WO2016204337A1 - Novel oil-soluble compound, photosensitive resin composition containing same, and color filter - Google Patents

Novel oil-soluble compound, photosensitive resin composition containing same, and color filter Download PDF

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Publication number
WO2016204337A1
WO2016204337A1 PCT/KR2015/008104 KR2015008104W WO2016204337A1 WO 2016204337 A1 WO2016204337 A1 WO 2016204337A1 KR 2015008104 W KR2015008104 W KR 2015008104W WO 2016204337 A1 WO2016204337 A1 WO 2016204337A1
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Prior art keywords
substituted
group
unsubstituted
fat
soluble compound
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PCT/KR2015/008104
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French (fr)
Korean (ko)
Inventor
최은정
박채원
신명엽
정의수
Original Assignee
삼성에스디아이 주식회사
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Priority to CN201580080997.9A priority Critical patent/CN107801394A/en
Publication of WO2016204337A1 publication Critical patent/WO2016204337A1/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/84—Nitriles
    • C07D213/85—Nitriles in position 3
    • 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
    • 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
    • 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
    • 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
    • C07D239/60—Three or more oxygen or sulfur atoms
    • 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

Definitions

  • Novel fat-soluble compound, photosensitive resin composition and color filter comprising same
  • the present disclosure relates to a novel fat-soluble compound, a photosensitive resin composition and a color filter comprising the same.
  • One embodiment is to provide novel fat-soluble compounds.
  • Another embodiment is to provide a photosensitive resin composition comprising the fat-soluble compound.
  • Yet another embodiment is to provide a color filter manufactured using the photosensitive resin composition.
  • One embodiment of the present invention provides a fat-soluble compound represented by the following 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 from 2 to 5
  • m is an integer from 0 to 5, provided that 2 ⁇ n + m ⁇ 5,
  • A is a substituted or unsubstituted C6 to C20 aromatic hetero ring or a substituted or unsubstituted C3 to C20 alicyclic hetero ring.
  • the aromatic hetero ring and alicyclic hetero ring may include at least one structure represented by the following Formula 2 in a sing-group ring.
  • the aromatic hetero ring may be represented by the following 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 hydrogen, a cyano group, a hydroxy group, a substituted or unsubstituted C1 to C20 alkyl group, or a substituted or unsubstituted C6 to C20 aryl groupidi-, xing-group
  • R 3 is a substituted or unsubstituted C1 to C20 alkyl group or a substituted or unsubstituted C6 to C20 aryl group
  • R 4 is a cyano group
  • R 5 is a substituted or unsubstituted C1 to C20 alkyl group or a substituted or unsubstituted C6 To C20 aryl group
  • R 6 may be a hydroxy group-.
  • the alicyclic hetero ring may be represented by the following formula (4).
  • R 7 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 Chemical Formula 1 may be represented by any one of compound compounds represented by Chemical Formulas 5 to 9.
  • the fat soluble compound may be a yellow dye.
  • Another embodiment provides a photosensitive resin composition comprising the oil-soluble compound.
  • the photosensitive resin composition may further include an alkali-soluble resin, a photopolymerizable compound, a photopolymerization initiator, and a solvent.
  • the sing-group photosensitive resin composition may further include 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.
  • substituted to "substituted” means that one or more hydrogen atoms of the functional group increase of the present Bill's name are halogen atoms (F, Br, Cl or I), hydroxy groups, nitro groups, cyano groups, Amino groups (NH 2 , NH (R 200 ) or N (R 20 l ) (R 202 ), where 200 , R 201 and R 202 are the same or different from each other, and are each independently C1 to C10 alkyl groups, amidino Groups, hydrazine groups, hydrazone groups, carboxyl groups, substituted or unsubstituted alkyl groups, substituted or unsubstituted alkenyl groups, substituted or unsubstituted alkynyl groups, substituted or unsubstituted alicyclic organic groups, substituted or unsubstituted aryls Means substituted with one or more substituents selected from the group consisting of
  • alkyl group means a C1 to C20 alkyl group, specifically means a C1 to C15 alkyl group
  • 'cycloalkyl group means a C3 to C20 cycloalkyl group, and specifically Means a C3 to C18 cycloalkyl group, 'an' alkoxy group 'means a C20 alkoxy group, specifically means a C1 to C18 alkoxy group
  • ''arylgroup' 1 means a C6 to C20 aryl group
  • alkenyl group and specifically means a C2 to C18 alkenyl group
  • alkylene group means a C1 to C20 alkylene group, specifically, it means a C1 to C18 alkylene group
  • arylene group ' Means a C6 to C20 arylene group, specifically means a C6 to C16 arylene group.
  • combination means “combination or copolymerization.”
  • Copolymerization means block copolymerization or random copolymerization
  • Copolymer means a block copolymer or a random copolymer. Unless otherwise defined in the formula in the present specification, when a chemical bond is not drawn at the position where the chemical bond is to be drawn,
  • maximum light absorption area means the area (range) which shows the maximum absorbance.
  • One embodiment provides a compound represented by Formula 1 below.
  • R ' 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 from 2 to 5
  • m is an integer from 0 to 5, provided that 2 ⁇ n + m ⁇ 5,
  • A is a substituted or unsubstituted C6 to C20 aromatic hetero ring or a substituted or unsubstituted C3 to C20 alicyclic hetero ring,
  • the fat-soluble compound according to one embodiment is represented by the formula (1), the benzene ring of the formula (1) by including at least two or more cyano groups, it may have an excellent contrast ratio and brightness while maintaining a wavelength band similar to the existing yellow dye .
  • the compound according to the embodiment is a solubility in organic solvents and excellent fat-soluble compound, and its structure and use differ from compounds containing a water-soluble hepatic-group (for example, sulfonic acid group, etc.) or salts thereof.
  • a water-soluble hepatic-group for example, sulfonic acid group, etc.
  • n may be an integer of 2 and m may be an integer of 0.
  • aromatic hetero ring and alicyclic hetero ring may be any aromatic hetero ring and alicyclic hetero ring.
  • aromatic hetero ring and alicyclic hetero ring may be any aromatic hetero ring and alicyclic hetero ring.
  • It may include at least one structure represented by the formula (2)-.
  • the sing -group aromatic hetero ring may be represented by the H group Formula 3. [Formula 3]
  • R 3 is hydrogen base-, substituted or unsubstituted C1 to C20 alkyl group, or 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.
  • the fat-soluble compound represented by Chemical Formula 1 may be represented by Hi-group Chemical Formula 1-1.
  • R 1 to R 6 , n and m are as described above.
  • R 3 is a substituted or unsubstituted ⁇ to C20 alkyl group or a substituted or unsubstituted C6 to C20 aryl group
  • a single-group R 4 is a cyano group
  • R 5 is a substituted or unsubstituted C1 to C20
  • the sing-group R 6 may be a hydroxy group.
  • the alicyclic hetero ring may be represented by the following formula (4).
  • R 7 and R 8 are each independently hydrogen-supported, substituted or unsubstituted C1 to C20 alkyl groups, or substituted or unsubstituted C6 to C20 aryl groups.
  • the fat-soluble compound represented by the single-group Formula 1 may be represented by the following Formula 1-2.
  • R ' ⁇ R ⁇ n and m are as described above.
  • the fat-soluble compound represented by Formula 1 includes, in addition to at least two or more cyano groups, an aromatic hetero ring represented by Formula 3 or an alicyclic hetero ring represented by Formula 4, thereby being similar to or shorter than the existing yellow pigment. It may have a maximum absorption region at the wavelength, and may have excellent heat resistance and colorability.
  • the fat-soluble compound represented by Chemical Formula 1 may be represented by any one of compounds represented by Chemical Formulas 5 to 9.
  • the fat-soluble compound according to one embodiment is a compound represented by Chemical Formula 1, for example, Chemical Formula 1-1 or Chemical Formula 1-2, and it is possible to express more vivid colors in a small amount, and when used as a colorant, for example, a dye It is possible to manufacture a display element having excellent color characteristics such as luminance niche contrast ratio.
  • the fat-soluble compound may be a yellow dye, for example, a dye having a maximum absorption region in the wavelength range of 150 nm to 450 nm, such as 350 nm to 450 nm.
  • the fat-soluble compound represented by Chemical Formula 1-1 (In Chemical Formula 1, A is Is an aromatic hetero ring, the aromatic hetero ring is a fat-soluble compound represented by the formula (3) may have a maximum absorption region in the wavelength range of 400nm to 450nm and the fat-soluble compound represented by the formula (1-2) , A is an alicyclic hetero ring, and the alicyclic hetero ring is a fat-soluble compound represented by Formula 4) may have a maximum absorption region in the wavelength range of 150 nm to 4 00 nm, for example, 350 nm to 400 nm.
  • a photosensitive resin composition comprising a fat-soluble compound according to the embodiment is provided.
  • the photosensitive resin composition may include a fat-soluble compound, an alkali-soluble resin, a photopolymerizable compound, a photopolymerization initiator, and a solvent according to a single-group embodiment.
  • the photosensitive resin composition may further include a pigment.
  • the fat-soluble compound according to a single-group embodiment may serve as a colorant such as a dye such as a yellowish color dye in the photosensitive resin composition, thereby expressing excellent color characteristics.
  • the fat-soluble compound according to one embodiment may be included in an amount of 1 wt% to 10 wt%, such as 3 wt% to 7 wt%, based on the total amount of the photosensitive resin composition.
  • the pigment may include, but is not limited to, a yellow pigment, a green pigment, a red pigment or a chopped-up thereof.
  • the 'group' pigment may be included in the sing-group photosensitive resin composition in the form of a pigment dispersion.
  • the sing-based pigment dispersion may include a solid pigment, a solvent, and a dispersant for uniformly dispersing the pigment in the solvent.
  • the pigment of the solid content is 1% by weight to 20% by weight based on the total amount of the pigment dispersion, For example, it may be included in an 8 increase% to 20% by weight, for example 15% to 20% by weight, for example 8 weight 0/0 to 15% by weight, for example 10% to 20 increase%, for example 10% by weight to 15% by weight .
  • a nonionic dispersant As the dispersant, a nonionic dispersant, anionic dispersant, cationic dispersant, etc. may be used.
  • the dispersant include polyalkylene glycols and esters thereof, polyoxyalkylenes, polyhydric alcohol ester alkylene oxide adducts, alcohol alkylene oxide adducts, sulfonic acid esters, sulfonic acid salts, carboxylic acid esters, and carboxylic acids. Salts, alkylamide alkylene oxide adducts, alkyl amines, and the like, and these may be used alone or in combination of two or more.
  • commercially available products of the dispersant include DISPERBYK- by ⁇ .
  • DISPERBYK— 130 DISPERBYK-140, DISPERBYK-160, DISPERBYK-161, DISPERBY-162, DISPERBYK-163, DISPERBYK-164, DISPERBYK-165,
  • the dispersant may be included in an amount of 1 wt% to 20 wt% based on the total amount of the pigment dispersion.
  • the dispersant is included in the above range, it is possible to maintain an appropriate viscosity to excellent dispersibility of the photosensitive resin composition, thereby maintaining the optical, physical and chemical quality in the product application.
  • Examples of the solvent for forming the pigment dispersion include ethylene glycol acetate,
  • Polyethylene glycol, cyclonucleanone, propylene glycol methyl ether and the like can be used.
  • the sing-based pigment dispersion may be included in an amount of 5% by weight to 30% by weight, such as 10% by weight to 25% by weight, based on the total amount of the sing'-group photosensitive resin composition.
  • the alkali-soluble resin may be an acrylic resin.
  • the acrylic resin is a copolymer of the first ethylenically unsaturated monomer and the second ethylenically unsaturated monomer copolymerizable therewith, and may be a resin including one or more acrylic repeating units.
  • the first ethylenically unsaturated monomer is an ethylenic ball-saturated monomer containing at least one carboxyl group, and specific examples thereof may include acrylic acid, methacrylic acid, maleic acid, itaconic acid, fumarcin, or a combination thereof.
  • the crab 1 ethylenically unsaturated monomer may be included in 5% by weight to 50% by weight, such as 10% by weight to 40% by weight, based on the total amount of the acrylic binder resin.
  • the second ethylenic saturated monomer may be selected from the group consisting of aromatic vinyl compounds such as styrene, ⁇ -methylstyrene, vinylluene and vinylbenzylmethyl ether; Methyl (meth) acrylate,
  • Unsaturated carboxylic ester compounds such as cy-cyclohexyl (meth) acrylate and phenyl (meth) acrylate; Unsaturated carboxylic acid amino alkyl ester compounds such as 2-aminoethyl (methacrylate and 2-dimethylaminoethyl (meth) acrylate), and carboxylic acid vinyl ester compounds such as vinyl acetate and vinyl benzoate;
  • Glycidyl unsaturated carboxylic acid glycidyl aster compounds such as methacrylate; vinyl cyanide compounds such as (meth) acrylonitrile; unsaturated amide compounds such as (meth) acrylamide); and the like. It can be used alone or in combination of two or more.
  • acrylic binder resin examples include polybenzyl methacrylate copolymer, (meth) acrylic acid / benzyl methacrylate copolymer,
  • the (meth) acrylic acid / benzyl methacrylate / styrene / 2-hydroxyethyl methacrylate copolymer etc. are mentioned, It is not limited to these, These can also be used individually or in combination of 2 or more types.
  • the weight average molecular weight of the alkali-soluble resin is 3,000 g / mol to 150,000 g / mol, such as 5,000 g / mol to 50,000 g / mol, such as 20,000 g / mol to 30,000 g mol.
  • the increase average molecular weight of the alkali-soluble resin is within the sing-group range, the physical and chemical physical properties of the photosensitive resin composition are excellent, the viscosity is appropriate, and the adhesion to the substrate is excellent when the color filter is manufactured.
  • the acid value of the singe-based alkali soluble resin is 15 mgKOH / g to 60 mgKOH / g, such as
  • the alkali-soluble resin may be included in 1% by weight to 30% by weight, such as 1% by weight to 15% by weight, based on the total amount of the photosensitive resin composition.
  • the alkali-soluble resin is included in the above range, it is excellent in developability in the production of color filters and crosslinkability is improved to obtain excellent surface smoothness.
  • the single-group photopolymerizable compound may be a monofunctional or polyfunctional ester of (meth) acrylic acid having at least one ethylenically unsaturated double bond.
  • the photopolymerizable compound Since the photopolymerizable compound has a single ethylenically unsaturated divalent bond, it causes sufficient polymerization during exposure in the pattern formation process to form a pattern excellent in heat resistance, light resistance and chemical resistance.
  • the photopolymerizable compound examples include ethylene glycol di (meth) acrylate, diethylene glycol di (meth) acrylate, triethylene glycol di (meth) acrylate, propylene glycol di (meth) acrylate, neomethyl glycol di Di (meth) acrylates (meth) acrylate, 1,4-butanedi di (meth) acrylate, di (meth) acrylate 1,6-nucleic acid di (meth) acrylate, bisphenol A di (meth) acrylate It is tri (meth) acrylate to pentaerythrate, tetra (meth) acrylate to pentaerythrite, nucleus (meth) acrylate to pentaerythritol, and di (meth) acrylate, dipenta to pentaerythritol Atritree tri (meth) acrylate, dipentaerythritol penta (meth) acrylate,
  • Tri (meth) acrylate Tris (meth) acryloyloxyethyl phosphate, a novolak epoxy (meth) acrylate, etc. are mentioned.
