it is usable to utilize resin obtained from carrying out micro-machined pigment dispersion method Black matrix.
Black matrix" involved by one embodiment of this specification can use black pigment or black dyes as color Material.For example, can be used alone carbon black, or carbon black and coloring pigment are used in mixed way, at this moment due to mixing light-proofness deficiency Coloring pigment, even if therefore increase the amount of colorant with having relativity, will not also reduce film strength or the adaptation to substrate The advantages of.
The display device for including the colour filter involved by this specification is provided.
Above-mentioned display device can be Plasmia indicating panel (Plasma Display Panel, PDP), light emitting diode (Light Emitting Diode, LED), organic illuminating element (Organic Light Emitting Diode, OLED), liquid Crystal device (Liquid Crystal Display, LCD), thin-film transistor LCD device (Thin FIlm Transistor-Liquid Crystal Display, LCD-TFT) and cathode-ray tube (Cathode Ray Tube, CRT any one in).
Below, enumerate embodiment in order to specifically be illustrated to this specification and be described in detail.But this theory Embodiment involved by bright book can be deformed into other various forms, and the scope of this specification should not be construed as limited to remember below The embodiment stated.The embodiment of this specification is provided to more completely illustrate this specification to those skilled in the art 's.
[experimental example 1]
The synthesis of compound
Compound 1 is generated by the reaction of such as following reaction equations 1.
Reaction equation 1
By 5g (8.710mmol) A-1,8.233g (34.838mmol) B-1,4.815g (34.5838mmol) K2CO3It is added in 100ml NMP, has been stirred at 95 DEG C 12 hours.Then, solvent is removed under a reduced pressure, in precipitate Middle addition 200ml water has stirred 1 hour.In addition, filtering precipitate under a reduced pressure, dried at 80 DEG C 12 hours.So Afterwards, dry precipitate is separated by column chromatography.(eluent-MC:MeOH)
As a result, obtain 6g (3.322mmol) compound 1, yield 72%.
Its result is as follows.
Ionization mode=:APCI+:M/z=949 [M+H]+, accurate mass (Exact Mass):948
Above-claimed cpd 11H-NMR measurement result is 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)
In addition, generate compound 2 by following reaction equations 2.
Reaction equation 2
By 5g (7.388mmol) acid red 289 and 4.09g (29.554mmol) K2CO3It is added to 100ml NMP In, stirred at 95 DEG C 12 hours.Then, solvent is removed under a reduced pressure, and salt solution (Brine) 100 is added in precipitate, Stir 1 hour.Then, precipitate is filtered under a reduced pressure, has been dried at 80 DEG C 12 hours.
As a result, obtain with the colorant 7.3g (6.945mmol) that compound 2 is main product, yield 94%.
In addition, generate compound 3 by following reaction equations 3.
Reaction equation 3
CHCl is added at 0 DEG C3, DMF 7.4g, be stirred.Add 2.479g (20.835mmol) SOCl2, enter at 0 DEG C One step has stirred 30 minutes.7.3g (6.945mmol) colorant with compound 2 for main product is slowly added dropwise.Then, rise Temperature has stirred 30 minutes 1 hour to 35 DEG C.It is then cooled to 0 DEG C, dropwise addition 2.693g (20.835mmol) 2 ethyl hexylamine, 7.028g (69.45mmol) Et is added dropwise3N, 16 hours in stirring at normal temperature.Remove solvent under a reduced pressure, addition water and MC is extracted.Organic layer is passed through into MgSO4Remove solvent under a reduced pressure afterwards, dried at 80 DEG C 12 hours.
As a result, obtain with the colorant 2.772g (2.431mmol) that compound 3 is main product, yield 35%.
In addition, generate compound 4 by following reaction equations 4.
Reaction equation 4
By 1.43g (2.732mmol) D-1,2.99g (9.490mmol) B-1,1.31g (9.490mmol) K2CO3 It is added in 20ml NMP, has been stirred at 95 DEG C 12 hours.Then, solvent is eliminated under a reduced pressure, is added in precipitate 200ml water, stir 1 hour.In addition, filtering precipitate under a reduced pressure, dried at 80 DEG C 12 hours.Then, will Dry precipitate is separated by column chromatography.(eluent-MC:MeOH)
As a result, 1.622g (1.912mmol) compound 4, yield 70% are obtained.
Ionization mode=:APCI+:M/z=977 [M+H]+, accurate mass:976
Then, compound 5 is generated by following reaction equations 5.
Reaction equation 5
By 1.608g (2.732mmol) E-1,2.99g (9.490mmol) B-1,1.31g (9.490mmol) K2CO3 It is added in 20ml NMP, has been stirred at 95 DEG C 12 hours.Then, solvent is removed under a reduced pressure, is added in precipitate 200ml water, stir 1 hour.In addition, filtering precipitate under a reduced pressure, dried at 80 DEG C 12 hours.Then, will Dry precipitate is separated by column chromatography.(eluent-MC:MeOH)
As a result, 1.526g (1.622mmol) compound 5, yield 59% are obtained.
