CN105801477B - Azo compound and polymer including it - Google Patents
Azo compound and polymer including it Download PDFInfo
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- CN105801477B CN105801477B CN201510649566.1A CN201510649566A CN105801477B CN 105801477 B CN105801477 B CN 105801477B CN 201510649566 A CN201510649566 A CN 201510649566A CN 105801477 B CN105801477 B CN 105801477B
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/84—Nitriles
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/84—Nitriles
- C07D213/85—Nitriles in position 3
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
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- C07D—HETEROCYCLIC COMPOUNDS
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- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/58—Amidines
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/34—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate
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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
- C09B43/00—Preparation of azo dyes from other azo compounds
- C09B43/30—Preparation of azo dyes from other azo compounds by esterification of —COOH or —SO3H groups
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/032—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders
- G03F7/033—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders the binders being polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. vinyl polymers
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/34—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate
- C08F220/343—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate in the form of urethane links
- C08F220/346—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate in the form of urethane links and further oxygen
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- Polymers & Plastics (AREA)
- Spectroscopy & Molecular Physics (AREA)
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
The present invention provides a kind of azo compound and the polymer including it, and azo compound is indicated by chemical formula 1.Azo compound and there is excellent yellow spectrum feature, high molar extinction coefficient and excellent solubility (about organic solvent) as the polymer of monomer including azo compound and can be used as dyestuff and be used to prepare photosensitive polymer combination used in colored filter, and the colored filter therefore, including the dyestuff can have excellent brightness and high contrast ratio.[chemical formula 1]
Description
The cross-reference of related application
This application claims No. 10-2015-0010127 to file an application in Korean Intellectual Property Office on January 12nd, 2015
The priority and right of South Korea patent application, the entire disclosure of the application are incorporated herein by reference.
Technical field
The present invention relates to a kind of novel azo compound and including its polymer.
Background technique
By using the colored filter of color type photosensitive polymer combination manufacture due to its pigment particle size in brightness and
It is restricted in terms of contrast ratio.In addition, color image forming apparatus used in imaging sensor needs lesser dispersion particle diameter to be formed
Fine pattern.In order to meet the requirements, by using the photoresist group for the dyestuff (and non-pigment) for including not formed particle
Object is closed to attempt to obtain the colored filter with improved color character (such as brightness and contrast ratio).Therefore, it is necessary to suitable
The unimolecule compound and polymer compound of dyestuff as photosensitive polymer combination are studied.
Summary of the invention
One embodiment provides a kind of compounds.
It includes polymer of the compound as monomer that another embodiment, which provides,.
One embodiment of the present of invention provides the compound indicated by chemical formula 1.
[chemical formula 1]
In chemical formula 1,
R1And R2It is substituted or unsubstituted C1 to C20 alkyl, *-C (=O) OR ' or *-OC (=O) each independently
R ',
R ' is substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C2 to C10 alkenyl or is taken
Generation or unsubstituted C6 to C20 aryl,
Its condition is R1And R2One of include the substituent group indicated by chemical formula 2, and
R3It is substituted or unsubstituted C1 to C20 alkyl.
[chemical formula 2]
In chemical formula 2,
R4It is hydrogen or substituted or unsubstituted C1 to C10 alkyl.
1 compound represented of chemical formula can be indicated by the chemical formula selected from chemical formula 3 to chemical formula 6.
[chemical formula 3]
[chemical formula 4]
[chemical formula 5]
[chemical formula 6]
In chemical formula 3 into chemical formula 6,
L1To L3It is independently that substituted or unsubstituted C1 to C10 alkylidene, substituted or unsubstituted C6 are arrived
C20 arlydene or *-L '-C (=O) O-L "-*,
L ' and L " is substituted or unsubstituted C1 to C5 alkylidene or substituted or unsubstituted each independently
C6 to C12 arlydene,
R3And R5It is substituted or unsubstituted C1 to C20 alkyl each independently, and
R4It is hydrogen or substituted or unsubstituted C1 to C10 alkyl.
Chemical formula 1 can be indicated by the chemical formula selected from chemical formula 7 to chemical formula 26.
[chemical formula 7]
[chemical formula 8]
[chemical formula 9]
[chemical formula 10]
[chemical formula 11]
[chemical formula 12]
[chemical formula 13]
[chemical formula 14]
[chemical formula 15]
[chemical formula 16]
[chemical formula 17]
[chemical formula 18]
[chemical formula 19]
[chemical formula 20]
[chemical formula 21]
[chemical formula 22]
[chemical formula 23]
[chemical formula 24]
[chemical formula 25]
[chemical formula 26]
The compound can be weld.
Weld can have about 400 nanometers of light absorption sections for arriving about 500 nano wave lengths.
It includes polymer of the repetitive unit as monomer shown in chemical formula 1 that another embodiment, which provides,.
That is, it includes the weight for arriving repetitive unit shown in chemical formula 30 selected from chemical formula 27 that another embodiment, which provides,
The polymer of multiple unit.
[chemical formula 27]
[chemical formula 28]
[chemical formula 29]
[chemical formula 30]
In chemical formula 27 into chemical formula 30,
L1To L3It is independently that substituted or unsubstituted C1 to C10 alkylidene, substituted or unsubstituted C6 are arrived
C20 arlydene or *-L '-C (=O) O-L "-*,
L ' and L " is substituted or unsubstituted C1 to C5 alkylidene or substituted or unsubstituted each independently
C6 to C12 arlydene,
R3And R5It is substituted or unsubstituted C1 to C20 alkyl each independently, and
R4It is hydrogen or substituted or unsubstituted C1 to C10 alkyl.
The polymer can further include repetitive unit shown in chemical formula 31 and chemical formula 32.
[chemical formula 31]
[chemical formula 32]
In chemical formula 31 and chemical formula 32,
R6It is hydrogen or substituted or unsubstituted C1 to C10 alkyl,
L4It is substituted or unsubstituted C1 to C10 alkylidene.