  • Examples of the monofunctional ester of (methicyl) acrylic acid include those of Toagosei Kagaku Kogyo Co., Ltd. Aronix M-101 ® , copper Mll ll ® , copper M-114 ®, etc .; Nihon Kayaku Co., Ltd.'s KAYARAD TC-11 OS ® , TC-120S ®, etc .; And V-158 ® and V-231 1 ® by Osaka Yuki Kagaku Kogyo Co., Ltd.
  • Examples of the difunctional ester of the above (meth) acrylic acid include, but are not limited to, Aronix M-210 ® M-240 ® , M-6200 ®, etc.
  • ester examples include Aronix M-309 ® , M-400 ® , M-405 ® , M-450 ® , -710 ® , M-8030 ® from Toagosei Kagaku Kogyo Co., Ltd. , Copper M-8060 ® and the like; Nihon
  • the photopolymerizable compound may be used by treating with an acid anhydride to impart better developability.
  • the photopolymerizable compound may be included in an amount of 1 wt% to 15 wt%, such as 5 wt% to 10 wt%, based on the total amount of the photosensitive resin composition.
  • a photopolymerizable compound is contained in the said range, hardening arises at the time of exposure in a pattern formation process, and it is excellent in reliability, and is excellent in developability to an alkaline developing solution.
  • Singh-based photopolymerization initiator is generally used in photosensitive resin composition
  • an acetophenone compound for example, an acetophenone compound, a benzophenone compound, a thioxanthone compound, a benzoin compound, an oxime compound or a combination thereof can be used.
  • acetophenone-based compound examples include 2,2'-dietospecific acetophenone, 2,2'-dibuspecial acetophenone, 2-hydroxy-2-methylpropiophenone and ⁇ -t-buryltriclo
  • acetophenone pt— butyldichloro acetophenone, 4-chloro acetophene, 2,2'-dichloro-4-phenoxy acetophenone, 2-methyl-1 '(4- (methylthio) phenyl) -2—
  • Morpholinopropane-1- is 2-benzyl-2-dimethylamino- 1- (4-morpholinophenyl) -butane-1-silver, etc .;
  • benzophenone-based compound examples include benzophenone, benzoyl benzoic acid, methyl benzoyl benzoate, 4-phenyl benzophenone, hydroxy benzophenone, acryl ash 'benzophenone, 4,4'-bis (dimethyl amino) benzophenone, 4 , 4'-bis (diethylamino) benzophenone, 4,4'- dimethylamino benzophenone, 4,4'- dichloro benzophenone, 3,3'- dimethyl- 2-methoxy benzophenone, etc. are mentioned. Can be.
  • thioxanthone-based compound examples include thioxanthone, 2-methyl thioxanthone and isopropyl thioxanthone, 2,4-diethyl thioxanthone, 2,4-diisopropyl thioxanthone, 2 -Chloro thioxanthone, etc. are mentioned.
  • benzoin compound examples include benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl ether, benzyldimethyl ketal and the like.
  • succinyl triazine compound examples include 2,4,6-trichloro-S-triazine, 2-phenyl 4,6-bis (trichloromethyl) -S-triazine, 2- (3 ', 4 '-Dimethoxystyryl) -4,6-bis (trichloromethyl) -S- triazine, 2- (4'-methoxynaphthyl) -4,6-bis (trichloromethyl) -S- Triazine, 2- (p-methoxyphenyl) -4,6-bis (trichloromethyl) -S-triazine, 2- (p-lryl) -4,6-bis (trichloromethyl) -s— Triazine,
  • oxime compounds include 0—acyl oxime compound, 2- ( ⁇ benzoyloxime) -1- [4- (phenylthio) phenyl] -1,2-octanedione, 1- ( 0 -acetyloxime) -1- [9-ethyl- 6- (2-methylbenzoyl) -9H-carbazole-
  • 3-yl] ethanone, 0-ethoxycarbonyl - ⁇ -oxyamino-1-phenylpropane-1-silver, etc. can be used.
  • Specific examples of the 0-acyl oxime compound include 1,2-octanedione, 2-dimethylamino—2- (4-methylbenzyl) —1- (4-morpholin-4-yl-phenyl) -butane 1 -Silver, phenylsulfanylphenyl) -butane -1,2-dione 2-oxime -0-benzoate, 1-(4-phenylsulfanylphenyl) -octane dione 2-oxime- 0-benzoate, 1- ( 4-phenylsulfanylphenyl) -octane -1-silver oxime -0-acetate, 1-(4-phenylsulfanylphenyl)-butane-1-onoxime-0-acetate, etc
  • the sing-group photopolymerization initiators include carbazole compounds, diketone compounds, sulfonium borate compounds, diazo compounds, imidazole compounds,
  • Biimidazole type compound etc. can be used-.
  • the photopolymerization initiator may be used together with a photosensitizer which causes a chemical reaction by absorbing light and transferring energy after being excited.
  • single-photosensitive sensitizer examples include tetraethyleneglycol bis-3-mercapto propionate pentaerythritol tetrakis-3-mercapto propionate, dipentaerytriol tetrakis- 3-mercapto propionate, etc. are mentioned.
  • Washing-machine photomultiplier sum initiator may be contained in the photosensitive resin composition for her total amount of 0.01% by weight increased to 10 0/0, for example 0, 1% to 5% increase.
  • the photo-heap-initiator is included in the above range, curing occurs during exposure in the pattern forming process to obtain excellent reliability, excellent heat resistance, light resistance and chemical resistance of the pattern, excellent resolution and adhesion, and unreacted. The fall of the transmittance
  • the solvent may be used a substance which has compatibility with the fat-soluble compound, the pigment, the alkali-soluble resin, the photopolymerizable compound and the photopolymerization initiator, but does not react.
  • the solvent may be an organic solvent.
  • solvent examples include methane and alcohols such as ethanol; Ethers such as dichloroethyl ether, ⁇ -butyl ether, diisoamyl ether, methylphenyl ether and tetrahydrofuran; Glycols 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; Methyl ethyl carbye, diethyl carbye, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol dimethyl ether, diethylene glycol methylethyl ether, diethylene glycol
  • Carbyls such as 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; Methyl ethyl ketone, cyclonucleanone, 4-hydroxy-
  • Ketones such as 4—methyl-2-3 ⁇ 4tanone, methyl-n-propylketone, methyl-n-butylketone, methyl-n-amylkeron and 2-heptanone; Saturated aliphatic monocarboxyl-alkyl esters such as ethyl acetate, n-butyl acetate, and isobutyl acetate; Lactic acid esters such as methyl lactate and ethyl lactate; Oxy acetic acid alkyl esters such as methyl oxy acetate, oxy acetic acid and butyl oxy acetate; Alkoxy acetic acid alkyl esters such as methyl acetate, methoxy acetic acid, methoxy butyl acetate, ethoxy methyl acetate, and ethoxy ethyl acetate; 3-oxy propionic acid alkyl esters such as methyl 3-oxy propionate and ethyl 3-oxypropionate
  • 3-alkoxy propionic acid alkyl esters such as ethyl propionate, ethyl 3-ethoxy propionate and methyl methyl propionate;
  • 2—oxy propionic acid alkyl esters such as methyl 2-oxy propionate, ethyl 2-oxypropionate and propyl 2-oxypropionic acid;
  • 2-methoxy 2-alkoxy propionic acid alkyl esters such as methyl propionate, ethyl 2-methoxy propionate, ethyl 2-propyne ethylpropionate and methyl 2-ethoxy propionate;
  • 2-oxy-2-methylpropionic acid esters such as 2 -oxy- 2 -methyl methyl propionate and 2 -oxy- 2 -methyl ethyl propionate, 2—methecoxy—2-methyl methyl propionate, 2-especial-2- mono-oxy monocarboxylic acid alkyl astro Terre flow of current-methylpropionic acid alky
  • Glycol ethers such as monoethyl ether; Ethylene glycol alkyl ether acetates such as ethyl cellosolve acetate; Esters such as 2—ethyl hydroxy propionate; Carbilol, such as diethylene glycol monomethyl ether; Propylene glycol alkylether acetates, such as propylene glycol monomethyl ether acetate and propylene glycol propylether i'acetate, can be used.
  • the solvent may be included in a balance, such as 30 wt% to 80 wt%, based on the total amount of the photosensitive resin composition.
  • the photosensitive resin composition When incorporated into group ranges washing-solvent washing jockey fairness in manufacturing the color filter right ⁇ depending on having a suitable viscosity photosensitive resin composition _ Hi _ di-, the photosensitive resin composition according to another embodiment, the substrate An epoxy compound may be further included in order to improve adhesiveness.
  • Examples of the sing-group epoxy compound include a phenol novolac epoxy compound, a tetramethyl biphenyl epoxy compound, a bisphenol A type epoxy compound, an alicyclic epoxy derivative, or a combination thereof.
  • the epoxy compound may be included in an amount of 0.01 to 20 parts by weight, such as 0.1 to 10 parts by weight, based on 100 parts by weight of the photosensitive resin composition. Epoxy When the compound is included in the above range, the adhesiveness, shelf life and the like are excellent.
  • the photosensitive resin composition may further include a silane coupling agent having a semi-aromatic substituent such as carboxyl group, methacryloyl group, isocyanate group, epoxy group, etc. in order to improve adhesion to the substrate.
  • a silane coupling agent having a semi-aromatic substituent such as carboxyl group, methacryloyl group, isocyanate group, epoxy group, etc. in order to improve adhesion to the substrate.
  • silane coupling agent examples include trimethicsilyl benzoic acid, ⁇ -methacryloxypropyl trimethicillin ', vinyl triacetic silane, vinyl trimethicylsilane, ⁇ -isocyanate propyl trieoxysilane, ⁇ - Glycidoxy propyl trimethoxysilane, (beta)-(3, 4- epoxycyclonuclear silane) ethyltrimethoxysilane, etc. are mentioned, These can be used individually or in mixture of 2 or more types.
  • the single-group silane coupling agent may be included in an amount of 0.01 parts by weight to 10 parts by weight with respect to the photosensitive resin composition loo part by weight.
  • the sing-based photosensitive resin composition may further include a surfactant for improving the coating property and preventing the occurrence of defects, if necessary.
  • surfactants examples include BM Chemie l: BM-1000 ® , BM-1100 ®, and the like; Mecha packs F 142D ® , F 172 ® , F 173 ® , F 183 ®, etc. of Dai Nippon Inki Chemical Co., Ltd .; M. Sumitomo Co. Pro rod FC-135 ® of ⁇ , copper FC- 170C ®, copper FC-430 ®, copper FC- 431 ®, and the like; Asahi Grass Co., Ltd.
  • the sing-based 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.
  • the surfactant is included in the above range, coating uniformity is ensured, staining does not occur, and wetting against the glass substrate is excellent.
  • the said photosensitive resin composition is in the range which does not inhibit physical property.
  • a color filter manufactured using the photosensitive resin composition according to the embodiment is provided.
  • the color filter may be a green color filter or a red color filter. It is not limited.
  • the pattern forming process in the color filter is as follows.
  • Synthesis Example 1 to Synthesis Example 5 and Comparative Synthesis Example 1 to Comparative Synthesis Example 3 Compounds synthesized in the UV-1800 UV-Vis Spectrometer was measured at the absorption wavelength ( ⁇ ) is shown in Table 2 below.
  • Synthesis Example 1 to Synthesis Example 5 and Comparative Synthesis Example 1 20 mg of the compound synthesized in Comparative Synthesis Example 3 was dissolved in Anone (Cyclohexanone) to make 20 g of a thick solution, and then diluted 0.1 g of the concentrated solution to 1 ( ⁇ ) to form a dilute solution of 0.001% by weight. After measuring the spectroscopy of the 0.001% by weight of the solution, the molar extinction coefficient was calculated from Equation 1 shown in Table 2 below.

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Abstract

Provided are an oil-soluble compound represented by a specific chemical formula, a photosensitive resin composition containing the same, and a color filter manufactured by using the photosensitive resin composition.

Description

【명세서】  【Specification】
【발명의 명칭】  [Name of invention]
신규한지용성 화합물, 이를 포함하는 감광성 수지 조성물 및 컬러필터 【기술분야】  Novel fat-soluble compound, photosensitive resin composition and color filter comprising same
본 기재는 신규한 지용성 화합물, 이를 포함하는 감광성 수지 조성물 및 컬러필터에 관한 것이다.  The present disclosure relates to a novel fat-soluble compound, a photosensitive resin composition and a color filter comprising the same.
【배경기술】 Background Art
안료형 감광성 수지 조성물로 제조된 컬러필터에서는 안료 입자 크기에서 비롯되는 휘도와 명암비의 힌 -계가 존재한디-. 또한 이미지 센서용 컬러 촬상 소자의 경우에는 미세한 패턴 형성을 위해 더 작은 분산입도를 요구하게 된다. 이와 같은 요구에 부웅하고자 안료 대신 입자를 이루지 않는 염료를 도입한 감광성 수지 조성물을 제조하여 휘도와 명암비 등의 색특성이 개선된 ¾러필터를 구현하려는 시도가 계속되고 있다.  In the color filter made of the pigment type photosensitive resin composition, there is a Hin-system of brightness and contrast ratio resulting from the pigment particle size. In addition, 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 satisfy such a demand, attempts have been made to implement a ¾ler filter in which color characteristics such as brightness and contrast ratio are improved by preparing a photosensitive resin composition incorporating a dye that does not form particles instead of a pigment.
따라서, 감광성 수지 조성물의 제조에 사용되는 염료로 적합한 화합물, 특히 조색용 염료 화합물에 대한 연구가 필요한 실정이다.  Therefore, there is a need for research on compounds suitable for the dyes used in the preparation of the photosensitive resin composition, especially dyeing compounds for coloration.
【발명의 상세한 설명】 [Detailed Description of the Invention]
【기술적 과제】  [Technical problem]
일 구현예는 신규한 지용성 화합물을 제공하기 위한 것이다.  One embodiment is to provide novel fat-soluble compounds.
다른 일 구현예는 상기 지용성 화합물을 포함하는 감광성 수지 조성물을 제공하기 위한 것이다.  Another embodiment is to provide a photosensitive resin composition comprising the fat-soluble compound.
또 다른 구현예는 상기 감광성 수지 조성물을 이용하여 제조된 컬러필터를 제공히-기 위한 것이디-.  Yet another embodiment is to provide a color filter manufactured using the photosensitive resin composition.
【기술적 해결방법】 Technical Solution
본 발명의 일 구현예는 하기 화학식 1로 표시되는 지용성 화합물을 제공한다.
Figure imgf000003_0001
One embodiment of the present invention provides a fat-soluble compound represented by the following formula (1).
