KR101790622B1 - Novel compound,novel polymer and colorant comprising the same - Google Patents
Novel compound,novel polymer and colorant comprising the same Download PDFInfo
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- KR101790622B1 KR101790622B1 KR1020150151183A KR20150151183A KR101790622B1 KR 101790622 B1 KR101790622 B1 KR 101790622B1 KR 1020150151183 A KR1020150151183 A KR 1020150151183A KR 20150151183 A KR20150151183 A KR 20150151183A KR 101790622 B1 KR101790622 B1 KR 101790622B1
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- 0 **1C=C(*(CN)c([n]c(C(c2ccc(*(C*COCC(C(CN)=O)=N)c(c(N)ccc3)c3N)cc2)=C(C=C2)C=CC2=*(CN)c(c(N)ccc2)c2N)c2-c3ccccc3)c2[Zn])C=CC=C1 Chemical compound **1C=C(*(CN)c([n]c(C(c2ccc(*(C*COCC(C(CN)=O)=N)c(c(N)ccc3)c3N)cc2)=C(C=C2)C=CC2=*(CN)c(c(N)ccc2)c2N)c2-c3ccccc3)c2[Zn])C=CC=C1 0.000 description 5
- KRVIQMDCGAKMRG-UHFFFAOYSA-N CCN(c([s]c(/C(/c(cc1)ccc1N(CCOC(C(C)=C)=O)c1c(C)cccc1C)=C(\C=C1)/C=C/C1=[N+](\CC)/c1c(C)cccc1C)c1-c2ccccc2)c1C#N)c1ccccc1 Chemical compound CCN(c([s]c(/C(/c(cc1)ccc1N(CCOC(C(C)=C)=O)c1c(C)cccc1C)=C(\C=C1)/C=C/C1=[N+](\CC)/c1c(C)cccc1C)c1-c2ccccc2)c1C#N)c1ccccc1 KRVIQMDCGAKMRG-UHFFFAOYSA-N 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/08—Hydrogen atoms or radicals containing only hydrogen and carbon atoms
- C07D333/10—Thiophene
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur 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
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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
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
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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
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
- C09B67/0084—Dispersions of dyes
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
Abstract
A cation and an anion, the cation being represented by the following formula (1), a polymer formed by the copolymerization reaction of the compound and the monomer, and a colorant comprising the compound or the polymer.
[Chemical Formula 1]
(Wherein each substituent is as defined in the specification).
Description
The present disclosure relates to novel compounds, novel polymers and colorants comprising them.
In order to facilitate the stable dispersion and fineness of the pigment dispersion, various studies have been conducted to make pigments having a particle size of a certain size through a process such as salt milling of the pigment obtained through synthesis. Further, in the case of a pigment, there is a limit of brightness and contrast ratio resulting from particle size, and in the case of a color imaging device for an image sensor, a smaller dispersion particle size is required for forming a fine pattern. Therefore, Studies have been made to improve physical properties such as brightness and contrast ratio by using a hybrid type colorant in which a pigment and a dye are mixed.
However, up to now, no coloring agent has been reported which has a greater effect of improving physical properties such as heat resistance and brightness as compared with conventional coloring agents and the like.
Therefore, it is necessary to study a compound suitable as a coloring agent used in the production of a photosensitive resin composition.
One embodiment is to provide a novel compound.
Another embodiment is to provide a polymer derived from said compound.
Another embodiment is to provide a colorant comprising the compound and / or the polymer.
One embodiment provides a compound comprising a cation and an anion, wherein the cation is represented by the following formula (1).
[Chemical Formula 1]
In Formula 1,
R 1 , R 2 , R 6 and R 7 are each independently a hydrogen atom, a substituted or unsubstituted C 1 to C 20 alkyl group, a substituted or unsubstituted C 6 to C 20 aryl group, a substituted or unsubstituted C 2 to C 20 heteroaryl group Or a substituent represented by the following formula (2)
Provided that at least one of R 1 , R 2 , R 6 and R 7 is a substituent represented by the following formula (2)
R 3 and R 4 are each independently a halogen atom or a substituted or unsubstituted C1 to C20 alkyl group,
R < 5 > is a substituted or unsubstituted C6 to C20 aryl group,
X is -O-, -S- or -NR 8 - (R 8 is a hydrogen atom, a substituted or unsubstituted C1 to C10 alkyl group or a substituted or unsubstituted C6 to C20 aryl group)
m and n are each independently an integer of 0 to 5,
(2)
In Formula 2,
L 1 to L 3 are each independently a single bond, a substituted or unsubstituted C1 to C20 alkylene group or a substituted or unsubstituted C6 to C20 arylene group,
R 9 is a hydrogen atom or a substituted or unsubstituted C1 to C10 alkyl group.
X may be -O- or -S-.
At least two of R 1 , R 2 , R 6 and R 7 must be represented by the formula (2).
At least three of R 1 , R 2 , R 6 and R 7 must be represented by the formula (2).
R 1 , R 2 , R 6 and R 7 may all be represented by the general formula (2).
The formula (2) may be represented by the following formula (2-1) or (2-2).
[Formula 2-1]
[Formula 2-2]
In the above Formulas (2-1) and (2-2)
L 4 to L 6 each independently represent a substituted or unsubstituted C1 to C10 alkylene group,
R 9 is a hydrogen atom or a substituted or unsubstituted C1 to C10 alkyl group.
The cation may be represented by the following formula (3) or (4).
