KR101858087B1 - Novel fat-soluble compound, photosensitive resin composition comprising the same, and color filter - Google Patents
Novel fat-soluble compound, photosensitive resin composition comprising the same, and color filter Download PDFInfo
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- KR101858087B1 KR101858087B1 KR1020150087289A KR20150087289A KR101858087B1 KR 101858087 B1 KR101858087 B1 KR 101858087B1 KR 1020150087289 A KR1020150087289 A KR 1020150087289A KR 20150087289 A KR20150087289 A KR 20150087289A KR 101858087 B1 KR101858087 B1 KR 101858087B1
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- YGTVWUPIFQQOHE-WCWDXBQESA-N CCCCN(C(C(C#N)=C1C)=O)C(O)=C1/N=N/c(cc1)cc(C#N)c1C#N Chemical compound CCCCN(C(C(C#N)=C1C)=O)C(O)=C1/N=N/c(cc1)cc(C#N)c1C#N YGTVWUPIFQQOHE-WCWDXBQESA-N 0.000 description 1
- KIHDFIYBROYKNP-QVIHXGFCSA-N Cc(cc1)ccc1N(C(C(C(N1c2ccc(C)cc2)=O)/N=N/c(cc2)cc(C#N)c2C#N)=O)C1=O Chemical compound Cc(cc1)ccc1N(C(C(C(N1c2ccc(C)cc2)=O)/N=N/c(cc2)cc(C#N)c2C#N)=O)C1=O KIHDFIYBROYKNP-QVIHXGFCSA-N 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/06—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton from hydroxy amines by reactions involving the etherification or esterification of hydroxy groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
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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
Abstract
A water-soluble compound represented by the following formula (1), a photosensitive resin composition containing the same, and a color filter manufactured using the photosensitive resin composition.
[Chemical Formula 1]
(Wherein each substituent is as defined in the specification).
Description
The present invention relates to a novel oil-soluble compound, a photosensitive resin composition containing the same, and a color filter.
In a color filter made of a pigment type photosensitive resin composition, there is a limit of luminance and contrast ratio resulting from the pigment particle size. Further, in the case of a color imaging device for an image sensor, a smaller dispersion particle size is required for forming a fine pattern. In order to meet such a demand, attempts have been made to fabricate a photosensitive resin composition in which a dye that does not form particles is introduced instead of a pigment, thereby realizing a color filter having improved color characteristics such as brightness and contrast ratio.
Therefore, it is necessary to study a compound suitable as a dye used in the production of a photosensitive resin composition, particularly a dye compound for dyeing.
One embodiment is to provide a novel lipophilic compound.
Another embodiment is to provide a photosensitive resin composition comprising the above-mentioned fat-soluble compound.
Another embodiment is to provide a color filter manufactured using the photosensitive resin composition.
An embodiment of the present invention provides a fat-soluble compound represented by the following formula (1).
[Chemical Formula 1]
In Formula 1,
R 1 is a cyano group,
R 2 is a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C2 to C20 alkylene group, or a substituted or unsubstituted C6 to C20 aryl group,
n is an integer of 2 to 5 and m is an integer of 0 to 5, provided that 2? n + m? 5,
A is a substituted or unsubstituted C6 to C20 aromatic heterocycle or a substituted or unsubstituted C3 to C20 cycloaliphatic heterocycle.
The aromatic heterocycle and the alicyclic heterocycle may include at least one structure represented by the following formula (2) in the ring.
(2)
The aromatic heterocycle may be represented by the following formula (3).
(3)
In Formula 3,
R 3 is a hydrogen atom, a substituted or unsubstituted C1 to C20 alkyl group, or a substituted or unsubstituted C6 to C20 aryl group,
R 4 to R 6 are each independently a hydrogen atom, a cyano group, a hydroxy group, a substituted or unsubstituted C1 to C20 alkyl group, or a substituted or unsubstituted C6 to C20 aryl group.
R 3 is a substituted or unsubstituted C 1 to C 20 alkyl group or a substituted or unsubstituted C 6 to C 20 aryl group, R 4 is a cyano group, R 5 is a substituted or unsubstituted C 1 to C 20 alkyl group, a substituted or unsubstituted C6 to C20 aryl ring, R 6 may be a hydroxyl group.
The alicyclic heterocycle may be represented by the following formula (4).
[Chemical Formula 4]
In Formula 4,
R 7 and R 8 are each independently a hydrogen atom, a substituted or unsubstituted C1 to C20 alkyl group, or a substituted or unsubstituted C6 to C20 aryl group.
The oil-soluble compound represented by the formula (1) may be represented by any one of the compounds represented by the following formulas (5) to (9).
[Chemical Formula 5]
[Chemical Formula 6]
(7)
[Chemical Formula 8]
[Chemical Formula 9]
The fat-soluble compound may be a yellow dye.
Another embodiment provides a photosensitive resin composition comprising the above-mentioned fat-soluble compound.
The photosensitive resin composition may further include an alkali-soluble resin, a photopolymerizable compound, a photopolymerization initiator, and a solvent.
The photosensitive resin composition may further comprise a pigment.
Another embodiment provides a color filter manufactured using the photosensitive resin composition.
The color filter may be a green color filter or a red color filter.
Other aspects of the present invention are included in the following detailed description.
