CN109456333A - Compounds, photosensitive polymer combination and colored filter including it - Google Patents
Compounds, photosensitive polymer combination and colored filter including it Download PDFInfo
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- CN109456333A CN109456333A CN201810883570.8A CN201810883570A CN109456333A CN 109456333 A CN109456333 A CN 109456333A CN 201810883570 A CN201810883570 A CN 201810883570A CN 109456333 A CN109456333 A CN 109456333A
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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
- C09B47/00—Porphines; Azaporphines
- C09B47/04—Phthalocyanines abbreviation: Pc
- C09B47/08—Preparation from other phthalocyanine compounds, e.g. cobaltphthalocyanineamine complex
- C09B47/085—Preparation from other phthalocyanine compounds, e.g. cobaltphthalocyanineamine complex substituting the central metal atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/22—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains four or more hetero rings
-
- 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
- C09B47/00—Porphines; Azaporphines
- C09B47/04—Phthalocyanines abbreviation: Pc
- C09B47/08—Preparation from other phthalocyanine compounds, e.g. cobaltphthalocyanineamine complex
- C09B47/10—Obtaining compounds having halogen atoms directly bound to the phthalocyanine skeleton
-
- 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
- C09B57/00—Other synthetic dyes of known constitution
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
- G02B5/22—Absorbing filters
- G02B5/223—Absorbing filters containing organic substances, e.g. dyes, inks or pigments
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/0005—Production of optical devices or components in so far as characterised by the lithographic processes or materials used therefor
- G03F7/0007—Filters, e.g. additive colour filters; Components for display devices
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
- G03F7/105—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers having substances, e.g. indicators, for forming visible images
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- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Optics & Photonics (AREA)
- Engineering & Computer Science (AREA)
- Architecture (AREA)
- Structural Engineering (AREA)
- Materials For Photolithography (AREA)
- Optical Filters (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The present invention discloses the colored filter of a kind of compound indicated by chemical formula 1 and photosensitive polymer combination and use photosensitive polymer combination manufacture comprising it.In chemical formula 1, each substituent group is identical as defined in specification.Compound disclosed by the invention is with splendid green spectral feature, high molar extinction coefficient and in organic solvent with splendid solubility.[chemical formula 1]
Description
Technical field
This disclosure relates to a kind of compounds and photosensitive polymer combination and colored filter comprising it.
Background technique
By using the colored filter of color type photosensitive polymer combination manufacture in brightness and right due to pigment particle size
There is limitation in terms of ratio.In addition, the color image forming apparatus for imaging sensor needs smaller dispersion particle diameter to be formed finely
Pattern.To respond the demand, continuously attempts to provide by preparing photosensitive polymer combination to have and improved color character
The colored filter of (such as brightness and contrast ratio), the photosensitive polymer combination include the dyestuff of not formed particle rather than face
Material.
Therefore, it is necessary to study a kind of compound, the compound is the change for being suitable for the dyestuff of photosensitive polymer combination
Close object.
Summary of the invention
One embodiment provides a kind of compounds.
Another embodiment provides a kind of photosensitive polymer combination comprising the compound.
Another embodiment provides a kind of colored filter manufactured using the photosensitive polymer combination.
One embodiment of the invention provides a kind of compound indicated by chemical formula 1.
[chemical formula 1]
In chemical formula 1,
R1To R16It independently is halogen atom, C1 to the C20 for being substituted or being unsubstituted alkyl, is substituted or is unsubstituted
C1 to C20 alkoxy, C6 to the C20 aryl for being substituted or being unsubstituted or C6 to the C20 virtue oxygen for being substituted or being unsubstituted
Base,
Restrictive condition is R1To R16In at least two indicated by chemical formula 2,
[chemical formula 2]
Wherein, in chemical formula 2,
R17For C1 to the C20 alkyl for being substituted or being unsubstituted, and
R18It is C1 to the C20 alkoxy for being substituted or being unsubstituted.
Chemical formula 2 can be indicated by chemical formula 3.
[chemical formula 3]
In chemical formula 3,
R17For C1 to the C20 alkyl for being substituted or being unsubstituted, and
R18For C1 to the C20 alkoxy for being substituted or being unsubstituted.
R17Can be tert-butyl (tert-butyl group).
R1To R16At least one of for C1 to the C20 alkoxy that is substituted or is unsubstituted.
R1To R4At least one of can be indicated by chemical formula 2, R5To R8At least one of can be indicated by chemical formula 2, R9
To R12At least one of can be indicated by chemical formula 2, and R13To R16At least one of can be indicated by chemical formula 2.
R1To R4At least one of can be C1 to the C20 alkoxy for being substituted or being unsubstituted, R5To R8In at least one
It is a to be indicated by chemical formula 2, R9To R12At least one of can be indicated by chemical formula 2, and R13To R16At least one of can be by
Chemical formula 2 indicates.
R1To R4It can be halogen atom, R5To R8At least one of can be indicated by chemical formula 2, R9To R12In at least one
It is a to be indicated by chemical formula 2, and R13To R16At least one of can be indicated by chemical formula 2.
R1To R8It can be halogen atom, R9To R12At least one of can be indicated by chemical formula 2, and R13To R16In at least
One can be indicated by chemical formula 2.
R1To R4It can be halogen atom, R5To R8At least one of can be indicated by chemical formula 2, R9To R12It can be former for halogen
Son, and R13To R16At least one of can be indicated by chemical formula 2.
The compound indicated by chemical formula 1 can be by chemical formula 4 a to expression in chemical formula 11.
[chemical formula 4]
[chemical formula 5]
[chemical formula 6]
[chemical formula 7]
[chemical formula 8]
[chemical formula 9]
[chemical formula 10]
[chemical formula 11]
The compound can be green dye.
The green dye can have maximum transmission rate in 445 nanometers to about 560 nanometers of wave-length coverage.
Another embodiment provides a kind of photosensitive polymer combination comprising the compound.
It can include the compound with the amount of 1 weight % to 10 weight % based on the total amount of photosensitive polymer combination.
Photosensitive polymer combination can additionally comprise alkali soluble resins, photopolymerizable compound, photopolymerization initiator and
Solvent.
Photosensitive polymer combination can additionally comprise pigment.
Pigment may include yellow uitramarine, viridine green or combinations thereof.
Another embodiment provides a kind of colored filter manufactured using the photosensitive polymer combination.
Other embodiments of the invention are contained in described in detail below.
There is splendid green spectral feature, high molar extinction coefficient (high molar according to the compound of an embodiment
Extinction coefficient) and there is splendid solubility in organic solvent, and therefore can be used as using in manufacture
Dyestuff during the green photonasty resin composition of colored filter, and therefore, the colored filter comprising dyestuff can have
There are premium brightness and splendid contrast ratio.
Specific embodiment
The embodiment of the present invention is described in detail below.However, these embodiments have demonstration, the present invention is unlimited
In this and the present invention be to be limited by the scope of the claims.
In the present specification, when in addition provide be specifically defined when, " being substituted " refer to by it is selected from the following at least
One substituent group substitutes at least one hydrogen of functional group: halogen (F, Br, Cl or I), hydroxyl, nitro, cyano, amido (NH2、
NH(R200) or N (R201)(R202), wherein R200、R201And R202It is identical or different, and independently be C1 to C10 alkyl), carbonamidine
Base, diazanyl, hydrazone group, carboxyl, the alkyl for being substituted or being unsubstituted, the alkenyl for being substituted or being unsubstituted, be substituted or without
Substituted alkynyl, the alicyclic ring organic group for being substituted or being unsubstituted, the aryl for being substituted or being unsubstituted and be substituted or
The heterocycle being unsubstituted.
In the present specification, when in addition offer is not specifically defined, " alkyl " refers to C1 to C20 alkyl, and specifically
It is C1 to C15 alkyl, " naphthenic base " refers to C3 to C20 naphthenic base, and specifically C3 to C18 naphthenic base, " alkoxy " are
Refer to C1 to C20 alkoxy, and specifically C1 to C18 alkoxy, " aryl " refer to C6 to C20 aryl, and specifically
C6 to C18 aryl, " alkenyl " refer to C2 to C20 alkenyl, and specifically C2 to C18 alkenyl, and " alkylidene " refers to C1 to C20
Alkylidene, and specifically C1 to C18 alkylidene, and " arlydene " refers to C6 to C20 arlydene, and specifically C6 is arrived
C16 arlydene.
In the present specification, when in addition offer is not specifically defined, " (methyl) acrylate ((meth) acrylate) "
Refer to " acrylate (acrylate) " and " methacrylate (methacrylate) " two, and " (methyl) acrylic acid
((meth) acrylic acid) " refers to " acrylic acid (acrylic acid) " and " methacrylic acid (methacrylic
acid)”。
In the present specification, when not otherwise provided definitions, " combination " refers to mixing or combined polymerization.In addition, " copolymerization " is
Finger block copolymerization is to random copolymerization, and " copolymer " refers to block copolymer to random copolymer.