In terms of polymer total amount, polymer may include about 40 weight % to about 60 weight % selected from chemical formula 27 to change
The repetitive unit of repetitive unit shown in formula 30；The repetition list of about 5 weight % to about 25 weight % indicated by chemical formula 31
Member；And about 25 weight % to about 45 weight % the repetitive unit indicated by chemical formula 32.
Polymer may include the repetitive unit that repetitive unit shown in chemical formula 52 is arrived selected from chemical formula 33.
Repetitive unit shown in chemical formula 27 can be selected from the repetitive unit indicated by chemical formula 33 to chemical formula 46.
[chemical formula 33]
[chemical formula 34]
[chemical formula 35]
[chemical formula 36]
[chemical formula 37]
[chemical formula 38]
[chemical formula 39]
[chemical formula 40]
[chemical formula 41]
[chemical formula 42]
[chemical formula 43]
[chemical formula 44]
[chemical formula 45]
[chemical formula 46]
Repetitive unit shown in chemical formula 28 can be repetitive unit shown in chemical formula 47 or chemical formula 48.
[chemical formula 47]
[chemical formula 48]
Repetitive unit shown in chemical formula 29 can be repetitive unit shown in chemical formula 49 or chemical formula 50.
[chemical formula 49]
[chemical formula 50]
Repetitive unit shown in chemical formula 30 can be repetitive unit shown in chemical formula 51 or chemical formula 52.
[chemical formula 51]
[chemical formula 52]
The other embodiment of the present invention includes in the following specific embodiments.
According to one embodiment, azo compound and including azo compound as monomer polymer have it is excellent
Yellow spectrum feature, high molar extinction coefficient and excellent solubility (about organic solvent) and can be used as dyestuff and be used for
Photosensitive polymer combination used in colored filter is prepared, and therefore, the colored filter including the dyestuff can have
There are excellent brightness and high contrast ratio.
Specific embodiment
The embodiment of the present invention is described in detail below.However, these embodiments are with exemplary and of the invention unlimited
In these embodiments.
Unless the context clearly determines otherwise, otherwise such as used in specification and appended claims, singular
" one ", " described " include multiple indicants.
As used herein, when in addition offer is not specifically defined, term " substituted " refers to be taken selected from following a
Replace (instead of at least one hydrogen in functional group) for base: halogen atom (F, Br, Cl or I), hydroxyl, nitro, cyano, amino
(NH2、NH(R200) or N (R201)(R202), wherein R200、R201And R202It is identical or different, and be independently C1 to C10 alkane
Base), amidino groups, diazanyl, hydrazone group, carboxyl, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, be substituted
Or unsubstituted alkynyl, substituted or unsubstituted alicyclic organic group, substituted or unsubstituted aryl and
Substituted or unsubstituted heterocycle.
As used herein, when in addition offer is not specifically defined, term " alkyl " refers to C1 to C20 alkyl, and specific
Ground says, C1 to C15 alkyl；Term " naphthenic base " refers to C3 to C20 naphthenic base, and specifically, C3 to C18 naphthenic base；Art
Language " alkoxy " refers to C1 to C20 alkoxy, and specifically, C1 to C18 alkoxy；Term " aryl " refers to C6 to C20
Aryl, and specifically, C6 to C18 aryl；Term " alkenyl " refers to C2 to C20 alkenyl, and specifically, C2 to C18
Alkenyl；Term " alkylidene " refers to C1 to C20 alkylidene, and specifically, C1 to C18 alkylidene；And term " sub- virtue
Base " refers to C6 to C20 arlydene, and specifically, C6 to C16 arlydene.
As used herein, when in addition provide be specifically defined when, " (methyl) acrylate " refer to " acrylate " and
" methacrylate " two, and " (methyl) acrylic acid " refers to " acrylic acid " and " methacrylic acid ".
As used herein, when in addition offer is not specifically defined, term " combination " refers to mixing or copolymerization.In addition, " altogether
It is poly- " refer to block copolymerization to random copolymerization, and term " copolymer " refers to block copolymer to random copolymer.
As used herein, be specifically defined unless otherwise provided, otherwise chemical bond is not shown position bond be hydrogen original
Son (otherwise a key occur in the position).
As used herein, when not otherwise provided definitions, " * " refers to the company between identical or different atom or chemical formula
Socket part point.
In addition, when not otherwise provided definitions, " absorption maximum section " indicates that display is as used herein in the present specification
Absorption maximum section section (range).
One embodiment provides 1 compound represented of chemical formula.
[chemical formula 1]
In chemical formula 1,
R1And R2It is substituted or unsubstituted C1 to C20 alkyl, *-C (=O) OR ' or *-OC (=O) each independently
R ',
R ' is substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C2 to C10 alkenyl or is taken
Generation or unsubstituted C6 to C20 aryl,
Its condition is R1And R2One of include the substituent group indicated by chemical formula 2, and
R3It is substituted or unsubstituted C1 to C20 alkyl.
1 compound represented of chemical formula is azo compound and disappears with excellent yellow spectrum feature and high mole
Backscatter extinction logarithmic ratio and also have excellent dissolubility (about organic solvent).Further, since R1And R2Any of be used as chemical formula
The substituent group of compound shown in 1 includes substituted or unsubstituted acrylate group certainly, therefore is changed shown in chemical formula 1
Conjunction object can have the machinability during excellent heat resistance, chemical resistance and manufacture colored filter.
[chemical formula 2]
In chemical formula 2,
R4It is hydrogen or substituted or unsubstituted C1 to C10 alkyl.
1 compound represented of chemical formula can be indicated by the chemical formula selected from chemical formula 3 to chemical formula 6.
[chemical formula 3]
[chemical formula 4]
[chemical formula 5]
[chemical formula 6]
In chemical formula 3 into chemical formula 6,
L1To L3It is independently that substituted or unsubstituted C1 to C10 alkylidene, substituted or unsubstituted C6 are arrived
C20 arlydene or *-L '-C (=O) O-L "-*,
L ' and L " is substituted or unsubstituted C1 to C5 alkylidene or substituted or unsubstituted each independently
C6 to C12 arlydene,
R3And R5It is substituted or unsubstituted C1 to C20 alkyl each independently, and
R4It is hydrogen or substituted or unsubstituted C1 to C10 alkyl.