Figure imgf000003_0001
상기 화학식 1에서,  In Chemical Formula 1,
R1은 시아노기이고， R 1 is a cyano group,
R2는 치환 또는 비치환된 C1 내지 C20 알킬기, 치환또는 비치환된 C2 내지 C20 알킬렌기 또는 치환 또는 비치환된 C6 내지 C20 아릴기이고, 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,
n은 2 내지 5의 정수이고, m은 0 내지 5의 정수이고, 단, 2≤n+m≤5이고， n is an integer from 2 to 5, m is an integer from 0 to 5, provided that 2≤n + m≤5,
A는 치환 또는 비치환된 C6 내지 C20 방향족 해테로 고리 또는 치환 또는 비치환된 C3 내지 C20 지환족 헤테로 고리이다. A is a substituted or unsubstituted C6 to C20 aromatic hetero ring or a substituted or unsubstituted C3 to C20 alicyclic hetero ring.
상기 방향족 헤테로 고리 및 지환족 헤테로 고리는 싱-기 고리 내에 하기 화학식 2로 표시되는 구조를 적어도 하나 이상 포함할 수 있다.  The aromatic hetero ring and alicyclic hetero ring may include at least one structure represented by the following Formula 2 in a sing-group ring.
2]
Figure imgf000003_0002
2]
Figure imgf000003_0002
상기 방향족 헤테로 고리는 하기 화학식 3으로 표시될 수 있다.  The aromatic hetero ring may be represented by the following formula (3).
Figure imgf000003_0003
Figure imgf000003_0003
상기 화학식 3에서,  In Chemical Formula 3,
R3은 수소 원자, 치환 또는 비치환된 C1 내지 C20 알킬기 또는 치환 또는 비치환된 C6 내지 C20 아릴기이고, 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,
R4 내지 R6은 각각 독립적으로, 수소 원지ᅳ, 시아노기, 히드록시기, 치환 또는 비치환된 C1 내지 C20 알킬기 또는 치환또는 비치환된 C6 내지 C20 아릴기이디-, 싱-기 화학식 3에서, R3은 치환 또는 비치환된 C1 내지 C20 알킬기 또는 치환 또는 비치환된 C6 내지 C20 아릴기이고, R4는 시아노기이고 , R5는 치환 또는 비치환된 C1 내지 C20 알킬기 또는 치환 또는 비치환된 C6 내지 C20 아릴기이고, R6는 히드록시기일 수 있다-. 상기 지환족 헤테로 고리는 하기 화학식 4로 표시될 수 있다. R 4 to R 6 are each independently hydrogen, a cyano group, a hydroxy group, a substituted or unsubstituted C1 to C20 alkyl group, or a substituted or unsubstituted C6 to C20 aryl groupidi-, xing-group In Formula 3, R 3 is a substituted or unsubstituted C1 to C20 alkyl group or a substituted or unsubstituted C6 to C20 aryl group, R 4 is a cyano group, R 5 is a substituted or unsubstituted C1 to C20 alkyl group or a substituted or unsubstituted C6 To C20 aryl group, R 6 may be a hydroxy group-. The alicyclic hetero ring may be represented by the following formula (4).
4]  4]
Figure imgf000004_0001
Figure imgf000004_0001
상기 화학식 4에서,  In Chemical Formula 4,
R7 및 은 각각 독립적으로 수소 원자, 치환또는 비치환된 C1 내지 C20 알킬기 또는 치환 또는 비치환된 C6 내지 C20 아릴기이다-. R 7 and 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.
상기 화학식 1로 표시되는 지용성 화합물은 하기 화학식 5 내지 화학식 9로 표시되는 화합물 증 어느 하나로 표시될 수 있다.  The fat-soluble compound represented by Chemical Formula 1 may be represented by any one of compound compounds represented by Chemical Formulas 5 to 9.
5]  5]
Figure imgf000004_0002
Figure imgf000004_0002
[화학식 6]  [Formula 6]
Figure imgf000004_0003
Figure imgf000004_0003
Figure imgf000004_0004
Figure imgf000004_0004
Figure imgf000005_0001
Figure imgf000005_0001
Figure imgf000005_0002
Figure imgf000005_0002
상기 지용성 화합물은 황색 염료일 수 있다.  The fat soluble compound may be a yellow dye.
다른 일 구현예는 상기 지용성 화합물을 포함하는 감광성 수지 조성물을 제공한다,  Another embodiment provides a photosensitive resin composition comprising the oil-soluble compound.
상기 감광성 수지 조성물은 알칼리 가용성 수지, 광중합성 화합물, 광중합 개시제 및 용매를 더 포함할 수 있디-.  The photosensitive resin composition may further include an alkali-soluble resin, a photopolymerizable compound, a photopolymerization initiator, and a solvent.
싱-기 감광성 수지 조성물은 안료를 더 포함할 수 있다.  The sing-group photosensitive resin composition may further include a pigment.
또 다른 일 구현예는 상기 감광성 수지 조성물을 이용하여 제조되는 컬러필터를 제공한다.  Another embodiment provides a color filter manufactured using the photosensitive resin composition.
상기 컬러필터는 녹색 컬러필터 또는 적색 컬러필터일 수 있다.  The color filter may be a green color filter or a red color filter.
기타 본 발명의 측면들의 구체적인 사항은 이하의 상세한 설명애 포함되어 있다. 【유리한 효과】  Other specific details of aspects of the present invention are included in the following detailed description. Advantageous Effects
일 구현예애 따른 지용성 화합물은 우수한 황색 분광 특성과 높은  The fat-soluble compound according to one embodiment has excellent yellow spectral properties and high
몰흡광계수를 가지고 유기 용매에 대한용해도가 우수하여, 컬러필터용 감광성 수지 조성물 제조 시 조색용 염료로 사용될 수 있고, 상기 조색용 염료를 포함하는 컬러필터, 특히 녹색 컬러필터 또는 적색 컬러필터는 우수한 휘도 및 명암비를 가질 수 있다 It has a molar extinction coefficient and excellent solubility in organic solvents, so that it can be used as a coloring dye when preparing a photosensitive resin composition for color filters, and a color filter including the coloring dye, in particular, a green color filter or a red color filter is excellent. Have brightness and contrast ratio Can
【발명의 실시를 위한 최선의 형태】 [Best form for implementation of the invention]
이하， 본 발명의 구현예를 상세히 설명하기로 한다, 다만, 이는 예시로서 제시되는 것으로， 이에 의해 본 발명이 제한되지는 않으며 본 발명은 후술할 청구범위의 범주에 의해 정의될 뿐이다.  Hereinafter, embodiments of the present invention will be described in detail, but it is presented by way of example, and the present invention is not limited thereto, and the present invention is defined only by the scope of the claims to be described later.
본 명세서에서 특별한 언급이 없는 한, "치환 " 내지 "치환된 "이란, 본 빌'명의 작용기 증의 하나 이상의 수소 원자가 할로겐 원자 (F, Br, Cl 또는 I), 히드록시기, 니트로기, 시아노기, 아미노기 (NH2, NH(R200) 또는 N(R20 l)(R202)이고, 여기서 200, R201 및 R202는 동일하거나 서로 상이하며, 각각 독립적으로 C1 내지 C10 알킬기임), 아미디노기， 하이드라진기, 하이드라존기, 카르복실기， 치환 또는 비치환된 알킬기, 치환 또는 비치환된 알케닐기, 치환또는 비치환된 알키닐기， 치환 또는 비치환된 지환족 유기기, 치환 또는 비치환된 아릴기 및 치환 또는 비치환된 헤테로고리기로 이루어진 군에서 선택되는 1종 이상의 치환기로 치환된 것을 의미한디-, Unless stated otherwise in the specification, "substituted" to "substituted" means that one or more hydrogen atoms of the functional group increase of the present Bill's name are halogen atoms (F, Br, Cl or I), hydroxy groups, nitro groups, cyano groups, Amino groups (NH 2 , NH (R 200 ) or N (R 20 l ) (R 202 ), where 200 , R 201 and R 202 are the same or different from each other, and are each independently C1 to C10 alkyl groups, amidino Groups, hydrazine groups, hydrazone groups, carboxyl groups, substituted or unsubstituted alkyl groups, substituted or unsubstituted alkenyl groups, substituted or unsubstituted alkynyl groups, substituted or unsubstituted alicyclic organic groups, substituted or unsubstituted aryls Means substituted with one or more substituents selected from the group consisting of a group and a substituted or unsubstituted heterocyclic group,
본 명세서에서 특별한 언급이 없는 한, "알킬기' '란 C1 내지 C20 알킬기를 의미하고， 구체적으로는 C1 내지 C15 알킬기를 의미하고, ' '사이클로알킬기"란 C3 내지 C20 사이클로알킬기를 의미하고, 구체적으로는 C3 내지 C18 사이클로알킬기를 의미하고, ' '알콕시기' '란 내지 C20 알콕시기를 의미하고， 구체적으로는 C1 내지 C18 알콕시기를 의미하고, ' '아릴기'1란 C6 내지 C20 아릴기를 의미하고, Unless stated otherwise in the present specification, "alkyl group" means a C1 to C20 alkyl group, specifically means a C1 to C15 alkyl group, and "'cycloalkyl group" means a C3 to C20 cycloalkyl group, and specifically Means a C3 to C18 cycloalkyl group, 'an' alkoxy group 'means a C20 alkoxy group, specifically means a C1 to C18 alkoxy group,''arylgroup' 1 means a C6 to C20 aryl group,
구체적으로는 C6 내지 C18 아릴기를 의미하고, ' '알케닐기"란 C2 내지 C20 Specifically, it refers to a C6 to C18 aryl group, 'an' alkenyl group 'means C2 to C20
알케닐기를 의미하고, 구체적으로는 C2 내지 C18 알케닐기를 의미하고, ' '알킬렌기"란 C1 내지 C20 알킬렌기를 의미하고, 구체적으로는 C1 내지 C18 알킬렌기를 의미하고 "아릴렌기' '란 C6 내지 C20 아릴렌기를 의미하고, 구체적으로는 C6 내지 C16 아릴렌기를 의미한다. It means an alkenyl group, and specifically means a C2 to C18 alkenyl group, "'alkylene group" means a C1 to C20 alkylene group, specifically, it means a C1 to C18 alkylene group and "arylene group"' Means a C6 to C20 arylene group, specifically means a C6 to C16 arylene group.
본 명세서에서 특별한 언급이 없는 한, " (메타)아크릴레이트 "는  Unless stated otherwise in the specification, "(meth) acrylate"
"아크릴레이트1'와 "메타크릴레이트" 둘 다 가능함을 의미하며, " (메타)아크릴산'1은 "아크릴산"과 "메타크릴산" 둘 다 가능함을 의미한다. "Acrylate 1 " and "methacrylate" mean that both are possible, and "(meth) acrylic acid" 1 means that both "acrylic acid" and "methacrylic acid" are possible.
본 명세서에서 별도의 정의가 없는 한, "조합' '이란 흔합 또는 공중합을 의미한다. 또한 "공중합"이란 블록 공중합 내지 랜덤 공중합을 의미하고,  Unless otherwise defined herein, "combination" means "combination or copolymerization." "Copolymerization" means block copolymerization or random copolymerization,
"공증합체"란 블록 공중합체 내지 랜덤 공중합체를 의미한다. 본 명세서 내 화학식에서 별도의 정의기- 없는 한， 화학 결합이 그려져야 하는 위치에 화학결합이 그려져 있지 않은 경우는 상기 위치에 수소 원자가 "Copolymer" means a block copolymer or a random copolymer. Unless otherwise defined in the formula in the present specification, when a chemical bond is not drawn at the position where the chemical bond is to be drawn,
결합되어 있음을 의미한다. It means that it is combined.
본 명세서에서 별도의 정의기 없는 한, ' 는 동일하거나 상이한 원자또는 화학식과 연결되는 부분을 의미한다.  In the present specification, unless otherwise defined, 'means a moiety connected to the same or different atoms or formulas.
또한, 본 명세서에서 별도의 정의가 없는 한, "최대 흡광영역"이란 최대 흡광도를 나타내는 영역 (범위)을 의미한다. 일 구현예는 하기 화학식 1로 표시되는 화합물을 제공한다.  In addition, unless otherwise defined in this specification, "maximum light absorption area" means the area (range) which shows the maximum absorbance. One embodiment provides a compound represented by Formula 1 below.
Figure imgf000007_0001
Figure imgf000007_0001
상기 화학식 1애서,  In Chemical Formula 1,
R'은 시아노기이고,  R 'is a cyano group,
R2는 치환 또는 비치환된 C1 내지 C20 알킬기, 치환 또는 비치환된 C2 내지 C20 알킬렌기 또는 치환 또는 비치환된 C6 내지 C20 아릴기이고, 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,
n은 2 내지 5의 정수이고, m은 0 내지 5의 정수이고, 단, 2≤n+m≤5이고， n is an integer from 2 to 5, m is an integer from 0 to 5, provided that 2≤n + m≤5,
A는 치환또는 비치환된 C6 내지 C20 방향족 해테로 고리 또는 치환또는 비치환된 C3 내지 C20 지환족 해테로 고리이다, A is a substituted or unsubstituted C6 to C20 aromatic hetero ring or a substituted or unsubstituted C3 to C20 alicyclic hetero ring,
일 구현예에 따른 지용성 화합물은 상기 화학식 1로 표시되고, 상기 화학식 1의 벤젠고리는 적어도 2개 이상의 시아노기를 반드시 포함함으로써, 기존 황색 염료와 유사한 파장대를 유지하면서도 우수한 명암비 및 휘도를 가질 수 있다. 또한 : 기존 황색 안료인 yellow G등과 대비하여도, 유사하거나 더 짧은 파장대를 기-지면서 : 높은 내열성 및 착색력을 가지고, 사이클로핵사논, PGMEA 등의 유기 용매에 대한 용해도도 우수하다. The fat-soluble compound according to one embodiment is represented by the formula (1), the benzene ring of the formula (1) by including at least two or more cyano groups, it may have an excellent contrast ratio and brightness while maintaining a wavelength band similar to the existing yellow dye . In addition: the group to Fig, similar or shorter wavelength as compared to a conventional yellow pigment yellow G-As: has a high heat resistance and tinting strength, it has excellent solubility in an organic solvent such as cyclo hex rice, PGMEA.
또한, 일 구현예에 따른 화합물은 유기 용매에 대한 용해도기ᅳ 우수한지용성 화합물로서, 수용성 치흰-기 (예컨대， 술폰산기 등)나 그 염을 포함하는 화합물과는 그 구조 및 용도가 상이하다.  In addition, the compound according to the embodiment is a solubility in organic solvents and excellent fat-soluble compound, and its structure and use differ from compounds containing a water-soluble hepatic-group (for example, sulfonic acid group, etc.) or salts thereof.
예컨대, 상기 화학식 1에서, n은 2의 정수이고, m은 0의 정수일 수 있다. For example, in Formula 1, n may be an integer of 2 and m may be an integer of 0.
예컨대 , 상기 방향족 해테로 고리 및.지환족 헤테로 고리는 상기  For example, the aromatic hetero ring and alicyclic hetero ring may be
하기 화학식 2로 표시되는 구조를 적어도 하나 이상 포함할수 있디-. It may include at least one structure represented by the formula (2)-.
