CN105801477A - Azo compound and polymer containing same - Google Patents
Azo compound and polymer containing same Download PDFInfo
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- CN105801477A CN105801477A CN201510649566.1A CN201510649566A CN105801477A CN 105801477 A CN105801477 A CN 105801477A CN 201510649566 A CN201510649566 A CN 201510649566A CN 105801477 A CN105801477 A CN 105801477A
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- 0 *C(C(N=NC1=CC=CCC1)=C(N(*)C1=O)O)=C1C#N Chemical compound *C(C(N=NC1=CC=CCC1)=C(N(*)C1=O)O)=C1C#N 0.000 description 3
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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
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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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- 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
- C07D213/24—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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- 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
- C07D213/24—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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- Materials For Photolithography (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
The invention provides an azo compound and a polymer containing the same. The azo compound is expressed by a chemical formula 1. The azo compound and the polymer containing the azo compound as monomer have excellent yellow spectral signature, high molar extinction coefficient and excellent solubility (related to organic solvent), and the azo compound and the polymer can be used as dyes to manufacture a photoresistive resin used in a color filter. Therefore, the color filter including the dye has excellent luminance and high contrast ratio. In the chemical formula, each substituent group is the same as defined in the specification.
Description
The cross reference of related application
The application advocates the priority of 10-2015-0010127 korean patent application and the right filed an application in Korean Intellectual Property Office on January 12nd, 2015, and the entire disclosure of described application is incorporated herein by reference.
Technical field
The present invention relates to a kind of novel azo compound and include its polymer.
Background technology
By using the colored filter of color type photosensitive polymer combination manufacture to be restricted in brightness and contrast ratio because of its pigment particle size.It addition, the color image forming apparatus used by imageing sensor needs less dispersion particle diameter to form fine pattern.In order to meet requirement, have passed through the colored filter using the photosensitive polymer combination of the dyestuff (and non-pigment) including not formed granule to attempt to obtain the color character (such as brightness and contrast ratio) with improvement.Accordingly, it would be desirable to the unimolecule compound of dyestuff and polymer compound being useful as photosensitive polymer combination is studied.
Summary of the invention
One embodiment provides a kind of compounds.
Another embodiment provides and includes the described compound polymer as monomer.
One embodiment of the present of invention provides the compound represented 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) R ' independently of one another,
R ' is substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C2 to C10 thiazolinyl or substituted or unsubstituted C6 to C20 aryl,
Its condition is, R1And R2One of include the substituent group that represented by chemical formula 2, and
R3It it 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.
Compound shown in chemical formula 1 can by selected from the chemical formula 3 chemical formulation to chemical formula 6.
[chemical formula 3]
[chemical formula 4]
[chemical formula 5]
[chemical formula 6]
In chemical formula 3 to chemical formula 6,
L1To L3It is substituted or unsubstituted C1 to C10 alkylidene, substituted or unsubstituted C6 to C20 arlydene or *-L '-C (=O) O-L independently "-*,
L ' and L " it is substituted or unsubstituted C1 to C5 alkylidene or substituted or unsubstituted C6 to C12 arlydene independently of one another,
R3And R5It is substituted or unsubstituted C1 to C20 alkyl independently of one another, and
R4It is hydrogen or substituted or unsubstituted C1 to C10 alkyl.
Chemical formula 1 can by selected from the chemical formula 7 chemical formulation 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]
Described compound can be weld.
Weld can have about 400 nanometers of light to about 500 nano wave lengths and absorb interval.
Another embodiment provides and includes the polymer as monomer of the repetitive shown in chemical formula 1.
It is to say, another embodiment provides the polymer including being selected from chemical formula 27 to the repetitive of the repetitive shown in chemical formula 30.
[chemical formula 27]
[chemical formula 28]
[chemical formula 29]
[chemical formula 30]
In chemical formula 27 to chemical formula 30,
L1To L3It is substituted or unsubstituted C1 to C10 alkylidene, substituted or unsubstituted C6 to C20 arlydene or *-L '-C (=O) O-L independently "-*,
L ' and L " it is substituted or unsubstituted C1 to C5 alkylidene or substituted or unsubstituted C6 to C12 arlydene independently of one another,
R3And R5It is substituted or unsubstituted C1 to C20 alkyl independently of one another, and
R4It is hydrogen or substituted or unsubstituted C1 to C10 alkyl.
Described polymer can also include the repetitive 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 it is substituted or unsubstituted C1 to C10 alkylidene.
With polymer total amount, polymer can include the repetitive selected from chemical formula 27 to the repetitive shown in chemical formula 30 of about 40 weight % to about 60 weight %；The repetitive represented by chemical formula 31 of about 5 weight % to about 25 weight %；And about 25 repetitives represented by chemical formula 32 of weight % to about 45 weight %.
Polymer can include the repetitive being selected from chemical formula 33 to the repetitive shown in chemical formula 52.
Repetitive shown in chemical formula 27 can select the repetitive that free chemical formula 33 represents 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 shown in chemical formula 28 can be the repetitive shown in chemical formula 47 or chemical formula 48.
[chemical formula 47]
[chemical formula 48]
Repetitive shown in chemical formula 29 can be the repetitive shown in chemical formula 49 or chemical formula 50.
[chemical formula 49]
[chemical formula 50]
Repetitive shown in chemical formula 30 can be the repetitive shown in chemical formula 51 or chemical formula 52.