Ionization mode=:APCI+:M/z=963 [M+H]+, accurate mass:962
The compound used as comparison other is as follows.
Comparative compound 1
Comparative compound 2
Above-mentioned comparative example 1 is Blue 7, and comparative example 2 is rhodamine 6G.
Embodiment and comparative example have been manufactured with the ratio of such as table 1 below.The input unit of compound is gram (g).
[table 1]
Substrate manufacture
Spin coating (spincoating) will be carried out on glass (5 × 5cm) by above-mentioned synthetically produced compound, 100 DEG C carry out prebake processing (prebake) 100 seconds and form film.It will be formed between the substrate and photomask (photo mask) of film Spacing be set to 250 μm, using exposure machine to the whole face of substrate with 40mJ/cm2Light exposure be irradiated.
Then, development 60 seconds, baking processing after being carried out at 230 DEG C in developer solution (KOH, 0.05%) by the substrate of exposure (post bake) 20 minutes and made substrate.
Evaluation of Heat Tolerance
The prebake made under conditions, as described above processing (prebake) substrate is utilized into spectrometer (MCPD-Otsuka Company) obtained 380nm to 780nm scope visible region Optical transmission spectrum.In addition, prebake is handled (prebake) further the baking after 230 DEG C handles (post bake) 20 minutes to substrate, in identical equipment and measurement range Optical transmission spectrum is obtained.
Using obtained Optical transmission spectrum and illuminant-C backlight, calculate △ Eab using obtained value E (L*, a*, b*) and show In table 2 below.
Δ E (L*, a*, b*)={ (Δ L*) 2+ (Δ a*) 2+ (Δ b*) 2 }/2
The small meaning color excellent heat resistance of Δ E values.
Compound and comparative example 1,2 to experimental example determine heat resistance, are as a result shown in Table 1.As shown in table 2, confirmationization For compound compared with comparative example 1,2, color change (△ Eab) is small.
[table 2]
ΔEab(PB-PrB)
Embodiment 1 2.02
Embodiment 2 1.98
Embodiment 3 2.15
Embodiment 4 2.30
Comparative example 1 26.52
Comparative example 2 23.95
In addition, Fig. 1 is the R for representing the chemical formula 1 involved by the embodiment of the application13And R14Respectively substitution has The situation of the phenyl of methyl, substitution have a situation of the phenyl of isopropyl and the transmissivity in the case that substitution has the phenyl of ethyl Chart.Understood with reference to figure 1, desired transmissivity can be obtained using the compound involved by the embodiment of the application.

Claims (16)

  1. A kind of 1. compound represented by following chemical formula 1:
    Chemical formula 1
    In the chemical formula 1,
    R1To R6It is each independently selected from hydrogen, deuterium, halogen atom, nitro, the straight chain of substituted or unsubstituted carbon number 1 to 30 Or the alkyl of side chain, the alkoxy of substituted or unsubstituted carbon number 1 to 30 and substituted or unsubstituted carbon number 6 To 30 monocyclic or polycyclic aryl and the monocyclic or polycyclic heteroaryl of substituted or unsubstituted carbon number 2 to 30,
    R7To R11It is each independently selected from hydrogen, deuterium, anionic property group, hydroxyl, substituted or unsubstituted carbon number 1 to 30 The alkyl of straight or branched, the monocyclic or polycyclic aryl of substituted or unsubstituted carbon number 6 to 30 and substitution do not take The monocyclic or polycyclic heteroaryl of the carbon number 2 to 30 in generation,
    The R7To R11In it is at least one be anionic property group,
    R12To R14Be each independently selected from hydrogen, deuterium, substituted or unsubstituted carbon number 6 to 30 monocyclic or polycyclic aryl, The monocyclic or polycyclic heteroaryl of substituted or unsubstituted carbon number 2 to 30 and two anhydride groups containing nitrogen-atoms,
    R15And R16It is each independently selected from hydrogen, deuterium, anionic property group, hydroxyl, substituted or unsubstituted carbon number 1 to 30 The alkyl of straight or branched, the monocyclic or polycyclic aryl of substituted or unsubstituted carbon number 6 to 30 and substitution do not take The monocyclic or polycyclic heteroaryl of the carbon number 2 to 30 in generation, or be combined with each other and form substituted or unsubstituted carbon atom The monocyclic or polycyclic aromatic series hydrocarbon ring of number 6 to 30 or substituted or unsubstituted carbon number 2 to 30 it is monocyclic or polycyclic Heterocycle,
    L1And L2It is each independently Direct Bonding or divalent linking group.