(3)
[Chemical Formula 4]
In the above formulas (3) and (4)
R 1 , R 2 , R 6 and R 7 are each independently a hydrogen atom, a substituted or unsubstituted C 1 to C 20 alkyl group, a substituted or unsubstituted C 6 to C 20 aryl group or a substituted or unsubstituted C 2 to C 20 heteroaryl group ego,
R 3 and R 4 are each independently a halogen atom or a substituted or unsubstituted C1 to C20 alkyl group,
R 9 is a hydrogen atom or a substituted or unsubstituted C1 to C10 alkyl group,
R 10 is a halogen atom, a nitro group or a substituted or unsubstituted C1 to C10 alkyl group,
X is -O-, -S- or -NR 8 - (R 8 is a hydrogen atom, a substituted or unsubstituted C1 to C10 alkyl group or a substituted or unsubstituted C6 to C20 aryl group)
m, n and p are each independently an integer of 0 to 5,
L 1 to L 3 are each independently a single bond, a substituted or unsubstituted C1 to C20 alkylene group or a substituted or unsubstituted C6 to C20 arylene group.
The cation may be represented by any one of the following formulas (5) to (7).
[Chemical Formula 5]
[Chemical Formula 6]
(7)
In the above Chemical Formulas 5 to 7,
R 1 , R 2 , R 6 and R 7 are each independently a hydrogen atom, a substituted or unsubstituted C 1 to C 20 alkyl group, a substituted or unsubstituted C 6 to C 20 aryl group or a substituted or unsubstituted C 2 to C 20 heteroaryl group ego,
R 3 and R 4 are each independently a halogen atom or a substituted or unsubstituted C1 to C20 alkyl group,
R 9 is a hydrogen atom or a substituted or unsubstituted C1 to C10 alkyl group,
R 10 is a halogen atom, a nitro group or a substituted or unsubstituted C1 to C10 alkyl group,
X is -O-, -S- or -NR 8 - (R 8 is a hydrogen atom, a substituted or unsubstituted C1 to C10 alkyl group or a substituted or unsubstituted C6 to C20 aryl group)
m, n and p are each independently an integer of 0 to 5,
L 1 to L 3 are each independently a single bond, a substituted or unsubstituted C1 to C20 alkylene group or a substituted or unsubstituted C6 to C20 arylene group.
The cation may be represented by the following general formula (8) or (9).
[Chemical Formula 8]
[Chemical Formula 9]
In the above formulas (8) and (9)
R 2 and R 7 are each independently a hydrogen atom, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C20 heteroaryl group,
R 3 and R 4 are each independently a halogen atom or a substituted or unsubstituted C1 to C20 alkyl group,
R 9 is a hydrogen atom or a substituted or unsubstituted C1 to C10 alkyl group,
R 10 is a halogen atom, a nitro group or a substituted or unsubstituted C1 to C10 alkyl group,
X is -O-, -S- or -NR 8 - (R 8 is a hydrogen atom, a substituted or unsubstituted C1 to C10 alkyl group or a substituted or unsubstituted C6 to C20 aryl group)
m, n and p are each independently an integer of 0 to 5,
L 1 to L 3 are each independently a single bond, a substituted or unsubstituted C1 to C20 alkylene group or a substituted or unsubstituted C6 to C20 arylene group.
The cation may be represented by any one selected from the group consisting of the following formulas (10-1) to (10-15).
[Formula 10-1]
[Formula 10-2]
[Formula 10-3]
[Formula 10-4]
[Formula 10-5]
[Formula 10-6]
[Formula 10-7]
[Formula 10-8]
[Chemical Formula 10-9]
[Chemical Formula 10-10]
[Chemical Formula 10-11]
[Chemical Formula 10-12]
[Chemical Formula 10-13]
[Chemical Formula 10-14]
[Chemical Formula 10-15]
In the above Chemical Formulas 10-1 to 10-15,
R 10 and R 11 are each independently a halogen atom, a nitro group or a substituted or unsubstituted C1 to C10 alkyl group,
q1 to q3 each independently represent an integer of 1 to 10,
p and s are each independently an integer of 0 to 5;
The anion may be represented by any one selected from the group consisting of the following chemical formulas (A) to (F).
(A)
[Chemical Formula B]
≪ RTI ID = 0.0 &
PW 12 O 40 3 -
[Chemical Formula D]
SiW 12 O 40 4 -
(E)
CF 3 SO 3 -
[Chemical Formula F]
ClO 4 -
The compound may have a maximum absorbance (? Max ) in the wavelength range of 550 nm to 700 nm.
The compound may have a maximum transmittance (T max ) in the wavelength range of 400 nm to 500 nm.
Another embodiment provides a polymer formed by the copolymerization reaction of the above compound with a multimer.
The monomer may be an ethylenically unsaturated monomer.
Wherein said ethylenically unsaturated monomer is at least one selected from the group consisting of an aromatic vinyl compound, an unsaturated carboxylic acid ester compound, an unsaturated carboxylic acid aminoalkyl ester compound, a carboxylic acid vinyl ester compound, an unsaturated carboxylic acid glycidyl ester compound, a vinyl cyanide compound, an unsaturated amide compound, It can be any one selected.
The polymer may be an acrylic polymer.
The polymer may have a weight average molecular weight of from 5,000 g / mol to 100,000 g / mol.
Another embodiment provides a colorant comprising the compound or the polymer.
The colorant may be a dye.
The dye may be a blue dye.
Other aspects of the present invention are included in the following detailed description.
The compounds and polymers according to one embodiment are excellent in tinting strength and heat resistance. When a photosensitive resin composition containing the above compound and polymer as a coloring agent is used, it is possible to manufacture a color filter having excellent luminance.