[chemical formula 51]
[chemical formula 52]
Other embodiments of the present invention include in the following specific embodiments.
According to an embodiment, azo compound and include azo compound, as the polymer of monomer, there is excellent yellow spectrum feature, high molar extinction coefficient and excellent solubility (about organic solvent) and can as dyestuff for preparing the photosensitive polymer combination used by colored filter, and therefore, can have excellent brightness and high contrast ratio including the colored filter of described dyestuff.
Detailed description of the invention
Embodiments of the invention are described in detail below.But, these embodiments have exemplary, and the invention is not restricted to these embodiments.
Unless the context clearly determines otherwise, used by otherwise in specification and appended claims, singulative " ", " described " include multiple indicant.
As used herein, when additionally do not provide be specifically defined time, term " is replaced " and refers to that being selected from each substituent group following replaces (replacing at least one hydrogen in functional group): halogen atom (F, Br, Cl or I), hydroxyl, nitro, cyano group, amino (NH2、NH(R200) or N (R201)(R202), wherein R200、R201And R202Identical or different, and be C1 to C10 alkyl independently), amidino groups, diazanyl, hydrazone group, carboxyl, substituted or unsubstituted alkyl, substituted or unsubstituted thiazolinyl, substituted or unsubstituted alkynyl, substituted or unsubstituted alicyclic organic group, substituted or unsubstituted aryl and substituted or unsubstituted heterocyclic radical.
As used herein, when additionally do not provide be specifically defined time, term " alkyl " refers to C1 to C20 alkyl, and specifically, C1 to C15 alkyl；Term " cycloalkyl " refers to C3 to C20 cycloalkyl, and specifically, C3 to C18 cycloalkyl；Term " alkoxyl " refers to C1 to C20 alkoxyl, and specifically, C1 to C18 alkoxyl；Term " aryl " refers to C6 to C20 aryl, and specifically, C6 to C18 aryl；Term " thiazolinyl " refers to C2 to C20 thiazolinyl, and specifically, C2 to C18 thiazolinyl；Term " alkylidene " refers to C1 to C20 alkylidene, and specifically, C1 to C18 alkylidene；And term " arlydene " refers to C6 to C20 arlydene, and specifically, C6 to C16 arlydene.
As used herein, when additionally offer is not specifically defined, " (methyl) acrylate " refers to " acrylate " and " methacrylate " two, and " (methyl) acrylic acid " refers to " acrylic acid " and " methacrylic acid ".
As used herein, when additionally offer is not specifically defined, term " combination " refers to mixing or copolymerization.Additionally, " copolymerization " refers to that block copolymerization is to random copolymerization, and term " copolymer " refers to that block copolymer is to random copolymer.
As used herein, it is specifically defined unless otherwise provided, is otherwise hydrogen atom (otherwise, described position occur a key) in the position bond of not shown chemical bond.
As used herein, when not otherwise provided definitions, " * " refers to the coupling part between identical or different atom or chemical formula.
It addition, when not otherwise provided definitions, " absorption maximum is interval " represents the interval (scope) showing that absorption maximum as used herein is interval in this manual.
One embodiment provides the compound shown in 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) R ' independently of one another,
R ' is substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C2 to C10 thiazolinyl or substituted or unsubstituted C6 to C20 aryl,
Its condition is, R1And R2One of include the substituent group that represented by chemical formula 2, and
R3It it is substituted or unsubstituted C1 to C20 alkyl.
Compound shown in chemical formula 1 is azo compound and has excellent yellow spectrum feature and high molar extinction coefficient and also have excellent dissolubility (about organic solvent).Additionally, due to R1And R2In any one certainly include substituted or unsubstituted acrylate group as the substituent group of compound shown in chemical formula 1, therefore the compound shown in chemical formula 1 can have the machinability during excellent thermostability, chemical resistance and manufacture colored filter.
[chemical formula 2]
In chemical formula 2,
R4It is hydrogen or substituted or unsubstituted C1 to C10 alkyl.
Compound shown in chemical formula 1 can by selected from the chemical formula 3 chemical formulation to chemical formula 6.
[chemical formula 3]
[chemical formula 4]
[chemical formula 5]
[chemical formula 6]
In chemical formula 3 to chemical formula 6,
L1To L3It is substituted or unsubstituted C1 to C10 alkylidene, substituted or unsubstituted C6 to C20 arlydene or *-L '-C (=O) O-L independently "-*,
L ' and L " it is substituted or unsubstituted C1 to C5 alkylidene or substituted or unsubstituted C6 to C12 arlydene independently of one another,
R3And R5It is substituted or unsubstituted C1 to C20 alkyl independently of one another, and
R4It is hydrogen or substituted or unsubstituted C1 to C10 alkyl.
For example, chemical formula 1, and specifically, chemical formula 3, it is possible to by selected from the chemical formula 7 chemical formulation to chemical formula 20, but it 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, it is possible to by the chemical formulation selected from chemical formula 21 or chemical formula 22, but it is not limited to these chemical formulas.
[chemical formula 21]
[chemical formula 22]
For example, chemical formula 1, and specifically, chemical formula 5, it is possible to by the chemical formulation selected from chemical formula 23 or chemical formula 24, but it is not limited to these chemical formulas.