2]
Figure imgf000008_0001
2]
Figure imgf000008_0001
예컨대, 싱-기 방향족 헤테로 고리는 히ᅵ기 화학식 3으로 표시될 수 있다. [화학식 3] For example, the sing -group aromatic hetero ring may be represented by the H group Formula 3. [Formula 3]
Figure imgf000008_0002
Figure imgf000008_0002
R3은 수소 원지-, 치환 또는 비치환된 C1 내지 C20 알킬기 또는 치환 또는 비치환된 C6 내지 C20 아릴기이고, R 3 is hydrogen base-, substituted or unsubstituted C1 to C20 alkyl group, or substituted or unsubstituted C6 to C20 aryl group,
R4 내지 R6은 각각 독립적으로, 수소 원자, 시아노기, 히드록시기, 치환또는 비치환된 C1 내지 C20 알킬기 또는 치환또는 비치환된 C6 내지 C20 아릴기이다. 예컨대, 상기 화학식 1로 표시되는 지용성 화합물은 히-기 화학식 1-1로 표시될 수 있다. 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 Chemical Formula 1 may be represented by Hi-group Chemical Formula 1-1.
1-1]  1-1]
Figure imgf000008_0003
Figure imgf000008_0003
상기 화학식 1-1에서  In Chemical Formula 1-1
R1 내지 R6, n 및 m은 전술한 바와 같다. R 1 to R 6 , n and m are as described above.
예컨대, 상기 R3은 치환 또는 비치환된 α 내지 C20 알킬기 또는 치환 또는 비치환된 C6 내지 C20 아릴기이고，싱-기 R4는 시아노기이고, 상기 R5는 치환또는 비치환된 C1 내지 C20 알킬기 또는 치환 또는 비치환된 C6 내지 C20 아릴기이고, 싱-기 R6는 히드록시기일 수 있다. For example, R 3 is a substituted or unsubstituted α to C20 alkyl group or a substituted or unsubstituted C6 to C20 aryl group, a single-group R 4 is a cyano group, and R 5 is a substituted or unsubstituted C1 to C20 An alkyl group or a substituted or unsubstituted C6 to C20 aryl group, and the sing-group R 6 may be a hydroxy group.
예컨대, 상기 지환족 해테로 고리는 하기 화학식 4로 표시될 수 있다.
Figure imgf000009_0001
For example, the alicyclic hetero ring may be represented by the following formula (4).
Figure imgf000009_0001
상기 화학식 4에서,  In Chemical Formula 4,
R7 및 R8은 각각 득립적으로 수소 원지-, 치환 또는 비치환된 C1 내지 C20 알킬기 또는 치환또는 비치환된 C6 내지 C20 아릴기이다. R 7 and R 8 are each independently hydrogen-supported, substituted or unsubstituted C1 to C20 alkyl groups, or substituted or unsubstituted C6 to C20 aryl groups.
예컨대, 싱-기 화학식 1로 표시되는 지용성 화합물은 하기 화학식 1-2로 표시될 수 있다.  For example, the fat-soluble compound represented by the single-group Formula 1 may be represented by the following Formula 1-2.
1_2]  1_2]
Figure imgf000009_0002
Figure imgf000009_0002
R'^^ ^ R^ n 및 m은 전술한 바와 같다. R '^^^ R ^ n and m are as described above.
상기 화학식 1로 표시되는 지용성 화합물은 적어도 2개 이상의 시아노기 외에, 상기 화학식 3으로 표시되는 방향족 해테로 고리 또는 화학식 4로 표시되는 지환족 헤테로 고리를 포함함으로써, 기존의 황색 안료와 유사하거나 더 짧은 파장에서 최대 흡광영역을 가지고, 우수한 내열성 및 착색력을 가질 수가 있다， 예컨대, 상기 화학식 1로 표시되는 지용성 화합물은 하기 화학식 5 내지 화학식 9로 표시되는 화합물 증 어느 하나로 표시될 수 있다,  The fat-soluble compound represented by Formula 1 includes, in addition to at least two or more cyano groups, an aromatic hetero ring represented by Formula 3 or an alicyclic hetero ring represented by Formula 4, thereby being similar to or shorter than the existing yellow pigment. It may have a maximum absorption region at the wavelength, and may have excellent heat resistance and colorability. For example, the fat-soluble compound represented by Chemical Formula 1 may be represented by any one of compounds represented by Chemical Formulas 5 to 9.
[화학식 5]  [Formula 5]
Figure imgf000009_0003
6]
Figure imgf000010_0001
Figure imgf000009_0003
6]
Figure imgf000010_0001
9]  9]
Figure imgf000010_0002
Figure imgf000010_0002
일 구현예에 따른 지용성 화합물은 상기 화학식 1, 예컨대 화학식 1-1 또는 화학식 1-2로 표시되는 화합물로서, 적은 양으로도 보다 선명한 색의 발현이 가능하여, 착색제， 예컨대 조색용 염료로 사용 시 휘도니ᅳ 명암비 등의 색특성이 우수한 디스플레이 소자의 제조가 가능하다. 예컨대, 상기 지용성 화합물은 황색 염료, 예¾대 150ηηι 내지 450nm, 예컨대 350nm 내지 450nm의 파장범위에서 최대 흡광영역을 가지는 염료일 수 있디-.  The fat-soluble compound according to one embodiment is a compound represented by Chemical Formula 1, for example, Chemical Formula 1-1 or Chemical Formula 1-2, and it is possible to express more vivid colors in a small amount, and when used as a colorant, for example, a dye It is possible to manufacture a display element having excellent color characteristics such as luminance niche contrast ratio. For example, the fat-soluble compound may be a yellow dye, for example, a dye having a maximum absorption region in the wavelength range of 150 nm to 450 nm, such as 350 nm to 450 nm.
예컨대, 상기 화학식 1-1로 표시되는 지용성 화합물 (상기 화학식 1에서 , Α가 방향족 헤테로 고리이고, 상기 방향족 해테로 고리는 상기 화학식 3으로 표시되는 지용성 화합물)은 400nm 내지 450nm의 파장범위에서 최대 흡광영역을 가질 수 있고 상기 화학식 1-2로 표시되는 지용성 화합물 (상기 화학식 1에서 , Α가 지환족 헤테로 고리이고, 상기 지환족 헤테로 고리는 상기 화학식 4로 표시되는 지용성 화합물)은 150nm 내지 400nm, 예컨대 350nm 내지 400nm의 파장범위에서 최대 흡광영역을 가질 수 있다. For example, the fat-soluble compound represented by Chemical Formula 1-1 (In Chemical Formula 1, A is Is an aromatic hetero ring, the aromatic hetero ring is a fat-soluble compound represented by the formula (3) may have a maximum absorption region in the wavelength range of 400nm to 450nm and the fat-soluble compound represented by the formula (1-2) , A is an alicyclic hetero ring, and the alicyclic hetero ring is a fat-soluble compound represented by Formula 4) may have a maximum absorption region in the wavelength range of 150 nm to 4 00 nm, for example, 350 nm to 400 nm.
일반적으로， 염료는 컬러필터 내에 사용되는 구성성분 중 가장 고가의 구성성분이다. 그러므로, 원하는 효괴., 예컨대 고휘도나 고명임-비 등을 달성하기 위해서는 고가의 염료를 더 많이 사용해야 히-기 때문에 생산 단가가 상승할 수 밖에 없었다. 그러니', 일 구현예에 따른 지용성 화합물을 컬러필터 내 염료, 예컨대 조색용 염료로사용하는 경우, 적은 양으로도 고휘도, 고명암비 등의 우수한 색특성을 달성할 수 있어 생산 단가의 절감이 가능하다. 다른 일 구현예에 따르면, 상기 일 구현예에 따른 지용성 화합물을 포함하는 감광성 수지 조성물을 제공한다.  In general, dyes are the most expensive of the components used in color filters. Therefore, in order to achieve the desired effect, for example, high brightness and high visibility-ratio, more expensive dyes have to be used. Therefore, when the fat-soluble compound according to one embodiment is used as a dye in a color filter, for example, a dye for dyeing, excellent color characteristics such as high brightness and high contrast ratio can be achieved with a small amount, thereby reducing the production cost. . According to another embodiment, a photosensitive resin composition comprising a fat-soluble compound according to the embodiment is provided.
예컨대, 상기 감광성 수지 조성물은 싱-기 일 구현예에 따른 지용성 화합물, 알칼리 가용성 수지, 광중합성 화합물， 광중합 개시제 및 용매를 포함할 수 있다. 또한, 상기 감광성 수지 조성물은 안료도 더 포함할 수 있다.  For example, the photosensitive resin composition may include a fat-soluble compound, an alkali-soluble resin, a photopolymerizable compound, a photopolymerization initiator, and a solvent according to a single-group embodiment. In addition, the photosensitive resin composition may further include a pigment.
싱-기 일 구현예에 따른 지용성 화합물은 감광성 수지 조성물 내에서 착색제, 예컨대 염료, 예컨대 황색 조색 염료로서의 역할을 하여, 우수한 색특성을 발현할 수 있다.  The fat-soluble compound according to a single-group embodiment may serve as a colorant such as a dye such as a yellowish color dye in the photosensitive resin composition, thereby expressing excellent color characteristics.
일 구현예에 따른 지용성 화합물은 상기 감광성 수지 조성물 총량에 대해 1 중량 % 내지 10 중량%, 예컨대 3 중량% 내지 7 증량%로 포함될 수 있다. 상기 범위로 일 구현예에 따른 화합물이 포함될 경우 색재현율 및 명암비가 우수해진다. 상기 안료는 황색 안료, 녹색 안료, 적색 안료 또는 이들의 조힙- 등을 포함할 수 있으나 이에 한정되는 것은 아니디-. 예컨대 싱'기 안료는 안료분산액의 형태로 싱-기 감광성 수지 조성물에 포함될 수 있다.  The fat-soluble compound according to one embodiment may be included in an amount of 1 wt% to 10 wt%, such as 3 wt% to 7 wt%, based on the total amount of the photosensitive resin composition. When the compound according to the embodiment is included in the above range, color reproducibility and contrast ratio are excellent. The pigment may include, but is not limited to, a yellow pigment, a green pigment, a red pigment or a chopped-up thereof. For example, the 'group' pigment may be included in the sing-group photosensitive resin composition in the form of a pigment dispersion.
싱-기 안료분산액은 고형분의 안료, 용제 및 상기 용제 내에 상기 안료를 균일하게 분산시키기 위한 분산제를 포함할 수 있다.  The sing-based pigment dispersion may include a solid pigment, a solvent, and a dispersant for uniformly dispersing the pigment in the solvent.
상기 고형분의 안료는 안료분산액 총량에 대하여 1 중량 % 내지 20 증량%, 예컨대 8 증량 % 내지 20 중량 %, 예컨대 15 중량% 내지 20 중량 %, 예컨대 8 중량0 /0 내지 15 중량%, 예컨대 10 중량 % 내지 20 증량 %, 예컨대 10 중량 % 내지 15 중량 %로 포함될 수 있다. The pigment of the solid content is 1% by weight to 20% by weight based on the total amount of the pigment dispersion, For example, it may be included in an 8 increase% to 20% by weight, for example 15% to 20% by weight, for example 8 weight 0/0 to 15% by weight, for example 10% to 20 increase%, for example 10% by weight to 15% by weight .
상기 분산제로는 비이온성 분산제, 음이온성 분산제, 양이온성 분산제 등을 사용할 수 있디-. 싱끼 분산제의 구체적인 예로는， 폴리알킬렌글리콜 및 이의 에스테르, 폴리옥시알킬렌, 다가알코을 에스테르 알킬렌 옥사이드 부가물, 알코을알킬렌 옥사이드 부가물, 술폰산 에스테르, 술폰산 염, 카르복실산 에스테르, 카르복실산 염, 알킬아미드 알킬렌 옥사이드 부가물, 알킬 아민 등을 들 수 있으며, 이들을 단독으로 또는 둘 이상흔합하여 사용할 수 있다.  As the dispersant, a nonionic dispersant, anionic dispersant, cationic dispersant, etc. may be used. Specific examples of the dispersant include polyalkylene glycols and esters thereof, polyoxyalkylenes, polyhydric alcohol ester alkylene oxide adducts, alcohol alkylene oxide adducts, sulfonic acid esters, sulfonic acid salts, carboxylic acid esters, and carboxylic acids. Salts, alkylamide alkylene oxide adducts, alkyl amines, and the like, and these may be used alone or in combination of two or more.
상기 분산제의 시판되는 제품을 예로 들면, ΒΥΚ 의 DISPERBYK- For example, commercially available products of the dispersant include DISPERBYK- by ΒΥΚ.
101, DISPERBYK— 130, DISPERBYK-140, DISPERBY -160, DISPERBYK-161, DISPERBY -162, DISPERBYK- 163, DISPERBYK- 164, DISPERBYK- 165, 101, DISPERBYK— 130, DISPERBYK-140, DISPERBYK-160, DISPERBYK-161, DISPERBY-162, DISPERBYK-163, DISPERBYK-164, DISPERBYK-165,
DISPERBYK- 166, DISPERBYK- 170, DISPERBYK-171 , DISPERBYK- 182, DISPERBYK- 166, DISPERBYK- 170, DISPERBYK-171, DISPERBYK- 182,
DISPERBYK— 2000, DISPERBYK-2001 등; EFKA 케미칼社의 EFKA— 47, EFKA- 47EA, EF A-48, EFKA-49, EFKA- 100, EFKA-400, EFKA-450 등； Zeneka社의 Solsperse 5000,Solsperse 12000, Solsperse 13240, Solsperse 13940, Solsperse 17000, Solsperse 20000, Solsperse24000GR, Solsperse 27000, Solsperse 28000 등; 또는 Ajinomoto社의 PB7U, PB821 등이 있다. DISPERBYK—2000, DISPERBYK-2001, and the like; EFKA- 47, EFKA- 47EA, EF A-48, EFKA-49, EFKA- 100, EFKA-400, EFKA-450, etc., from EFKA Chemical Co., Ltd .; 17000, Solsperse 20000, Solsperse 24000GR, Solsperse 27000, Solsperse 28000, and the like; Or PB7U, PB821 from Ajinomoto.
상기 분산제는 안료분산액 총량에 대하여 1 중량 % 내지 20 중량 %로 포함될 수 있다. 분산제가 상기 범위 내로 포함될 경우, 적절한 점도를 유지할 수 있어 감광성 수지 조성물의 분산성이 우수하며 이로 인해 제품 적용시 광학적, 물리적 및 화학적 품질을 유지할 수 있다.  The dispersant may be included in an amount of 1 wt% to 20 wt% based on the total amount of the pigment dispersion. When the dispersant is included in the above range, it is possible to maintain an appropriate viscosity to excellent dispersibility of the photosensitive resin composition, thereby maintaining the optical, physical and chemical quality in the product application.
상기 안료분산액을 형성하는 용제로는 에틸렌글리콜 아세테이트,  Examples of the solvent for forming the pigment dispersion include ethylene glycol acetate,
에틸셀로솔브 ,프로필렌글리콜 모노메틸에테르아세테이트, 에틸락테이트, Ethyl cellosolve, propylene glycol monomethyl ether acetate, ethyl lactate,
폴리에틸렌글리콜,사이클로핵사논, 프로필렌글리콜 메틸에테르 등을 사용할 수 있다. Polyethylene glycol, cyclonucleanone, propylene glycol methyl ether and the like can be used.