Soluble compound according to one embodiment has excellent yellow spectral characteristics and a high molar extinction coefficient and is excellent in solubility in an organic solvent and can be used as a coloring dye in the production of a photosensitive resin composition for a color filter, Color filters, especially green color filters, can have excellent luminance and contrast ratios.
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.
Unless otherwise specified herein, "substituted" to "substituted" means that at least one hydrogen atom of the functional group of the present invention is a halogen atom (F, Br, Cl, or I), a hydroxy group, a nitro 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 group), an amidino 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, A substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic group, and 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.
Further, unless otherwise defined in this specification, the " maximum light absorbing region " means a region (range) showing the maximum absorbance.
An embodiment provides a compound represented by the following formula (1).
[Chemical Formula 1]
In Formula 1,
R 1 is a cyano group,
R 2 is a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C2 to C20 alkylene group, or a substituted or unsubstituted C6 to C20 aryl group,
n is an integer of 2 to 5 and m is an integer of 0 to 5, provided that 2? n + m? 5,
A is a substituted or unsubstituted C6 to C20 aromatic heterocycle or a substituted or unsubstituted C3 to C20 cycloaliphatic heterocycle.
The fat-soluble compound according to one embodiment is represented by the formula (1), and the benzene ring of the formula (1) necessarily contains at least two or more cyano groups, so that it can have excellent contrast ratio and brightness while maintaining a wavelength band similar to that of a conventional yellow dye . In addition, it has a similar or shorter wavelength band as compared with the conventional yellow pigment, such as yellow G, and has high heat resistance and coloring power, and is excellent in solubility in organic solvents such as cyclohexanone and PGMEA.
In addition, the compound according to one embodiment is a lipophilic compound having excellent solubility in an organic solvent, and has a different structure and use from a compound containing a water-soluble substituent (e.g., a sulfonic acid group or the like) or a salt thereof.
For example, in Formula 1,
n is an integer of 2, and m may be an integer of 0.
For example, the aromatic heterocyclic ring and the alicyclic heterocyclic ring may contain at least one structure represented by the following formula (2) in the ring.
(2)
For example, the aromatic heterocyclic ring may be represented by the following formula (3).
(3)
In Formula 3,
R 3 is a hydrogen atom, a substituted or unsubstituted C1 to C20 alkyl group, or a substituted or unsubstituted C6 to C20 aryl group,
R 4 to R 6 are each independently a hydrogen atom, a cyano group, a hydroxy group, a substituted or unsubstituted C1 to C20 alkyl group, or a substituted or unsubstituted C6 to C20 aryl group.
For example, the fat-soluble compound represented by Formula 1 may be represented by Formula 1-1 below.
[Formula 1-1]
In Formula 1-1,
R 1 to R 6 , n, and m are as described above.
For example, R 3 is a substituted or unsubstituted C 1 to C 20 alkyl group or a substituted or unsubstituted C 6 to C 20 aryl group, R 4 is a cyano group, and R 5 is a substituted or unsubstituted C 1 to C 20 alkyl group or A substituted or unsubstituted C6 to C20 aryl group, and R < 6 > may be a hydroxy group.
For example, the alicyclic heterocycle may be represented by the following formula (4).
[Chemical Formula 4]
In Formula 4,
R 7 and R 8 are each independently a hydrogen atom, a substituted or unsubstituted C1 to C20 alkyl group, or a substituted or unsubstituted C6 to C20 aryl group.
For example, the fat-soluble compound represented by Formula 1 may be represented by Formula 1-2.
[Formula 1-2]
In Formula 1-2,
R 1 , R 2 , R 7 , R 8 , n, and m are as described above.
The oil-soluble compound represented by the formula (1) contains an aromatic heterocyclic ring represented by the formula (3) or an alicyclic heterocyclic ring represented by the formula (4) in addition to at least two cyano groups, Absorbing region, and can have excellent heat resistance and coloring power.
For example, the oil-soluble compound represented by the formula (1) may be represented by one of the compounds represented by the following formulas (5) to (9).
[Chemical Formula 5]
[Chemical Formula 6]
(7)
[Chemical Formula 8]
[Chemical Formula 9]
The oil-soluble compound according to one embodiment is a compound represented by the above formula (1), for example, a compound represented by the formula (1-1) or (1-2), and a clear color can be expressed with a small amount. It is possible to manufacture a display device having excellent color characteristics such as luminance and contrast ratio. For example, the oil-soluble compound may be a yellow dye, for example, a dye having a maximum light absorption region in a wavelength range of 150 nm to 450 nm, for example, 350 nm to 450 nm.
For example, the oil-soluble compound represented by Formula 1-1 (in Formula 1, A is an aromatic heterocycle and the aromatic heterocycle is a lipophilic compound represented by Formula 3) has a maximum absorption region in a wavelength range of 400 nm to 450 nm, Soluble lipophilic compound represented by Formula 1-2, wherein A is an alicyclic heterocycle and the alicyclic heterocycle is a lipophilic compound represented by Formula 4, is 150 nm to 400 nm, for example, And may have a maximum light absorption region in a wavelength range of 350 nm to 400 nm.
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 oil-soluble compound according to one embodiment is used as a dye in a color filter, for example, a coloring dye, it is possible to achieve excellent color characteristics such as high luminance and high contrast ratio even in a small amount, thereby reducing the production cost.