[chemical formula 23]
[chemical formula 24]
For example, chemical formula 1, and specifically, chemical formula 6, it is possible to by the chemical formulation selected from chemical formula 25 or chemical formula 26, but it is not limited to these chemical formulas.
[chemical formula 25]
[chemical formula 26]
Compound according to an embodiment is the azo compound including acrylate group for specified substituent, and therefore just can realize more transparent colour on a small quantity, and therefore can have the display device of good color feature (such as brightness, contrast ratio etc.) as coloring agent for manufacture.For example, described compound can be coloring agent, for instance dyestuff, for instance the weld that display wavelength absorption maximum in about 400 nanometers to about 500 nanometers (specifically, about 410 nanometers to about 450 nanometers) scopes is interval.
For example, described compound can be the dyestuff that display wavelength absorption maximum in about 400 nanometers to about 500 nanometers (specifically, about 410 nanometers to about 450 nanometers) scopes is interval.
In general, dyestuff is the most expensive in component used by colored filter.Therefore, dye dosage should be relatively big to obtain desired effect, for instance high brightness, high contrast ratio etc., but causes that manufacturing cost increases.But, when the compound according to an embodiment is used as the dyestuff in colored filter, described compound can use and reduce manufacturing cost on a small quantity, and realizes excellent color character, for instance high brightness, high contrast ratio etc..
According to another embodiment, it is provided that a kind of compound included according to an embodiment is as the polymer of monomer.
It is to say, described polymer includes the compound shown in chemical formula 1 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) R ' independently of one another,
R ' is substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C2 to C10 thiazolinyl or substituted or unsubstituted C6 to C20 aryl,
Its condition is, R1And R2One of include the substituent group shown in chemical formula 2,
[chemical formula 2]
In chemical formula 2,
R4It is hydrogen or substituted or unsubstituted C1 to C10 alkyl, and
R3It it is substituted or unsubstituted C1 to C20 alkyl.
Described polymer can have the weight average molecular weight of about 10,000 grams/mol to about 100,000 grams/mol.
For example, in the polymer, the monomer shown in chemical formula 1 can be represented to the repetitive of the repetitive shown in chemical formula 30 by selected from chemical formula 27.It is to say, described polymer can include the repetitive being selected from chemical formula 27 to the repetitive shown in chemical formula 30.
[chemical formula 27]
[chemical formula 28]
[chemical formula 29]
[chemical formula 30]
In chemical formula 27 to chemical formula 30,
L1To L3It is substituted or unsubstituted C1 to C10 alkylidene, substituted or unsubstituted C6 to C20 arlydene or *-L '-C (=O) O-L independently "-*,
L ' and L " it is substituted or unsubstituted C1 to C5 alkylidene or substituted or unsubstituted C6 to C12 arlydene independently of one another,
R3And R5It is substituted or unsubstituted C1 to C20 alkyl independently of one another, and
R4It is hydrogen or substituted or unsubstituted C1 to C10 alkyl.
Described polymer can also include the repetitive 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 it is substituted or unsubstituted C1 to C10 alkylidene.
With polymer total amount, polymer can include the repetitive selected from chemical formula 27 to the repetitive shown in chemical formula 30 of about 40 weight % to about 60 weight %；The repetitive represented by chemical formula 31 of about 5 weight % to about 25 weight %；And about 25 repetitives represented by chemical formula 32 of weight % to about 45 weight %.When polymer includes every kind of repetitive in described weight range, polymer can produce dissolubility and structural stability is had favorable influence.
For example, the repetitive shown in chemical formula 27 can be chosen from the chemical formula 33 repetitive to the repetitive shown in 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 shown in chemical formula 28 can be the repetitive shown in chemical formula 47 or chemical formula 48.
[chemical formula 47]
[chemical formula 48]
Repetitive shown in chemical formula 29 can be the repetitive shown in chemical formula 49 or chemical formula 50.
[chemical formula 49]
[chemical formula 50]
Repetitive shown in chemical formula 30 can be the repetitive shown in chemical formula 51 or chemical formula 52.
[chemical formula 51]
[chemical formula 52]
Described compound and/or polymer can as in the coloring agent photosensitive polymer combinations for colored filter.
The technique forming pattern in colored filter is as follows.
Described technique includes using the methods such as spin coating, slot coated, ink jet printing to be coated by photosensitive polymer combination on support substrate；The dry photosensitive polymer combination being coated with is to form photosensitive polymer combination layer；Photosensitive polymer combination layer is exposed；The photosensitive polymer combination exposed is made to develop to obtain photosensitive resin film with alkaline aqueous solution；And photosensitive resin film is carried out heat treatment.Process conditions etc. are in the related art it is widely known that and unspecified in this manual.
The present invention is illustrated in greater detail below with reference to example.But, these examples should not be construed as restriction the scope of the present invention in all senses.
(compou nd synthesis)
Synthesis example 1: the compound that synthesis is represented by chemical formula 7
3.12 grams of PABAs, 75.6 ml deionized water and 17.28 milliliters of HCl (35%) are stirred in 125 milliliters of triangle flasks, in ice bath.Then, it is added dropwise over 14.4 milliliters of sodium nitrite in aqueous solution (1 millimolar concentration) wherein, and stirs mixture 3 hours under ice bath.