싱-기 안료분산액은 싱'기 감광성 수지 조성물 총량에 대하여 5 증량 % 내지 30 중량%, 예컨대 10 중량 % 내지 25 중량%로 포함될 수 있다. 싱-기  The sing-based pigment dispersion may be included in an amount of 5% by weight to 30% by weight, such as 10% by weight to 25% by weight, based on the total amount of the sing'-group photosensitive resin composition. Singh-ki
안료분산액이 싱-기 범위 내로 포함될 경우, 공정마진 확보에 유리하고, 색재현율 및 명암비가 우수해진디-. 상기 알칼리 가용성 수지는 아크릴계 수지일 수 있디-. When the pigment dispersion is included in the sing-base range, it is advantageous to secure process margins, and the color reproducibility and contrast ratio are excellent. The alkali-soluble resin may be an acrylic resin.
상기 아크릴계 수지는 제 1 에틸렌성 불포화 단량체 및 이와 공중합 가능한 제 2 에틸렌성 블포화 단량체의 공중합체로, 하나 이상의 아크릴계 반복단위를 포함하는 수지일 수 있다.  The acrylic resin is a copolymer of the first ethylenically unsaturated monomer and the second ethylenically unsaturated monomer copolymerizable therewith, and may be a resin including one or more acrylic repeating units.
상기 제 1 에틸렌성 불포화 단량체는 하나 이상의 카르복시기를 함유하는 에틸렌성 볼포화 단량체이며， 이의 구체적인 예로는 아크릴산， 메타크릴산, 말레산, 이타콘산, 푸마르신ᅳ, 또는 이들의 조합을 들 수 있다.  The first ethylenically unsaturated monomer is an ethylenic ball-saturated monomer containing at least one carboxyl group, and specific examples thereof may include acrylic acid, methacrylic acid, maleic acid, itaconic acid, fumarcin, or a combination thereof.
상기 게 1 에틸렌성 불포화 단량체는 상기 아크릴계 바인더 수지 총량에 대하여 5 중량% 내지 50 중량%, 예컨대 10 중량 % 내지 40 증량%로 포함될 수 있다.  The crab 1 ethylenically unsaturated monomer may be included in 5% by weight to 50% by weight, such as 10% by weight to 40% by weight, based on the total amount of the acrylic binder resin.
상기 제 2 에틸렌성 붙포화 단량체는 스티렌 , α-메틸스티렌, 비닐를루엔, 비닐벤질메틸에테르 등의 방향족 비닐 화합물; 메틸 (메타)아크릴레이트, The second ethylenic saturated monomer may be selected from the group consisting of aromatic vinyl compounds such as styrene, α -methylstyrene, vinylluene and vinylbenzylmethyl ether; Methyl (meth) acrylate,
에틸 (메타)아크릴레이트, 부틸 (메타)아크릴레이트, 2-히드록시에틸 (메타)아크릴레이트, 2-히드록시 부틸 (메타)아크릴레이트, 벤질 (메타)아크릴레이트, Ethyl (meth) acrylate, butyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, 2-hydroxy butyl (meth) acrylate, benzyl (meth) acrylate,
시 -이클로핵실 (메타)아크릴레이트, 페닐 (메타)아크릴레이트 등의 불포화 카르복시산 에스테르 화합물; 2-아미노에틸 (메티 아크릴레이트, 2- 디메틸아미노에틸 (메타)아크릴레이트 등의 불포화 카르복시산 아미노 알킬 에스테르 화합물; 초산비닐, 안식향산 비닐 등의 카르복시산 비닐 에스테르 화합물; Unsaturated carboxylic ester compounds such as cy-cyclohexyl (meth) acrylate and phenyl (meth) acrylate; Unsaturated carboxylic acid amino alkyl ester compounds such as 2-aminoethyl (methacrylate and 2-dimethylaminoethyl (meth) acrylate), and carboxylic acid vinyl ester compounds such as vinyl acetate and vinyl benzoate;
글리시딜 (메티 아크릴레이트 등의 불포화 카르복시산 글리시딜 애스테르 화합물; (메.타)아크릴로니트릴 등의 시안화 비닐 화합물; (메타)아크릴아미드 등의 불포화 아미드 화합물; 등을 들 수 있으며, 이들을 단독으로 또는 들 이상흔합하여 사용할 수 있다. Glycidyl (unsaturated carboxylic acid glycidyl aster compounds such as methacrylate; vinyl cyanide compounds such as (meth) acrylonitrile; unsaturated amide compounds such as (meth) acrylamide); and the like. It can be used alone or in combination of two or more.
상기 아크릴계 바인더 수지의 구체적인 예로는 폴리벤질메타크릴레이트 공중합체, (메타)아크릴산 /벤질메타크릴레이트 공중합체,  Specific examples of the acrylic binder resin include polybenzyl methacrylate copolymer, (meth) acrylic acid / benzyl methacrylate copolymer,
(메타)아크릴산 /벤질메타크릴레이트 /스티렌 공중합체, (Meth) acrylic acid / benzyl methacrylate / styrene copolymer,
(메타)아크릴산 /벤질메타크릴레이트 /2-히드록시에틸메타크릴레이트 공중합체 ,  (Meth) acrylic acid / benzyl methacrylate / 2-hydroxyethyl methacrylate copolymer,
(메타)아크릴산 /벤질메티'크릴레이트 /스티렌 /2-히드록시에틸메타크릴레이트 공중합체 등을 들 수 있으니ᅳ, 이애 한정되는 것은 아니며, 이들을 단독 또는 2종 이상을 배합하여 사용할 수도 있다. The (meth) acrylic acid / benzyl methacrylate / styrene / 2-hydroxyethyl methacrylate copolymer etc. are mentioned, It is not limited to these, These can also be used individually or in combination of 2 or more types.
상기 알칼리 가용성 수지의 중량평균 분자량은 3,000 g/mol 내지 150,000 g/mol, 예컨대 5,000 g/mol 내지 50,000 g/mol, 예컨대 20,000 g/mol 내지 30,000 g mol 일 수 있다. 상기 알칼리 가용성 수지의 증량평균 분자량이 싱-기 범위 내일 경우, 상기 감광성 수지 조성물의 물리적 및 화학적 물성이 우수하고 점도가 적절하며, 컬러필터 제조시 기판과의 밀착성이 우수하다. The weight average molecular weight of the alkali-soluble resin is 3,000 g / mol to 150,000 g / mol, such as 5,000 g / mol to 50,000 g / mol, such as 20,000 g / mol to 30,000 g mol. When the increase average molecular weight of the alkali-soluble resin is within the sing-group range, the physical and chemical physical properties of the photosensitive resin composition are excellent, the viscosity is appropriate, and the adhesion to the substrate is excellent when the color filter is manufactured.
싱-기 알칼리 가용성 수지의 산가는 15 mgKOH/g 내지 60 mgKOH/g, 예컨대 The acid value of the singe-based alkali soluble resin is 15 mgKOH / g to 60 mgKOH / g, such as
20 mgKOH/g 내지 50 mgKOH/g 일 수 있디-. 알칼리 가용성 수지의 산가가 상기 범위 내일 경우 픽셀 패턴의 해상도가 우수하다. 20 mgKOH / g to 50 mgKOH / g. When the acid value of alkali-soluble resin is in the said range, the resolution of a pixel pattern is excellent.
상기 알칼리 가용성 수지는 상기 감광성 수지 조성물 총량에 대하여 1 중량 % 내지 30 중량 %, 예컨대 1 중량% 내지 15 증량 %로 포함될 수 있다. 알칼리 가용성 수지가 상기 범위 내로 포함될 경우, 컬러필터 제조시 현상성이 우수하며 가교성이 개선되어 우수한 표면 평활도를 얻을 수 있디-.  The alkali-soluble resin may be included in 1% by weight to 30% by weight, such as 1% by weight to 15% by weight, based on the total amount of the photosensitive resin composition. When the alkali-soluble resin is included in the above range, it is excellent in developability in the production of color filters and crosslinkability is improved to obtain excellent surface smoothness.
싱-기 광중합성 화합물은 적어도 1개의 에틸렌성 불포화 이중결합을 가지는 (메타)아크릴산의 일관능 또는 다관능 에스테르가사용될 수 있다.  The single-group photopolymerizable compound may be a monofunctional or polyfunctional ester of (meth) acrylic acid having at least one ethylenically unsaturated double bond.
광중합성 화합물은 싱ᅳ기 에틸렌성 불포화 이증결합을 가짐으로써, 패턴 형성 공정애서 노광시 충분한 중합을 일으킴으로써 내열성, 내광성 및 내화학성이 우수한 패턴을 형성할 수 있다.  Since the photopolymerizable compound has a single ethylenically unsaturated divalent bond, it causes sufficient polymerization during exposure in the pattern formation process to form a pattern excellent in heat resistance, light resistance and chemical resistance.
광중합성 화합물의 구체적인 예로는， 에틸렌 글리콜 디 (메타)아크릴레이트, 디에틸렌 글리콜 디 (메타)아크릴레이트, 트리에틸렌 글리콜 디 (메타)아크릴레이트， 프로필렌 글리콜 디 (메타)아크릴레이트, 네오 틸 글리콜 디 (메타)아크릴레이트 , 1,4- 부탄디을 디 (메타)아크릴레이트, 1 ,6-핵산디을 디 (메타)아크릴레이트, 비스페놀 A 디 (메타)아크릴레이트, 펜타에리트리를 디 (메타)아크릴레이트, 펜타에리트리를 트리 (메티ᅳ)아크릴레이트， 펜타에리트리를 테트라 (메타)아크릴레이트, 펜타에리트리를 핵사 (메타)아크릴레이트, 디펜타에리트리를 디 (메타)아크릴레이트, 디펜타애리트리를 트리 (메타)아크릴레이트, 디펜타에리트리를 펜타 (메타)아크릴레이트,  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, neomethyl glycol di Di (meth) acrylates (meth) acrylate, 1,4-butanedi di (meth) acrylate, di (meth) acrylate 1,6-nucleic acid di (meth) acrylate, bisphenol A di (meth) acrylate It is tri (meth) acrylate to pentaerythrate, tetra (meth) acrylate to pentaerythrite, nucleus (meth) acrylate to pentaerythritol, and di (meth) acrylate, dipenta to pentaerythritol Atritree tri (meth) acrylate, dipentaerythritol penta (meth) acrylate,
디펜타에리트리를 핵사 (메타)아크릴레이트, 비스페놀 A 애폭시 (메티-)아크릴레이트, 에틸렌 글리콜 모노메틸에테르 (메타)아크릴레이트, 트리메틸을 프로판 It is propane to nucleate (meth) acrylate, bisphenol A epoxy (meth-) acrylate, ethylene glycol monomethyl ether (meth) acrylate, trimethyl
트리 (메타)아크릴레이트, 트리스 (메타)아크릴로일옥시에틸 포스페이트, 노볼락에폭시 (메타)아크릴레이트 등을 들 수 있다. Tri (meth) acrylate, tris (meth) acryloyloxyethyl phosphate, a novolak epoxy (meth) acrylate, etc. are mentioned.
광증합성 화합물의 시판되는 제품을 예로 들면 다음과 같다. 상기  Examples of commercially available products of the photopolymerizable compounds are as follows. remind
(메티ᅳ)아크릴산의 일관능 에스테르의 예로는, 도아 고세이 가가꾸 고교 (주)社의 아로닉스 M-101®, 동 M-l l l®, 동 M-114® 등; 니혼 가야꾸 (주)社의 KAYARAD TC- 11 OS®, 동 TC-120S®등; 오사카 유끼 가가꾸 고교 (주)社의 V-158®, V-231 1®등을 들 수 있다. 상기 (메타)아크릴산의 이관능 에스테르의 예로는, 도아 고세이 가가꾸 고교 (주)社의 아로닉스 M-210® 동 M-240®, 동 M-6200® 등; 니흔 가야꾸 (주)社의 I AYARAD HDDA®, 동 HX-220®, 동 R-604® 등; 오사카유끼 가가꾸 고교 (주)社의 V- 260®, V-312®, V-335 HP® 등을 들 수 있다. 상기 (메타)아크릴산의 삼관능 Examples of the monofunctional ester of (methicyl) acrylic acid include those of Toagosei Kagaku Kogyo Co., Ltd. Aronix M-101 ® , copper Mll ll ® , copper M-114 ®, etc .; Nihon Kayaku Co., Ltd.'s KAYARAD TC-11 OS ® , TC-120S ®, etc .; And V-158 ® and V-231 1 ® by Osaka Yuki Kagaku Kogyo Co., Ltd. Examples of the difunctional ester of the above (meth) acrylic acid include, but are not limited to, Aronix M-210 ® M-240 ® , M-6200 ®, etc. manufactured by Toagosei Kagaku Kogyo Co., Ltd .; Nihon Kayak Co., Ltd. I AYARAD HDDA ® , HX-220 ® , R-604 ®, etc .; And V-260 ® , V-312 ® , and V-335 HP ® from Osaka Yugaku Kagaku Kogyo Co., Ltd. Trifunctionality of the (meth) acrylic acid
에스테르의 예로는, 도아 고세이 가가꾸 고교 (주)社의 아로닉스 M-309®, 동 M-400®, 동 M-405®, 동 M-450®, 동 -710®, 동 M-8030®, 동 M-8060® 등; 니흔 Examples of the ester include Aronix M-309 ® , M-400 ® , M-405 ® , M-450 ® , -710 ® , M-8030 ® from Toagosei Kagaku Kogyo Co., Ltd. , Copper M-8060 ® and the like; Nihon
가야꾸 (주) St의 KAYARAD TMPTA®, 동 DPCA-20®, 동 -30®, 동— 60®, 동 -120®등; KAYARAD TMPTA ® , DPCA-20 ® , -30 ® ,-60 ® , -120 ® etc. from St. Kayak Co .;
오사카 유끼 가야꾸 고교 (주)社의 V-295®, 동 -300®, 동 -360®, 동— GPT®, 동 -3PA®, 동- 400® 등을 들 수 있다. 상기 제품을 단독 사용 또는 2종 이상 함께 사용할 수 있다. And V-295 ® , East -300 ® , East -360 ® , East-GPT ® , East -3PA ® and East-400 ® by Osaka Yuki Kayaku Kogyo Co., Ltd. The above products can be used alone or in combination of two or more.
상기 광증합성 화합물은 보다 우수한 현상성을 부여히-기 위하여 산무수물로 처리하여 사용할 수도 있디-.  The photopolymerizable compound may be used by treating with an acid anhydride to impart better developability.