In the present specification, when not otherwise provided definitions, when not drawing chemical bond, hydrogen is speculating at the position provided
Bond.
In the present specification, when in addition offer is not specifically defined, " * " instruction connects identical or different atom or chemical formula
Point.
One embodiment provides a kind of compound indicated by chemical formula 1.
[chemical formula 1]
In chemical formula 1,
R1To R16It independently is halogen atom, C1 to the C20 for being substituted or being unsubstituted alkyl, is substituted or is unsubstituted
C1 to C20 alkoxy, C6 to the C20 aryl for being substituted or being unsubstituted or C6 to the C20 virtue oxygen for being substituted or being unsubstituted
Base,
Restrictive condition is R1To R16In at least two indicated by chemical formula 2,
[chemical formula 2]
In chemical formula 2,
R17It is C1 to the C20 alkyl for being substituted or being unsubstituted, and
R18It is C1 to the C20 alkoxy for being substituted or being unsubstituted.
For example, work as R17And R18When being all alkyl or alkoxy, it may be difficult to realize the green for being used for colored filter
Pixel.
There is splendid green spectral feature and high molar extinction coefficient by the compound that chemical formula 1 indicates.In addition, by chemistry
The compound that formula 1 indicates must include at least two substituent groups indicated by chemical formula 2 and therefore can show in organic solvent
Splendid solubility and in addition when be applied to colored filter when premium brightness and splendid contrast ratio.
For example, when the compound indicated by above-mentioned chemical formula 1 includes the substituent group that only one is indicated by chemical formula 2
When, solubility, brightness and contrast ratio in organic solvent greatly deteriorate and therefore can be used as the sense for colored filter
Colorant in photosensitive resin composition.
Chemical formula 2 can be indicated by chemical formula 3.
[chemical formula 3]
In chemical formula 3,
R17For C1 to the C20 alkyl for being substituted or being unsubstituted, and
R18For C1 to the C20 alkoxy for being substituted or being unsubstituted.
There is the substituent group indicated by chemical formula 3 an alkyl and an alkoxy, one alkyl to be present in ortho position
Place, and one alkoxy is present at contraposition, and therefore can be further improved brightness and contrast ratio.For example, when
One alkyl is present at contraposition, and when an alkoxy is present at ortho position, it may be difficult to realize for colored filter
Green pixel.
For example, R17It can be tert-butyl.Compared to working as R17When being branched-chain alkyl, such as tert-butyl and the like,
Work as R17Whens being straight chained alkyl, such as methyl, ethyl, normal-butyl etc., adequate brightness and contrast ratio can get.
R1To R16At least one of can be C1 to the C20 alkoxy for being substituted or being unsubstituted.For example, changing
In formula 1, compared to " in R1To R16In two indicated by chemical formula 2, when other substituent groups are all halogen atoms ", " in R1
To R16In two simultaneously indicated by chemical formula 2, R1To R16At least one of when being alkoxy " sufficient dissolution can be obtained
Degree.
In addition, in chemical formula 1, as " R1To R16In at least four be by chemical formula 2 indicate (for example, R1To R4In
At least one can indicate by chemical formula 2, R5To R8At least one of can be indicated by chemical formula 2, R9To R12In at least one
It is a to be indicated by chemical formula 2, R13To R16At least one of indicated by chemical formula 2) " when, compound can have optimal dissolution
Degree.
R1To R4At least one of can be indicated by chemical formula 2, R5To R8At least one of can be by 2 table of chemical formula
Show, R9To R12At least one of can be indicated by chemical formula 2 and R13To R16At least one of can be by 2 table of chemical formula
Show.For example, R2And R3At least one of can be indicated by chemical formula 2, R6And R7At least one of can be by chemical formula
2 indicate, R10And R11At least one of can be indicated by chemical formula 2 and R14And R15At least one of can be by chemical formula
2 indicate.
R1To R4At least one of can be C1 to the C20 alkoxy for being substituted or being unsubstituted, R5To R8In at least
One can be indicated by chemical formula 2, R9To R12At least one of can be indicated by chemical formula 2 and R13To R16In at least
One can be indicated by chemical formula 2.For example, R2And R3At least one of can be the C1 for being substituted or being unsubstituted and arrive
C20 alkoxy, R6And R7At least one of can be indicated by chemical formula 2, R10And R11At least one of can be by chemical formula 2
Expression and R14And R15At least one of can be indicated by chemical formula 2.
R1To R4It can be halogen atom, R5To R8At least one of can be indicated by chemical formula 2, R9To R12In
At least one can be indicated by chemical formula 2 and R13To R16At least one of can be indicated by chemical formula 2.For example, R1
To R4It can be halogen atom, R6And R7At least one of can be indicated by chemical formula 2, R10And R11At least one of can
To be indicated by chemical formula 2 and R13To R16It can be halogen atom.
R1To R8It can be halogen atom, R9To R12At least one of can be indicated by chemical formula 2 and R13To R16
At least one of can be indicated by chemical formula 2.For example, R1To R8It can be halogen atom, R10And R11In at least
One can be C1 to the C20 alkoxy and R for being substituted or being unsubstituted14And R15At least one of can be by chemical formula
2 indicate.
R1To R4It can be halogen atom, R5To R8At least one of can be indicated by chemical formula 2, R9To R12It can be with
It is halogen atom and R13To R16At least one of can be indicated by chemical formula 2.For example, R1To R4It can be halogen
Atom, R6And R7At least one of can be indicated by chemical formula 2, R9To R12It can be halogen atom and R14And R15In
At least one can be indicated by chemical formula 2.
For example, the compound indicated by chemical formula 1 can by chemical formula 4 to one in chemical formula 11 expression, but
It is without being limited thereto.
[chemical formula 4]
[chemical formula 5]
[chemical formula 6]
[chemical formula 7]
[chemical formula 8]
[chemical formula 9]
[chemical formula 10]
[chemical formula 11]
The substituent group indicated by chemical formula 2 is contained at least two according to the compound of an embodiment and therefore can be with small amount
Realize apparent color, and therefore when be used as colorant when, can manufacture with splendid color character (such as premium brightness,
Splendid contrast ratio etc.) display device.For example, the compound can be colorant, such as dyestuff, such as green dye
Material, such as with the dyestuff of maximum transmission rate in 445 nanometers to 560 nanometers of wave-length coverage.
In general, dyestuff is most expensive in the component for colored filter.Therefore, expensive dyestuff may need more
To realize required effect, such as high brightness, high contrast etc., and therefore increase the unit cost of production.However, when according to one
When the compound of embodiment is used as dyestuff in colored filter, splendid color characteristic is may be implemented in the compound, such as high
Brightness, high contrast etc., and the unit cost of production is reduced, even if being used with small amount.
According to another embodiment, a kind of photosensitive polymer combination comprising compound according to the embodiment is provided.
For example, photosensitive polymer combination may include compound according to the embodiment, alkali soluble resins, photopolymerizable
Compound, photopolymerization initiator and solvent.
Colorant (such as dyestuff, such as green are played in photosensitive polymer combination according to the compound of an embodiment
Dyestuff) effect and splendid color character may be implemented.
It, can be with 1 weight % to 10 weight %, such as 3 weight % to 7 weight % based on the total amount of photosensitive polymer combination
Amount include according to the compound of an embodiment.When comprising in the range according to the compound of an embodiment, color is again
Existing property and contrast ratio are improved.
Photosensitive polymer combination can additionally comprise pigment, such as yellow uitramarine, viridine green or combinations thereof.
Yellow uitramarine may include C.I. pigment yellow 13 8, C.I. pigment yellow 13 9, C.I. pigment yellow 150 in color index
Deng, and can be used alone or form of mixtures with two or greater than two uses.
Viridine green may include C.I. pigment green 36, C.I. naphthol green 58, C.I. naphthol green 59 etc. in color index, and
And it can be used alone or form of mixtures with two or greater than two uses.
Pigment can be contained in the photosensitive polymer combination in the form of dispersible pigment dispersion.
Dispersible pigment dispersion may include solid pigment, solvent and the dispersion for being homogeneously dispersed in pigment in solvent
Agent.
, can be with 1 weight % to 20 weight % based on the total amount of dispersible pigment dispersion, such as 8 weight % to 20 weight %, such as
The solid content of 8 weight % to 15 weight %, such as 10 weight % to 20 weight %, such as 10 weight % to 15 weight % includes
Pigment.
Dispersing agent can be non-ionic dispersing agent, anionic dispersing agents, cation dispersing agent etc..The specific example of dispersing agent
It can be poly- alkane glycol (polyalkylene glycol) and its ester, polyoxyalkylene (polyoxyalkylene), polyol ester
Alkylene oxide (polyhydric alcohol ester alkylene oxide) addition product, alcohol alkylene oxide
(alcoholalkylene oxide) addition product, sulphonic acid ester (sulfonate ester), sulfonate (sulfonate
Salt), carboxylate (carboxylate ester), carboxylate (carboxylate salt), alkylamide alkylene oxide
(alkylamide alkylene oxide) addition product, alkylamine (alkyl amine) etc., and can be used alone or
Form of mixtures with two or greater than two uses.