According to another embodiment, there is provided a photosensitive resin composition comprising a fat-soluble compound according to one embodiment.
For example, the photosensitive resin composition may include a water-soluble compound, an alkali-soluble resin, a photopolymerizable compound, a photopolymerization initiator, and a solvent according to one embodiment.
The photosensitive resin composition may further comprise a pigment.
The oil-soluble compound according to one embodiment of the present invention functions as a coloring agent such as a dye, for example, a yellow coloring dye in the photosensitive resin composition, and can exhibit excellent color characteristics.
The fat-soluble compound according to one embodiment may be included in an amount of 1 wt% to 10 wt%, for example, 3 wt% to 7 wt% with respect to the total amount of the photosensitive resin composition. When the compound according to one embodiment is included in the above range, the color reproducibility and the contrast ratio are excellent .
The pigments may include, but are not limited to, yellow pigments, green pigments, red pigments, or combinations thereof. For example, the pigment may be included in the photosensitive resin composition in the form of a pigment dispersion.
The pigment dispersion may include a solid pigment, a solvent, and a dispersant for uniformly dispersing the pigment in the solvent.
The solid pigment may be present in the pigment dispersion in an amount ranging from 1% to 20%, such as 8% to 20%, such as 15% to 20%, such as 8% to 15% 20% by weight, such as 10% by weight to 15% by weight.
As the dispersing agent, a nonionic dispersing agent, an anionic dispersing agent, a cationic dispersing agent and the like can be used. Specific examples of the dispersing agent include polyalkylene glycols and esters thereof, polyoxyalkylene, polyhydric alcohol ester alkylene oxide adduct, alcohol alkylene oxide adduct, sulfonic acid ester, sulfonic acid salt, carboxylic acid ester, carboxylic acid Salts, alkylamide alkylene oxide adducts, and alkylamines. These may be used singly or in combination of two or more.
DISPERBYK-161, DISPERBYK-160, DISPERBYK-160, DISPERBYK-161, DISPERBYK-162, DISPERBYK-163, DISPERBYK-164, DISPERBYK-160, DISPERBYK-130, DISPERBYK- -166, DISPERBYK-170, DISPERBYK-171, DISPERBYK-182, DISPERBYK-2000, DISPERBYK-2001 and the like; EFKA-47, EFKA-47EA, EFKA-48, EFKA-49, EFKA-100, EFKA-400 and EFKA-450 of EFKA Chemical Co., Solsperse 5000, Solsperse 12000, Solsperse 13240, Solsperse 13940, Solsperse 17000, Solsperse 20000, Solsperse24000GR, Solsperse 27000, Solsperse 28000 from Zeneka; Or Ajinomoto's PB711 and PB821.
The dispersing agent may be contained in an amount of 1 to 20% by weight based on the total amount of the pigment dispersion. When the dispersing agent is contained within the above range, the dispersibility of the photosensitive resin composition can be maintained because an appropriate viscosity can be maintained, so that optical, physical and chemical quality can be maintained when the product is applied.
As the solvent for forming the pigment dispersion, ethylene glycol acetate, ethyl cellosolve, propylene glycol monomethyl ether acetate, ethyl lactate, polyethylene glycol, cyclohexanone, propylene glycol methyl ether and the like can be used.
The pigment dispersion may be contained in an amount of 5% by weight to 30% by weight, for example, 10% by weight to 25% by weight based on the total amount of the photosensitive resin composition. When the pigment dispersion is contained within the above range, it is advantageous in securing a process margin and excellent color reproduction ratio and contrast ratio.
The alkali-soluble resin may be an acrylic resin.
The acrylic resin is a copolymer of a first ethylenically unsaturated monomer and a second ethylenically unsaturated monomer copolymerizable with the first ethylenically unsaturated monomer, and may be a resin containing at least one acrylic repeating unit.
The first ethylenically unsaturated monomer is an ethylenically unsaturated monomer containing at least one carboxyl group, and specific examples thereof include acrylic acid, methacrylic acid, maleic acid, itaconic acid, fumaric acid, and combinations thereof.
The first ethylenically unsaturated monomer may be included in an amount of 5% by weight to 50% by weight, for example, 10% by weight to 40% by weight based on the total amount of the acrylic binder resin.
The second 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; These may be used singly or in combination of two or more.
Specific examples of the acrylic binder resin include polybenzyl methacrylate copolymer, (meth) acrylic acid / benzyl methacrylate copolymer, (meth) acrylic acid / benzyl methacrylate / styrene copolymer, (meth) acrylic acid / benzyl methacrylate (Meth) acrylic acid / benzyl methacrylate / styrene / 2-hydroxyethyl methacrylate copolymer, but are not limited thereto, and they may be used alone or in combination of two or more. Two or more kinds may be used in combination.
The weight-average molecular weight of the alkali-soluble resin may be from 3,000 g / mol to 150,000 g / mol, such as from 5,000 g / mol to 50,000 g / mol, such as from 20,000 g / mol to 30,000 g / mol. When the weight average molecular weight of the alkali-soluble resin is within the above range, the photosensitive resin composition has excellent physical and chemical properties, is suitable in viscosity, and has excellent adhesion with a substrate in the production of a color filter.