For example, chemical formula 1, and specifically, chemical formula 3, it can be by the change selected from chemical formula 7 to chemical formula 20
Formula indicates, but is not limited to these chemical formulas.
[chemical formula 7]
[chemical formula 8]
[chemical formula 9]
[chemical formula 10]
[chemical formula 11]
[chemical formula 12]
[chemical formula 13]
[chemical formula 14]
[chemical formula 15]
[chemical formula 16]
[chemical formula 17]
[chemical formula 18]
[chemical formula 19]
[chemical formula 20]
For example, chemical formula 1, and specifically, chemical formula 4, can be by selected from chemical formula 21 or chemical formula 22
Chemical formula indicates, but is not limited to these chemical formulas.
[chemical formula 21]
[chemical formula 22]
For example, chemical formula 1, and specifically, chemical formula 5, can be by selected from chemical formula 23 or chemical formula 24
Chemical formula indicates, but is not limited to these chemical formulas.
[chemical formula 23]
[chemical formula 24]
For example, chemical formula 1, and specifically, chemical formula 6, can be by selected from chemical formula 25 or chemical formula 26
Chemical formula indicates, but is not limited to these chemical formulas.
[chemical formula 25]
[chemical formula 26]
Compound according to one embodiment is the azo chemical combination including acrylate group for specified substituent
Object, and therefore can realize more transparent colour on a small quantity, and therefore can be used as colorant for manufacture with excellent
The display device of color character (such as brightness, contrast ratio etc.).For example, the compound can be colorant, such as
Dyestuff, such as display wavelength is in about 400 nanometers to about 500 nanometers (specifically, about 410 nanometers to about 450 nanometers) ranges
Absorption maximum section weld.
For example, the compound can be display wavelength at about 400 nanometers to about 500 nanometers (specifically, about
410 nanometers to about 450 nanometers) dyestuff in absorption maximum section in range.
It in general, is most expensive in dyestuff component used in colored filter.Therefore, dye dosage should it is larger with
Desired effect, such as high brightness, high contrast ratio etc. are obtained, but manufacturing cost is caused to increase.However, when according to a reality
Apply example compound be used as colored filter in dyestuff when, the compound can on a small quantity using and reduce manufacture at
This, and realize excellent color character, such as high brightness, high contrast ratio etc..
According to another embodiment, providing a kind of includes polymer according to the compound of one embodiment as monomer.
That is, the polymer includes 1 compound represented of chemical formula as monomer.
[chemical formula 1]
In chemical formula 1,
R1And R2It is substituted or unsubstituted C1 to C20 alkyl, *-C (=O) OR ' or *-OC (=O) each independently
R ',
R ' is substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C2 to C10 alkenyl or is taken
Generation or unsubstituted C6 to C20 aryl,
Its condition is R1And R2One of include chemical formula 2 shown in substituent group,
[chemical formula 2]
In chemical formula 2,
R4It is hydrogen or substituted or unsubstituted C1 to C10 alkyl, and
R3It is substituted or unsubstituted C1 to C20 alkyl.
The polymer can have about 10,000 grams/mol to about 100,000 grams/mol of weight average molecular weight.
For example, in the polymer, monomer shown in chemical formula 1 can be as selected from shown in chemical formula 27 to chemical formula 30
Repetitive unit repetitive unit indicate.That is, the polymer may include selected from chemical formula 27 to 30 institute of chemical formula
The repetitive unit of the repetitive unit shown.
[chemical formula 27]
[chemical formula 28]
[chemical formula 29]
[chemical formula 30]
In chemical formula 27 into chemical formula 30,
L1To L3It is independently that substituted or unsubstituted C1 to C10 alkylidene, substituted or unsubstituted C6 are arrived
C20 arlydene or *-L '-C (=O) O-L "-*,
L ' and L " is substituted or unsubstituted C1 to C5 alkylidene or substituted or unsubstituted each independently
C6 to C12 arlydene,
R3And R5It is substituted or unsubstituted C1 to C20 alkyl each independently, and
R4It is hydrogen or substituted or unsubstituted C1 to C10 alkyl.
The polymer can further include repetitive unit shown in chemical formula 31 and chemical formula 32.
[chemical formula 31]
[chemical formula 32]
In chemical formula 31 and chemical formula 32,
R6It is hydrogen or substituted or unsubstituted C1 to C10 alkyl, and
L4It is substituted or unsubstituted C1 to C10 alkylidene.
In terms of polymer total amount, polymer may include about 40 weight % to about 60 weight % selected from chemical formula 27 to change
The repetitive unit of repetitive unit shown in formula 30；The repetition list of about 5 weight % to about 25 weight % indicated by chemical formula 31
Member；And about 25 weight % to about 45 weight % the repetitive unit indicated by chemical formula 32.When polymer includes the weight
When every kind of repetitive unit in range, polymer can produce dissolubility and have favorable influence to structural stability.
For example, repetitive unit shown in chemical formula 27 can be to arrive selected from chemical formula 33 and repeat shown in chemical formula 46
The repetitive unit of unit.
[chemical formula 33]
[chemical formula 34]
[chemical formula 35]
[chemical formula 36]
[chemical formula 37]
[chemical formula 38]
[chemical formula 39]
[chemical formula 40]
[chemical formula 41]
[chemical formula 42]
[chemical formula 43]
[chemical formula 44]
[chemical formula 45]
[chemical formula 46]
Repetitive unit shown in chemical formula 28 can be repetitive unit shown in chemical formula 47 or chemical formula 48.
[chemical formula 47]
[chemical formula 48]
Repetitive unit shown in chemical formula 29 can be repetitive unit shown in chemical formula 49 or chemical formula 50.