The commercial examples of dispersing agent may include the DISPERBYK- of Societe BIC S.A. (BYK Co., Ltd.) manufacture
101、DISPERBYK-130、DISPERBYK-140、DISPERBYK-160、DISPERBYK-161、DISPERBYK-162、
DISPERBYK-163、DISPERBYK-164、DISPERBYK-165、DISPERBYK-166、DISPERBYK-170、
DISPERBYK-171, DISPERBYK-182, DISPERBYK-2000, DISPERBYK-2001 etc.；Efka chemical company
EFKA-47, EFKA-47EA, EFKA-48, EFKA-49, EFKA-100, EFKA- of (EFKA Chemicals Co.) manufacture
400, EFKA-450 etc.；Ze Neika company (Zeneka Co.) manufacture Solsperse 5000, Solsperse 12000,
Solsperse 13240、Solsperse 13940、Solsperse 17000、Solsperse 20000、Solsperse
24000GR, Solsperse27000, Solsperse 28000 etc.；Or Ajincomoto Co., Inc (Ajinomoto Inc) manufacture
PB711, PB821.
It can include dispersing agent with the amount of 1 weight % to 20 weight % by the total weight of dispersible pigment dispersion.When comprising described
When dispersing agent in range, the dispersion liquid of photosensitive polymer combination is improved due to viscosity appropriate, and therefore, when
When photosensitive polymer combination is applied in product, optics, physics and chemical quality can be kept.
Be used to form dispersible pigment dispersion solvent can be Ethylene glycol acetate (ethylene glycol acetate),
Ethyl cellosolve (ethylcellosolve), propylene glycol methyl ether acetate (propylene glycol
Methyletheracetate), ethyl lactate (ethyllactate), polyethylene glycol (polyethylene glycol), hexamethylene
Ketone (cyclohexanone), propylene glycol monomethyl ether (propylene glycol methylether) etc..
It, can be with 10 weight % to 20 weight % (such as 12 weight % to 18 weights based on the total amount of photosensitive polymer combination
Measure %) amount include dispersible pigment dispersion.When comprising dispersible pigment dispersion in the range, it can be ensured that processing range, and mention
High colorrendering quality and contrast ratio.
Alkali soluble resins can be acrylic resinoid.
Propylene based binder resin is the first alkene system unsaturated monomer and can be unsaturated with the diene series of its combined polymerization
The copolymer of monomer, and be the resin comprising at least one propylene base class repetitive unit.
First alkene system unsaturated monomer is the alkene system unsaturated monomer comprising at least one carboxyl.The example packet of monomer
Containing acrylic acid, methacrylic acid, maleic acid (maleic acid), itaconic acid (itaconic acid), fumaric acid
(fumaric acid) or combinations thereof.
It, can be with 5 weight % to 50 weight % (such as 10 weight % to 40 weights based on the total amount of propylene based binder resin
Measure %) amount include the first alkene system unsaturated monomer.
Diene series unsaturated monomer can be aromatic ethenyl compound, such as styrene (styrene), Alpha-Methyl
Styrene (α-methylstyrene), vinyltoluene (vinyl toluene), vinyl benzene dimethyl cellosolve
(vinylbenzylmethylether) etc.；Unsaturated carboxylic ester compound, such as (methyl) methyl acrylate (methyl
(meth) acrylate), (methyl) ethyl acrylate (ethyl (meth) acrylate), (methyl) butyl acrylate (butyl
(meth) acrylate), (methyl) acrylic acid 2- hydroxyl ethyl ester (2-hydroxyethyl (meth) acrylate), (methyl) propylene
Sour 2- hydroxy butyl ester (2-hydroxy butyl (meth) acrylate), (methyl) benzyl acrylate (benzyl (meth)
Acrylate), (methyl) cyclohexyl acrylate (cyclohexyl (meth) acrylate), (methyl) phenyl acrylate
(phenyl (meth) acrylate) etc.；Unsaturated carboxylic acid aminoalkyl ester compounds, such as (methyl) acrylic acid 2- amido second
Ester (2-aminoethyl (meth) acrylate), (methyl) acrylic acid 2- dimethylamino ethyl ester (2-
Dimethylaminoethyl (meth) acrylate) etc.；Generating vinyl carboxylate ester compounds, such as vinyl acetate (vinyl
Acetate), vinyl benzoate () etc.；Unsaturated carboxylic acid epihydric alcohol ester compound, such as the shrink of (methyl) acrylic acid are sweet
Grease (vinyl benzoate) etc.；Vinyl cyanide (vinyl cyanide) compound, such as (methyl) acrylonitrile ((meth)
Acrylonitrile) etc.；Unsaturated acyl amine compounds, such as (methyl) acrylamide ((meth) acrylamide) etc.；Deng.
These can be used alone or the form of mixtures with two kinds or greater than two kinds uses.
The specific example of acrylic resinoid can be (methyl) acrylic acid/benzyl methacrylate copolymer, (first
Base) acrylic acid/benzyl methacrylate/styrol copolymer, (methyl) acrylic acid/benzyl methacrylate/methyl-prop
Olefin(e) acid 2- hydroxyl ethyl ester copolymer, (methyl) acrylic acid/benzyl methacrylate/styrene/methacrylic acid 2- hydroxyl ethyl ester are total
Polymers etc., but it is not limited to these.These can be used alone or the form of mixtures with two kinds or greater than two kinds uses.
The weight average molecular weight of alkali soluble resins can be in 3,000 grams/mol to 150,000 grams/mol, such as 5,000
Gram/mol to 50,000 grams/mol, such as 20, in the range of 000 gram/mol to 30,000 gram/mol.Work as alkali soluble resins
When with weight average molecular weight in the range, photosensitive polymer combination can have splendid physics and chemical characteristic
And proper viscosity, appropriate developability and sensibility are maintained, and show splendid and substrate during colored filter manufacture
Close contact property.
The alkali soluble resins can have the acid value of 15mgKOH/g to 60mgKOH/g, such as 20mgKOH/g is arrived
50mgKOH/g.When the alkali soluble resins has the acid value in the range, pixel has splendid resolution ratio.
It, can be with 1 weight % to 30 weight %, such as 1 weight % to 20 weights based on the total amount of photosensitive polymer combination
The amount for measuring % includes alkali soluble resins.When comprising alkali soluble resins in the above range, can be improved developability and
Colored filter manufacture during can due to raising crosslinking and improve excellent surface smoothness.
Photopolymerizable compound can be single official of (methyl) acrylic acid comprising at least one ethylene system unsaturated double-bond
It can ester or multifunctional ester.
Photopolymerizable compound has alkene system unsaturated double-bond, therefore can draw during the exposure in patterning process
It rises and polymerize enough and form the pattern with splendid heat resistance, light resistance and chemical resistance.
The specific example of photopolymerizable compound can be two (methyl) acrylic acid glycol ester (ethylene glycol
Di (meth) acrylate), two (methyl) acrylic acid binaryglycol ester (diethylene glycol di (meth)
Acrylate), two (methyl) acrylic acid triglycol esters (triethylene glycol di (meth) acrylate), two (first
Base) propylene acid propylene glycol ester (propylene glycol di (meth) acrylate), two (methyl) acrylic acid neopentyl glycol ester
(neopentyl glycol di (meth) acrylate), two (methyl) acrylic acid 1,4- butanediol ester (1,4-butanediol
Di (meth) acrylate), two (methyl) acrylic acid 1,6-HD ester (1,6-hexanediol di (meth)
Acrylate), bisphenol-A two (methyl) acrylate (bisphenol A di (meth) acrylate), two (methyl) acrylic acid
Pentaerythritol ester (pentaerythritol di (meth) acrylate), three (methyl) acrylate, pentaerythritols
(pentaerythritol tri (meth) acrylate), four (methyl) acrylate, pentaerythritol (pentaerythritol
Tetra (meth) acrylate), six (methyl) acrylate, pentaerythritol (pentaerythritol hexa (meth)
Acrylate), two (methyl) acrylic acid dipentaerythritol esters (dipentaerythritol di (meth) acrylate), three
(methyl) acrylic acid dipentaerythritol ester (dipentaerythritol tri (meth) acrylate), five (methyl) acrylic acid
Dipentaerythritol ester (dipentaerythritol penta (meth) acrylate), six (methyl) acrylic acid dipentaerythritols
Ester (dipentaerythritol hexa (meth) acrylate), bisphenol A epoxide resin (methyl) acrylate
(bisphenol A epoxy (meth) acrylate), ethylene glycol single methyl ether (methyl) acrylate (ethylene
Glycol monomethylether (meth) acrylate), trimethylolpropane tris (methyl) acrylate
(trimethylol propane tri (meth) acrylate), tricresyl phosphate (methyl) acryloyloxyethyl ester (tris (meth)
Acryloyloxyethyl phosphate), novolac epoxy resin (methyl) acrylate (novolacepoxy (meth)
Acrylate) etc..