Make 4.35 grams of cyan-acetic esters and 4.97 grams of ethylhexylamine backflows and react 2 hours at 110 DEG C.Subsequently, it is added thereto to 5 grams of ethyl acetoacetates and 3.76 grams of piperidines, and makes the backflow of gained mixture and react overnight.
After utilizing TLC to check gains, with acid treatment and wash them with water several times, be synthetically derived pyridinone compounds 1.
4.722 grams of pyridinone compounds 1 are added in 20 ml deionized water, and is added thereto to NaOH aqueous solution (pH8) to be dissolved.The pyridinone compounds 1 dissolved is positioned in above-mentioned 125 milliliters of triangle flasks, and uses in sodium carbonate (10%) aqueous solution and the pH of mixture.The product neutralized is filtered and purifies and vacuum drying with water, it is thus achieved that compound 2.
5.5 g of compound 2 are positioned in 250 ml flasks, are added thereto to 2.09 grams of GMA, 2.16 grams of TBAB and 70 milliliters of acetonitriles, and make mixture backflow and react overnight at 90 DEG C.Gains MC/ water processes and carries out chromatographic column purification, is synthetically derived the compound represented by chemical formula 7 (CF7).
1HNMR (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 represented by chemical formula 8
3.12 grams of PABAs, 75.6 ml deionized water and 17.28 milliliters of HCl (35%) are stirred in 125 milliliters of triangle flasks, in ice bath.Then, it is added dropwise over 14.4 milliliters of sodium nitrite in aqueous solution (1 millimolar concentration) wherein, and stirs mixture 3 hours under ice bath.
By carrying out pyridine synthesis ketonic compound 3 with butylamine displacement according to the ethylhexylamine of synthesis example 1.3.69 grams of pyridinone compounds 3 are added in 20 ml deionized water, and is added thereto to NaOH aqueous solution (pH8) to be dissolved.The pyridinone compounds 3 dissolved is added in above-mentioned 125 milliliters of triangle flasks, and uses in sodium carbonate (10%) aqueous solution and the pH of mixture.Filter gains and purify with water, then vacuum drying, it is thus achieved that compound 4.
4.8 g of compound 4 are positioned in 250 ml flasks, are added thereto to 2.09 grams of GMA, 2.16 grams of TBAB and 70 milliliters of acetonitriles, and make mixture backflow and react overnight at 90 DEG C.Gains MC/ water processes and carries out chromatographic column purification, is synthetically derived the compound represented by chemical formula 8 (CF8).
1HNMR (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 represented by chemical formula 9
3.12 grams of 3-amino benzoic Acid, 75.6 ml deionized water and 17.28 milliliters of HCl (35%) are stirred in 125 milliliters of triangle flasks, in ice bath.Then, it is added dropwise over 14.4 milliliters of sodium nitrite in aqueous solution (1 millimolar concentration) wherein, and stirs mixture 3 hours under ice bath.
4.722 grams of gained pyridinone compounds 1 added in 20 ml deionized water and dissolved by being added thereto to NaOH aqueous solution (pH8).The pyridinone compounds 1 dissolved is added in above-mentioned 125 milliliters of triangle flasks, and uses in sodium carbonate (10%) aqueous solution and the pH of mixture.Filter gains and purify with water, then vacuum drying, it is thus achieved that compound 5.
5.5 g of compound 5 are positioned in 250 ml flasks, are added thereto to 2.09 grams of GMA, 2.16 grams of TBAB and 70 milliliters of acetonitriles, and make mixture backflow and react overnight at 90 DEG C.Gains MC/ water processes and carries out chromatographic column purification, is synthetically derived the compound represented by chemical formula 9 (CF9).
GC-MS (DI) m/z:552.26
Synthesis example 4: the compound that synthesis is represented by chemical formula 10
3.12 grams of 3-amino benzoic Acid, 75.6 ml deionized water and 17.28 milliliters of HCl (35%) are stirred in 125 milliliters of triangle flasks, in ice bath.Then, it is added dropwise over 14.4 milliliters of sodium nitrite in aqueous solution (1 millimolar concentration) wherein, and stirs mixture 3 hours under ice bath.
3.69 grams of pyridinone compounds 3 added in 20 ml deionized water and dissolved by being added thereto to NaOH aqueous solution (pH8).The pyridinone compounds 3 dissolved is added in above-mentioned 125 milliliters of triangle flasks, and uses in sodium carbonate (10%) aqueous solution and the pH of mixture.Filter gains and purify with water, then vacuum drying, it is thus achieved that compound 6.
4.8 g of compound 6 are positioned in 250 ml flasks, are added thereto to 2.09 grams of GMA, 2.16 grams of TBAB and 70 milliliters of acetonitriles, and make mixture backflow and react overnight at 90 DEG C.Gains MC/ water processes and carries out chromatographic column purification, it is thus achieved that the compound represented by chemical formula 10 (CF10).
GC-MS (DI) m/z:494.22
Synthesis example 5: the compound that synthesis is represented by chemical formula 25
1.5 grams of PABA isobutyl esters, 32 ml deionized water and 7.5 milliliters of HCl (35%) are stirred in 20 milliliters of bottles, in ice bath.Then, it is added dropwise over 6 milliliters of sodium nitrite in aqueous solution (1 millimolar concentration) wherein, and stirs mixture 3 hours under ice bath.