1 is a graph showing the absorbance of the compound represented by the formula (22-1) according to the wavelength.
Hereinafter, embodiments of the present invention will be described in detail. However, it should be understood that the present invention is not limited thereto, and the present invention is only defined by the scope of the following claims.
Means that at least one hydrogen atom of the functional group of the present invention is substituted with a halogen atom (F, Br, Cl or I), a hydroxy group, a nitro group, a cyano group, an amino group NH 2, NH (R 200), or N (R 201) (R 202), wherein R 200, R 201 and R 202 are the same or different, each independently being a C1 to C10 alkyl groups), amidino group, A substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted alicyclic alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl group, And a substituted or unsubstituted heterocyclic group substituted with at least one substituent selected from the group consisting of a substituted or unsubstituted heterocyclic group.
Unless otherwise specified in the specification, "alkyl group" means C1 to C20 alkyl group, specifically C1 to C15 alkyl group, "cycloalkyl group" means C3 to C20 cycloalkyl group, specifically C3 Refers to a C1 to C20 alkoxy group, specifically, a C1 to C18 alkoxy group, and an "aryl group" means a C6 to C20 aryl group, specifically, a C6 to C20 aryl group, Refers to a C 2 to C 20 alkenyl group, specifically, a C 2 to C 18 alkenyl group, and the "alkylene group" refers to a C 1 to C 20 alkylene group, specifically, a C1 Refers to a C6 to C20 arylene group, and specifically refers to a C6 to C16 arylene group.
(Meth) acrylate "refers to both" acrylic acid "and" methacrylic acid " It means both are possible.
As used herein, unless otherwise defined, "combination" means mixing or copolymerization. "Copolymerization" means block copolymerization or random copolymerization, and "copolymer" means block copolymer or random copolymer.
Unless otherwise defined in the chemical formulas in this specification, when no chemical bond is drawn at the position where the chemical bond should be drawn, it means that the hydrogen atom is bonded at the above position.
Unless otherwise defined herein, "*" means the same or different atom or moiety connected to a formula.
One embodiment provides a compound comprising a cation and an anion, wherein the cation is represented by the following formula (1).
[Chemical Formula 1]
In Formula 1,
R 1 , R 2 , R 6 and R 7 are each independently a hydrogen atom, a substituted or unsubstituted C 1 to C 20 alkyl group, a substituted or unsubstituted C 6 to C 20 aryl group, a substituted or unsubstituted C 2 to C 20 heteroaryl group Or a substituent represented by the following formula (2)
Provided that at least one of R 1 , R 2 , R 6 and R 7 is a substituent represented by the following formula (2)
R 3 and R 4 are each independently a halogen atom or a substituted or unsubstituted C1 to C20 alkyl group,
R < 5 > is a substituted or unsubstituted C6 to C20 aryl group,
X is -O-, -S- or -NR 8 - (R 8 is a hydrogen atom, a substituted or unsubstituted C1 to C10 alkyl group or a substituted or unsubstituted C6 to C20 aryl group)
m and n are each independently an integer of 0 to 5,
(2)
In Formula 2,
L 1 to L 3 are each independently a single bond, a substituted or unsubstituted C1 to C20 alkylene group or a substituted or unsubstituted C6 to C20 arylene group,
R 9 is a hydrogen atom or a substituted or unsubstituted C1 to C10 alkyl group.
For example, X may be -O- or -S-.
In recent years, in order to produce a color filter having a high luminance and a high contrast ratio, researches have been actively conducted to synthesize dyes excellent in durability than pigments and to achieve high luminance and high contrast ratio of color filters using a composition containing the dyes have. Among the dyes, many studies using triarylmethane compounds known as blue dyes have been conducted. The triarylmethane dye has an advantage that it has a high luminance in a wavelength range of 420 nm to 450 nm, but has a disadvantage in that it has poor solubility in organic solvents such as PGMEA and heat resistance. In order to overcome the weak heat resistance, attempts have been made to use anions such as naphthalenesulfonic acid and naphthylamine sulfonic acid in triarylmethane dyes, but the heat resistance has not been greatly improved.
The compound according to one embodiment contains cations represented by the formula (1) and has excellent spectroscopic characteristics and a high molar extinction coefficient as compared with a compound used as a conventional colorant, such as a triarylmethane compound, and has excellent coloring ability and heat resistance, The solubility in organic solvents such as cyclohexanone and PGMEA is also excellent. In particular, a compound according to one embodiment has three rings linked to a central carbon, wherein one of the three rings has an aromatic heterocycle comprising a cyano group, so that a composition comprising a compound according to one embodiment It is possible to provide a color filter excellent in luminance and durability.
For example, at least two of R 1 , R 2 , R 6, and R 7 may be represented by Formula 2.
For example, at least three of R 1 , R 2 , R 6 and R 7 must be represented by the formula (2).
For example, R 1 , R 2 , R 6 and R 7 may all be represented by the general formula (2).
The formula (2) may be represented by the following formula (2-1) or (2-2).
[Formula 2-1]
[Formula 2-2]
In the above Formulas (2-1) and (2-2)
L 4 to L 6 each independently represent a substituted or unsubstituted C1 to C10 alkylene group,
R 9 is a hydrogen atom or a substituted or unsubstituted C1 to C10 alkyl group.
For example, the cation may be represented by the following formula (3) or (4).