상기 광중합성 화합물은 상기 감광성 수지 조성물 총량에 대하여 1 증량% 내지 15 중량%, 예컨대 5 중량 % 내지 10 증량 %로 포함될 수 있다. 광증합성 화합물이 상기 범위 내로 포함될 경우, 패턴 형성 공정에서 노광 시 경화가층분히 일어나 신뢰성이 우수하며, 알칼리 현상액에의 현상성이 우수하다.  The photopolymerizable compound may be included in an amount of 1 wt% to 15 wt%, such as 5 wt% to 10 wt%, based on the total amount of the photosensitive resin composition. When a photopolymerizable compound is contained in the said range, hardening arises at the time of exposure in a pattern formation process, and it is excellent in reliability, and is excellent in developability to an alkaline developing solution.
싱-기 광중합 개시제는 감광성 수지 조성물애 일반적으로사용되는  Singh-based photopolymerization initiator is generally used in photosensitive resin composition
개시제로서, 예를 들어 아세토페논계 화합물, 벤조페논계 화합물, 티오크산톤계 화합물, 벤조인계 화합물, 옥심계 화합물 또는 이들의 조합을사용할 수 있다-. As the initiator, for example, an acetophenone compound, a benzophenone compound, a thioxanthone compound, a benzoin compound, an oxime compound or a combination thereof can be used.
상기 아세토페논계의 화합물의 예로는 , 2,2'-디에특시 아세토페논, 2,2'-디부특시 아세토페논, 2-히드록시 -2-메틸프로피오페논 , ρ-t-부릴트리클로로 아세토페논 , p-t— 부틸디클로로 아세토페논, 4-클로로 아세토페는, 2,2'-디클로로 -4-페녹시 아세토페논, 2- 메틸 -1ᅳ(4- (메틸티오)페닐) -2—모폴리노프로판 -1-은, 2-벤질 -2-디메틸아미노— 1-(4- 모플리노페닐) -부탄 -1-은 등을 들 수 있디-.  Examples of the acetophenone-based compound include 2,2'-dietospecific acetophenone, 2,2'-dibuspecial acetophenone, 2-hydroxy-2-methylpropiophenone and ρ-t-buryltriclo With acetophenone, pt— butyldichloro acetophenone, 4-chloro acetophene, 2,2'-dichloro-4-phenoxy acetophenone, 2-methyl-1 '(4- (methylthio) phenyl) -2— Morpholinopropane-1- is 2-benzyl-2-dimethylamino- 1- (4-morpholinophenyl) -butane-1-silver, etc .;
상기 벤조페논계 화합물의 예로는, 벤조페논, 벤조일 안식향산, 벤조일 안식향산 메틸， 4—페닐 벤조페논, 히드록시 벤조페논, 아크릴회' 벤조페논, 4,4'— 비스 (디메틸 아미노)벤조페논, 4,4'-비스 (디에틸아미노)벤조페논, 4,4'- 디메틸아미노벤조페논, 4,4'-디클로로벤조페논, 3,3'-디메틸 -2-메특시벤조페논 등을 들 수 있다. Examples of the benzophenone-based compound include benzophenone, benzoyl benzoic acid, methyl benzoyl benzoate, 4-phenyl benzophenone, hydroxy benzophenone, acryl ash 'benzophenone, 4,4'-bis (dimethyl amino) benzophenone, 4 , 4'-bis (diethylamino) benzophenone, 4,4'- dimethylamino benzophenone, 4,4'- dichloro benzophenone, 3,3'- dimethyl- 2-methoxy benzophenone, etc. are mentioned. Can be.
상기 티오크산톤계 화합물의 예로는, 티오크산톤, 2-메틸티오크산톤, 이소프로필.티오크산톤, 2,4-디에틸 티오크산톤， 2,4-디이소프로필 티오크산론， 2- 클로로티오크산톤 등을 들 수 있다.  Examples of the thioxanthone-based compound include thioxanthone, 2-methyl thioxanthone and isopropyl thioxanthone, 2,4-diethyl thioxanthone, 2,4-diisopropyl thioxanthone, 2 -Chloro thioxanthone, etc. are mentioned.
상기 벤조인계 화합물의 예로는, 벤조인, 벤조인 메틸 에테르, 벤조인 에틸 에테르, 벤조인 이소프로필 에테르, 벤조인 이소부틸 에테르， 벤질디메틸케탈 등을 들 수 있다.  Examples of the benzoin compound include benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl ether, benzyldimethyl ketal and the like.
싱ᅳ기 트리아진계 화합물의 예로는 , 2,4,6-트리클로로 -S-트리아진, 2-페닐 4,6- 비스 (트리클로로메틸) -S-트리아진, 2-(3', 4'-디메특시스티릴) -4,6-비스 (트리클로로메틸) -S- 트리아진， 2-(4'-메록시나프틸 )-4,6-비스 (트리클로로메틸) -S-트리아진, 2-(p-메톡시페닐) - 4,6 -비스 (트리클로로메틸) -S-트리아진, 2-(p-를릴) -4,6-비스 (트리클로로 메틸) -s—트리아진, Examples of the succinyl triazine compound include 2,4,6-trichloro-S-triazine, 2-phenyl 4,6-bis (trichloromethyl) -S-triazine, 2- (3 ', 4 '-Dimethoxystyryl) -4,6-bis (trichloromethyl) -S- triazine, 2- (4'-methoxynaphthyl) -4,6-bis (trichloromethyl) -S- Triazine, 2- (p-methoxyphenyl) -4,6-bis (trichloromethyl) -S-triazine, 2- (p-lryl) -4,6-bis (trichloromethyl) -s— Triazine,
2-비페닐 4,6-비스 (트리클로로 메틸) -S-트리아진， 비스 (트리클로로메틸 >6-스티릴 -S- 트리아진， 2— (나프토- 1 -일) -4,6-비스 (트리클로로메틸 )-s-트리아진 , 2-(4-메록시나프토— 1 - 일) -4,6-비스 (트리클로로메틸)— s-트리아진， 2-4-비스 (트리클로로메틸) -6-피페로닐 트리아진, 2-4-비스 (트리클로로메틸) 6-(4-메톡시스티릴) 트리아진 등을 들 수 있디-. 상기 옥심계 화합물의 예로는 , 0—아실옥심계 화합물 , 2-(ο벤조일옥심) -1-[4- (페닐티오)페닐]—1 ,2—옥탄디온, 1 -(0-아세틸옥심) -1-[9-에틸 -6-(2-메틸벤조일) -9H-카르바졸-2-biphenyl 4,6-bis (trichloromethyl) -S-triazine, bis (trichloromethyl> 6-styryl-S-triazine, 2— (naphtho- 1 -yl) -4,6 -Bis (trichloromethyl) -s-triazine, 2- (4-methoxynaphtho— 1 -yl) -4,6-bis (trichloromethyl)-s-triazine, 2-4-bis ( Trichloromethyl) -6-piperonyl triazine, 2-4-bis (trichloromethyl) 6- (4-methoxystyryl) triazine, etc. Examples of the oxime compounds include 0—acyl oxime compound, 2- (οbenzoyloxime) -1- [4- (phenylthio) phenyl] -1,2-octanedione, 1- ( 0 -acetyloxime) -1- [9-ethyl- 6- (2-methylbenzoyl) -9H-carbazole-
3-일]에탄온 , 0-에록시카르보닐 -α—옥시아미노 -1-페닐프로판 -1—은 등을 사용할 수 있디-. 상기 0-아실옥심계 화합물의 구체적인 예로는 , 1 ,2-옥탄디온, 2-디메틸아미노—2-(4- 메틸벤질 )— 1 -(4-모르폴린 -4-일-페닐) -부탄 1 -은, 페닐술파닐페닐) -부탄 -1 ,2-디온 2- 옥심 -0-벤조에이트, 1 -(4—페닐술파닐페닐) -옥탄 디온 2—옥심— 0-벤조에이트, 1-(4- 페닐술파닐페닐) -옥탄 -1—은옥심 -0-아세테이트, 1 -(4-페닐술파닐페닐) -부탄 -1—온옥심 -0— 아세테이트 등을 들 수 있다. 3-yl] ethanone, 0-ethoxycarbonyl -α-oxyamino-1-phenylpropane-1-silver, etc. can be used. Specific examples of the 0-acyl oxime compound include 1,2-octanedione, 2-dimethylamino—2- (4-methylbenzyl) —1- (4-morpholin-4-yl-phenyl) -butane 1 -Silver, phenylsulfanylphenyl) -butane -1,2-dione 2-oxime -0-benzoate, 1-(4-phenylsulfanylphenyl) -octane dione 2-oxime- 0-benzoate, 1- ( 4-phenylsulfanylphenyl) -octane -1-silver oxime -0-acetate, 1-(4-phenylsulfanylphenyl)-butane-1-onoxime-0-acetate, etc. are mentioned.
싱-기 광증합 개시제는 싱-기 화합물 이외에도 카바졸계 화합물, 디케톤류 화합물, 술포늄 보레이트계 화합물, 디아조계 화합물, 이미다졸계 화합물,  In addition to the sing-group compounds, the sing-group photopolymerization initiators include carbazole compounds, diketone compounds, sulfonium borate compounds, diazo compounds, imidazole compounds,
비이미다졸계 화합물 등을 사용할수 있디-. Biimidazole type compound etc. can be used-.
상기 광중합 개시제는 빛을 흡수하여 들뜬 상태가 된 후 그 에너지를 전달함으로써 화학반응을 일으키는 광 증감제와 함께 사용될 수도 있다.  The photopolymerization initiator may be used together with a photosensitizer which causes a chemical reaction by absorbing light and transferring energy after being excited.
싱-기 광 증감제의 예로는, 테트라에틸렌글리콜 비스 -3-머캡토 프로피오네이트 펜타에리트리롤 테트라키스 -3-머캡토 프로피오네이트， 디펜타에리트리롤 테트라키스- 3-머캡토 프로피오네이트 등을 들 수 있다. Examples of the single-photosensitive sensitizer include tetraethyleneglycol bis-3-mercapto propionate pentaerythritol tetrakis-3-mercapto propionate, dipentaerytriol tetrakis- 3-mercapto propionate, etc. are mentioned.
싱-기 광증합 개시제는 상기 감광성 수지 조성물 총량애 대하여 0.01 중량 % 내지 10 증량0 /0, 예컨대 0, 1 중량 % 내지 5 증량 %로 포함될 수 있다. 광증힙- 개시제가 상기 범위 내로 포함될 경우, 패턴 형성 공정에서 노광시 경화가 층분히 일어나 우수한 신뢰성을 얻을 수 있으며, 패턴의 내열성, 내광성 및 내화학성이 우수하고， 해상도 및 밀착성 또한우수하며, 미반응 개시제로 인한 투과율의 저하를 막을 수 있다. Washing-machine photomultiplier sum initiator may be contained in the photosensitive resin composition for her total amount of 0.01% by weight increased to 10 0/0, for example 0, 1% to 5% increase. When the photo-heap-initiator is included in the above range, curing occurs during exposure in the pattern forming process to obtain excellent reliability, excellent heat resistance, light resistance and chemical resistance of the pattern, excellent resolution and adhesion, and unreacted. The fall of the transmittance | permeability by an initiator can be prevented.
상기 용매는 일 구현예에 따른 지용성 화합물, 안료, 알칼리 가용성 수지, 광중합성 화합물 및 광중합 개시제와의 상용성을 가지되 반응하지 않는 물질들이 사용될 수 있다， 상기 용매는 유기 용매일 수 있다.  The solvent may be used a substance which has compatibility with the fat-soluble compound, the pigment, the alkali-soluble resin, the photopolymerizable compound and the photopolymerization initiator, but does not react. The solvent may be an organic solvent.
상기 용매의 예로는, 메탄을, 에탄올 등의 알코올류; 디클로로에틸 에테르 , η- 부틸 에테르, 디이소아밀 에테르, 메틸페닐 애테르, 테트라히드로퓨란 등의 에테르류; 에틸렌 글리콜 모노메틸에테르, 에틸렌 글리콜 모노애틸에테르 등의 글리콜  Examples of the solvent include methane and alcohols such as ethanol; Ethers such as dichloroethyl ether, η-butyl ether, diisoamyl ether, methylphenyl ether and tetrahydrofuran; Glycols such as ethylene glycol monomethyl ether and ethylene glycol monoethyl ether
에테르류; 메틸 샐로솔브 아세테이트, 에틸 셀로솔브 아세테이트, 디애틸 샐로솔브 아세테이트 등의 샐로솔브 아세테이트류; 메틸에틸 카르비를， 디에틸 카르비를, 디에틸렌 글리콜 모노메틸에테르， 디에틸렌 글리콜 모노에틸에테르， 디에틸렌 글리콜 디메틸에테르, 디애틸렌 글리콜 메틸에틸에테르, 디에틸렌 글리콜 Ethers; Cellosolve acetates such as methyl cellosolve acetate, ethyl cellosolve acetate, and diethyl cellosolve acetate; Methyl ethyl carbye, diethyl carbye, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol dimethyl ether, diethylene glycol methylethyl ether, diethylene glycol
디에틸에테르 등의 카르비를류; 프로필렌 글리콜 메틸에테르 아세테이트, 프로필렌 글리콜 프로필에테르 아세테이트 등의 프로필렌 글리콜 알킬에테르 아세테이트류; 를루엔, 크실렌 등의 방향족 탄화수소류; 메틸에틸케톤,사이클로핵사논, 4-히드록시-Carbyls such as 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; Methyl ethyl ketone, cyclonucleanone, 4-hydroxy-
4—메틸 -2-¾타논, 메틸 -n-프로필케톤, 메틸 -n-부틸케톤, 메틸 -n-아밀케론， 2-헵타논 등의 케톤류; 초산 에틸, 초산 -nᅳ부틸, 초산 이소부틸 등의 포화 지방족 모노카르복실신- 알킬 에스테르류; 젖산 메틸, 젖산 에틸 등의 젖산 에스테르류; 옥시 초산 메틸， 옥시 초산 애틸， 옥시 초산 부틸 등의 옥시 초산 알킬 에스테르류; 메특시 초산 메틸, 메록시 초산 애틸, 메톡시 초산 부틸, 에록시 초산 메틸， 에록시 초산 에틸 등의 알콕시 초산 알킬 에스테르류; 3-옥시 프로피온산 메틸， 3-옥시 프로피온산 에틸 등의 3-옥시 프로피은산 알킬에스테르류; 3-메록시 프로피온산 메틸, 3-메특시 Ketones such as 4—methyl-2-¾tanone, methyl-n-propylketone, methyl-n-butylketone, methyl-n-amylkeron and 2-heptanone; Saturated aliphatic monocarboxyl-alkyl esters such as ethyl acetate, n-butyl acetate, and isobutyl acetate; Lactic acid esters such as methyl lactate and ethyl lactate; Oxy acetic acid alkyl esters such as methyl oxy acetate, oxy acetic acid and butyl oxy acetate; Alkoxy acetic acid alkyl esters such as methyl acetate, methoxy acetic acid, methoxy butyl acetate, ethoxy methyl acetate, and ethoxy ethyl acetate; 3-oxy propionic acid alkyl esters such as methyl 3-oxy propionate and ethyl 3-oxypropionate; 3-methoxy methyl propionate, 3-methoxy
프로피온산 에틸, 3-에톡시 프로피온산 에틸, 3-에특시 프로피은산 메틸 등의 3- 알큭시 프로피온산 알킬 에스테르류; 2-옥시 프로피온산 메틸, 2—옥시 프로피온산 에틸, 2-옥시 프로피은산 프로필 등의 2—옥시 프로피온산 알킬 에스테르류; 2-메록시 프로피온산 메틸, 2-메톡시 프로피온산 에틸, 2-에특시 프로피은산 에틸， 2-에록시 프로피온산 메틸 등의 2-알콕시 프로피온산 알킬 에스테르류; 2-옥시 -2-메틸 프로피온산 메틸, 2-옥시 -2-메틸 프로피온산 에틸 등의 2-옥시ᅳ 2-메틸 프로피온산 에스테르류 , 2—메특시—2-메틸 프로피온산 메틸, 2-에특시 -2-메틸 프로피온산 에틸 등의 2알콕시 -2-메틸 프로피온산 알킬류의 모노옥시 모노카르복실산 알킬 애스테르류; 2- 히드록시 프로피온산 에틸, 2—히드록시 -2-메틸 프로피온산 에틸, 히드톡시 초산 에틸, 2_히드록시—3-메틸 부탄산 메틸 등의 에스테르류; 피루빈산 에틸 등의 케톤산 에스테르류 등이 있으며 , 또한 , Ν-메틸포름아미드 , Ν,Ν-디메틸포름아미드, N- 메틸포름아닐라드, Ν-메틸아세트아미드, Ν,Ν-디메틸아세트아미드, Ν-메틸피를리돈, 디메틸술폭시드， 벤질애틸에테르, 디핵실에테르, 아세틸아세톤, 이소포론, 카프론산, 카프릴산, 1 -옥탄을 , 1—노난을, 벤질알코을, 초산 벤질, 안식향산 에틸, 옥살산 디에틸, 말레인산 디에틸 , γ-부티로락톤, 탄산 에틸렌, 탄산 프로필렌, 페닐 셀로솔브 아세테이트 등의 고비점 용매를 들 수 있다. 3-alkoxy propionic acid alkyl esters such as ethyl propionate, ethyl 3-ethoxy propionate and methyl methyl propionate; 2—oxy propionic acid alkyl esters such as methyl 2-oxy propionate, ethyl 2-oxypropionate and propyl 2-oxypropionic acid; 2-methoxy 2-alkoxy propionic acid alkyl esters such as methyl propionate, ethyl 2-methoxy propionate, ethyl 2-propyne ethylpropionate and methyl 2-ethoxy propionate; 2-oxy-2-methylpropionic acid esters, such as 2 -oxy- 2 -methyl methyl propionate and 2 -oxy- 2 -methyl ethyl propionate, 2—methecoxy—2-methyl methyl propionate, 2-especial-2- mono-oxy monocarboxylic acid alkyl astro Terre flow of current-methylpropionic acid alkyl 2-alkoxy, such as methyl propionate, ethyl-2; 2-hydroxy ethyl, 2-hydroxy-2-methylpropionic acid ethyl, hydroxy-ethoxy-ethyl, 2-hydroxy-3-methylbutoxy _ esters, such as methyl carbonate; Ketone acid esters such as ethyl pyruvate, and the like, and Ν-methylformamide, Ν, Ν-dimethylformamide, N-methylformanilade, Ν-methylacetamide, Ν, Ν-dimethylacetamide , Ν-methylpyridone, dimethyl sulfoxide, benzyl ethyl ether, dinuclear ether, acetylacetone, isophorone, caproic acid, caprylic acid, 1-octane, 1-nonane, benzyl alcohol, benzyl acetate, benzoic acid High boiling point solvents, such as ethyl, diethyl oxalate, diethyl maleate, (gamma) -butyrolactone, ethylene carbonate, propylene carbonate, and phenyl cellosolve acetate, are mentioned.