The example of commercially available photopolymerizable compound is as follows.Mono-functional (methyl) acrylate may include Ah's Knicks
(Aronix)(East Asia synthetic chemical industry Co., Ltd (Toagosei Chemistry
Industry Co.,Ltd.))；KAYARAD(Nippon Kayaku K. K)；(Osaka organic chemistry Co., Ltd (Osaka Organic Chemical Ind., Ltd.)) etc..Function
The example of abnormal (methyl) acrylate of energy may include Aronix(East Asia synthesizes chemical work
Industry Co., Ltd), KAYARAD (Nippon Kayaku K. K),(Osaka organic chemistry Co., Ltd) etc..The example of trifunctional (methyl) acrylate can
Include Aronix (East Asia synthesis
Chemical industry Co., Ltd), KAYARAD (day
This chemical drug Co., Ltd.), (Osaka is by the big life of disproportionation medicine
Co., Ltd (Osaka Yuki Kayaku Kogyo Co.Ltd.)) etc..These can be used alone or with two kinds or greater than two
The form of mixtures of kind uses.
The photopolymerizable compound can be handled through acid anhydrides to improve developability.
It, can be with 1 weight % to 15 weight %, such as 5 weight % to 10 weights based on the total amount of photosensitive polymer combination
The amount for measuring % includes photopolymerizable compound.When comprising photopolymerizable compound in the range, photopolymerizable monomer exists
Sufficiently solidify during exposure in patterning process and there is splendid reliability, and the aobvious of alkaline-based developer can be improved
Shadow.
Photopolymerization initiator can be photopolymerization initiator conventionally used in photosensitive polymer combination, such as acetophenone
Class compound, Benzophenone class compound, thioxanthene ketone class compound, styrax class compound, compound in triazine class, oxime compound
Deng.
The example of acetophenone compounds can be 2,2'- diethoxy acetophenone, 2,2'- dibutoxy acetophenone, 2-
Hydroxy-2-methyl propiophenone, to tert-butyl trichloroacetophenone, chloro- to tert-butyl dichloroacetophenone, 4- chloro-acetophenone, 2,2'- bis-
4- metaphenoxy acetophenone, 2- methyl-1-(4- (methyl mercapto) phenyl)-2- morpholinyl propyl- 1- ketone, 2- benzyl-2- dimethylamino-
1- (4- morpholino phenyl)-butyl- 1- ketone etc..
The example of Benzophenone class compound can be Benzophenone, benzoilbenzoate, phenylamino benzoic acid formoxyl methyl esters, 4-
Phenyl Benzophenone, Viosorb 110, propylene are acidified Benzophenone, bis- (dimethyl amido) Benzophenones of 4,4'-, the bis- (diethyl of 4,4'-
Amido) Benzophenone, 4,4'- dimethylamino benzophenone, 4,4'- dichloro benzophenone, 3,3'- dimethyl -2- methoxyl group hexichol
Ketone etc..
The example of thioxanthene ketone class compound can be thioxanthones, 2- methyl thioxanthones, isopropyl thioxanthone, 2,4- diethyl thiophene
Ton ketone, 2,4- diisopropylthioxanthone, 2-chlorothioxanthone etc..
The example of styrax class compound can be styrax, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether,
Benzoin isobutyl ether, benzyl dimethyl ketal etc..
The example of compound in triazine class can be bis- (the trichloromethyl)-s- of 2,4,6- trichloto-s-triazine, 2- phenyl -4,6-
Triazine, bis- (the trichloromethyl)-s- triazines of 2- (3', 4'- dimethoxy-styryl) -4,6-, 2- (4'- methoxyl group naphthalene) -4,
Bis- (the trichloromethyl)-s- triazines of 6-, bis- (the trichloromethyl)-s- triazines of 2- (p-methoxyphenyl) -4,6-, 2- (p-methylphenyl) -4,
Bis- (the trichloromethyl)-s- triazines of 6-, bis- (the trichloromethyl)-s- triazines of 2- phenylbenzene -4,6-, bis- (trichloromethyl) -6- styrene
Base-s- triazine, bis- (the trichloromethyl)-s- triazines of 2- (naphthols-yl) -4,6-, 2- (4- methoxynaphthol-yl) bis- (trichlorines of -4,6-
Methyl)-s- triazine, bis- (trichloromethyl) -6- piperonyl (the piperonyl)-s- triazines of 2-4-, bis- (the trichloromethyl) -6- of 2-4-
(4- methoxyl-styrene)-s- triazine etc..
The example of oxime compound can be O- acyl group oxime compound, 2- (o-benzoyl base oxime) -1- [4- (thiophenyl) benzene
Base] -1,2- acetyl caproyl, 1- (adjacent acetyl oxime) -1- [9- ethyl -6- (2- methyl benzoyl) -9H- carbazole -3- base] ethyl ketone, O-
Carbethoxyl group-α-oxygen amido -1- phenyl propyl- 1- ketone etc..The specific example of O- acyl group oxime compound can be 1,2- acetyl caproyl,
2- dimethyl amido -2- (4- methylbenzyl) -1- (4- morpholine -4- base-phenyl)-butyl- 1- ketone, 1- (4- Phenylsulfanylphenyl) -
Butane -1,2- diketone 2- oxime-O- benzoic ether, 1- (4- Phenylsulfanylphenyl)-octane -1,2- diketone 2- oxime-O- benzoic ether, 1-
(4- Phenylsulfanylphenyl)-octyl- 1- ketoxime-O- acetic acid esters, 1- (4- Phenylsulfanylphenyl)-butyl- 1- ketoxime-O- acetic acid esters etc..
In addition to the compound, Photoepolymerizationinitiater initiater can additionally comprise carbazole compound, cyclohexadione compounds, boric acid
Sulfonium class compound, weight nitrogen compound, glyoxaline compound, bisglyoxaline class compound, compound of fluorene class etc..
The Photoepolymerizationinitiater initiater can be used together with emulsion, and the emulsion can be by absorbing light and becoming sharp
It sends out state and then shifts its energy and cause to chemically react.
The example of emulsion can -3-thiopropionate, pentaerythrite four -3-thiopropionate, two seasons double for tetraethylene glycol
Penta four -3-thiopropionate of tetrol etc..
It, can be with 0.01 weight % to 10 weight %, such as 0.1 weight % to 5 based on the total amount of photosensitive polymer combination
The amount of weight % includes photopolymerization initiator.When comprising photopolymerization initiator in the range, in pattern forming method
Sufficient photopolymerization occurs during exposure, splendid reliability can be able to achieve, the heat resistance, light resistance and resistance toization of pattern can be improved
The property learned, resolution ratio and close contact property, and due to non-reaction initiator, transmittance degradation can be prevented.
Solvent be with according to the compound of an embodiment, pigment, alkali soluble resins, photopolymerizable compound and photopolymerization
The material that initiator etc. has compatibility but do not react with it.