[chemical formula 49]
[chemical formula 50]
Repetitive unit shown in chemical formula 30 can be repetitive unit shown in chemical formula 51 or chemical formula 52.
[chemical formula 51]
[chemical formula 52]
The compound and/or polymer can be used as photosensitive polymer combination of the colorant for colored filter
In.
The technique that pattern is formed in colored filter is as follows.
The technique includes being coated on photosensitive polymer combination using the methods of spin coating, slot coated, ink jet printing
On supporting substrate；Dry be coated with photosensitive polymer combination is to form photosensitive polymer combination layer；By photoresist
Composition layer exposure；Exposed photosensitive polymer combination is set to develop to obtain photosensitive resin film with alkaline aqueous solution；With
And photosensitive resin film is heat-treated.Process conditions etc. are in the related art it is widely known that and in the present specification
It is unspecified.
Below with reference to the present invention is described in more detail in example.However, these examples should not be construed as in any sense
It limits the scope of the invention.
(compound synthesis)
Synthesis example 1: the compound that synthesis is indicated by chemical formula 7
3.12 grams of 4-aminobenzoic acid, 75.6 ml deionized waters and 17.28 milliliters of HCl (35%) are in 125 milliliters of triangles
It is stirred in shape flask, in ice bath.Then, 14.4 milliliters of sodium nitrite in aqueous solution (1 millimolar concentration) is added dropwise thereto,
And it is stirred mixture 3 hours under ice bath.
Make 4.35 grams of cyan-acetic esters and 4.97 grams of ethylhexylamine reflux and is reacted 2 hours at 110 DEG C.Then, to
5 grams of ethyl acetoacetates and 3.76 grams of piperidines are wherein added, and so that gained mixture is flowed back and reacts overnight.
After checking gains using TLC, it is handled with acid and is washed with water several times, synthesis obtains pyridine assimilation
Close object 1.
4.722 grams of pyridinone compounds 1 are added in 20 ml deionized waters, and NaOH aqueous solution is added thereto
(pH8) to be dissolved.The pyridinone compounds 1 dissolved are placed in above-mentioned 125 milliliters of triangle flasks, and are used
In sodium carbonate (10%) aqueous solution and the pH of mixture.The product neutralized is filtered and is purified and is dried in vacuo with water,
Obtain compound 2.
5.5 g of compound 2 are placed in 250 milliliters of flasks, thereto be added 2.09 grams of GMA, 2.16 grams of TBAB and
70 milliliters of acetonitriles, and mixture is made to flow back and stay overnight in 90 DEG C of reactions.Gains MC/ water process and carry out chromatographic column
Purification, synthesis obtain the compound indicated by chemical formula 7 (CF 7).
1H NMR (DMSO): 15.02 (s, 1H), 8.1 (m, 1H), 7.94 (m, 1H), 7.73 (m, 1H), 7.55 (m, 1H),
6.65 (m, 1H), 6.17 (m, 1H), 4.7 (m, 1H), 4.3 (m, 2H), 3.9 (m, 2H), 2.03 (s, 1H) 1.73 (m, 3H), 1.96
(m, 3H), 1.81 (m, 1H), 1.28 (m, 8H), 0.91 (m, 6H)
Synthesis example 2: the compound that synthesis is indicated by chemical formula 8
3.12 grams of 4-aminobenzoic acid, 75.6 ml deionized waters and 17.28 milliliters of HCl (35%) are in 125 milliliters of triangles
It is stirred in shape flask, in ice bath.Then, 14.4 milliliters of sodium nitrite in aqueous solution (1 millimolar concentration) is added dropwise thereto,
And it is stirred mixture 3 hours under ice bath.
By replacing the ethylhexylamine according to synthesis example 1 with butylamine come pyridine synthesis ketone compound 3.By 3.69 grams of pyridines
Ketone compound 3 is added in 20 ml deionized waters, and NaOH aqueous solution (pH 8) is added thereto to be dissolved.Institute is molten
The pyridinone compounds 3 of solution are added in above-mentioned 125 milliliters of triangle flasks, and using in sodium carbonate (10%) aqueous solution and mixed
Close the pH of object.It filters gains and is purified with water, is then dried in vacuo, obtain compound 4.
4.8 g of compound 4 are placed in 250 milliliters of flasks, thereto be added 2.09 grams of GMA, 2.16 grams of TBAB and
70 milliliters of acetonitriles, and mixture is made to flow back and stay overnight in 90 DEG C of reactions.Gains MC/ water process and carry out chromatographic column
Purification, synthesis obtain the compound indicated by chemical formula 8 (CF 8).
1H NMR (DMSO) 15.02 (s, 1H), 8.1 (m, 1H), 7.94 (m, 1H), 7.73 (m, 1H), 7.55 (m, 1H),
6.65 (m, 1H), 6.17 (m, 1H), 4.7 (m, 1H), 4.3 (m, 2H), 3.9 (m, 2H), 2.03 (s, 1H) 1.73 (m, 3H), 1.96
(m, 3H), 1.28 (m, 4H), 0.9 (m, 3H)
Synthesis example 3: the compound that synthesis is indicated by chemical formula 9
3.12 grams of 3- aminobenzoic acids, 75.6 ml deionized waters and 17.28 milliliters of HCl (35%) are in 125 milliliters of triangles
It is stirred in shape flask, in ice bath.Then, 14.4 milliliters of sodium nitrite in aqueous solution (1 millimolar concentration) is added dropwise thereto,
And it is stirred mixture 3 hours under ice bath.
4.722 grams of gained pyridinone compounds 1 are added in 20 ml deionized waters and by the way that NaOH is added thereto
Aqueous solution (pH 8) and dissolved.The pyridinone compounds 1 dissolved are added in above-mentioned 125 milliliters of triangle flasks, and
And use the pH in sodium carbonate (10%) aqueous solution with mixture.It filters gains and is purified with water, be then dried in vacuo, obtain
Obtain compound 5.