1.46 grams of pyridinone compounds 7 added in 20 ml deionized water and dissolved by being added thereto to NaOH aqueous solution (pH8).The pyridinone compounds 7 dissolved is added in above-mentioned 20 milliliters of bottles, and uses in sodium carbonate (10%) aqueous solution and the pH of mixture.Filter gains and purify and vacuum drying with water, it is thus achieved that compound 8.
1 g of compound 8 is positioned in 100 ml flasks, is added thereto to 0.766 gram of TEA, 0.154 gram of DMAP and 0.457 gram of acryloyl chloride and 10 milliliters of acetonitriles, and makes mixture at room temperature react overnight.Gains MC/ water processes, and then carries out chromatographic column purification, is synthetically derived the compound represented by chemical formula 25 (CF25).
1HNMR (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 represented by chemical formula 26
The compound (GC-MS (DI) m/z:466.19) represented by chemical formula 26 is according to the method synthesis identical with synthesis example 5, but wherein uses methacrylic chloride, and the acryloyl chloride in non-synthetic example 5.
Synthesis example 7: the compound that synthesis is represented by chemical formula 11
The compound (GC-MS (DI) m/z:552.26) represented by chemical formula 11 is according to the method synthesis identical with synthesis example 1, but wherein uses 2-amino benzoic Acid but not PABA.
Synthesis example 8: the compound that synthesis is represented by chemical formula 12
The compound (GC-MS (DI) m/z:480.20) represented by chemical formula 12 is according to the method synthesis identical with synthesis example 1, but wherein uses 2-aminopropane. and ethylhexylamine in non-synthetic example 1.
Synthesis example 9: the compound that synthesis is represented by chemical formula 13
The compound (GC-MS (DI) m/z:494.22) represented by chemical formula 13 is according to the method synthesis identical with synthesis example 1, but wherein uses isobutyl amine and ethylhexylamine in non-synthetic example 1.
Synthesis example 10: the compound that synthesis is represented by chemical formula 14
The compound (GC-MS (DI) m/z:508.23) represented by chemical formula 14 is according to the method synthesis identical with synthesis example 1, but wherein uses isobutylcarbylamine and ethylhexylamine in non-synthetic example 1.
Synthesis example 11: the compound that synthesis is represented by chemical formula 15
Compound 2 is according to the method synthesis identical with synthesis example 1.Make the DCC of the compound 2 of identical equivalent and Isosorbide-5-Nitrae-dihydroxy benzenes and 1.5 equivalents in THF solvent, at room temperature react.After utilizing TLC to check reaction, gains EA/ water processes and carries out chromatographic column purification.Then, identical with synthesis example 5, TEA, DMAP, acryloyl chloride and acetonitrile are added in gained compound, and makes mixture at room temperature react overnight.Gains MC/ water processes and carries out chromatographic column purification, is synthetically derived the compound (GC-MS (DI) m/z:556.23) represented by chemical formula 15.
Synthesis example 12: the compound that synthesis is represented by chemical formula 16
The compound (GC-MS (DI) m/z:570.24) represented by chemical formula 16 is according to the method synthesis identical with synthesis example 11, but wherein uses methacrylic chloride, and the acryloyl chloride in non-synthetic example 11.
Synthesis example 13: the compound that synthesis is represented by chemical formula 21
Azo coupling is to carry out according to the synthesis identical method of example 1, but wherein uses 3-amino-phenol and PABA in non-synthetic example 1.Then, according to the method identical with synthesis example 5, TEA, DMAP, acryloyl chloride and acetonitrile are added in compound, and makes mixture at room temperature react overnight.Gains MC/ water processes and carries out chromatographic column purification, is synthetically derived the compound (GC-MS (DI) m/z:436.21) represented by chemical formula 21.
Synthesis example 14: the compound that synthesis is represented by chemical formula 22
The compound (GC-MS (DI) m/z:450.23) represented by chemical formula 22 is according to the method synthesis identical with synthesis example 13, but wherein uses methacrylic chloride, and the acryloyl chloride in non-synthetic example 13.
Synthesis example 15: the compound that synthesis is represented by chemical formula 23
Azo coupling is to carry out according to the synthesis identical method of example 1, but wherein uses 3-amino-phenol and PABA in non-synthetic example 1.Make the gained azo compound of identical equivalent and 4-HBA and 1.5 equivalent DCC in THF solvent, at room temperature carry out esterification.After utilizing TLC to check reaction, gains EA/ water processes and carries out chromatographic column purification.Then, according to the method identical with synthesis example 5, TEA, DMAP, acryloyl chloride and acetonitrile are added in gained compound, and makes mixture at room temperature react overnight.Gains MC/ water processes and carries out chromatographic column purification, is synthetically derived the compound (GC-MS (DI) m/z:556.23) represented by chemical formula 23.
Synthesis example 16: the compound that synthesis is represented by chemical formula 24
The compound (GC-MS (DI) m/z:570.25) represented by chemical formula 24 is according to the method synthesis identical with synthesis example 15, but wherein uses methacrylic chloride, and the acryloyl chloride in non-synthetic example 15.
Synthesis example 17: the compound that synthesis is represented by chemical formula 17
Compound 2 is according to the method synthesis identical with synthesis example 1.Then make the DCC of the compound 2 of identical equivalent and ethylene glycol and 1.5 equivalents in THF solvent, at room temperature react.After utilizing TLC to check reaction, gains EA/ water processes and carries out chromatographic column purification.Then, according to the method identical with synthesis example 5, TEA, DMAP, acryloyl chloride and acetonitrile are added in gained compound, at room temperature maintains overnight.Gains MC/ water processes and carries out chromatographic column purification, is synthetically derived the compound (GC-MS (DI) m/z:508.23) represented by chemical formula 17.