The example of solvent may include alcohol, such as methanol, ethyl alcohol etc.；Ether, such as dichloroether, n-butyl ether, isoamyl ether, first
Base phenyl ether, tetrahydrofuran etc.；Glycol ethers, such as glycol monoethyl ether, ethylene glycol monoethyl ether etc.；Cellosolve acetate, such as
Cellosolve methyl acetate, cellosolve ethyl acetate, cellosolve diethyl acetate etc.；Carbitol (carbitols), such as methyl second
Base carbitol, diethyl carbitol, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol dimethyl ether, diethylene glycol first
Benzyl ethyl ether, diethylene glycol diethyl ether etc.；Propylene glycol alkyl ether acetic acid ester, such as propylene glycol methyl ether acetate, propylene glycol propyl ether
Acetic acid esters etc.；Aromatic hydrocarbon, such as toluene, dimethylbenzene etc.；Ketone, such as methyl ethyl ketone, cyclohexanone, 4- hydroxy-4-methyl -2-
The positive acetone of pentanone, methyl, methyl n-butyl ketone, Methylpentanone, 2-HEPTANONE etc.；Representative examples of saturated aliphatic monocarboxylic acid Arrcostab, such as second
Acetoacetic ester, n-butyl acetate, isobutyl acetate etc.；Lactate, such as methyl lactate, ethyl lactate etc.；Ethoxyacetic acid Arrcostab,
Such as ethoxyacetic acid methyl esters, ethoxyacetic acid ethyl ester, ethoxyacetic acid butyl ester etc.；Alkoxy acetic acid Arrcostab, such as methoxyacetic acid
Methyl esters, ethyl methoxyacetate, methoxyacetic acid butyl ester, ethoxy acetate, ethoxy ethyl acetate etc.；3- oxygroup propionic acid
Arrcostab, such as 3- oxygroup methyl propionate, 3- oxygroup ethyl propionate etc.；3- alkoxypropan acid alkyl ester, such as 3- methoxy propyl
Sour methyl esters, 3- methoxypropionate, 3- ethoxyl ethyl propionate, 3- ethoxypropanoate etc.；2- oxygroup alkyl propionates,
Such as 2- oxygroup methyl propionate, 2- oxygroup ethyl propionate, 2- oxygroup propyl propionate etc.；2- alkoxypropan acid alkyl ester, such as 2-
Methoxy methyl propionate, 2- methoxypropionate, 2- ethoxyl ethyl propionate, 2- ethoxypropanoate etc.；2- oxygroup -2-
Methylpropionate, such as 2- oxygroup -2 Methylpropionic acid methyl esters, 2- oxygroup -2 Methylpropionic acid ethyl ester etc.；2- alkoxy -2- methyl
Single oxygroup monocarboxylic acid Arrcostab of alkyl propionate, such as 2- methoxyl group -2 Methylpropionic acid methyl esters, 2- ethyoxyl -2- methyl-prop
Acetoacetic ester etc.；Ester, such as propionic acid 2- hydroxy methacrylate, propionic acid 2- hydroxyl -2- methyl ethyl, acetic acid hydroxy methacrylate, butyric acid 2- hydroxyl -
3- carboxylic acid methyl ester etc.；Keto ester, such as ethyl pyruvate etc..Alternatively, it is also possible to use high boiling solvent, such as N- methyl formyl
Amine (N-methylformamide), N,N-dimethylformamide (N, N-dimethylformamide), N- methyl formyl aniline
(N-methylformanilide), N- methylacetamide (N-methylacetamide), DMAC N,N' dimethyl acetamide (N, N-
Dimethylacetamide), N-Methyl pyrrolidone (N-methylpyrrolidone), dimethyl sulfoxide
(dimethylsulfoxide), benzyl ether (benzylethylether), two hexyl ethers (dihexylether), levulinic
Ketone (acetylacetone), isophorone (isophorone), caproic acid (caproic acid), octanoic acid (caprylic
Acid), 1- octanol (1-octanol), 1 nonyl alcohol (1-nonanol), benzyl alcohol (benzylalcohol), phenylmethyl acetate
(benzyl acetate), ethyl benzoate (ethyl benzoate), diethy-aceto oxalate (diethyl oxalate), suitable fourth
Enedioic acid diethylester (diethyl maleate), gamma-butyrolacton (γ-butyrolactone), ethylene carbonate (ethylene
Carbonate), propylene carbonate (propylene carbonate), ethylene glycol ethyl ether phenylacetate (phenyl
Cellosolve acetate) etc..
In view of compatibility and reactivity, glycol ethers, such as ethylene glycol monoethyl ether etc. can be preferably used；Ethylene glycol alkane
Base ether acetic acid ester, such as ethohexadiol acetic acid ether etc.；Ester, such as propionic acid 2- hydroxy methacrylate etc.；Carbitol, such as diethyl two
Alcohol monomethyl ether etc.；Propylene glycol alkyl ether acetic acid ester, such as propylene glycol methyl ether acetate, propylene glycol propyl ether acetic acid esters；And/or
Ketone, such as cyclohexanone.
Solvent is used with surplus, such as based on the total amount of photosensitive polymer combination 30 weight % to 80 weight %.Work as packet
When containing solvent in the range, photosensitive polymer combination can have proper viscosity, to improve the painting of colored filter
Cloth feature.
Photosensitive polymer combination according to another embodiment can additionally comprise epoxide, tight with substrate to improve
Close contact performance.
The example of the epoxide may include novolak type epoxy compound (phenol novolac epoxy
Compound), tetramethyl phenylbenzene epoxide, Bisphenol A epoxides, alicyclic epoxide compound or combinations thereof.
It, can be with 0.01 parts by weight to 20 parts by weight and such as 0.1 weight based on the photosensitive polymer combination of 100 parts by weight
The amount of part to 10 parts by weight includes epoxide.When comprising epoxide in the range, it can improve and closely connect
Touch characteristic, storage characteristics etc..
In addition, photosensitive polymer combination can additionally comprise have for example carboxyl, methylacryloyl, isocyanate group,
The silane coupling agent of epoxy group isoreactivity substituent group, to improve its adhesion with substrate.
The example of silanes coupling agent may include trimethoxy silane yl benzoic acid, γ-methylpropenyl propoxyl group front three
Oxysilane, vinyltriacetoxy silane, vinyltrimethoxysilane, γ-isocyanate propyl triethoxysilane,
γ-glycidoxypropyltrimewasxysilane, β-(3,4- epoxycyclohexyl) ethyl trimethoxy silane etc..These can be with
It is used alone or the form of mixtures with two kinds or greater than two kinds uses.
It can include silane with the amount of 0.01 parts by weight to 10 parts by weight based on the photosensitive polymer combination of 100 parts by weight
Coupling agent.When comprising silane coupling agent in the range, close contact property, storage characteristics etc. can be splendid.
In addition, optionally, photosensitive polymer combination can additionally comprise surfactant to improve coating characteristic and prevent
Defect.
The example of surfactant can beWith(BM chemical company (BM Chemie
Inc.))；MEGAFACEAnd(big Japanese ink chemical company (Dainippon
Ink Kagaku Kogyo Co.,Ltd.))；FULORADFULORADFULORADAnd
FULORAD(Sumitomo 3M Co., Ltd. (Sumitomo 3M Co., Ltd.))；SURFLONSURFLONSURFLONSURFLONAnd SURFLON(Asahi Glass Co., Ltd (ASAHI Glass
Co.,Ltd.))；AndAndDeng (the beautiful silica gel in east is limited
Company (Toray Silicone Co., Ltd.))；The F- of big Japanese ink chemical industry Co., Ltd (DIC Co., Ltd)
482, F-484, F-478, F-554 etc..
It can include surface with the amount of 0.001 parts by weight to 5 parts by weight based on the photosensitive polymer combination of 100 parts by weight
Activating agent.When comprising surfactant in the range, it is ensured that coating uniformity does not find dyeing and glass substrate
Wetting characteristics is splendid.
In addition, photosensitive polymer combination can additionally comprise other additives, such as oxidation retarder, stabilization with predetermined amount
Agent etc., unless deterioration in characteristics.
According to another embodiment, a kind of colorized optical filtering manufactured using photosensitive polymer combination according to the embodiment is provided
Piece.
The pattern forming method of colored filter is as follows.
The method includes will be according to the photoresist of an embodiment with the methods of spin coating, slot coated, ink jet printing
Composition is applied in support substrate；Dry be coated with positive type photosensitive organic compound is to form photosensitive polymer combination
Film；Positive type photosensitive organic compound film is exposed；The normal Photosensitive resin combination for developing in alkaline aqueous solution exposed
Object film is to obtain photo-sensitive resin；And heat treatment photo-sensitive resin.Condition for patterning method is the relevant technologies
In it is known and will not elaborate in the present specification.
Hereinafter, the present invention is described in more detail in reference example, however, but these examples not with any meaning explanation be limited
The scope of the present invention processed.
(synthesis compound)
Synthesize example 1-1: the synthesis chloro- 5- of 3,4,6- tri- (4- methoxyl group -2- methyl-phenoxv)-phthalonitrile
By 3,4,5,6- tetrachloro phthalonitrile (3,4,5,6-tetrachlorophthalonitrile) (5 grams), 4- first
Oxygroup -2- cresols (4-methoxy-2-methylphenol) (3.12 grams), K2CO3(3.9 grams) and N, N- dimethyl formyl
Amine (25 milliliters) is placed in 100 milliliters of flask and then heats while stirring at 70 DEG C.When the reactions are completed, EA (acetic acid
Ethyl ester, ethyl acetate) for extracting.After extraction, solid is obtained by concentration.Herein, make solid obtained molten
Solution is washed several times in a small amount of methylene chloride with hexane, is filtered and is dried in vacuo to obtain 3,4,6- tri- chloro- 5- (4- methoxies
Base -2- methyl-phenoxv)-phthalonitrile.
Synthesize example 1-2: the synthesis chloro- phthalonitrile of 4- (2- tert-butyl -4- Difluoro-phenoxy) -3,5,6- three
By 3,4,5,6- tetrachloro phthalonitrile (5 grams), 2- tert-butyl -4- metoxyphenol (4.07 grams), K2CO3(3.9
Gram), N,N-dimethylformamide (25 milliliters) be placed in 100 milliliters of flask and then at 70 DEG C heat and meanwhile stir.When
When reaction is completed, EA (ethyl acetate) is for extracting.After extraction, solid is obtained by concentration.Herein, make obtained solid
Body is dissolved in a small amount of methylene chloride, is washed several times with hexane, is filtered and is dried in vacuo to obtain 4- (2- tert-butyl -4- first
Oxygroup-phenoxy group) three chloro- phthalonitrile of -3,5,6-.