5.5 g of compound 5 are placed in 250 milliliters of flasks, thereto be added 2.09 grams of GMA, 2.16 grams of TBAB and
70 milliliters of acetonitriles, and mixture is made to flow back and stay overnight in 90 DEG C of reactions.Gains MC/ water process and carry out chromatographic column
Purification, synthesis obtain the compound indicated by chemical formula 9 (CF 9).
GC-MS (DI) m/z:552.26
Synthesis example 4: the compound that synthesis is indicated by chemical formula 10
3.12 grams of 3- aminobenzoic acids, 75.6 ml deionized waters and 17.28 milliliters of HCl (35%) are in 125 milliliters of triangles
It is stirred in shape flask, in ice bath.Then, 14.4 milliliters of sodium nitrite in aqueous solution (1 millimolar concentration) is added dropwise thereto,
And it is stirred mixture 3 hours under ice bath.
3.69 grams of pyridinone compounds 3 are added in 20 ml deionized waters and by the way that NaOH aqueous solution is added thereto
(pH8) it is dissolved.The pyridinone compounds 3 dissolved are added in above-mentioned 125 milliliters of triangle flasks, and use carbon
In sour sodium (10%) aqueous solution and the pH of mixture.It filters gains and is purified with water, is then dried in vacuo, obtain compound
6。
4.8 g of compound 6 are placed in 250 milliliters of flasks, thereto be added 2.09 grams of GMA, 2.16 grams of TBAB and
70 milliliters of acetonitriles, and mixture is made to flow back and stay overnight in 90 DEG C of reactions.Gains MC/ water process and carry out chromatographic column
Purification obtains the compound indicated by chemical formula 10 (CF 10).
GC-MS (DI) m/z:494.22
Synthesis example 5: the compound that synthesis is indicated by chemical formula 25
1.5 grams of 4-aminobenzoic acid isobutyl esters, 32 ml deionized waters and 7.5 milliliters of HCl (35%) are in 20 milliliters of bottles
In, stir in ice bath.Then, 6 milliliters of sodium nitrite in aqueous solution (1 millimolar concentration) is added dropwise thereto, and in ice
Bath lower stirring mixture 3 hours.
1.46 grams of pyridinone compounds 7 are added in 20 ml deionized waters and by the way that NaOH aqueous solution is added thereto
(pH8) it is dissolved.The pyridinone compounds 7 dissolved are added in above-mentioned 20 milliliters of bottles, and use sodium carbonate
(10%) in aqueous solution and the pH of mixture.It filters gains and is purified and be dried in vacuo with water, obtain compound 8.
1 g of compound 8 is placed in 100 milliliters of flasks, thereto be added 0.766 gram of TEA, 0.154 gram of DMAP and
0.457 gram of acryloyl chloride and 10 milliliters of acetonitriles, and react mixture at room temperature overnight.Gains MC/ water process, connects
Carry out chromatographic column purification, synthesis obtain by chemical formula 25 (CF 25) indicate compound.
1H NMR (DMSO): 14.38 (s, 1H), 8.03 (m, 1H), 7.85 (m, 1H), 7.8 (m, 1H), 7.6 (m, 1H),
6.5 (m, 1H), 6.26 (m, 1H), 5.94 (m, 1H), 4.4 (m, 2H), 4.1 (m, 2H), 3.9 (s, 2H), 2.64 (m, 1H), 2.01
(s, 1H), 1.73 (m, 3H), 1.21 (m, 6H)
Synthesis example 6: the compound that synthesis is indicated by chemical formula 26
The compound (GC-MS (DI) m/z:466.19) indicated by chemical formula 26 is according to side identical with example 5 is synthesized
Method synthesis, but methacrylic chloride is wherein used, and the acryloyl chloride in non-synthetic example 5.
Synthesis example 7: the compound that synthesis is indicated by chemical formula 11
The compound (GC-MS (DI) m/z:552.26) indicated by chemical formula 11 is according to side identical with example 1 is synthesized
Method synthesis, but wherein use 2- aminobenzoic acid rather than 4-aminobenzoic acid.
Synthesis example 8: the compound that synthesis is indicated by chemical formula 12
The compound (GC-MS (DI) m/z:480.20) indicated by chemical formula 12 is according to side identical with example 1 is synthesized
Method synthesis, but the wherein ethylhexylamine in non-synthetic example 1 using isopropylamine.
Synthesis example 9: the compound that synthesis is indicated by chemical formula 13
The compound (GC-MS (DI) m/z:494.22) indicated by chemical formula 13 is according to side identical with example 1 is synthesized
Method synthesis, but the wherein ethylhexylamine in non-synthetic example 1 using isobutyl amine.
Synthesis example 10: the compound that synthesis is indicated by chemical formula 14
The compound (GC-MS (DI) m/z:508.23) indicated by chemical formula 14 is according to side identical with example 1 is synthesized
Method synthesis, but the wherein ethylhexylamine in non-synthetic example 1 using iso-amylamine.
Synthesis example 11: the compound that synthesis is indicated by chemical formula 15
Compound 2 is synthesized according to method identical with synthesis example 1.Make the compound 2 and Isosorbide-5-Nitrae-dihydroxy of identical equivalent
Base benzene reacts in THF solvent, at room temperature with the DCC of 1.5 equivalents.After checking reaction using TLC, gains EA/ water
Processing and progress chromatographic column purification.Then, identical as synthesis example 5, gained is added in TEA, DMAP, acryloyl chloride and acetonitrile
In compound, and react mixture at room temperature overnight.Gains MC/ water process and chromatographic column purification is carried out, closed
At the compound (GC-MS (DI) m/z:556.23) for obtaining being indicated by chemical formula 15.
Synthesis example 12: the compound that synthesis is indicated by chemical formula 16
The compound (GC-MS (DI) m/z:570.24) indicated by chemical formula 16 is according to side identical with example 11 is synthesized
Method synthesis, but methacrylic chloride is wherein used, and the acryloyl chloride in non-synthetic example 11.