Synthesis example 18: the compound that synthesis is represented by chemical formula 18
The compound (GC-MS (DI) m/z:522.25) represented by chemical formula 18 is according to the method synthesis identical with synthesis example 17, but wherein uses methacrylic chloride, and the acryloyl chloride in non-synthetic example 17.
Synthesis example 19: the compound that synthesis is represented by chemical formula 19
Compound 2 is according to the method synthesis identical with synthesis example 1.Then, make the compound 2 of identical equivalent and 4-HBA and 1.5 equivalent DCC in THF solvent, at room temperature carry out esterification.After utilizing TLC to check reaction, gains EA/ water processes and carries out chromatographic column purification.Then, according to the method identical with synthesis example 1, GMA, TBAB and acetonitrile are added in compound, and make mixture backflow and react overnight at 90 DEG C.Gains MC/ water processes and carries out chromatographic column purification, is synthetically derived the compound (GC-MS (DI) m/z:610.26) represented by chemical formula 19.
Synthesis example 20: the compound that synthesis is represented by chemical formula 20
Compound 2 is according to the method synthesis identical with synthesis example 1.Then, make the compound 2 of identical equivalent and 4-glycolic and 1.5 equivalent DCC in THF solvent, at room temperature carry out esterification.After utilizing TLC to check reaction, gains EA/ water processes and carries out chromatographic column purification.Then, according to the method identical with synthesis example 1, GMA, TBAB and acetonitrile are added in compound, and make mixture backflow and react overnight at 90 DEG C.Gains MC/ water processes and carries out chromatographic column purification, is synthetically derived the compound (GC-MS (DI) m/z:658.26) represented by chemical formula 20.
Synthesis example 21: include the synthesis of the polymer of the repetitive represented by chemical formula 33
Synthetic polymer, described polymer include 50 weight % according to the synthesis compound represented by chemical formula 7 of example 1 and the methacrylic acid (big-and-middle chemistry and metal company limited (DaejungChemicals&MetalsCo., Ltd.)) of 15 weight % and the benzyl methacrylate (Hitachi, Ltd (HitachLtd.)) of 35 weight % as every kind of monomer.
Specifically, by 1.5 grams of V601 (with Optical Chemical Company (WakoChemicals, Inc.)) it is positioned in 100 ml beakers as initiator, and with 30 grams of total monomer weight, sequentially add the benzyl methacrylate (Hitachi Ltd) according to the synthesis compound represented by chemical formula 7 of example 1, the methacrylic acid (big-and-middle chemistry and metal company limited) of 15 weight % and 35 weight % of 50 weight % wherein.Then, it is possible to additionally incorporate 72 grams of Ketohexamethylene wherein as solvent, and stir mixture 30 minutes, until dye monomer and initiator are completely dissolved, thus preparing monomer solution.Subsequently, 54 grams of solvents are positioned over and are equipped with in 250 milliliters of glass reactors of cooler to carry out polyreaction and to be heated to 85 DEG C, and last 3 hours in reactor and be added dropwise over prepared monomer solution.When having added, mixture is made to react 9 hours at the same temperature and be cooled to room temperature, thus completing reaction.Carry out polyreaction under nitrogen atmosphere.According to the chromatograph of gel permeation (gelpermeationchromatography manufactured by Waters (WatersCo.)；GPC), polymer has the weight average molecular weight of 10,800 grams/mol.
Synthesis example 22: include the synthesis of the polymer of the repetitive represented by chemical formula 35
According to synthesizing the polymer of repetitive including being represented by chemical formula 35 with the synthesis identical method of example 21, but wherein use the compound represented by chemical formula 9 of 50 weight %, and the compound represented by chemical formula 7 of 50 weight % in non-synthetic example 21.When using the chromatograph of gel permeation (GPC) that Waters manufactures to measure, polymer has the weight average molecular weight of 9,300 grams/mol.
Synthesis example 23: include the synthesis of the polymer of the repetitive represented by chemical formula 47
According to synthesizing the polymer of repetitive including being represented by chemical formula 47 with the synthesis identical method of example 21, but wherein use the compound represented by chemical formula 21 of 50 weight %, and the compound represented by chemical formula 7 of 50 weight % in non-synthetic example 21.When using the chromatograph of gel permeation (GPC) that Waters manufactures to measure, polymer has the weight average molecular weight of 9,700 grams/mol.
Synthesis example 24: include the synthesis of the polymer of the repetitive represented by chemical formula 49
According to synthesizing the polymer of repetitive including being represented by chemical formula 49 with the synthesis identical method of example 21, but wherein use the compound represented by chemical formula 23 of 50 weight %, and the compound represented by chemical formula 7 of 50 weight % in non-synthetic example 21.When using the chromatograph of gel permeation (GPC) that Waters manufactures to measure, polymer has the weight average molecular weight of 10,100 grams/mol.