Synthesis example 1: the compound that synthesis is indicated by chemical formula 4
It will be according to the chloro- 5- of 3,4,6- tri- (4- methoxyl group -2- methyl-phenoxv)-phthalonitrile (2 of synthesis example 1-1
Gram), 1,8- diazabicyclo, 11-7- alkene (1.04 grams) and 1- pentenol (10 grams) be placed in 100 milliliters of flask, and with
It is heated at 90 DEG C afterwards and carrys out dissolved solid, zinc acetate (0.25 gram) is added to wherein, and heat the mixing at 140 DEG C
Object stirs simultaneously.When the reactions are completed, precipitating is confirmed by methanol, filtered and is dried in vacuo.Dry solid passes through column color
Spectrometry purifying.After purification, methylene chloride is suitably added to obtained solid to make it dissolve, and is added to it methanol for tying
It is brilliant.Filtering for crystallizing solid and vacuum drying to obtain the compound indicated by chemical formula 4.
[chemical formula 4]
Maldi-tof MS:1527.82m/z
Synthesis example 2: the compound that synthesis is indicated by chemical formula 5
It will be according to the chloro- 5- of 3,4,6- tri- (4- methoxyl group -2- methyl-phenoxv)-phthalonitrile of synthesis example 1-1
(1.5 grams), 3,4,5,6- tetrachloro phthalonitrile (0.36 gram), 11-7- alkene of 1,8- diazabicyclo (1.04 grams) and 1-
Pentenol (14 grams) is placed in 100 milliliters of flask and heating is at 90 DEG C to dissolve the solid, by zinc acetate (0.25 gram)
It is added to wherein, and heats mixture at 140 DEG C and stir simultaneously.When the reactions are completed, precipitating by methanol confirmation, filtered with
And vacuum drying.Dry solid passes through column chromatography eluting.After purification, methylene chloride is suitably added to obtained solid
It makes it dissolve, and is added to it methanol for crystallizing.Filtering for crystallizing solid and vacuum drying to obtain the change indicated by chemical formula 5
Close object.
[chemical formula 5]
Maldi-tof MS:1425.72m/z
Synthesis example 3: the compound that synthesis is indicated by chemical formula 6
It will be according to the chloro- 5- of 3,4,6- tri- (4- methoxyl group -2- methyl-phenoxv)-phthalonitrile of synthesis example 1-1
(1.1 grams), 3,4,5,6- tetrachloro phthalonitrile (0.80 gram), 11-7- alkene of 1,8- diazabicyclo (1.14 grams) and 1-
Pentenol (14 grams) is placed in 100 milliliters of flask and heating is at 90 DEG C to dissolve the solid, by zinc acetate (0.27 gram)
It is added to wherein, and heats obtained mixture at 140 DEG C and stir simultaneously.When the reactions are completed, precipitating is by methanol confirmation, warp
Filtering and vacuum drying.Dry solid passes through column chromatography eluting.After purification, dichloro is suitably added to obtained solid
Methane makes it dissolve, and is added to it methanol for crystallizing.Filtering for crystallizing solid and vacuum drying to obtain by 6 table of chemical formula
The compound shown.
[chemical formula 6]
Maldi-tof MS:1323.64m/z
Synthesis example 4: the compound that synthesis is indicated by chemical formula 7
It will be according to the chloro- 5- of 3,4,6- tri- (4- methoxyl group -2- methyl-phenoxv)-phthalonitrile of synthesis example 1-1
The chloro- 5- amoxy-phthalonitrile (0.43 gram) of (1.5 grams), 3,4,6- tri-, 11-7- alkene (1.04 of 1,8- diazabicyclo
Gram) and 1- pentenol (14 grams) be placed in 100 milliliters of flask and heated at 90 DEG C, after solid dissolution, by second
Sour zinc (0.25 gram) is added to wherein, and heats obtained mixture at 140 DEG C and stir simultaneously.When the reactions are completed, it sinks
It forms sediment by methanol confirmation, filtered and be dried in vacuo.Dry solid passes through column chromatography eluting.After purification, to being consolidated
Body adds methylene chloride suitably to make it dissolve, and is added to it methanol for crystallizing.Filtering for crystallizing solid and vacuum drying
To obtain the compound indicated by chemical formula 7.
[chemical formula 7]
Maldi-tof MS:1477.84m/z
Synthesis example 5: the compound that synthesis is indicated by chemical formula 8
It will be according to the chloro- phthalonitrile of 4- (2- tert-butyl -4- Difluoro-phenoxy) -3,5,6- three of synthesis example 1-2
(2 grams), 1,8- diazabicyclo, 11-7- alkene (0.93 gram) and 1- pentenol (10 grams) are placed in 100 milliliters of flask, and
It is then heated at 90 DEG C and carrys out dissolved solid, zinc acetate (0.22 gram) is added to wherein, and heat and obtained at 140 DEG C
Mixture stirs simultaneously.When the reactions are completed, precipitating is confirmed by methanol, filtered and is dried in vacuo.Dry solid passes through
It is column chromatography eluting.After purification, it adds methylene chloride suitably to obtained solid to make it dissolve, and is added to it methanol use
In crystallization.Filtering for crystallizing solid and vacuum drying to obtain the compound indicated by chemical formula 8.
[chemical formula 8]
Maldi-tof MS:1696.01m/z
Synthesis example 6: the compound that synthesis is indicated by chemical formula 9
It will be according to the chloro- phthalonitrile of 4- (2- tert-butyl -4- Difluoro-phenoxy) -3,5,6- three of synthesis example 1-2
(1.5 grams), 3,4,5,6- tetrachloro phthalonitrile (0.32 gram), 11-7- alkene of 1,8- diazabicyclo (0.93 gram) and 1-
Pentenol (14 grams) is placed in 100 milliliters of flask and heating is at 90 DEG C to dissolve the solid, by zinc acetate (0.22 gram)
It is added to wherein, and heats obtained mixture at 140 DEG C and stir simultaneously.When the reactions are completed, precipitating is by methanol confirmation, warp
Filtering and vacuum drying.Dry solid passes through column chromatography eluting.After purification, methylene chloride is suitably added to and is obtained
Solid, and add methanol to wherein to crystallize.Filtering for crystallizing solid and vacuum drying is indicated with obtaining by chemical formula 9
Compound.
[chemical formula 9]
Maldi-tof MS:1551.87m/z
Synthesis example 7: the compound that synthesis is indicated by chemical formula 10
It will be according to the chloro- phthalonitrile of 4- (2- tert-butyl -4- Difluoro-phenoxy) -3,5,6- three of synthesis example 1-2
(1.1 grams), 3,4,5,6- tetrachloro phthalonitrile (0.71 gram), 11-7- alkene of 1,8- diazabicyclo (1.02 grams) and 1-
Pentenol (14 grams) is placed in 100 milliliters of flask and heating is at 90 DEG C to dissolve the solid, by zinc acetate (0.25 gram)
It is added to wherein, and heats obtained mixture at 140 DEG C and stir simultaneously.When the reactions are completed, precipitating is by methanol confirmation, warp
Filtering and vacuum drying.Dry solid passes through column chromatography eluting.After purification, dichloro is suitably added to obtained solid
Methane makes it dissolve, and is added to it methanol for crystallizing.Filtering for crystallizing solid and vacuum drying to obtain by chemical formula 10
The compound of expression.
[chemical formula 10]
Maldi-tof MS:1407.73m/z
Synthesis example 8: the compound that synthesis is indicated by chemical formula 11
It will be according to the chloro- 5- of 3,4,6- tri- (4- methoxyl group -2- methyl-phenoxv)-phthalonitrile of synthesis example 1-1
The chloro- 5- amoxy-phthalonitrile (0.39 gram) of (1.5 grams), 3,4,6- tri-, 11-7- alkene (0.93 of 1,8- diazabicyclo
Gram) and 1- pentenol (14 grams) is placed in 100 milliliters of flask and heating is at 90 DEG C to dissolve the solid, by zinc acetate
(0.22 gram) is added to wherein, and heats obtained mixture at 140 DEG C and stir simultaneously.When the reactions are completed, precipitating is by first
Alcohol confirmation is filtered and is dried in vacuo.Dry solid passes through column chromatography eluting.After purification, suitably by methylene chloride
It is added to obtained solid to make it dissolve, and is added to it methanol for crystallizing.Filtering for crystallizing solid and vacuum drying to obtain
The compound indicated by chemical formula 11.
[chemical formula 11]
Maldi-tof MS:1603.98m/z
Compare synthesis example 1: the compound that synthesis is indicated by chemical formula C-1
By three chloro- phthalonitrile (1 gram) of 4- (2- sec-butyl-phenoxy group)-3,5,6-, 1,8- diazabicyclo 11-
7- alkene (0.30 gram), 1- pentenol (7 grams), zinc acetate (0.12 gram) are placed in 100 milliliters of flask and heat at 140 DEG C
It stirs simultaneously.When the reactions are completed, gains are concentrated and by column chromatography eluting.After purification, obtained liquid is concentrated to obtain
Obtain solid.Crystalline solid is dried in vacuo to obtain the compound indicated by chemical formula C-1.