The acid value of the alkali-soluble resin may be from 15 mgKOH / g to 60 mgKOH / g, for example, from 20 mgKOH / g to 50 mgKOH / g. When the acid value of the alkali-soluble resin is within the above range, the resolution of the pixel pattern is excellent.
The alkali-soluble resin may be contained in an amount of 1% by weight to 30% by weight, for example, 1% by weight to 15% by weight based on the total amount of the photosensitive resin composition. When the alkali-soluble resin is contained within the above-mentioned range, the color filter is excellent in developability in the production of a color filter, and the cross-linkability is improved, whereby excellent surface smoothness can be obtained.
The photopolymerizable compound may be a monofunctional or polyfunctional ester of (meth) acrylic acid having at least one ethylenically unsaturated double bond.
By having the ethylenically unsaturated double bond, the photopolymerizable compound can form a pattern having excellent heat resistance, light resistance and chemical resistance by causing sufficient polymerization during exposure in the pattern formation step.
Specific examples of the photopolymerizable compound include ethylene glycol di (meth) acrylate, diethylene glycol di (meth) acrylate, triethylene glycol di (meth) acrylate, propylene glycol di (meth) acrylate, neopentyl glycol di (Meth) acrylate, 1,6-hexanediol di (meth) acrylate, bisphenol A di (meth) acrylate, pentaerythritol di (meth) acrylate, (Meth) acrylate, pentaerythritol tri (meth) acrylate, pentaerythritol tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, pentaerythritol hexa (Meth) acrylate, dipentaerythritol hexa (meth) acrylate, bisphenol A epoxy (meth) acrylate, ethylene glycol monomethacrylate (Meth) acrylate, trimethylolpropane tri (meth) acrylate, tris (meth) acryloyloxyethyl phosphate, novolac epoxy (meth) acrylate and the like.
Examples of commercially available products of photopolymerizable compounds are as follows. The (meth) acrylic acid is one example of a polyfunctional ester, such as doah Gosei Kagaku Kogyo's (primary)社Aronix M-101 ®, the same M-111 ®, the same M-114 ®; KAYARAD TC-110S ® and TC-120S ® from Nihon Kayaku Co., Ltd.; Osaka yukki the like Kagaku Kogyo (main)社of V-158 ®, V-2311 ®. The (meth) transfer function of an example esters of acrylic acid are, doah Gosei Kagaku Kogyo (Note)社of Aronix M-210 ®, copper or the like M-240 ®, the same M-6200 ®; KAYARAD HDDA ® , HX-220 ® and R-604 ® from Nihon Kayaku Corporation; Osaka yukki the like Kagaku Kogyo Co., Ltd. of 社V-260 ®, V- 312 ®, V-335 HP ®. Examples of the tri-functional ester of (meth) acrylic acid, doah Gosei Kagaku Kogyo (Note)社of Aronix M-309 ®, the same M-400 ®, the same M-405 ®, the same M-450 ®, Dong M -710 ® , copper M-8030 ® , copper M-8060 ® and the like; Nippon Kayaku (Note)社of KAYARAD TMPTA ®, copper DPCA-20 ®, ® copper -30, -60 ® copper, copper ® -120 and the like; Osaka yukki Kayaku high (primary)社of V-295 ®, copper ® -300, -360 ® copper, copper -GPT ®, copper -3PA ®, and the like copper -400 ®. These products may be used alone or in combination of two or more.
The photopolymerizable compound may be treated with an acid anhydride so as to give better developing properties.
The photopolymerizable compound may be contained in an amount of 1 wt% to 15 wt%, for example, 5 wt% to 10 wt% with respect to the total amount of the photosensitive resin composition. When the photopolymerizable compound is contained within the above-mentioned range, the pattern forming process sufficiently cures upon exposure to light, which is excellent in reliability and developability in an alkaline developer.
The photopolymerization initiator may be, for example, an acetophenone-based compound, a benzophenone-based compound, a thioxanthone-based compound, a benzoin-based compound, an oxime-based compound, or a combination thereof as an initiator generally used in a photosensitive resin composition .
Examples of the acetophenone-based compound include 2,2'-diethoxyacetophenone, 2,2'-dibutoxyacetophenone, 2-hydroxy-2-methylpropiophenone, pt-butyltrichloroacetophenone, dichloro-4-phenoxyacetophenone, 2-methyl-1- (4- (methylthio) phenyl) -2-morpholinopropanone, p-butyldichloroacetophenone, 1-one, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butan-1-one.
Examples of the benzophenone compound include benzophenone, benzoyl benzoic acid, methyl benzoyl benzoate, 4-phenylbenzophenone, hydroxybenzophenone, acrylated benzophenone, 4,4'-bis (dimethylamino) benzophenone, '-Bis (diethylamino) benzophenone, 4,4'-dimethylaminobenzophenone, 4,4'-dichlorobenzophenone, and 3,3'-dimethyl-2-methoxybenzophenone.
Examples of the thioxanthone compound include thioxanthone, 2-methylthioxanthone, isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-diisopropylthioxanthone, 2- Chlorothioxanthone and the like.
Examples of the benzoin compound include benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl ether, and benzyl dimethyl ketal.