(3)
[Chemical Formula 4]
In the above formulas (3) and (4)
R 1 , R 2 , R 6 and R 7 are each independently a hydrogen atom, a substituted or unsubstituted C 1 to C 20 alkyl group, a substituted or unsubstituted C 6 to C 20 aryl group or a substituted or unsubstituted C 2 to C 20 heteroaryl group ego,
R 3 and R 4 are each independently a halogen atom or a substituted or unsubstituted C1 to C20 alkyl group,
R 9 is a hydrogen atom or a substituted or unsubstituted C1 to C10 alkyl group,
R 10 is a halogen atom, a nitro group or a substituted or unsubstituted C1 to C10 alkyl group,
X is -O-, -S- or -NR 8 - (R 8 is a hydrogen atom, a substituted or unsubstituted C1 to C10 alkyl group or a substituted or unsubstituted C6 to C20 aryl group)
m, n and p are each independently an integer of 0 to 5,
L 1 to L 3 are each independently a single bond, a substituted or unsubstituted C1 to C20 alkylene group or a substituted or unsubstituted C6 to C20 arylene group.
For example, the cation may be represented by any one of the following formulas (5) to (7).
[Chemical Formula 5]
[Chemical Formula 6]
(7)
In the above Chemical Formulas 5 to 7,
R 1 , R 2 , R 6 and R 7 are each independently a hydrogen atom, a substituted or unsubstituted C 1 to C 20 alkyl group, a substituted or unsubstituted C 6 to C 20 aryl group or a substituted or unsubstituted C 2 to C 20 heteroaryl group ego,
R 3 and R 4 are each independently a halogen atom or a substituted or unsubstituted C1 to C20 alkyl group,
R 9 is a hydrogen atom or a substituted or unsubstituted C1 to C10 alkyl group,
R 10 is a halogen atom, a nitro group or a substituted or unsubstituted C1 to C10 alkyl group,
X is -O-, -S- or -NR 8 - (R 8 is a hydrogen atom, a substituted or unsubstituted C1 to C10 alkyl group or a substituted or unsubstituted C6 to C20 aryl group)
m, n and p are each independently an integer of 0 to 5,
L 1 to L 3 are each independently a single bond, a substituted or unsubstituted C1 to C20 alkylene group or a substituted or unsubstituted C6 to C20 arylene group.
For example, the cation may be represented by the following formula (8) or (9).
[Chemical Formula 8]
[Chemical Formula 9]
In the above formulas (8) and (9)
R 2 and R 7 are each independently a hydrogen atom, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C20 heteroaryl group,
R 3 and R 4 are each independently a halogen atom or a substituted or unsubstituted C1 to C20 alkyl group,
R 9 is a hydrogen atom or a substituted or unsubstituted C1 to C10 alkyl group,
R 10 is a halogen atom, a nitro group or a substituted or unsubstituted C1 to C10 alkyl group,
X is -O-, -S- or -NR 8 - (R 8 is a hydrogen atom, a substituted or unsubstituted C1 to C10 alkyl group or a substituted or unsubstituted C6 to C20 aryl group)
m, n and p are each independently an integer of 0 to 5,
L 1 to L 3 are each independently a single bond, a substituted or unsubstituted C1 to C20 alkylene group or a substituted or unsubstituted C6 to C20 arylene group.
For example, the halogen atom may be F, Cl or Br.
For example, the cation may be represented by any one selected from the group consisting of the following formulas (10-1) to (10-15).
[Formula 10-1]
[Formula 10-2]
[Formula 10-3]
[Formula 10-4]
[Formula 10-5]
[Formula 10-6]
[Formula 10-7]
[Formula 10-8]
[Chemical Formula 10-9]
[Chemical Formula 10-10]
[Chemical Formula 10-11]
[Chemical Formula 10-12]
[Chemical Formula 10-13]
[Chemical Formula 10-14]
[Chemical Formula 10-15]
In the above Chemical Formulas 10-1 to 10-15,
R 10 and R 11 are each independently a halogen atom, a nitro group or a substituted or unsubstituted C1 to C10 alkyl group,
q1 to q3 each independently represent an integer of 1 to 10,
p and s are each independently an integer of 0 to 5;
The compound according to an embodiment includes an anion, and the anion may be represented by any one selected from the group consisting of the following formulas (A) to (F), but is not limited thereto.
(A)
[Chemical Formula B]
≪ RTI ID = 0.0 &
PW 12 O 40 3 -
[Chemical Formula D]
SiW 12 O 40 4 -
(E)
CF 3 SO 3 -
[Chemical Formula F]
ClO 4 -
Since the compound according to one embodiment contains the cation represented by the formula (1), it is possible to express a clearer color even in a small amount, and it is possible to manufacture a display device having excellent color characteristics such as luminance and contrast ratio when used as a colorant Do. For example, the compound may be a dye having a maximum absorbance (? Max ) in the wavelength range of 550 nm to 700 nm, for example in the wavelength range of 600 nm to 650 nm, such as a dye such as a dye such as a blue dye. For example, the compound may be a dye having a T max in the wavelength range of 400 nm to 500 nm, for example in the wavelength range of 420 nm to 500 nm, for example in the wavelength range of 430 nm to 480 nm. Tmax can mean maximum transmittance.
According to another embodiment, there is provided a polymer formed by the copolymerization reaction of a compound according to this embodiment and another monomer.
The monomer may be an ethylenically unsaturated monomer.