[chemical formula C-1]
Maldi-tof MS:1584.04m/z
Compare synthesis example 2: the compound that synthesis is indicated by chemical formula C-2
By 3,4,5,6- tetrachloro phthalonitrile (5 grams), 2,4- xylenol (2.75 grams), K2CO3(3.9 grams) and
N,N-dimethylformamide (25 milliliters) is placed in 100 milliliters of flask and then heats while stirring at 70 DEG C.Work as reaction
When completion, EA (ethyl acetate) is for extracting.After extraction, solid is obtained by concentration.Herein, make solid obtained molten
Solution is washed several times in a small amount of methylene chloride with hexane, is filtered and is dried in vacuo to obtain 3,4,6- tri- chloro- 5- (2,4- bis-
Methyl-phenoxv)-phthalonitrile.
By 3,4,6- tri- chloro- 5- (2,4- Dimehtyl-phenoxy)-phthalonitrile (1 gram), 1,8- diazabicylo ten
One -7- alkene (1.08 grams) and 1- pentenol (14 grams) are placed in 100 milliliters of flask and heat at 90 DEG C to dissolve
Solid is stated, zinc acetate (0.26 gram) is added to wherein, and heats mixture at 140 DEG C and stirs simultaneously.When reaction is completed
When, precipitating is confirmed by methanol, filtered and is dried in vacuo.Dry solid passes through column chromatography eluting.After purification, to being obtained
It obtains solid and adds methylene chloride suitably to make it dissolve, and be added to it methanol for crystallizing.Filtering for crystallizing solid and vacuum
Drying is to obtain the compound indicated by chemical formula C-2.
[chemical formula C-2]
Maldi-tof MS:1463.84m/z
Compare synthesis example 3: the compound that synthesis is indicated by chemical formula C-3
By 3,4,5,6- tetrachloro phthalonitrile (5 grams), 2,4- xylenol (3.47 grams), K2CO3(3.9 grams) and
N,N-dimethylformamide (25 milliliters) is placed in 100 milliliters of flask and then heats while stirring at 70 DEG C.Work as reaction
When completion, ethyl acetate (EA) is for extracting.After extraction, solid is obtained by concentration.Herein, make solid obtained molten
Solution is washed several times in a small amount of methylene chloride with hexane, is filtered and is dried in vacuo to obtain 3,4,6- tri- chloro- 5- (2,4- bis-
Difluoro-phenoxy)-phthalonitrile.
By 3,4,6- tri- chloro- 5- (2,4- Dimethoxv-phenoxy)-phthalonitrile (2 grams), 1,8- diazabicylo ten
One -7- alkene (0.99 gram) and 1- pentenol (14 grams) are placed in 100 milliliters of flask and heat at 90 DEG C to dissolve
Solid is stated, zinc acetate (0.24 gram) is added to wherein, and heats mixture at 140 DEG C and stirs simultaneously.When reaction is completed
When, precipitating is confirmed by methanol, filtered and is dried in vacuo.Dry solid passes through column chromatography eluting.After purification, by dichloro
Methane is suitably added to obtained solid and makes it dissolve, and is added to it methanol for crystallizing.Filtering for crystallizing solid and vacuum
Drying is to obtain the compound indicated by chemical formula C-3.
[chemical formula C-3]
Maldi-tof MS:1591.80m/z
Compare synthesis example 4: the compound that synthesis is indicated by chemical formula C-4
It will be according to the chloro- phthalonitrile of 4- (2- tert-butyl -4- Difluoro-phenoxy) -3,5,6- three of synthesis example 1-2
(0.7 gram), 3,4,5,6- tetrachloro phthalonitrile (1.45 grams), 11-7- alkene of 1,8- diazabicyclo (1.38 grams) and 1-
Pentenol (14 grams) is placed in 100 milliliters of flask and heating is added to it zinc acetate to dissolve the solid at 90 DEG C
(0.33 gram), and heat the mixture at 140 DEG C while stirring.When the reactions are completed, precipitating is confirmed by methanol, through filtering
And vacuum drying.Dry solid passes through column chromatography eluting.After purification, methylene chloride is suitably added to obtained solid
It makes it dissolve, and is added to it methanol for crystallizing.Filtering for crystallizing solid and vacuum drying indicated with obtaining by chemical formula C-4
Compound.
[chemical formula C-4]
Maldi-tof MS:1237.54m/z
Assessment 1: dissolubility
Retarder thinner (PGMEA) is added to 0.5 gram according to synthesis example 1 to synthesis example 8 and compares synthesis example 1
Into each compound for comparing synthesis example 4, thus obtained each corresponding solution uses mixed rotor (mixed rotor VMR-5, well
Nei ShengSakaetang Co., Ltd. (Iuchi Seieido Co., Ltd.)) it is stirred 1 hour under 25 DEG C and 100 revs/min, and eachization
The dissolubility result for closing object is showed in table 1.
Dissolubility assessment reference
Dissolve the compound (solute) for being greater than or equal to 10 weight % based on the total amount of retarder thinner:
Dissolution is greater than or equal to 5 weight % and the compound (solute) less than 10 weight % based on the total amount of retarder thinner:
△
Dissolve the compound (solute) based on the total amount of retarder thinner less than 5 weight %: X
[table 1]
(unit: weight %)
| Dissolubility | |
| Synthesize example 1 | ○ |
| Synthesize example 2 | △ |
| Synthesize example 3 | △ |
| Synthesize example 4 | ○ |
| Synthesize example 5 | ○ |
| Synthesize example 6 | △ |
| Synthesize example 7 | △ |
| Synthesize example 8 | ○ |
| Compare synthesis example 1 | X |
| Compare synthesis example 2 | X |
| Compare synthesis example 3 | X |
| Compare synthesis example 4 | X |
Referring to table 1, compared to synthesis example 1 is compared to the compound for comparing synthesis example 4, synthesis example 1 is real to synthesis
Therefore the compound of example 8 ought be used as showing splendid dissolubility in organic solvent according to the compound of an embodiment
Splendid color character is shown whens photosensitive polymer combination etc..
(synthesis photosensitive polymer combination)
Example 1
Following components is mixed in the photosensitive resin composition prepared in the composition shown in table 2 according to example 1
Object.
Specifically, photopolymerization initiator is dissolved in solvent, solution is stirred at room temperature 2 hours, adds thereto
Alkali soluble resins and photopolymerizable compound, and obtained mixture is stirred at room temperature 2 hours.Then, example 1 will be synthesized
Compound (compound indicated by chemical formula 4) is added to reactant as colorant and pigment (dispersible pigment dispersion), and in room
Temperature lower stirring obtained mixture 1 hour.Then, filtering products therefrom is three times to remove impurity, to prepare photoresist
Composition.
[table 2]
(unit: weight %)
Example 2
Except the compound for using the compound (compound indicated by chemical formula 5) of synthesis example 2 to replace synthesizing example 1
(compound indicated by chemical formula 4) outside, photosensitive polymer combination is prepared according to method identical with example 1.
Example 3
Except the compound for using the compound (compound indicated by chemical formula 6) of synthesis example 3 to replace synthesizing example 1
(compound indicated by chemical formula 4) outside, photosensitive polymer combination is prepared according to method identical with example 1.
Example 4
Except the compound for using the compound (compound indicated by chemical formula 7) of synthesis example 4 to replace synthesizing example 1
(compound indicated by chemical formula 4) outside, photosensitive polymer combination is prepared according to method identical with example 1.
Example 5
Except the compound for using the compound (compound indicated by chemical formula 8) of synthesis example 5 to replace synthesizing example 1
(compound indicated by chemical formula 4) outside, photosensitive polymer combination is prepared according to method identical with example 1.
Example 6
Except the compound for using the compound (compound indicated by chemical formula 9) of synthesis example 6 to replace synthesizing example 1
(compound indicated by chemical formula 4) outside, photosensitive polymer combination is prepared according to method identical with example 1.
Example 7
Except the compound for using the compound (compound indicated by chemical formula 10) of synthesis example 7 to replace synthesizing example 1
(compound indicated by chemical formula 4) outside, photosensitive polymer combination is prepared according to method identical with example 1.
Example 8
Except the compound for using the compound (compound indicated by chemical formula 11) of synthesis example 8 to replace synthesizing example 1
(compound indicated by chemical formula 4) outside, photosensitive polymer combination is prepared according to method identical with example 1.
Comparative example 1
Except the change for using the compound (compound indicated by chemical formula C-1) for comparing synthesis example 1 to replace synthesizing example 1
Close object (compound indicated by chemical formula 4) outside, photosensitive polymer combination is prepared according to method identical with example 1.