Examples of the triazine-based compound include 2,4,6-trichloro-s-triazine, 2-phenyl 4,6-bis (trichloromethyl) (Trichloromethyl) -s-triazine, 2- (4'-methoxynaphthyl) -4,6-bis (trichloromethyl) Bis (trichloromethyl) -s-triazine, 2- (p-tolyl) -4,6-bis (trichloromethyl) Bis (trichloromethyl) -s-triazine, bis (trichloromethyl) -6-styryl-s-triazine, 2- (naphtho- Bis (trichloromethyl) -s-triazine, 2- (4-methoxynaphtho-1-yl) (Trichloromethyl) -6- (4-methoxystyryl) -s-triazine, and the like.
Examples of the oxime compounds include O-acyloxime compounds, 2- (o-benzoyloxime) -1- [4- (phenylthio) phenyl] -1,2-octanedione, 1- ) -1- [9-ethyl-6- (2-methylbenzoyl) -9H-carbazol-3-yl] ethanone, O-ethoxycarbonyl- Etc. may be used. Specific examples of the O-acyloxime-based compound include 1,2-octanedione, 2-dimethylamino-2- (4-methylbenzyl) -1- (4-morpholin- (4-phenylsulfanylphenyl) -butane-1,2-dione 2-oxime-O-benzoate, 1- -Oxime-O-benzoate, 1- (4-phenylsulfanylphenyl) -octane-1-one oxime-O-acetate and 1- (4-phenylsulfanylphenyl) Acetate and the like.
The photopolymerization initiator may be a carbazole compound, a diketone compound, a sulfonium borate compound, a diazo compound, an imidazole compound, or a nonimidazole compound in addition to the above compounds.
The photopolymerization initiator may be used in combination with a photosensitizer that generates a chemical reaction by absorbing light to be in an excited state and transferring its energy.
Examples of the photosensitizer include tetraethylene glycol bis-3-mercaptopropionate, pentaerythritol tetrakis-3-mercaptopropionate, dipentaerythritol tetrakis-3-mercaptopropionate and the like .
The photopolymerization initiator may be included in an amount of 0.01 wt% to 10 wt%, for example, 0.1 wt% to 5 wt% with respect to the total amount of the photosensitive resin composition. When the photopolymerization initiator is contained within the above range, the photopolymerization initiator is sufficiently cured upon exposure in the pattern formation step to obtain excellent reliability, and the pattern is excellent in heat resistance, light resistance, chemical resistance, resolution and adhesion, It is possible to prevent the transmittance from being lowered.
The solvent may be a lipophilic compound, a pigment, an alkali-soluble resin, a photopolymerizable compound, and a material that does not react with the photopolymerization initiator but does not react with the photopolymerization initiator. The solvent may be an organic solvent or a solvent.
Examples of the solvent include alcohols such as methanol and ethanol; Ethers such as dichloroethyl ether, n-butyl ether, diisobutyl ether, methylphenyl ether and tetrahydrofuran; Glycol ethers such as ethylene glycol monomethyl ether and ethylene glycol monoethyl ether; Cellosolve acetates such as methyl cellosolve acetate, ethyl cellosolve acetate and diethyl cellosolve acetate; Carbitols such as methylethylcarbitol, diethylcarbitol, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol dimethyl ether, diethylene glycol methyl ethyl ether and diethylene glycol diethyl ether; Propylene glycol alkyl ether acetates such as propylene glycol methyl ether acetate and propylene glycol propyl ether acetate; Aromatic hydrocarbons such as toluene and xylene; Ketones such as methyl ethyl ketone, cyclohexanone, 4-hydroxy-4-methyl-2-pentanone, methyl-n-propyl ketone, methyl- ; Saturated aliphatic monocarboxylic acid alkyl esters such as ethyl acetate, n-butyl acetate and isobutyl acetate; Lactic acid esters such as methyl lactate and ethyl lactate; Oxyacetic acid alkyl esters such as methyl oxyacetate, ethyl oxyacetate and butyl oxyacetate; Alkoxyacetic acid alkyl esters such as methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, and ethyl ethoxyacetate; 3-oxypropionic acid alkyl esters such as methyl 3-oxypropionate and ethyl 3-oxypropionate; 3-alkoxypropionic acid alkyl esters such as methyl 3-methoxypropionate, ethyl 3-methoxypropionate, ethyl 3-ethoxypropionate and methyl 3-ethoxypropionate; 2-oxypropionic acid alkyl esters such as methyl 2-oxypropionate, ethyl 2-oxypropionate and propyl 2-oxypropionate; 2-alkoxypropionic acid alkyl esters such as methyl 2-methoxypropionate, ethyl 2-methoxypropionate, ethyl 2-ethoxypropionate and methyl 2-ethoxypropionate; 2-methylpropionic acid esters such as methyl 2-oxy-2-methylpropionate and ethyl 2-oxy-2-methylpropionate, methyl 2-methoxy- Monooximonocarboxylic acid alkyl esters of 2-alkoxy-2-methylpropionic acid alkyls such as ethyl methyl propionate; Esters such as ethyl 2-hydroxypropionate, ethyl 2-hydroxy-2-methylpropionate, ethyl hydroxyacetate and methyl 2-hydroxy-3-methylbutanoate; Ketone acid esters such as ethyl pyruvate, and the like, and also include N-methylformamide, N, N-dimethylformamide, N-methylformanilide, N-methylacetamide, N, N-dimethylacetamide , N-methylpyrrolidone, dimethylsulfoxide, benzyl ethyl ether, dihexyl ether, acetylacetone, isophorone, caproic acid, caprylic acid, 1-octanol, 1-nonanol, benzyl alcohol, benzyl acetate, And high boiling solvents such as ethyl acetate, diethyl oxalate, diethyl maleate,? -Butyrolactone, ethylene carbonate, propylene carbonate, and phenyl cellosolve acetate.