이들 증 좋게는 상용성 및 반웅성을 고려하여, 에틸렌 글리콜  Ethylene glycol, in view of their good compatibility and reaction
모노에틸에테르 등의 글리콜 에테르류; 에틸 셀로솔브 아세테이트 등의 에틸렌 글리콜 알킬에테르 아세테이트류 ; 2—히드록시 프로피온산 에틸 등의 에스테르류; 디에틸렌 글리콜 모노메틸에테르 등의 카르비롤류; 프로필렌 글리콜 모노메틸에테르 아세테이트, 프로필렌 글리콜 프로필에테르 이'세테이트 등의 프로필렌 글리콜 알킬에테르 아세테이트류가사용될 수 있다. Glycol ethers such as monoethyl ether; Ethylene glycol alkyl ether acetates such as ethyl cellosolve acetate; Esters such as 2—ethyl hydroxy propionate; Carbilol, such as diethylene glycol monomethyl ether; Propylene glycol alkylether acetates, such as propylene glycol monomethyl ether acetate and propylene glycol propylether i'acetate, can be used.
상기 용매는 상기 감광성 수지 조성물 총량에 대하여 잔부량, 예컨대 30 중량 % 내지 80 중량%로 포함될 수 있다-. 용매가 싱-기 범위 내로 포함될 경우 싱-기 감광성 수지 조성물이 적절한 점도를 가짐에 따라 컬러필터 제조 시 공정성이 우^수 _히_디-, 다른 일 구현예에 따른 감광성 수지 조성물은 기판과의 밀착성 등을 개선하기 위해 에폭시 화합물을 더 포함할 수 있다. The solvent may be included in a balance, such as 30 wt% to 80 wt%, based on the total amount of the photosensitive resin composition. When incorporated into group ranges washing-solvent washing jockey fairness in manufacturing the color filter right ^ depending on having a suitable viscosity photosensitive resin composition _ Hi _ di-, the photosensitive resin composition according to another embodiment, the substrate An epoxy compound may be further included in order to improve adhesiveness.
싱-기 에폭시 화합물의 예로는, 페놀 노볼락 에폭시 화합물, 테트라메틸 비페닐 에폭시 화합물, 비스페놀 Α형 에폭시 화합물, 지환족 에폭시 희.합물 또는 이들의 조합을 들 수 있다.  Examples of the sing-group epoxy compound include a phenol novolac epoxy compound, a tetramethyl biphenyl epoxy compound, a bisphenol A type epoxy compound, an alicyclic epoxy derivative, or a combination thereof.
상기 에폭시 화합물은 감광성 수지 조성물 100 중량부에 대하여 0.01 중량부 내지 20 중량부, 예컨대 0.1 중량부 내지 10 중량부로 포함될 수 있다. 에폭시 화합물이 상기 범위 내로 포함될 경우 밀착성, 저장성 등이 우수하다. The epoxy compound may be included in an amount of 0.01 to 20 parts by weight, such as 0.1 to 10 parts by weight, based on 100 parts by weight of the photosensitive resin composition. Epoxy When the compound is included in the above range, the adhesiveness, shelf life and the like are excellent.
또한 상기 감광성 수지 조성물은 기판과의 접착성을 향상시키기 위해 카르복실기, 메타크릴로일기, 이소시아네이트기 , 에폭시기 등의 반웅성 치환기를 갖는 실란 커플링제를 더 포함할 수 있디-.  In addition, the photosensitive resin composition may further include a silane coupling agent having a semi-aromatic substituent such as carboxyl group, methacryloyl group, isocyanate group, epoxy group, etc. in order to improve adhesion to the substrate.
상기 실란 커플링제의 예로는, 트리메특시실릴 벤조산 , γ-메타크릴 옥시프로필 트리메특시실린', 비닐 트리아세특시실란, 비닐 트리메특시실란 , γ-이소시아네이트 프로필 트리에특시실란， γ-글리시독시 프로필 트리메록시실란 , β-(3,4- 에폭시사이클로핵실)에틸트리메록시실란 등을 들 수 있으며, 이들을 단독 또는 2종 이상 흔합하여 사용할 수 있다.  Examples of the silane coupling agent include trimethicsilyl benzoic acid, γ-methacryloxypropyl trimethicillin ', vinyl triacetic silane, vinyl trimethicylsilane, γ-isocyanate propyl trieoxysilane, γ- Glycidoxy propyl trimethoxysilane, (beta)-(3, 4- epoxycyclonuclear silane) ethyltrimethoxysilane, etc. are mentioned, These can be used individually or in mixture of 2 or more types.
싱-기 실란 커플링제는 감광성 수지 조성물 loo 중량부에 대하여 0.01 중량부 내지 10 중량부로 포함될 수 있디-, 실란 커플링제가 상기 범위 내로 포함될 경우 밀착성, 저장성 등이 우수하다.  The single-group silane coupling agent may be included in an amount of 0.01 parts by weight to 10 parts by weight with respect to the photosensitive resin composition loo part by weight.
또한 싱-기 감광성 수지 조성물은 필요에 따라 코팅성 향상 및 결점 생성 방지 효과를 위해 계면 활성제를 더 포함할 수 있다.  In addition, the sing-based photosensitive resin composition may further include a surfactant for improving the coating property and preventing the occurrence of defects, if necessary.
상기 계면활성제의 예로는， BM Chemie l:의 BM-1000®, BM-1100® 등; 다이 닛폰 잉키 가가꾸 고교 (주)社의 메카 팩 F 142D®, 동 F 172®, 동 F 173®, 동 F 183®등; 스미토모 스리엠 (주)肚의 프로라드 FC-135®, 동 FC— 170C®, 동 FC-430®, 동 FC— 431® 등; 아사히 그라스 (주)社의 사프론 S-112®, 동 S-113®, 동 Sᅳ 131®, 동 S-141®, 동 S- 145® 등; 도레이 실리콘 (주)社의 SH-28PA®, 동 -190®, 동 -193®, SZ-6032®, SF-8428® 등의 명칭으로 시판된고 있는 불소계 계면 활성제를 사용할 수 있디-. Examples of the surfactants include BM Chemie l: BM-1000 ® , BM-1100 ®, and the like; Mecha packs F 142D ® , F 172 ® , F 173 ® , F 183 ®, etc. of Dai Nippon Inki Chemical Co., Ltd .; M. Sumitomo Co. Pro rod FC-135 ® of肚, copper FC- 170C ®, copper FC-430 ®, copper FC- 431 ®, and the like; Asahi Grass Co., Ltd. Saffron S-112 ® , S-113 ® , S-131 ® , S-141 ® , S-145 ®, etc .; Toray Silicone Co., Ltd. can use commercially available fluorine-based surfactants under the names SH-28PA ® , -190 ® , -193 ® , SZ-6032 ® and SF-8428 ® .
싱-기 계면 활성제는 감광성 수지 조성물 100 증량부에 대하여 0.001 중량부 내지 5 증량부로사용될 수 있다. 계면 활성제가 상기 범위 내로 포함될 경우 코팅 균일성이 확보되고, 얼룩이 발생하지 않으며, 유리 기판에 대힌- 습윤성 (wetting)이 우수하다.  The sing-based 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 included in the above range, coating uniformity is ensured, staining does not occur, and wetting against the glass substrate is excellent.
또한 상기 감광성 수지 조성물은 물성을 저해하지 않는 범위 내에서  Moreover, the said photosensitive resin composition is in the range which does not inhibit physical property.
산화방지제, 안정제 등의 기타 첨가제가 일정량 첨가될 수도 있디-. 또 다른 일 구현예에 따르면, 상기 일 구현예에 따른 감광성 수지 조성물을 이용하여 제조된 컬러필터를 제공한다. Certain amounts of other additives such as antioxidants and stabilizers may be added. According to another embodiment, a color filter manufactured using the photosensitive resin composition according to the embodiment is provided.
상기 컬러필터는 녹색 컬러필터 또는 적색 컬러필터일 수 있으니ᅳ, 이에 한정되는 것은 아니다. The color filter may be a green color filter or a red color filter. It is not limited.
상기 컬러필터 내 패턴 형성 공정은 다음과 같다.  The pattern forming process in the color filter is as follows.
상기 감광성 수지 조성물을 지지 기판상에 스핀 코팅, 슬릿 코팅, 잉크젯 프린팅 등으로 도포하는 공정; 상기 도포된 감광성 수지 조성물을 건조하여 감광성 수지 조성물 막을 형성하는 공정; 상기 감광성 수지 조성물 막을 노광하는 공정; 상기 노광된 감광성 수지 조성물 막을 알칼리 수용액으로 현상하여 감광성 수지막을 제조하는 공정; 및 상기 감광성 수지막을 가열 처리하는 공정을 포함한다. 상기 공정 상의 조건 등에 대하여는 당해 분야에서 널리 알려진 사항이므로, 본 명세서에서 자세한 설명은 생략하기로 한다,  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 heat-processing the said photosensitive resin film. Since the process conditions and the like are well known in the art, detailed descriptions thereof will be omitted herein.
【발명의 실시를 위한 형태】 [Form for implementation of invention]
이히 ·, 실시예를 들어 본 발명에 대해서 더욱 상세하게 설명할 것이나, 하기의 실시예는 본 발명의 바람직한 실시예일 뿐 본 발명이 히-기 실시예에 한정되는 것은 아니디-.  Hereafter, the present invention will be described in more detail with reference to examples, but the following examples are only preferred embodiments of the present invention, but the present invention is not limited to the hi-group embodiments.
(지용성 화합물의 합성) (Synthesis of fat-soluble compound)
합성예 1: 화학식 5로 표시되는 지용성 화합물의 합성  Synthesis Example 1 Synthesis of Fat-Soluble Compound Represented by Chemical Formula 5
Figure imgf000020_0001
Figure imgf000020_0001
4-Aminophthalonitrile (2.5 mmol)°H 염산 (2.5 mL)과 소듐 나이트레이트 (1.25M 수용액 2 mL)를 넣어 아조늄 이온으로 만든 후, 이를 2ᅳ에틸핵실기가 치환된 피리돈 화합물 (2.5 mmol)을 NaOH 수용액으로 녹인 약염기성 수용액에 넣어 아조 화합물을 만들었다. 이때 얻어진 고체를 여과하고 정제 및 진공 건조하여 하기 화학식 5로 표시되는 지용성 화합물을 얻었다.
Figure imgf000021_0001
4-Aminophthalonitrile (2.5 mmol) ° H Hydrochloric acid (2.5 mL) and sodium nitrate (2 mL of 1.25M aqueous solution) were added to form azonium ions, which were then substituted with 2? Ethylnucleosilyl substituted pyridone compounds (2.5 mmol). Was added to a weakly basic aqueous solution dissolved in an aqueous NaOH solution to prepare an azo compound. The solid obtained at this time was filtered, purified, and vacuum dried to obtain a fat-soluble compound represented by the following formula (5).
Figure imgf000021_0001
Ή NMR (300 MHz, CDC13) 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). NMR (300 MHz, CDC1 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 (6 H).