For example, the ethylenically unsaturated monomer may be an aromatic vinyl compound, an unsaturated carboxylic acid ester compound, an unsaturated carboxylic acid aminoalkyl ester compound, a carboxylic acid vinyl ester compound, an unsaturated carboxylic acid glycidyl ester compound, a vinyl cyanide compound, an unsaturated amide compound, Lt; / RTI >
For example, the ethylenically unsaturated monomer may be an aromatic vinyl compound such as styrene,? -Methylstyrene, vinyltoluene, or vinylbenzyl methyl ether; (Meth) acrylate, 2-hydroxyethyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, benzyl (meth) acrylate, Unsaturated carboxylic acid ester compounds such as cyclohexyl (meth) acrylate and phenyl (meth) acrylate; Unsaturated carboxylic acid aminoalkyl ester compounds such as 2-aminoethyl (meth) acrylate and 2-dimethylaminoethyl (meth) acrylate; Carboxylic acid vinyl ester compounds such as vinyl acetate and vinyl benzoate; Unsaturated carboxylic acid glycidyl ester compounds such as glycidyl (meth) acrylate; A vinyl cyanide compound such as (meth) acrylonitrile; Unsaturated amide compounds such as (meth) acrylamide, or combinations thereof.
The polymer may be an acrylic polymer. That is, the polymer may be formed by a copolymerization reaction of a compound containing a cation represented by Formula 1 and the ethylenically unsaturated monomer.
The polymer may have a weight average molecular weight of from 5,000 g / mol to 100,000 g / mol.
The polymer according to another embodiment of the present invention is capable of expressing a clearer color in a small amount by copolymerizing a cation-containing compound represented by the above formula (1) with another monomer, and thus, when used as a colorant, It is possible to manufacture such an excellent display device. For example, the polymer may be a colorant, such as a dye, such as a blue dye.
In general, dyes are the most expensive component of the components used in color filters. Therefore, in order to achieve a desired effect, for example, a high luminance and a high contrast ratio, it is necessary to use more expensive dye, so that the production cost has to be increased. However, when the compound and / or the polymer according to one embodiment is used as a colorant in a color filter, for example, a dye, excellent color characteristics such as high luminance and high contrast ratio can be achieved in a small amount, .
Another embodiment provides a colorant comprising the compound or the polymer.
As mentioned above, the colorant may be a dye, such as a blue dye.
The colorant may further comprise, in addition to the compound or the polymer, an organic solvent-soluble dye.
Examples of the organic solvent soluble dyes include triarylmethane compounds, anthraquinone compounds, benzylidene compounds, cyanine compounds, phthalocyanine compounds, azapphyrin compounds, and indigo compounds.
The colorant may further comprise a pigment in addition to the compound and / or the polymer.
The pigment may include a blue pigment, a purple pigment, a red pigment, a green pigment, a yellow pigment and the like.
Examples of the blue pigments include C.I. Blue pigment 15: 6, C.I. Blue pigment 15, C.I. Blue pigment 15: 1, C.I. Blue pigment 15: 2, C.I. Blue pigment 15: 3, C.I. Blue pigment 15: 4, C.I. Blue pigment 15: 5, C.I. Blue pigment 16, C.I. Blue pigment 22, C.I. Blue pigment 60, C.I. Blue pigment 64, C.I. Blue pigment 80, or a combination thereof.
Examples of the purple pigments include CI violet pigment 1, CI violet pigment 19, CI violet pigment 23, CI violet pigment 27, CI violet pigment 29, CI violet pigment 30, CI violet pigment 32, CI violet pigment 37, CI violet pigment 40, CI violet pigment 42, CI violet pigment 50, or a combination thereof.
Examples of the red pigment include pigments such as perylene pigments, anthraquinone pigments, dianthraquinone pigments, azo pigments, diazo pigments, quinacridone pigments, anthracene pigments, and the like. . Specific examples of the red pigments include perylene pigments, quinacridone pigments, naphthol AS, sikomine pigments, anthraquinone (sudan I, II, III, R), dianthraquinone, bis Azo (azo), benzopyran and the like.
Examples of the green pigment include halogenated phthalocyanine pigments such as chlorophthalocyanine chloride, zinc chlorophthalocyanine and / or chlorinated zinc phthalocyanine bromide.
Examples of the yellow pigments include C.I. Pigment yellow 139, C.I. Pigment yellow 138, C.I. Pigment yellow 150 and the like.
The coloring agent may be a component of the photosensitive resin composition for a color filter.
A pattern forming process in a color filter manufactured by using a photosensitive resin composition containing a colorant is as follows.
Applying the photosensitive resin composition on a support substrate by spin coating, slit coating, inkjet printing or the like; Drying the applied photosensitive resin composition to form a photosensitive resin composition film; Exposing the photosensitive resin composition film; Developing the exposed photosensitive resin composition film with an aqueous alkali solution to produce a photosensitive resin film; And a step of heat-treating the photosensitive resin film. The process conditions and the like are well known in the art, and therefore, detailed description thereof will be omitted herein.
Hereinafter, preferred embodiments of the present invention will be described. However, the following examples are only a preferred embodiment of the present invention, and the present invention is not limited by the following examples.
(Compound synthesis)
Synthetic example A-1: Synthesis of Formula 21-1
An intermediate (a) having a hydroxy group at the terminal is synthesized using a known synthesis method. Triethylamine (1.1 eq.) And methacrylic anhydride (1.1 eq.) Are added to the intermediate (a) to obtain a compound (b) having methacrylate. Compound (d) is synthesized by adding 1 equivalent of a substituted thiophene compound (c) and 4 equivalents of phosphorus chloride to the resulting compound (b). Compound (d) in the form of a chlorine salt was reacted (ion-exchanged) with lithium bistrifluoromethane sulfonimide to synthesize a compound represented by the following formula (21-1).