  2. 2. compound according to claim 1, wherein, the chemical formula 1 is represented by following chemical formula 2:
    Chemical formula 2
    In the chemical formula 2,
    R1To R11、R13To R16、L1And L2It is identical with the definition in the chemical formula 1,
    R17And R18It is each independently selected from hydrogen, deuterium, anionic property group, hydroxyl, substituted or unsubstituted carbon number 1 to 30 The alkyl of straight or branched, the monocyclic or polycyclic aryl of substituted or unsubstituted carbon number 6 to 30 and substitution do not take The monocyclic or polycyclic heteroaryl of the carbon number 2 to 30 in generation, or be combined with each other and form substituted or unsubstituted carbon atom The monocyclic or polycyclic aromatic series hydrocarbon ring of number 6 to 30 or substituted or unsubstituted carbon number 2 to 30 it is monocyclic or polycyclic Heterocycle.
  3. 3. compound according to claim 1, wherein, the chemical formula 1 is represented by following chemical formula 3:
    Chemical formula 3
    In the chemical formula 3,
    R1To R14、L1And L2It is identical with the definition in the chemical formula 1,
    R19Selected from hydrogen, deuterium, the straight or branched alkyl of substituted or unsubstituted carbon number 1 to 30, substituted or unsubstituted carbon The alkoxy of atomicity 1 to 30, the monocyclic or polycyclic aryl of substituted or unsubstituted carbon number 6 to 30, substitution do not take Monocyclic or polycyclic heteroaryl, halogen atom, nitro, phenoxy group, carboxyl, carboxylic acid ester groups, the carboxylic acid of the carbon number 2 to 30 in generation Alkali, alkoxy carbonyl, hydroxyl, sulfonic group, sulfonate group, sulphonate-base ,-SO2NHR21Base and-SO2NR22R23,
    The R21To R23The alkyl of carbon number 1 to 30 is each independently,
    M is 1 to 4 integer, when m is more than 2, R19It is same to each other or different to each other.
  4. 4. compound according to claim 1, wherein, the chemical formula 1 is represented by following chemical formula 4:
    Chemical formula 4
    In the chemical formula 4,
    R1To R11、R13、R14、L1And L2It is identical with the definition in the chemical formula 1,
    R19And R20Be each independently selected from hydrogen, deuterium, substituted or unsubstituted carbon number 1 to 30 straight or branched alkyl, take Generation or alkoxy, the monocyclic or polycyclic virtue of substituted or unsubstituted carbon number 6 to 30 of unsubstituted carbon number 1 to 30 Base, the monocyclic or polycyclic heteroaryl of substituted or unsubstituted carbon number 2 to 30, halogen atom, nitro, phenoxy group, carboxyl, Carboxylic acid ester groups, carboxylate group, alkoxy carbonyl, hydroxyl, sulfonic group, sulfonate group, sulphonate-base ,-SO2NHR21Base and- SO2NR22R23,
    M is 1 to 4 integer,
    N is 1 to 4 integer,
    When m is more than 2, R19It is same to each other or different to each other,
    When n is more than 2, R20It is same to each other or different to each other.
  5. 5. compound according to claim 1, wherein, the anionic property group is selected from-OH ,-SO3 -、-SO3H、- SO3 -Z+、-CO2H、-CO2 -Z+、-CO2Ra、-SO3Rb and-SO3It is at least one in NRcRd, Z+Represent+N(Re)4、Na+Or K+, Ra Represent the straight or branched alkyl selected from substituted or unsubstituted carbon number 1 to 30, substitution independently of one another to Re or do not take The monocyclic or polycyclic aryl of the carbon number 6 to 30 in generation and substituted or unsubstituted carbon number 2 to 30 it is monocyclic or more It is at least one in the heteroaryl of ring.
  6. 6. compound according to claim 1, wherein, the compound represented by the chemical formula 1 is by following chemical formula In any one represent compound：
  7. 7. compound according to claim 1, wherein, R13And R14It is each independently by alkyl-substituted carbon number 6 To 10 phenyl.
  8. 8. compound according to claim 1, wherein, R13And R14It is each independently 2,6- 3,5-dimethylphenyls.
  9. 9. a kind of colorant composition is comprising compound any one of claim 1 to 8.
  10. 10. colorant composition according to claim 9, wherein, also comprising at least one of dyestuff and pigment.
  11. 11. a kind of resin combination is comprising chemical combination represented by chemical formula 1 any one of claim 1 to 8 Thing, adhesive resin, multi-functional monomer, light trigger and solvent.
  12. 12. resin combination according to claim 11, wherein, with the gross weight of the solid constituent in the resin combination On the basis of amount, the content of the compound represented by the chemical formula 1 is 5 weight % to 60 weight %, described adhesive resin Content is 1 weight % to 60 weight %, and the content of the light trigger is 0.1 weight % to 20 weight %, described multi-functional The content of monomer is 0.1 weight % to 50 weight %.
  13. 13. resin combination according to claim 11, wherein, also comprising antioxidant.
  14. 14. a kind of photosensitive material, manufactured using the resin combination described in claim 11.
  15. 15. a kind of colour filter is comprising photosensitive material described in claim 14.
  16. 16. a kind of display device is comprising colour filter described in claim 15.
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