Synthesis example 13: the compound that synthesis is indicated by chemical formula 21
Azo coupling be carried out according to the identical method of synthesis example 1, but wherein using 3- amino-phenol rather than
Synthesize the 4-aminobenzoic acid in example 1.Then, according to method identical with synthesis example 5, by TEA, DMAP, acryloyl chloride
And acetonitrile is added in compound, and reacts mixture at room temperature overnight.Gains MC/ water process and carry out chromatography
Column purification, synthesis obtain the compound (GC-MS (DI) m/z:436.21) indicated by chemical formula 21.
Synthesis example 14: the compound that synthesis is indicated by chemical formula 22
The compound (GC-MS (DI) m/z:450.23) indicated by chemical formula 22 is according to side identical with example 13 is synthesized
Method synthesis, but methacrylic chloride is wherein used, and the acryloyl chloride in non-synthetic example 13.
Synthesis example 15: the compound that synthesis is indicated by chemical formula 23
Azo coupling be carried out according to the identical method of synthesis example 1, but wherein using 3- amino-phenol rather than
Synthesize the 4-aminobenzoic acid in example 1.Make the gained azo compound and 4-HBA and 1.5 equivalents of identical equivalent
DCC in THF solvent, carry out esterification at room temperature.Using TLC check reaction after, gains EA/ water process and
Carry out chromatographic column purification.Then, according to method identical with synthesis example 5, TEA, DMAP, acryloyl chloride and acetonitrile are added
In gained compound, and react mixture at room temperature overnight.It gains MC/ water process and carries out chromatographic column and mentions
Pure, synthesis obtains the compound (GC-MS (DI) m/z:556.23) indicated by chemical formula 23.
Synthesis example 16: the compound that synthesis is indicated by chemical formula 24
The compound (GC-MS (DI) m/z:570.25) indicated by chemical formula 24 is according to side identical with example 15 is synthesized
Method synthesis, but methacrylic chloride is wherein used, and the acryloyl chloride in non-synthetic example 15.
Synthesis example 17: the compound that synthesis is indicated by chemical formula 17
Compound 2 is synthesized according to method identical with synthesis example 1.Then make the compound 2 and second two of identical equivalent
Alcohol reacts in THF solvent, at room temperature with the DCC of 1.5 equivalents.After checking reaction using TLC, at gains EA/ water
Reason and progress chromatographic column purification.Then, according to method identical with synthesis example 5, TEA, DMAP, acryloyl chloride and acetonitrile are added
Enter in gained compound, maintains at room temperature overnight.Gains MC/ water process and chromatographic column purification is carried out, synthesis obtains
The compound (GC-MS (DI) m/z:508.23) indicated by chemical formula 17.
Synthesis example 18: the compound that synthesis is indicated by chemical formula 18
The compound (GC-MS (DI) m/z:522.25) indicated by chemical formula 18 is according to side identical with example 17 is synthesized
Method synthesis, but methacrylic chloride is wherein used, and the acryloyl chloride in non-synthetic example 17.
Synthesis example 19: the compound that synthesis is indicated by chemical formula 19
Compound 2 is synthesized according to method identical with synthesis example 1.Then, make the compound 2 and 4- hydroxyl of identical equivalent
Yl benzoic acid and 1.5 equivalent DCC in THF solvent, carry out esterification at room temperature.After checking reaction using TLC, gained
Object EA/ water process and carry out chromatographic column purification.Then, according to the identical method of synthesis example 1, by GMA, TBAB and
Acetonitrile is added in compound, and mixture is made to flow back and stay overnight in 90 DEG C of reactions.Gains MC/ water process and carry out color
Column purification is composed, synthesis obtains the compound (GC-MS (DI) m/z:610.26) indicated by chemical formula 19.
Synthesis example 20: the compound that synthesis is indicated by chemical formula 20
Compound 2 is synthesized according to method identical with synthesis example 1.Then, make the compound 2 and 4- hydroxyl of identical equivalent
Acetic acid and 1.5 equivalent DCC in THF solvent, carry out esterification at room temperature.After checking reaction using TLC, gains are used
EA/ water process and progress chromatographic column purification.Then, according to method identical with synthesis example 1, GMA, TBAB and acetonitrile are added
Enter in compound, and mixture is made to flow back and stay overnight in 90 DEG C of reactions.It gains MC/ water process and carries out chromatographic column and mentions
Pure, synthesis obtains the compound (GC-MS (DI) m/z:658.26) indicated by chemical formula 20.
Synthesize example 21: the polymer including the repetitive unit indicated by chemical formula 33 synthesizes
Synthetic polymer, the polymer include the chemical combination indicated by chemical formula 7 according to synthesis example 1 of 50 weight %
Object and 15 weight % methacrylic acid (big-and-middle chemistry and metal Co., Ltd (Daejung Chemicals&Metals Co.,
Ltd.)) and the benzyl methacrylate of 35 weight % (Hitachi, Ltd (Hitach Ltd.)) is used as every kind of monomer.
Specifically, 1.5 grams of V601 (and Optical Chemical Company (Wako Chemicals, Inc.)) are placed as initiator
In 100 milliliters of beakers, and with 30 grams of total monomer weights, be sequentially added thereto 50 weight % according to synthesis example 1
The compound indicated by chemical formula 7,15 weight % methacrylic acid (big-and-middle chemistry and metal Co., Ltd) and 35 weights
Measure the benzyl methacrylate (Hitachi Ltd) of %.Then, 72 grams of cyclohexanone are additionally incorporated thereto as solvent, and
And stirring mixture 30 minutes, until dye monomer and initiator are completely dissolved, to prepare monomer solution.Then, will
54 grams of solvents are placed in 250 milliliters of glass reactors equipped with cooler to carry out polymerization reaction and be heated to 85 DEG C,
And it lasts and prepared monomer solution is added dropwise within 3 hours into reactor.When addition is completed, make mixture mutually synthermal
It is lower to react 9 hours and be cooled to room temperature, to complete to react.Polymerization reaction is carried out under nitrogen atmosphere.According to Waters public affairs
Take charge of gel permeation chromatograph (gel permeation chromatography manufactured by (Waters Co.)；GPC), it polymerize
Object has 10,800 grams/mol of weight average molecular weight.