Comparative example 2
Except the change for using the compound (compound indicated by chemical formula C-2) for comparing synthesis example 2 to replace synthesizing example 1
Close object (compound indicated by chemical formula 4) outside, photosensitive polymer combination is prepared according to method identical with example 1.
Comparative example 3
Except the change for using the compound (compound indicated by chemical formula C-3) for comparing synthesis example 3 to replace synthesizing example 1
Close object (compound indicated by chemical formula 4) outside, photosensitive polymer combination is prepared according to method identical with example 1.
Comparative example 4
Except the change for using the compound (compound indicated by chemical formula C-4) for comparing synthesis example 4 to replace synthesizing example 1
Close object (compound indicated by chemical formula 4) outside, photosensitive polymer combination is prepared according to method identical with example 1.
Comparative example 5
In addition to using composition shown in table 3 to replace composition shown in table 1, photosensitive polymer combination is basis
It is prepared by identical with example 1 method.
[table 3]
(unit: weight %)
Comparative example 6
In addition to using dispersible pigment dispersion pigment G36 to replace dispersible pigment dispersion pigment G58, photosensitive polymer combination is basis
It is prepared by identical with comparative example 5 method.
Assessment 2: hue coordinate, brightness and contrast ratio
The photosensitive polymer combination of example 1 to example 8 and comparative example 1 to comparative example 6 is respectively coated and is arrived for 1 micron
In 3 microns of thickness to 1 millimeters thick degreasing and clean glass substrate, and then on 90 DEG C of hot plates dry 2 minutes it is each to obtain
Film.Then, film is exposed by using the high-pressure sodium lamp with 365 nanometers of dominant wavelengths.Then, film is dry in 200 DEG C of forced convertions
5 minutes are dried in dry boiler to obtain sample.The brightness (Y) of pixel layer and contrast ratio are by using spectrophotometer
(MCPD3000, great Zhong Electronics Co., Ltd (Otsuka Electronics Co., Ltd.)) measurement, and result is showed in table
In 4.
[table 4]
| Brightness (Y) | Contrast ratio | |
| Example 1 | 62.7 | 15,700 |
| Example 2 | 62.5 | 15,400 |
| Example 3 | 62.8 | 15,500 |
| Example 4 | 62.4 | 15,300 |
| Example 5 | 62.6 | 15,300 |
| Example 6 | 62.3 | 15,000 |
| Example 7 | 62.5 | 14,900 |
| Example 8 | 62.3 | 15,200 |
| Comparative example 1 | 61.0 | 14,400 |
| Comparative example 2 | 60.8 | 14,600 |
| Comparative example 3 | 60.1 | 14,300 |
| Comparative example 4 | 59.7 | 14,100 |
| Comparative example 5 | 60.9 | 13,300 |
| Comparative example 6 | 58.6 | 13,600 |
Referring to table 4, compared to the photosensitive resin composition for arriving comparative example 6 according to comparative example 1 for not including the compound
Object, the photosensitive polymer combination comprising the embodiment compound as dyestuff according to example 1 to example 8 show splendid color
Feature.
Although describing the present invention in conjunction with the content for being presently considered as practical practical embodiments, it should be appreciated that the present invention is not
It is limited to the disclosed embodiments, but on the contrary, it is intended to covering includes in the spirit and scope of the appended claims
Various modifications and equivalent arrangements.
Claims (18)
1. a kind of compound, which is characterized in that indicated by chemical formula 1:
[chemical formula 1]
Wherein, in chemical formula 1,
R1To R16It independently is halogen atom, C1 to the C20 for being substituted or being unsubstituted alkyl, the C1 for being substituted or being unsubstituted
To C20 alkoxy, C6 to the C20 aryl for being substituted or being unsubstituted or C6 to the C20 aryloxy group for being substituted or being unsubstituted,
Restrictive condition is R1To R16In at least two indicated by chemical formula 2,
[chemical formula 2]
Wherein, in chemical formula 2,
R17For C1 to the C20 alkyl for being substituted or being unsubstituted, and
R18For C1 to the C20 alkoxy for being substituted or being unsubstituted.
2. compound according to claim 1, which is characterized in that chemical formula 2 is indicated by chemical formula 3:
[chemical formula 3]
Wherein, in chemical formula 3,
R17For C1 to the C20 alkyl for being substituted or being unsubstituted, and
R18For C1 to the C20 alkoxy for being substituted or being unsubstituted.
3. compound according to claim 1, which is characterized in that R17For tert-butyl.
4. compound according to claim 1, which is characterized in that R1To R16At least one of be to be substituted or without taking
C1 to the C20 alkoxy in generation.
5. compound according to claim 1, which is characterized in that R1To R4At least one of indicated by chemical formula 2,
R5To R8At least one of indicated by chemical formula 2,
R9To R12At least one of indicated by chemical formula 2, and
R13To R16At least one of indicated by chemical formula 2.
6. compound according to claim 1, which is characterized in that
R1To R4At least one of for C1 to the C20 alkoxy that is substituted or is unsubstituted,
R5To R8At least one of indicated by chemical formula 2,
R9To R12At least one of indicated by chemical formula 2, and
R13To R16At least one of indicated by chemical formula 2.
7. compound according to claim 1, which is characterized in that
R1To R4For halogen atom,
R5To R8At least one of indicated by chemical formula 2,
R9To R12At least one of indicated by chemical formula 2, and
R13To R16At least one of indicated by chemical formula 2.
8. compound according to claim 1, which is characterized in that
R1To R8For halogen atom,
R9To R12At least one of indicated by chemical formula 2, and
R13To R16At least one of indicated by chemical formula 2.
9. compound according to claim 1, which is characterized in that
R1To R4For halogen atom,
R5To R8At least one of indicated by chemical formula 2,
R9To R12For halogen atom, and
R13To R16At least one of indicated by chemical formula 2.
10. compound according to claim 1, which is characterized in that the compound indicated by chemical formula 1 is by chemical formula
4 indicate to one in chemical formula 11.
[chemical formula 4]
[chemical formula 5]
[chemical formula 6]
[chemical formula 7]
[chemical formula 8]
[chemical formula 9]
[chemical formula 10]
[chemical formula 11]
11. compound according to claim 1, which is characterized in that the compound is green dye.
12. compound according to claim 11, which is characterized in that the green dye is at 445 nanometers to 560 nanometers
There is maximum transmission rate in wave-length coverage.
13. a kind of photosensitive polymer combination, which is characterized in that including according to claim 1 to change described in any one of 12
Close object.
14. photosensitive polymer combination according to claim 13, which is characterized in that press the photosensitive polymer combination
Total amount meter, with the amount of 1 weight % to 10 weight % include the compound.
15. photosensitive polymer combination according to claim 13, which is characterized in that the photosensitive polymer combination is also
Including alkali soluble resins, photopolymerizable compound, photopolymerization initiator and solvent.
16. photosensitive polymer combination according to claim 15, which is characterized in that the photosensitive polymer combination is also
Including pigment.
17. photosensitive polymer combination according to claim 16, which is characterized in that the pigment include yellow uitramarine,
Viridine green or combinations thereof.
18. a kind of colored filter, which is characterized in that made using photosensitive polymer combination according to claim 13
It makes.
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| KR1020170113931A KR102149968B1 (en) | 2017-09-06 | 2017-09-06 | Novel compound,photosensitive resin composition comprising the same and color filter |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101373329A (en) * | 2007-08-24 | 2009-02-25 | 住友化学株式会社 | Colored cured composition |
| CN103323897A (en) * | 2012-03-22 | 2013-09-25 | 株式会社日本触媒 | Light selective transmitting filter, resin sheet and solid state image sensor |
| KR20160005258A (en) * | 2014-07-04 | 2016-01-14 | 엘지디스플레이 주식회사 | Color filter comprising Green Dye and Display Device using the same |
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| JP2016124888A (en) * | 2014-12-26 | 2016-07-11 | 東洋インキＳｃホールディングス株式会社 | Color filter pigment, coloring composition and color filter |
| KR101837563B1 (en) * | 2015-06-23 | 2018-03-12 | 삼성에스디아이 주식회사 | Novel compound, photosensitive resin composition comprising the same, and color filter |
| KR101768895B1 (en) * | 2015-10-30 | 2017-08-18 | 엘지디스플레이 주식회사 | Pigment-dye dispersion, green color filter and display device fabricated from the dispersion |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101373329A (en) * | 2007-08-24 | 2009-02-25 | 住友化学株式会社 | Colored cured composition |
| CN103323897A (en) * | 2012-03-22 | 2013-09-25 | 株式会社日本触媒 | Light selective transmitting filter, resin sheet and solid state image sensor |
| KR20160005258A (en) * | 2014-07-04 | 2016-01-14 | 엘지디스플레이 주식회사 | Color filter comprising Green Dye and Display Device using the same |
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| KR20190027185A (en) | 2019-03-14 |
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| TW201912648A (en) | 2019-04-01 |
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