Synthesis example 25: include the synthesis of the polymer of the repetitive represented by chemical formula 52
According to synthesizing the polymer of repetitive including being represented by chemical formula 52 with the synthesis identical method of example 21, but wherein use the compound represented by chemical formula 26 of 50 weight %, and the compound represented by chemical formula 7 of 50 weight % in non-synthetic example 21.When using the chromatograph of gel permeation (GPC) that Waters manufactures to measure, polymer has the weight average molecular weight of 9,900 grams/mol.
Comparative synthesis example 1
1000 grams of Ketohexamethylene (are won a Chemical Co., Ltd. (ShinyChemicalIndustrialCo., Ltd.) in the 10 liters of polymer reactors be equipped with reflux cooler and agitator, it is heated to 80 DEG C, and last 3 hours and thermotropism polymer reactor is slowly added to by by 300 g of compound 12, 300 grams of benzyl methacrylate (Hitachi Ltd), 106 grams of methacrylic acids (big-and-middle chemistry and metal company limited) and 92 gram 2, 2 '-azodiisobutyronitrile (and Optical Chemical Company) is dissolved in 5000 grams of Ketohexamethylene (victory-Chemical Co., Ltd.) solution obtained.When the addition is complete, stirring mixture 14 hours, it is thus achieved that include the polymer of the repetitive represented by chemical formula B.When using the chromatograph of gel permeation (GPC) that Waters manufactures to measure, polymer has the weight average molecular weight of 9,800 grams/mol.
[chemical formula B]
In chemical formula B, a=2, b=2 and c=1.
Evaluate 1: dissolubility
Retarder thinner (PGMEA) is separately added into according in synthesis example 1 to the every kind of compound and the 0.5 gram of compound represented by chemical formula A that synthesize example 20；Use the MixrotarVMR-5 that Jing Nei company (IuchiInc.) manufactures, every kind of corresponding solution is stirred under 25 DEG C and 100 revs/min, and check the dissolved state (meltage of compound) of compound, and result is provided in the following table in 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 |
(compound represented by chemical formula A has a structure that
[chemical formula A]
)
Dissolubility evaluation reference
>=20wt% (in PGMEA): zero
< 20wt% (in PGMEA): X
Referring to table 1, according to the compound of an embodiment, there is excellent dissolubility (about organic solvent)；Compared to the photosensitive polymer combination not including described compound, it is easy to anticipate that including described compound shows excellent color character as the photosensitive polymer combination of dyestuff.
(synthesis of photosensitive polymer combination)
Example 1
According to the composition provided in table 2 below, Photoepolymerizationinitiater initiater is dissolved in solvent, and at room temperature agitating solution 2 hours.Then, it is added thereto to adhesive resin and photopolymerizable monomer, and at room temperature stirs gained mixture 2 hours.Then, being added thereto to the compound represented by synthesis example 21, gained mixture at room temperature stirs one hour, is added thereto to silane coupling agent, and gained mixture at room temperature stirs one hour.Filtering solution three times, and remove impurity therein, thus the photosensitive polymer combination that preparation is according to example 1.
[table 2]
(unit: gram)
Example 2
Photosensitive polymer combination according to example 2 is to prepare according to the method identical with example 1, but wherein uses the compound of synthesis example 22 and the compound of non-synthetic example 21.
Example 3
Photosensitive polymer combination according to example 3 is to prepare according to the method identical with example 1, but wherein uses the compound of synthesis example 23, and the compound of non-synthetic example 21.
Example 4
Photosensitive polymer combination according to example 4 is to prepare according to the method identical with example 1, but wherein uses the compound of synthesis example 24, and the compound of non-synthetic example 21.
Example 5
Photosensitive polymer combination according to example 5 is to prepare according to the method identical with example 1, but wherein uses the compound of synthesis example 25, and the compound of non-synthetic example 21.
Comparative example 1
Photosensitive polymer combination according to comparative example 1 is to prepare according to the method identical with example 1, but wherein uses the polymer of comparative synthesis example 1, and the compound of non-synthetic example 21.
Evaluate 2: hue coordinate, brightness and contrast ratio
By being respectively coated 1 micron to 3 microns thickness in defat scrubbed glass substrate and drying 2 minutes on 90 DEG C of hot plates in 1 millimeters thick of every kind of photosensitive polymer combination according to example 1 to example 5 and comparative example 1, it is thus achieved that film.Subsequently, the high voltage mercury lamp with 365 nanometers of dominant wavelengths is used to be exposed by film.Film is dried 5 minutes in the forced convertion drying oven of 200 DEG C.Then, spectrophotometer (MCPD3000, great Zhong Electronics Co., Ltd. (OtsukaElectronicCo., Ltd.)) is used to measure the hue coordinate (x of gained pixel layer, y), brightness (Y) and contrast ratio, and result is provided in the following table in 3.
[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 not including compound or the polymer photosensitive polymer combination as dyestuff according to comparative example 1, show excellent color character according to the include compound according to an embodiment or the polymer of example 1 to example 5 as the photosensitive polymer combination of dyestuff.
Those skilled in the art is it is appreciated that the many variants of the present invention relevant with the present invention and other embodiments, and it has the benefit of the teachings presented in preceding description.It will be understood, therefore, that the invention is not restricted to disclosed specific embodiment and wish that its variant and other embodiments are included in the scope of the appended claims.Although being used herein particular term, but they only use in general and descriptive meaning and are not used in the purpose of restriction, and the scope of the present invention limits in detail in the claims.