Among them, glycol ethers such as ethylene glycol monoethyl ether and the like are preferably used in consideration of compatibility and reactivity; Ethylene glycol alkyl ether acetates such as ethyl cellosolve acetate; Esters such as ethyl 2-hydroxypropionate; Carbitols such as diethylene glycol monomethyl ether; Propylene glycol alkyl ether acetates such as propylene glycol monomethyl ether acetate and propylene glycol propyl ether acetate can be used.
The solvent may be contained in an amount of 30% by weight to 80% by weight based on the total amount of the photosensitive resin composition. When the solvent is contained within the above range, the photosensitive resin composition has an appropriate viscosity, and thus the processability in the production of the color filter is excellent.
The photosensitive resin composition according to another embodiment may further include an epoxy compound to improve adhesion with the substrate.
Examples of the epoxy compound include a phenol novolak epoxy compound, a tetramethylbiphenyl epoxy compound, a bisphenol A type epoxy compound, an alicyclic epoxy compound, or a combination thereof.
The epoxy compound may be contained in an amount of 0.01 to 20 parts by weight, for example, 0.1 to 10 parts by weight based on 100 parts by weight of the photosensitive resin composition. When the epoxy compound is contained within the above range, the adhesiveness and storage stability are excellent.
The photosensitive resin composition may further include a silane coupling agent having a reactive substituent such as a carboxyl group, a methacryloyl group, an isocyanate group or an epoxy group in order to improve the adhesiveness to the substrate.
Examples of the silane coupling agent include trimethoxysilylbenzoic acid,? -Methacryloxypropyltrimethoxysilane, vinyltriacetoxysilane, vinyltrimethoxysilane,? -Isocyanatepropyltriethoxysilane,? -Glycidoxine (3,4-epoxycyclohexyl) ethyltrimethoxysilane, etc. These may be used alone or in combination of two or more.
The silane coupling agent may be contained in an amount of 0.01 to 10 parts by weight based on 100 parts by weight of the photosensitive resin composition. When the silane coupling agent is contained within the above range, the adhesion and storage stability are excellent.
The above-mentioned photosensitive resin composition may further contain a surfactant for improving coatability and preventing defect formation if necessary.
Examples of the surfactants include, BM Chemie BM-1000 ® of社, BM-1100 ®, and the like; Mechacup F 142D ® , copper F 172 ® , copper F 173 ® , copper F 183 ® and the like manufactured by Dainippon Ink & Chemicals Incorporated; Sumitomo M. (Note)社Pro rod FC-135 ®, the same FC-170C ®, copper FC-430 ®, the same FC-431 ®, and the like; Asahi Grass Co., Saffron S-112 ® of社, such S-113 ®, the same S-131 ®, the same S-141 ®, the same S-145 ®, and the like; Toray silicone (Note)社SH-28PA ®, copper -190 ®, may be used copper ® -193, fluorine-based surfactants and commercially available under the name, such as SZ-6032 ®, SF-8428 ®.
The surfactant may be used in an amount of 0.001 part by weight to 5 parts by weight based on 100 parts by weight of the photosensitive resin composition. When the surfactant is contained within the above range, uniformity of coating is ensured, no staining occurs, and wetting of the glass substrate is excellent.
The photosensitive resin composition may contain a certain amount of other additives such as an antioxidant and a stabilizer within a range that does not impair the physical properties.
According to another embodiment, there is provided a color filter manufactured using the photosensitive resin composition according to one embodiment.
The color filter may be a green color filter or a red color filter, but is not limited thereto.
The pattern forming process in the color filter 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.
EXAMPLES Hereinafter, the present invention will be described in more detail with reference to Examples. However, the following Examples are only the preferred embodiments of the present invention, and the present invention is not limited to the following Examples.
(Synthesis of a fat-soluble compound)
Synthetic example 1: Synthesis of a lipid-soluble compound represented by the formula (5)
4-Aminophthalonitrile (2.5 mmol) was added with hydrochloric acid (2.5 mL) and sodium nitrate (2 mL of 1.25 M aqueous solution) to give an azonium ion. The pyridone compound (2.5 mmol) substituted with 2-ethylhexyl group NaOH aqueous solution to prepare an azo compound. At this time, the obtained solid was filtered, purified and vacuum-dried to obtain a fat-soluble compound represented by the following formula (5).
[Chemical Formula 5]
1 H NMR (300 MHz, CDCl 3 ) 7.88-7.85 (2H), 7.73-7.69 (1H), 3.87 (2H), 2.60 (3H), 1.79 (1H), 1.40-1.15 (8H), 0.93-0.88 6H).
GC / MS 416 m / z.