Synthesize example 22: the polymer including the repetitive unit indicated by chemical formula 35 synthesizes
The polymer of the repetitive unit including being indicated by chemical formula 35 is synthesized according to method identical with synthesis example 21,
But wherein use 50 weight % the compound indicated by chemical formula 9, and 50 weight % in non-synthetic example 21 by chemistry
The compound that formula 7 indicates.When being measured using the gel permeation chromatograph (GPC) that Waters manufacture, polymer has 9,300
Gram/mol weight average molecular weight.
Synthesize example 23: the polymer including the repetitive unit indicated by chemical formula 47 synthesizes
The polymer of the repetitive unit including being indicated by chemical formula 47 is synthesized according to method identical with synthesis example 21,
But wherein use 50 weight % the compound indicated by chemical formula 21, and 50 weight % in non-synthetic example 21 by chemistry
The compound that formula 7 indicates.When being measured using the gel permeation chromatograph (GPC) that Waters manufacture, polymer has 9,700
Gram/mol weight average molecular weight.
Synthesize example 24: the polymer including the repetitive unit indicated by chemical formula 49 synthesizes
The polymer of the repetitive unit including being indicated by chemical formula 49 is synthesized according to method identical with synthesis example 21,
But wherein use 50 weight % the compound indicated by chemical formula 23, and 50 weight % in non-synthetic example 21 by chemistry
The compound that formula 7 indicates.When being measured using the gel permeation chromatograph (GPC) that Waters manufacture, polymer has 10,
100 grams/mol of weight average molecular weight.
Synthesize example 25: the polymer including the repetitive unit indicated by chemical formula 52 synthesizes
The polymer of the repetitive unit including being indicated by chemical formula 52 is synthesized according to method identical with synthesis example 21,
But wherein use 50 weight % the compound indicated by chemical formula 26, and 50 weight % in non-synthetic example 21 by chemistry
The compound that formula 7 indicates.When being measured using the gel permeation chromatograph (GPC) that Waters manufacture, polymer has 9,900
Gram/mol weight average molecular weight.
Comparative synthesis example 1
By 1000 grams of cyclohexanone, (victory one Chemical Co., Ltd. (Shiny Chemical Industrial Co., Ltd.) exists
Be heated to 80 DEG C in 10 liters of polymer reactors equipped with reflux cooler and blender, and last 3 hours it is anti-to thermal polymerization
It answers and is slowly added in device by by 300 g of compound, 12,300 grams of benzyl methacrylates (Hitachi Ltd), 106 grams of first
Base acrylic acid (big-and-middle chemistry and metal Co., Ltd) and 92 gram 2,2 '-azodiisobutyronitriles (and Optical Chemical Company) are dissolved in
Solution obtained in 5000 grams of cyclohexanone (victory-Chemical Co., Ltd.).When the addition is complete, it stirs mixture 14 hours, obtains
It must include by the polymer of the chemical formula B repetitive unit indicated.The gel permeation chromatograph (GPC) manufactured using Waters
When measurement, polymer has 9,800 grams/mol of weight average molecular weight.
[chemical formula B]
In chemical formula B, a=2, b=2 and c=1.
Evaluation 1: dissolubility
Retarder thinner (PGMEA) is separately added into according to synthesis example 1 to every kind of compound of synthesis example 20 and 0.5 gram
In the compound indicated by chemical formula A；The MixrotarVMR-5 manufactured using Jing Nei company (Iuchi Inc.), at 25 DEG C and
Every kind of corresponding solution is stirred under 100 revs/min, and checks the dissolved state (meltage of compound) of compound, and tie
Fruit is provided in the following table 1.
[table 1]
| Compound | Dissolubility |
| Chemical formula 7 | ○ |
| Chemical formula 9 | ○ |
| Chemical formula 11 | ○ |
| Chemical formula 14 | ○ |
| Chemical formula 15 | ○ |
| Chemical formula 16 | ○ |
| Chemical formula 21 | ○ |
| Chemical formula 22 | ○ |
| Chemical formula 23 | ○ |
| Chemical formula 24 | ○ |
| Chemical formula 17 | ○ |
| Chemical formula 18 | ○ |
| Chemical formula 19 | ○ |
| Chemical formula 20 | ○ |
| Chemical formula A | X |
It (is had a structure that by the compound that chemical formula A is indicated
[chemical formula A]
)
Dissolubility evaluation reference
>=20wt% (in PGMEA): zero
< 20wt% (in PGMEA): X
Referring to table 1, excellent dissolubility (about organic solvent) is had according to the compound of one embodiment；Compared to not
Photosensitive polymer combination including the compound is easy to anticipate the photoresist including the compound as dyestuff
Composition shows excellent color character.
(synthesis of photosensitive polymer combination)
Example 1
According to composition provided in the following table 2, Photoepolymerizationinitiater initiater is dissolved in solvent, and is stirred at room temperature molten
Liquid 2 hours.Then, adhesive resin and photopolymerizable monomer are added thereto, and it is small that gained mixture 2 is stirred at room temperature
When.Then, the compound indicated by synthesizing example 21 is added thereto, gained mixture is stirred at room temperature one hour, Xiang Qi
Middle addition silane coupling agent, and gained mixture is stirred at room temperature one hour.Filtering solution three times, and removes wherein
Impurity, so that preparation is according to the photosensitive polymer combination of example 1.
[table 2]
(unit: gram)
Example 2
Photosensitive polymer combination according to example 2 is to be prepared according to method identical with example 1, but wherein use synthesis
The compound of example 22 and the compound of non-synthetic example 21.
Example 3
Photosensitive polymer combination according to example 3 is to be prepared according to method identical with example 1, but wherein use synthesis
The compound of example 23, and the compound of non-synthetic example 21.