[Formula 21-1]
[NMR data of the cations in the compound represented by the formula (21-1)
1 H NMR (300MHz, CDCl 3 ): δ = 7.59-7.02 (20H), 6.92 (2H), 6.09 (1H), 5.95 (2H), 5.59 (1H), 4.21 (2H), 4.10 (2H), 3.75 (4H), 2.03 (12H), 1.95 (3H), 1.40 (3H), 1.24
[LC / MS data of cations in the compound represented by the formula (21-1)] [
UPLC / TQMS API + mode, [M] + = 847.52
Synthetic example A-2: Synthesis of formula (22-1)
Synthesis Example A-1 was synthesized in the same manner as in Synthesis Example A-1 except that a fluoro group was used in place of the methyl group in the substituent group 2,6-dimethylaniline to synthesize a compound represented by the following Formula 22-1 .
[Formula 22-1]
[LC / MS data of cations in the compound represented by the formula (22-1)
UPLC / TQMS API + mode, [M] + = 863.38
Synthetic example A-3: Synthesis of Compound (25-1)
An intermediate (a ') having a hydroxy group at the terminal is synthesized using a known synthetic method. Triethylamine (1.1 eq.) And methacrylic anhydride (1.1 eq.) Are added to the intermediate (a ') to obtain a compound (c') having methacrylate. Compound (d ') is synthesized by using 1 equivalent of a substituted benzophenone compound (b') and 4 equivalent of phosphorous chloride to the obtained compound (c '). Compound (d ') in the form of a chlorine salt was reacted (ion-exchanged) with lithium bistrifluoromethane sulfonimide to synthesize a compound represented by the following Chemical Formula 25-1.
[Formula 25-1]
[LC / MS data of cations in the compound represented by Formula 25-1]
UPLC / TQMS API + mode, [M] + = 847.63
Synthetic example A-4: Synthesis of Compound (26-1)
Synthesis Example A-3 was synthesized in the same manner as in Synthesis Example A-3 except that a fluoro group was used in place of the methyl group in the substituent group 2,6-dimethylaniline to synthesize a compound represented by the following Formula 26-1 .
[Formula 26-1]
[LC / MS data of cations in the compound represented by Formula 26-1]
UPLC / TQMS API + mode, [M] + = 863.47
Synthetic example A-5: Synthesis of Compound (27-1)
Synthesis Example A-3 was synthesized in the same manner as in Synthesis Example A-3 except that N-isopropylaniline was used in place of N-ethyl-2,6-dimethylaniline as a substituent in the above Synthesis Example A-3, Was synthesized.
[Formula 27-1]
[LC / MS data of cations in the compound represented by the formula (27-1)
UPLC / TQMS API + mode, [M] + = 819.50
Synthetic example A-6: Synthesis of formula (33-1)
An intermediate (a ") having a hydroxy group at the terminal is synthesized using a known synthetic method. Triethylamine (2.2 equivalents) and methacrylic anhydride (2.2 equivalents) are added to the intermediate (a ") to obtain a compound (b") having methacrylate. Compound (d ") is synthesized by adding 1 equivalent of a substituted thiophene compound (c) and 4 equivalents of phosphorus chloride to the resulting compound (b"). Compound (d '') in the form of a chlorine salt was reacted (ion-exchanged) with lithium bistrifluoromethane sulfonimide to synthesize a compound represented by the following formula (33-1).
(33-1)
[LC / MS data of the cations in the compound represented by the formula (33-1)
UPLC / TQMS API + mode, [M] + = 931.58
Synthetic example A-7: Synthesis of Compound (34-1)
Synthesis Example A-6 was synthesized in the same manner as in Synthesis Example A-6 except that a fluoro group was used in place of the methyl group in the substituent group 2,6-dimethylaniline to synthesize a compound represented by the following Formula 34-1 .
(34-1)
[LC / MS data of cations in the compound represented by the formula (34-1)
UPLC / TQMS API + mode, [M] + = 947.30
Synthetic example A-8: Synthesis of Compound (29-1)
An intermediate (a '' ') having a hydroxy group at the terminal is synthesized using a known synthetic method. Triethylamine (1.1 eq.) And methacrylic anhydride (1.1 eq.) Are added to the intermediate (a '' ') to obtain a compound (c' '') having methacrylate. Compound (d '' ') is synthesized by using 1 equivalent of substituted benzophenone compound (b') and 4 equivalents of phosphorous chloride to the obtained compound (c '' '). Compound (d '' ') in the form of a chlorine salt was reacted (ion-exchanged) with lithium bistrifluoromethane sulfonimide to synthesize a compound represented by the following Chemical Formula 29-1.
[Chemical Formula 29-1]
[LC / MS data of the cations in the compound represented by the formula (29-1)
UPLC / TQMS API + mode, [M] + = 923.45
Synthetic example A-9: Synthesis of Compound (30-1)
Synthesis Example A-8 was synthesized in the same manner as in Synthesis Example A-8 except that a fluoro group was used in place of the methyl group in the substituent group 2,6-dimethylaniline to synthesize a compound represented by the following Formula 30-1 .
(30-1)
[LC / MS data of cations in the compound represented by formula (30-1)
UPLC / TQMS API + mode, [M] + = 939.49
Synthetic example A-10: Synthesis of (31-1)
Was synthesized in the same manner as in Synthesis Example A-8 except that N-isopropylaniline was used in place of the substituent N-ethyl-2,6-dimethyl aniline in Synthesis Example A-8 to obtain Was synthesized.