Claims (15)
1. an azo compound, is represented by chemical formula 1:
Wherein, in chemical formula 1
R1And R2It is substituted or unsubstituted C1 to C20 alkyl, *-C (=O) OR ' or *-OC (=O) R ' independently of one another,
R ' is substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C2 to C10 thiazolinyl or substituted or unsubstituted C6 to C20 aryl,
Its condition is, R1And R2One of include the substituent group that represented by chemical formula 2, and
R3It is substituted or unsubstituted C1 to C20 alkyl,
Wherein, in chemical formula 2,
R4It is hydrogen or substituted or unsubstituted C1 to C10 alkyl.
2. azo compound according to claim 1, the compound wherein represented by chemical formula 1 is by selected from the chemical formula 3 chemical formulation to chemical formula 6:
Wherein, in chemical formula 3 to chemical formula 6,
L1To L3It is substituted or unsubstituted C1 to C10 alkylidene, substituted or unsubstituted C6 to C20 arlydene or *-L '-C (=O) O-L independently "-*,
L ' and L " it is substituted or unsubstituted C1 to C5 alkylidene or substituted or unsubstituted C6 to C12 arlydene independently of one another,
R3And R5It is substituted or unsubstituted C1 to C20 alkyl independently of one another, and
R4It is hydrogen or substituted or unsubstituted C1 to C10 alkyl.
3. azo compound according to claim 1, wherein chemical formula 1 is by selected from the chemical formula 7 chemical formulation to chemical formula 20:
4. azo compound according to claim 1, wherein chemical formula 1 is by selected from the chemical formula 21 chemical formulation to chemical formula 24:
5. azo compound according to claim 1, wherein chemical formula 1 is by the chemical formulation selected from chemical formula 25 or chemical formula 26:
6. azo compound according to claim 1, wherein said compound is weld.
7. azo compound according to claim 6, wherein said weld is the compound with the absorption maximum interval that wave-length coverage is 400 nanometers to 500 nanometers.
8. comprising a polymer for azo compound, described azo compound is by the be shown as monomer of chemical formula 1:
Wherein, in chemical formula 1,
R1And R2It is substituted or unsubstituted C1 to C20 alkyl, *-C (=O) OR ' or *-OC (=O) R ' independently of one another,
R ' is substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C2 to C10 thiazolinyl or substituted or unsubstituted C6 to C20 aryl,
Its condition is, R1And R2One of include the substituent group that represented by chemical formula 2, and
R3It is substituted or unsubstituted C1 to C20 alkyl,
Wherein, in chemical formula 2,
R4It is hydrogen or substituted or unsubstituted C1 to C10 alkyl.
9. the polymer comprising azo compound according to claim 8, wherein said polymer comprises the repetitive selected from the repetitive shown in chemical formula 27 to chemical formula 30:
Wherein, in chemical formula 27 to chemical formula 30,
L1To L3It is substituted or unsubstituted C1 to C10 alkylidene, substituted or unsubstituted C6 to C20 arlydene or *-L '-C (=O) O-L independently "-*,
L ' and L " it is substituted or unsubstituted C1 to C5 alkylidene or substituted or unsubstituted C6 to C12 arlydene independently of one another,
R3And R5It is substituted or unsubstituted C1 to C20 alkyl independently of one another, and
R4It is hydrogen or substituted or unsubstituted C1 to C10 alkyl.
10. the polymer comprising azo compound according to claim 9, wherein said polymer also comprises the repetitive shown in chemical formula 31 and 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 it is substituted or unsubstituted C1 to C10 alkylidene.
11. the polymer comprising azo compound according to claim 10, wherein said polymer comprises:
The repetitive selected from chemical formula 27 to the repetitive shown in chemical formula 30 of 40 weight % to 60 weight %；
The repetitive represented by chemical formula 31 of 5 weight % to 25 weight %；And
The repetitive represented by chemical formula 32 of 25 weight % to 45 weight %.
12. the polymer comprising azo compound according to claim 9, the wherein said repetitive represented by chemical formula 27 is chosen from the repetitive represented by chemical formula 33 to chemical formula 46:
13. the polymer comprising azo compound according to claim 9, the wherein said repetitive represented by chemical formula 28 is to be represented by chemical formula 47 or chemical formula 48:
14. the polymer comprising azo compound according to claim 9, the wherein said repetitive represented by chemical formula 29 is the repetitive shown in chemical formula 49 or chemical formula 50:
15. the polymer comprising azo compound according to claim 9, the wherein said repetitive represented by chemical formula 30 is the repetitive shown in chemical formula 51 or chemical formula 52:
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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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| WO2018099416A1 (en) * | 2016-11-30 | 2018-06-07 | 东莞东阳光科研发有限公司 | Azo-compound, polymer and preparation method and use of same |
| CN109641855A (en) * | 2016-11-30 | 2019-04-16 | 东莞东阳光科研发有限公司 | Azo-compound, polymer and their Preparation method and use |
| CN109641855B (en) * | 2016-11-30 | 2022-04-29 | 东莞东阳光医疗智能器件研发有限公司 | Azo compounds, polymers, and processes for their preparation and use |
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| CN105801477B (en) | 2019-04-16 |
| KR20160090168A (en) | 2016-07-29 |
| TW201627413A (en) | 2016-08-01 |
| KR101788089B1 (en) | 2017-10-19 |
| TWI580737B (en) | 2017-05-01 |
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