Example 4
Photosensitive polymer combination according to example 4 is to be prepared according to method identical with example 1, but wherein use synthesis
The compound of example 24, and the compound of non-synthetic example 21.
Example 5
Photosensitive polymer combination according to example 5 is to be prepared according to method identical with example 1, but wherein use synthesis
The compound of example 25, and the compound of non-synthetic example 21.
Comparative example 1
Photosensitive polymer combination according to comparative example 1 is to be prepared according to method identical with example 1, but wherein use
The polymer of comparative synthesis example 1, and the compound of non-synthetic example 21.
Evaluation 2: hue coordinate, brightness and contrast ratio
It will be de- in the warp of 1 millimeters thick according to every kind of photosensitive polymer combination of example 1 to example 5 and comparative example 1
It is respectively coated on rouge and washed glass substrate to 1 micron to 3 microns thickness and 2 minutes dry on 90 DEG C of hot plates, is obtained
Film.Then, film is exposed using the high-pressure sodium lamp with 365 nanometers of dominant wavelengths.By film in 200 DEG C of forced convertion drying oven
It is 5 minutes dry.Then, using spectrophotometer (MCPD3000, great Zhong Electronics Co., Ltd. (Otsuka Electronic
Co., Ltd.)) hue coordinate (x, y), brightness (Y) and the contrast ratio of measurement gained pixel layer, and result is provided in the following table 3
In.
[table 3]
| Hue coordinate (x, y) | Brightness (Y) | Contrast ratio | |
| Example 1 | 0.269,0.620 | 51.3 | 11250 |
| Example 2 | 0.267,0.620 | 51.1 | 11224 |
| Example 3 | 0.265,0.620 | 50.5 | 11263 |
| Example 4 | 0.266,0.620 | 51.0 | 11165 |
| Example 5 | 0.263,0.620 | 50.8 | 11180 |
| Comparative example 1 | 0.267,0.620 | 49.1 | 9850 |
Referring to table 3, compared to according to comparative example 1 not including the photoresist of compound or polymer as dyestuff
Composition, what it is according to example 1 to example 5 includes photonasty tree according to the compound or polymer of one embodiment as dyestuff
Oil/fat composition shows excellent color character.
Those skilled in the art will expect many variants of the present invention related to the present invention and other embodiments, tool
There is the benefit of the teachings presented in preceding description.It will be understood, therefore, that the present invention is not limited to disclosed specific embodiments
And wish that its variant and other embodiments are included in the scope of the appended claims.Although specific art is used herein
Language, but they only in general and descriptive meaning using and be not used in the purpose of limitation, the scope of the present invention is being weighed
It is limited in sharp claim.
Claims (6)
1. a kind of azo compound, by the change selected from chemical formula 7, chemical formula 9, chemical formula 11 and chemical formula 14 to chemical formula 20
Formula indicates:
[chemical formula 7]
[chemical formula 9]
[chemical formula 11]
[chemical formula 14]
[chemical formula 15]
[chemical formula 16]
[chemical formula 17]
[chemical formula 18]
[chemical formula 19]
[chemical formula 20]
2. azo compound according to claim 1, wherein the compound is weld.
3. azo compound according to claim 2, wherein it is 400 nanometers that the weld, which is with wave-length coverage,
To the compound in 500 nanometers of absorption maximum section.
4. a kind of polymer comprising azo compound, comprising being selected from shown in chemical formula 33, chemical formula 35 and chemical formula 49
The repetitive unit of repetitive unit:
[chemical formula 33]
[chemical formula 35]
[chemical formula 49]
5. the polymer according to claim 4 comprising azo compound, wherein the polymer also includes chemical formula
31 and chemical formula 32 shown in repetitive unit:
[chemical formula 31]
[chemical formula 32]
Wherein, in above-mentioned chemical formula 31 and chemical formula 32,
R6It is hydrogen or substituted or unsubstituted C1 to C10 alkyl, and
L4It is substituted or unsubstituted C1 to C10 alkylidene.
6. the polymer according to claim 5 comprising azo compound, wherein the polymer includes:
The repetition list selected from chemical formula 33, chemical formula 35 and repetitive unit shown in chemical formula 49 of 40 weight % to 60 weight %
Member；
The repetitive unit that by chemical formula 31 is indicated of the 5 weight % to 25 weight %；And
The repetitive unit that by chemical formula 32 is indicated of the 25 weight % to 45 weight %.
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| KR102378563B1 (en) * | 2019-04-17 | 2022-03-23 | 삼성에스디아이 주식회사 | Photosensitive resin composition and photosensitive resin layer using the same, color filter |
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|---|---|---|---|---|
| US5578419A (en) * | 1991-12-12 | 1996-11-26 | Mitsui Toatsu Chemicals, Incorporated | Dyes for color filters, and photosensitive resist resin composition containing the same |
| CN103068929A (en) * | 2010-08-07 | 2013-04-24 | 默克专利有限公司 | Particles for electrophoretic displays |
| CN103173068A (en) * | 2011-12-26 | 2013-06-26 | 第一毛织株式会社 | Pigment dispersion composition, photosensitive resin composition including the same and color filter using the same |
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| US20070207331A1 (en) * | 2006-03-06 | 2007-09-06 | Pearson Jason C | Azo compounds and coating compositions containing the azo compounds |
| JP6065547B2 (en) * | 2011-11-28 | 2017-01-25 | 三菱化学株式会社 | Colored resin composition, color filter, liquid crystal display device and organic EL display device |
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| US5578419A (en) * | 1991-12-12 | 1996-11-26 | Mitsui Toatsu Chemicals, Incorporated | Dyes for color filters, and photosensitive resist resin composition containing the same |
| CN103068929A (en) * | 2010-08-07 | 2013-04-24 | 默克专利有限公司 | Particles for electrophoretic displays |
| CN103173068A (en) * | 2011-12-26 | 2013-06-26 | 第一毛织株式会社 | Pigment dispersion composition, photosensitive resin composition including the same and color filter using the same |
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| KR20160090168A (en) | 2016-07-29 |
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