(31-1)
[LC / MS data of cations in the compound represented by the formula (31-1)] [
UPLC / TQMS API + mode, [M] + = 895.53
( Polymer synthesis)
Synthetic example B-1
1.5 g of V-601 (Wako) as an initiator was added to a 100 ml beaker equipped with a stirrer, and then 40% by weight of a dye compound represented by the formula (21-1) in Synthesis Example A-1, 15% by weight of acrylic acid (made by purified gold) and 45% by weight of methyl methacrylate were added in this order. 72 g of Cyclohexanone as a solvent was further added and stirred for 30 minutes until the dye compound and the initiator were completely dissolved to prepare a monomer solution. In order to proceed the polymerization reaction, 54 g of the above solvent was added to a 250 ml glass reactor equipped with a condenser, and the temperature was raised to 85 ° C. Then, the monomer solution was added dropwise to the reactor for 3 hours. After completion of dropwise addition, the reaction was carried out at the same temperature for 9 hours, the temperature was lowered to room temperature, and the reaction was terminated to obtain a polymer.
Polystyrene equivalent weight average molecular weight (Mw) = 9,800 g / mol
Synthetic example B-2
A polymer was obtained in the same manner as in Synthesis Example B-1, except that the compound of Formula 22-1 was used instead of the compound of Formula 21-1.
Polystyrene equivalent weight average molecular weight (Mw) = 10,200 g / mol
Synthetic example B-3
A polymer was obtained in the same manner as in Synthesis Example B-1, except that the compound of Formula 25-1 was used instead of the compound of Formula 21-1.
Polystyrene equivalent weight average molecular weight (Mw) = 9,900 g / mol
Synthetic example B-4
A polymer was obtained in the same manner as in Synthesis Example B-1, except that the compound of Formula 26-1 was used instead of the compound of Formula 21-1.
Polystyrene equivalent weight average molecular weight (Mw) = 10,500 g / mol
Synthetic example B-5
A polymer was obtained in the same manner as in Synthesis Example B-1, except that the compound of Formula 27-1 was used instead of the compound of Formula 21-1.
Polystyrene equivalent weight average molecular weight (Mw) = 10,200 g / mol
Synthetic example B-6
A polymer was obtained in the same manner as in Synthesis Example B-1, except that the compound of Formula 33-1 was used instead of the compound of Formula 21-1.
Polystyrene equivalent weight average molecular weight (Mw) = 11,700 g / mol
Synthetic example B-7
A polymer was obtained in the same manner as in Synthesis Example B-1, except that the compound of Formula 34-1 was used instead of the compound of Formula 21-1.
Polystyrene equivalent weight average molecular weight (Mw) = 12,600 g / mol
Synthetic example B-8
A polymer was obtained in the same manner as in Synthesis Example B-1, except that the compound of Formula 29-1 was used instead of the compound of Formula 21-1.
Polystyrene equivalent weight average molecular weight (Mw) = 10,600 g / mol
Synthetic example B-9
A polymer was obtained in the same manner as in Synthesis Example B-1, except that the compound of Formula 30-1 was used instead of the compound of Formula 21-1.
Polystyrene equivalent weight average molecular weight (Mw) = 10,800 g / mol
Synthetic example B-10
A polymer was obtained in the same manner as in Synthesis Example B-1, except that the compound of Formula 31-1 was used instead of the compound of Formula 21-1.
Polystyrene equivalent weight average molecular weight (Mw) = 10,300 g / mol
While the present invention has been described with reference to the preferred embodiments thereof, it is to be understood that the invention is not limited thereto and that various changes and modifications may be made within the scope of the appended claims, It is natural to belong.
Claims (20)
Wherein the cation is a compound represented by the following Formula 1:
[Chemical Formula 1]
In Formula 1,
R 1 , R 2 , R 6 and R 7 are each independently a hydrogen atom, a substituted or unsubstituted C 1 to C 20 alkyl group, a substituted or unsubstituted C 6 to C 20 aryl group, a substituted or unsubstituted C 2 to C 20 heteroaryl group Or a substituent represented by the following formula (2)
Provided that at least one of R 1 , R 2 , R 6 and R 7 is a substituent represented by the following formula (2)
R 3 and R 4 are each independently a halogen atom or a substituted or unsubstituted C1 to C20 alkyl group,
R < 5 > is a substituted or unsubstituted C6 to C20 aryl group,
X is -O-, -S- or -NR 8 - (R 8 is a hydrogen atom, a substituted or unsubstituted C1 to C10 alkyl group or a substituted or unsubstituted C6 to C20 aryl group)
m and n are each independently an integer of 0 to 5,
(2)
In Formula 2,
L 1 to L 3 are each independently a single bond, a substituted or unsubstituted C1 to C20 alkylene group or a substituted or unsubstituted C6 to C20 arylene group,
R 9 is a hydrogen atom or a substituted or unsubstituted C1 to C10 alkyl group.
Wherein X is -O- or -S-.
Wherein at least two of R 1 , R 2 , R 6 and R 7 are necessarily substituents represented by the general formula (2).
Wherein at least three of R 1 , R 2 , R 6 and R 7 are necessarily substituents represented by the above formula (2).
(2) is a compound represented by the following formula (2-1) or (2-2):
[Formula 2-1]
[Formula 2-2]
In the above Formulas (2-1) and (2-2)
L 4 to L 6 each independently represent a substituted or unsubstituted C1 to C10 alkylene group,
R 9 is a hydrogen atom or a substituted or unsubstituted C1 to C10 alkyl group.