Synthetic example 2: Synthesis of the oil-soluble compound represented by the formula (6)
3-Aminophthalonitrile (2.5 mmol) was added with hydrochloric acid (2.5 mL) and sodium nitrate (1.25M aqueous solution, 2 mL) to give an azonium ion. The pyridone compound (2.5 mmol) substituted with 2-ethylhexyl group NaOH aqueous solution to prepare an azo compound. At this time, the obtained solid was filtered, purified and vacuum-dried to obtain a fat-soluble compound represented by the following formula (6).
[Chemical Formula 6]
GC / MS 416 m / z.
Synthetic example 3: Synthesis of the oil-soluble compound represented by the formula (7)
4-Aminophthalonitrile (2.5 mmol) was added with hydrochloric acid (2.5 mL) and sodium nitrate (1.25M aqueous solution, 2 mL) to prepare an azonium ion. The pyridone compound (2.5 mmol) substituted with n-butyl group was dissolved in an aqueous solution of NaOH In a weak basic aqueous solution to prepare an azo compound. At this time, the obtained solid was filtered, purified and vacuum-dried to obtain a fat-soluble compound represented by the following formula (7).
(7)
1 H NMR (300 MHz, CDCl 3 ) 7.88-7.85 (2H), 7.73-7.69 (1H), 3.86 (2H), 2.60 (3H), 1.50-1.12 (4H), 0.96-0.92 (3H).
Synthetic example 4: Synthesis of the oil-soluble compound represented by the formula (8)
4-Aminophthalonitrile (2.5 mmol) was added with hydrochloric acid (2.5 mL) and sodium nitrate (1.25M aqueous solution, 2 mL) to make an azonium ion. This was added to a weakly basic aqueous solution of barbituric acid (2.5 mmol) Azo compound. The resulting solid was filtered, purified and vacuum-dried, and then 1-iodobutane (5.5 mmol) and potassium carbonate (7.5 mmol) were added thereto. The reaction was carried out in a DMF solvent, followed by purification and vacuum drying to obtain a fat-
[Chemical Formula 8]
1 H NMR (300 MHz, CDCl 3 ) 14.3 (1H), 7.95-7.94 (1H), 7.86-7.80 (2H), 4.03-3.87 (4H), 1.78-1.62 (4H), 1.46-1.36 1.01-0.94 (6H).
Synthetic example 5: Synthesis of the oil-soluble compound represented by the formula (9)
4-Aminophthalonitrile (2.5 mmol) was added with hydrochloric acid (2.5 mL) and sodium nitrate (1.25M aqueous solution, 2 mL) to make an azonium ion. This was added to a weakly basic aqueous solution of barbituric acid (2.5 mmol) Azo compound. The resulting solid was filtered, purified and vacuum-dried, and 4-iodotoluene (5.5 mmol) and potassium carbonate (7.5 mmol) were added thereto, followed by reaction in DMF solvent, purification, and vacuum drying to obtain a fat-
[Chemical Formula 9]
1 H NMR (300 MHz, CDCl 3 ) 14.3 (1H), 7.95-7.94 (1H), 7.86-7.80 (2H), 7.21 (2H), 7.06 (2H), 2.36
compare Synthetic example 1: To 10 Synthesis of displayed compounds
4-Aminophenol (2.5 mmol) was added with hydrochloric acid (2.5 mL) and sodium nitrate (1.25 M aqueous solution, 2 mL) to make an azonium ion. This was added to a weakly basic aqueous solution of barbituric acid (2.5 mmol) Azo compound. The resulting solid was filtered, purified and vacuum-dried, and then 1-iodobutane (5.5 mmol) and potassium carbonate (7.5 mmol) were added thereto, followed by reaction in DMF solvent, purification, and vacuum drying to obtain a fat-
[Chemical formula 10]
GC / MS 360 m / z.
compare Synthetic example 2: Synthesis of Compound Represented by Formula 11
Aniline (2.5 mmol) was added with hydrochloric acid (2.5 mL) and sodium nitrate (1.25M aqueous solution, 2 mL) to give an azonium ion. The pyridone compound (2.5 mmol) substituted with a 2-ethylhexyl group was dissolved in an aqueous solution of NaOH In a weak basic aqueous solution to prepare an azo compound. At this time, the obtained solid was filtered, purified and vacuum-dried to obtain a fat-soluble compound represented by the following formula (11).
(11)
1 H NMR (300 MHz, CDCl 3 ) 7.53 (2H), 7.44 (2H), 7.36 (1H), 3.87 (2H), 2.60 (3H), 1.79 (6H).
compare Synthetic example 3: Synthesis of the compound represented by the formula (12)
Aniline (2.5 mmol) was added with hydrochloric acid (2.5 mL) and sodium nitrate (1.25 M aqueous solution, 2 mL) to make an azonium ion. The azo compound was added to a weakly basic aqueous solution in which barbituric acid (2.5 mmol) . The resulting solid was filtered, purified and vacuum-dried, and then 1-iodobutane (5.5 mmol) and potassium carbonate (7.5 mmol) were added thereto, followed by reaction in DMF solvent, purification, and vacuum drying to obtain a fat-
[Chemical Formula 12]
1 H NMR (300 MHz, CDCl 3 ) 14.1 (1H), 7.71 (2H), 7.59 (2H), 7.46 (1H), 4.03-3.87 (4H), 1.78-1.62 , 1.01-0.94 (6H).
(evaluation)
Evaluation 1: Solubility of organic solvent
Diluted solvent (Anone) was added to 0.5 g of the compound synthesized in Synthesis Examples 1 to 5 and Comparative Synthesis Examples 1 to 3, and the solution was mixed with a mix rotor (MIXROTAR VMR-5) After stirring at 25 DEG C and 100 rpm for 1 hour, the solubility of each compound was determined. (Anone means cyclohexanone.)