Wherein the cation is represented by the following formula 3 or 4:
(3)
[Chemical Formula 4]
In the above formulas (3) and (4)
R 1 , R 2 , R 6 and R 7 are each independently a hydrogen atom, a substituted or unsubstituted C 1 to C 20 alkyl group, a substituted or unsubstituted C 6 to C 20 aryl group or a substituted or unsubstituted C 2 to C 20 heteroaryl group ego,
R 3 and R 4 are each independently a halogen atom or a substituted or unsubstituted C1 to C20 alkyl group,
R 9 is a hydrogen atom or a substituted or unsubstituted C1 to C10 alkyl group,
R 10 is a halogen atom, a nitro group or a substituted or unsubstituted C1 to C10 alkyl group,
X is -O-, -S- or -NR 8 - (R 8 is a hydrogen atom, a substituted or unsubstituted C1 to C10 alkyl group or a substituted or unsubstituted C6 to C20 aryl group)
m, n and p are each independently an integer of 0 to 5,
L 1 to L 3 are each independently a single bond, a substituted or unsubstituted C1 to C20 alkylene group or a substituted or unsubstituted C6 to C20 arylene group.
Wherein the cation is represented by any one selected from the group consisting of the following Chemical Formulas 5 to 7:
[Chemical Formula 5]
[Chemical Formula 6]
(7)
In the above Chemical Formulas 5 to 7,
R 1 , R 2 , R 6 and R 7 are each independently a hydrogen atom, a substituted or unsubstituted C 1 to C 20 alkyl group, a substituted or unsubstituted C 6 to C 20 aryl group or a substituted or unsubstituted C 2 to C 20 heteroaryl group ego,
R 3 and R 4 are each independently a halogen atom or a substituted or unsubstituted C1 to C20 alkyl group,
R 9 is a hydrogen atom or a substituted or unsubstituted C1 to C10 alkyl group,
R 10 is a halogen atom, a nitro group or a substituted or unsubstituted C1 to C10 alkyl group,
X is -O-, -S- or -NR 8 - (R 8 is a hydrogen atom, a substituted or unsubstituted C1 to C10 alkyl group or a substituted or unsubstituted C6 to C20 aryl group)
m, n and p are each independently an integer of 0 to 5,
L 1 to L 3 are each independently a single bond, a substituted or unsubstituted C1 to C20 alkylene group or a substituted or unsubstituted C6 to C20 arylene group.
The cation is a compound represented by the following general formula (8) or (9):
[Chemical Formula 8]
[Chemical Formula 9]
In the above formulas (8) and (9)
R 2 and R 7 are each independently a hydrogen atom, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C20 heteroaryl group,
R 3 and R 4 are each independently a halogen atom or a substituted or unsubstituted C1 to C20 alkyl group,
R 9 is a hydrogen atom or a substituted or unsubstituted C1 to C10 alkyl group,
R 10 is a halogen atom, a nitro group or a substituted or unsubstituted C1 to C10 alkyl group,
X is -O-, -S- or -NR 8 - (R 8 is a hydrogen atom, a substituted or unsubstituted C1 to C10 alkyl group or a substituted or unsubstituted C6 to C20 aryl group)
m, n and p are each independently an integer of 0 to 5,
L 1 to L 3 are each independently a single bond, a substituted or unsubstituted C1 to C20 alkylene group or a substituted or unsubstituted C6 to C20 arylene group.
Wherein the cation is represented by any one selected from the group consisting of the following Chemical Formulas 10-1 to 10-15:
[Formula 10-1]
[Formula 10-2]
[Formula 10-3]
[Formula 10-4]
[Formula 10-5]
[Formula 10-6]
[Formula 10-7]
[Formula 10-8]
[Chemical Formula 10-9]
[Chemical Formula 10-10]
[Chemical Formula 10-11]
[Chemical Formula 10-12]
[Chemical Formula 10-13]
[Chemical Formula 10-14]
[Chemical Formula 10-15]
In the above Chemical Formulas 10-1 to 10-15,
R 10 and R 11 are each independently a halogen atom, a nitro group or a substituted or unsubstituted C1 to C10 alkyl group,
q1 to q3 each independently represents an integer of 1 to 10,
p and s are each independently an integer of 0 to 5;
Wherein said anion is represented by any one selected from the group consisting of the following formulas (A) to (F).
(A)
[Chemical Formula B]
≪ RTI ID = 0.0 &
PW 12 O 40 3 -
[Chemical Formula D]
SiW 12 O 40 4 -
(E)
CF 3 SO 3 -
[Chemical Formula F]
ClO 4 -
Wherein said compound has a maximum absorbance (? Max ) in the wavelength range of 550 nm to 700 nm.
Wherein the compound has a maximum transmittance (T max ) in a wavelength range of 400 nm to 500 nm.
Wherein the monomer is an ethylenically unsaturated monomer.
Wherein said ethylenically unsaturated monomer is at least one selected from the group consisting of an aromatic vinyl compound, an unsaturated carboxylic acid ester compound, an unsaturated carboxylic acid aminoalkyl ester compound, a carboxylic acid vinyl ester compound, an unsaturated carboxylic acid glycidyl ester compound, a vinyl cyanide compound, an unsaturated amide compound, The polymer is any one selected.
Wherein the polymer is an acrylic polymer.
Wherein the polymer has a weight average molecular weight of from 5,000 g / mol to 100,000 g / mol.
Wherein the coloring agent is a dye.
Wherein the dye is a blue dye.
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