Solubility evaluation criteria
2.5% by weight or more of the compound (solute) dissolved in the total amount of the diluting solvent: ○
Less than 2.5% by weight of compound (solute) dissolved in total diluent solvent Dissolution: X
It can be seen from Table 1 that the compounds of Synthesis Examples 1 to 5 which are the compounds according to one embodiment are superior to the compounds of Comparative Synthesis Examples 1 to 3 in solubility in an organic solvent, It can be confirmed that the color characteristics can be expressed.
Evaluation 2: Coloring power
The maximum absorption wavelength (? Max ) of the compounds synthesized in Synthesis Examples 1 to 5 and Comparative Synthesis Examples 1 to 3 was measured with a UV-1800 UV-Vis spectrometer and is shown in Table 2 below. 20 mg of the compound synthesized in Synthesis Examples 1 to 5 and Comparative Synthesis Examples 1 to 3 was dissolved in anion (cyclohexanone) to make 20 g of a concentrated solution. Then, 0.1 g of the concentrated solution was added again to 10 g to make a 0.001 wt% dilute solution. The spectroscopic measurement of the 0.001% by weight solution at room temperature was carried out, and the molar extinction coefficient was calculated from the following equation (1).
[Equation 1]
A = ecl
(A: maximum absorbance, e: molar extinction coefficient, c: molar concentration, l: optical path length)
It can be seen from Table 2 that unlike the compounds of Comparative Synthesis Examples 1 to 3, the compounds of Synthesis Examples 1 to 5, which are compounds according to one embodiment, contain a cyano group, It can be confirmed that it has better coloring power.
While the present invention has been particularly shown and described with reference to exemplary embodiments thereof, it is to be understood that the invention is not limited to the disclosed exemplary embodiments, but, on the contrary, And it goes without saying that the invention belongs to the scope of the invention.
Claims (12)
[Chemical Formula 1]
[Chemical Formula 5]
[Chemical Formula 6]
(7)
In Formula 1,
R 1 is a cyano group,
R 2 is a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C2 to C20 alkenyl group, or a substituted or unsubstituted C6 to C20 aryl group,
n is an integer of 2 to 5 and m is an integer of 0 to 5, provided that 2? n + m? 5,
A is an alicyclic heterocycle represented by the following formula (4)
[Chemical Formula 4]
In Formula 4,
R 7 and R 8 are each independently a hydrogen atom, a substituted or unsubstituted C1 to C20 alkyl group, or a substituted or unsubstituted C6 to C20 aryl group.
The fat-soluble compound represented by the formula (1) is represented by the following formula (8) or (9).
[Chemical Formula 8]
[Chemical Formula 9]
Wherein said oil-soluble compound is a yellow dye.
Wherein the photosensitive resin composition further comprises an alkali-soluble resin, a photopolymerizable compound, a photopolymerization initiator, and a solvent.
Wherein the photosensitive resin composition further comprises a pigment.
Wherein the color filter is a green color filter or a red color filter.
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| KR1020150087289A KR101858087B1 (en) | 2015-06-19 | 2015-06-19 | Novel fat-soluble compound, photosensitive resin composition comprising the same, and color filter |
| PCT/KR2015/008104 WO2016204337A1 (en) | 2015-06-19 | 2015-08-03 | Novel oil-soluble compound, photosensitive resin composition containing same, and color filter |
| CN201580080997.9A CN107801394A (en) | 2015-06-19 | 2015-08-03 | Fat-soluble compound, the photosensitive resin composition and colored filter containing the compound of novelty |
| TW105106822A TWI585078B (en) | 2015-06-19 | 2016-03-07 | Novel fat-soluble compound, photosensitive resin composition comprising the same and color filter |
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| JP2012208474A (en) | 2011-03-14 | 2012-10-25 | Jsr Corp | Colored composition for color filter, color filter and display element |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CH555932A (en) * | 1971-05-25 | 1974-11-15 | ||
| DE2163378A1 (en) * | 1971-12-21 | 1973-06-28 | Bayer Ag | Yellow azo dyes contg substd 6-hydroxy-2-pyridone residues - for dyeing/printing hydrophobic fibres, eg polyesters |
| DE2340569C2 (en) * | 1973-08-10 | 1982-12-02 | Bayer Ag, 5090 Leverkusen | Azo dyes |
| DE2516032C2 (en) * | 1975-04-12 | 1984-10-04 | Bayer Ag, 5090 Leverkusen | Process for diazotizing aromatic amines |
| JPS6044556A (en) * | 1983-08-22 | 1985-03-09 | Nippon Kayaku Co Ltd | Water-insoluble monoazo compound and dyeing using it |
| JPH05142863A (en) * | 1991-11-18 | 1993-06-11 | Ricoh Co Ltd | Electrophotographic toner |
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| TW201700460A (en) | 2017-01-01 |
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