GC/MS 416 m/z. 합성예 2: 화학식 6으로 표시되는지용성 화합물의 합성  GC / MS 416 m / z. Synthesis Example 2 Synthesis of Soluble Compound
Figure imgf000021_0002
Figure imgf000021_0002
3-Aminophthalonitrile (2.5 mmol)°l] 염산 (2.5 mL)과 소듐 나이트레이트 (1.25M 수용액 2 mL)를 넣어 아조늄 이은으로 만든 후, 이를 2-에틸핵실기가 치환된 피리돈 화합물 (2.5 mmol)을 NaOH 수용액으로 녹인 약염기성 수용액에 넣어 아조 화합물을 만들었디-. 이띠 Γ얻어진 고체를 여과하고 정제 및 진공 건조하여 하기 화학식 6으로 표시되는 지용성 화합물을 얻었다.  3-Aminophthalonitrile (2.5 mmol) ° l] Pyridone compound (2.5 mmol) substituted with 2-ethylnucleosil group by adding hydrochloric acid (2.5 mL) and sodium nitrate (2 mL of 1.25M aqueous solution) to azonium silver. ) Was added to a weakly basic aqueous solution dissolved in aqueous NaOH solution to make an azo compound. The solid obtained was obtained by filtration, purification and vacuum drying to obtain a fat-soluble compound represented by the following formula (6).
6]  6]
Figure imgf000021_0003
Figure imgf000021_0003
GC/MS 416 m/z. 합성예 3: 화학식 7로 표시되는지용성 화합물의 합성
Figure imgf000022_0001
GC / MS 416 m / z. Synthesis Example 3 Synthesis of Soluble Compound
Figure imgf000022_0001
4-Aminophthalonitrile (2.5 mmol)°H 염산 (2.5 mL)과 소듐 나이트레이트 (1.25M 수용액 2 mL)를 넣어 아조늄 이온으로 만든 후, 이를 n-부틸기가 치환된 피리돈 화합물 (2,5 mmol)을 NaOH 수용액으로 녹인 약염기성 수용액에 넣어 이-조 화합물을 만들었디ᅳ. 이때 얻어진 고체를 여과하고 정제 및 진공 건조하여 하기 화학식 7로 표시되는 지용성 화합물을 얻었다.  4-Aminophthalonitrile (2.5 mmol) ° H Hydrochloric acid (2.5 mL) and sodium nitrate (2 mL of 1.25M aqueous solution) were added to form azonium ions, which were then substituted with n-butyl group (2,5 mmol). Was added to a weakly basic aqueous solution dissolved in an aqueous NaOH solution to give a di-crude compound. The solid obtained at this time was filtered, purified, and vacuum dried to obtain a fat-soluble compound represented by the following formula (7).
[화학식 7]  [Formula 7]
Figure imgf000022_0002
Figure imgf000022_0002
Ή NMR (300 MHz, CDC13) 7.88-7.85 (2H), 7.73-7.69 (1Η), 3.86 (2H), 2.60 (3H), 1.50- 1.12 (4H), 0.96-0.92 (3H). 합성예 4: 화학식 8로 표시되는지용성 화합 합성 NMR (300 MHz, CDC1 3 ) 7.88-7.85 (2H), 7.73-7.69 (1Η), 3.86 (2H), 2.60 (3H), 1.50- 1.12 (4H), 0.96-0.92 (3H). Synthesis Example 4 Soluble Compound Synthesis
Figure imgf000022_0003
Figure imgf000022_0003
4-Aminophthalonitrile (2.5 mmol)에 염산 (2.5 mL)과 소듐 나이트레이트 (1.25M 수용액 2 mL)를 넣어 아조늄 이온으로 만든 후 5 이를 barbituric acid(2.5 mmol)를 NaOH수용액으로 녹인 약염기성 수용액에 넣어 아조 화합물을 만들었다. 이때 얻어진 고체를 여과하고 정제 및 진공 건조 후 l- dobutane (5.5 mmol)과 To 4-Aminophthalonitrile (2.5 mmol), add hydrochloric acid (2.5 mL) and sodium nitrate (2 mL of 1.25M aqueous solution) to make azonium ions, and 5 place it in a weakly basic aqueous solution of barbituric acid (2.5 mmol) dissolved in aqueous NaOH solution. Azo compound was made. The solid obtained at this time was filtered, purified and dried in vacuo and then l-dobutane (5.5 mmol) and
포타슘카보네이트 (7.5 mmol)을 넣고 DMF 용매하에서 반웅 후 정제 및 Potassium carbonate (7.5 mmol) was added and reaction was carried out in DMF solvent, followed by purification and
진공건조하여 하기 화학식 8로 표시되는 지용성 화합물을 얻었다-.
Figure imgf000023_0001
It was dried in vacuo to obtain a fat-soluble compound represented by the following formula (8).
Figure imgf000023_0001
Ή NMR (300 MHz, CDC13) 14.3 (IH), 7.95-7.94 (IH), 7.86-7.80 (2H), 4.03-3.87 (4H) 1.78-1.62 (4H), 1.46-1.36 (4H), 1.01-0,94 (6H). 5: 화학식 9로 표시되는지용성 화합물의 합성 NMR (300 MHz, CDC1 3 ) 14.3 (IH), 7.95-7.94 (IH), 7.86-7.80 (2H), 4.03-3.87 (4H) 1.78-1.62 (4H), 1.46-1.36 (4H), 1.01- 0,94 (6 H). 5: Synthesis of Soluble Compounds
Figure imgf000023_0002
Figure imgf000023_0002
4-Aminophthalomtrile (2.5 mmol)에 염산 (2.5 mL)과 소듐 나이트레이트 (1.25M 수용액 2 mL)를 넣어 아조늄 이은으로 만든 후, 이를 barbituric acid(2,5 mmol)를 NaOH 수용액으로 녹인 약염기성 수용액에 넣어 아조 화합물을 만들었다. 이때 얻어진 고체를 여과하고 정제 및 진공 건조 후 4-iodotoluene (5.5 mmol)과  Hydrochloric acid (2.5 mL) and sodium nitrate (2 mL of 1.25M aqueous solution) were added to 4-Aminophthalomtrile (2.5 mmol) to make azonium di- silver. To azo compound. The solid obtained at this time was filtered, purified and dried in vacuo, then 4-iodotoluene (5.5 mmol) and
포타슴카보네이트 (7.5 mmol)을 넣고 DMF 용매하에서 반옹 후 정제 및 Potassium carbonate (7.5 mmol) was added and the reaction was carried out in DMF solvent to purify and
진공건조하여 하기 화학식 9로 표시되는 지용성 화합물을 얻었다. It was dried in vacuo to obtain a fat-soluble compound represented by the following formula (9).
9]  9]
Figure imgf000023_0003
Figure imgf000023_0003
H NMR (300 MHz, CDC13) 14.3 (1H), 7.95-7.94 (1H), 7.86-7.80 (2H), 7.21 (2H), 7.06 (2H), 2,36 (3H). 교 합성예 1: 화학식 10로표시되는 화합물의 합성 H NMR (300 MHz, CDC1 3 ) 14.3 (1H), 7.95-7.94 (1H), 7.86-7.80 (2H), 7.21 (2H), 7.06 (2H), 2,36 (3H). Synthesis Example 1 Synthesis of Compound Represented by Chemical Formula 10
Figure imgf000024_0001
Figure imgf000024_0001
4-Aminophenol (2.5 mmol)에 염산 (2.5 mL)과 소듐 나이트레이트 (1.25M 수용액 2 mL)를 넣어 아조늄 이온으로 만든 후, 이를 barbituric acid(2.5 mmol)* NaOH 수용액으로 녹인 약염기성 수용액에 넣어 아조 화합물을 만들었디-. 이때 얻어진 고체를 여과하고 정제 및 진공 건조 후 1-iodobutane (5,5 mmol)과 포타슴카보네이트 (7.5 mmol)를 넣고 DMF 용매 하에서 반웅 후 정제 및 진공 건조하여 5 하기 화학식 10으로 표시되는 지용성 화합물을 얻었다. Hydrochloric acid (2.5 mL) and sodium nitrate (2 mL of 1.25M aqueous solution) are added to 4-Aminophenol (2.5 mmol) to make azonium ions, which are then dissolved in a weakly aqueous solution of barbituric acid (2.5 mmol) * NaOH solution. I made an azo compound. The resulting solid was filtered and purified and then vacuum-dried into a 1-iodobutane (5,5 mmol) and Porta thoracic carbonate (7.5 mmol) to 5 to give a vacuum and then dried under banung DMF solvent to oil-soluble compound represented by the formula (10) Got it.
10]  10]
Figure imgf000024_0002
Figure imgf000024_0002
GC/MS 360 m/z. 비교 합성예 2: 화학식 11로표시되는 화합물의 합성  GC / MS 360 m / z. Comparative Synthesis Example 2 Synthesis of Compound Represented by Formula (11)
Figure imgf000024_0003
Figure imgf000024_0003
Aniline (2.5 mmol)에 염산 (2.5 mL)과 소듐 나이트레이트 (1.25M 수용액 2 mL)를 넣어 아조늄 이은으로 만든후, 이를 2-에틸핵실기가 치환된 피리돈 화합물 (2,5 mmol)을 NaOH수용액으로 녹인 약염기성 수용액에 넣어 이ᅳ조 화합물을 만들었다. 이때 얻어진 고체를 여과하고 정제 및 진공 건조하여, 히ᅳ기 화학식 11로 는 지용성 화합물을 얻었다. Hydrochloric acid (2.5 mL) and sodium nitrate (2 mL of 1.25M aqueous solution) were added to aniline (2.5 mmol) to make azonium silver, which was then converted to a pyridone compound (2,5 mmol) substituted with 2-ethylnuclear group. It was added to a weakly basic aqueous solution dissolved in an aqueous NaOH solution to prepare a compound. The solid obtained at this time was filtered, purified and dried in vacuo to a chemical formula 11 Obtained a fat-soluble compound.
11]  11]
Figure imgf000025_0001
Figure imgf000025_0001
'H NMR (300 MHz, CDC13) 7.53 (2H), 7.44 (2H), 7.36 (1H)5 3.87 (2H), 2,60 (3H), 1.79 (1H); 1.40-1.15 (8H), 0.93-0.88 (6H). 비교 합성예 3: 화학식 12로 표시되는 화합물의 합성 'H NMR (300 MHz, CDC1 3 ) 7.53 (2H), 7.44 (2H), 7.36 (1H) 5 3.87 (2H), 2,60 (3H), 1.79 (1H) ; 1.40-1.15 (8H), 0.93-0.88 (6H). Comparative Synthesis Example 3: Synthesis of Compound Represented by Chemical Formula 12
Figure imgf000025_0002
Figure imgf000025_0002
Figure imgf000025_0003
염산 (2.5 mL)과 소듐 나이트레이트 (1 .25M 수용액 2 mL)를 넣어 아조늄 이은으로 만든 후, 이를 barbituric acid(2.5 mmol)를 NaOH 수용액으로 녹인 약염기성 수용액에 넣어 아조 화합물을 만들었다. 이때 얻어진 고체를 여과하고 정제 및 진공 건조 후 l-iodobutane (5.5 mmol)과 포타슘카보네이트 (7.5 mmol)를 넣고 DMF 용매 하에서 반응 후 정제 및 진공 건조하여, 하기 화학식 12로 표시되는 지용성 화합물을 얻었다.
Figure imgf000025_0003
Hydrochloric acid (2.5 mL) and sodium nitrate (2 mL of 1.25M aqueous solution) were added to make azonium silver, which was then added to a weakly basic aqueous solution of barbituric acid (2.5 mmol) in an aqueous NaOH solution to form an azo compound. The solid obtained was filtered, purified and dried in vacuo, l-iodobutane (5.5 mmol) and potassium carbonate (7.5 mmol) were added thereto, reacted in a DMF solvent, purified and dried in vacuo to obtain a fat-soluble compound represented by Chemical Formula 12.
I2] I 2 ]
Figure imgf000025_0004
Figure imgf000025_0004
'H NM (300 MHz, CDC13) 14.1 (1H), 7.71 (2H), 7.59 (2H), 7.46 (1H), 4.03-3.87 (4H); 1.78-1.62 (4H), 1.46-1.36 (4H), 1.01-0.94 (6H). (평가) 'H NM (300 MHz, CDC1 3 ) 14.1 (1H), 7.71 (2H), 7.59 (2H), 7.46 (1H), 4.03-3.87 (4H) ; 1.78-1.62 (4H), 1.46-1.36 (4H), 1.01-0.94 (6H). (evaluation)
평가 유기용매 대한용해도 합성예 1 내지 합성예 5 및 비교 합성예 1 내지 비교 합성예 3에서 합성한 화합물 0.5g에, 희석 용제 (Anone)를 각각 첨가하고, 해당 용액을 믹스 로터 (iuchi 주식회사, MIXROTAR VMR— 5)로 25 °C , 100 rpm로 1시간 동안 교반한 후, 각각의 화합물의 용해도 확인 결과를 하기 표 ᅵ 나타내었다. (Anone은 cyclohexanone을 의미한디 -.) 용해도 평기- 기준 Evaluation of Solubility in Organic Solvents To 0.5 g of the compound synthesized in Synthesis Example 1 to Synthesis Example 5 and Comparative Synthesis Example 1 to Comparative Synthesis Example 3, a diluent solvent (Anone) was added, respectively, and the solution was mixed with a mix rotor (iuchi Co., MIXROTAR VMR-5). After stirring for 1 hour at 25 ° C, 100 rpm, the solubility of each compound is shown below. (Anone means cyclohexanone.) Solubility Grade-based
희석용제 총량애 대해 화합물 (용질)이 2.5 중량 % 이상 용해: o  At least 2.5% by weight of compound (solute) dissolved in the total amount of diluent solvent: o
희석용제 총량에 대해 화합물 (용질)이 2.5 중량 % 미만 용해 : X  Dissolve less than 2.5% by weight of compound (solute) based on the total amount of diluted solvent: X
[표 1]TABLE 1
Figure imgf000026_0001
상기 표 1로부터, 일 구현예에 띠'른 화합물인 합성예 1 내지 합성예 5의 화합물은 비교 합성예 1 내지 비교 합성예 3의 화합물보다 유기용매에 대한 용해도가 우수하여, 감광성 수지 조성물 등에 사용 시 우수한 색특성을 나타낼 수 있음을 확인할 수 있다. 평가 2: 착색력
Figure imgf000026_0001
From Table 1, the compounds of Synthesis Examples 1 to 5, which are compounds according to one embodiment, have better solubility in organic solvents than the compounds of Comparative Synthesis Examples 1 to 3, and thus are used in photosensitive resin compositions and the like. It can be seen that it can exhibit excellent color characteristics. Evaluation 2: coloring power
합성예 1 내지 합성예 5 및 비교 합성예 1 내지 비교 합성예 3에서 합성한 화합물을 UV-1800 UV-Vis Spectrometer장비로 최디ᅵ 흡수 파장 (λ 을 측정하여, 하기 표 2에 나타내었다. 또한, 상기 합성예 1 내지 합성예 5 및 비교 합성예 1 내지 비교 합성예 3에서 합성한 화합물 20 mg을 Anone(Cyclohexanone)에 녹여 20 g의 진한 용액을 만든 후, 상기 진한 용액 0.1 g을 다시 1(^이 되도록 묽혀 0.001 중량%의 묽은 용액을 만든다. 상온에서 상기 0.001 중량 %의 용액의 분광을 측정한 후， 하기 수학식 1로부터 몰흡광계수를 계산하여, 하기 표 2에 나타내었다. Synthesis Example 1 to Synthesis Example 5 and Comparative Synthesis Example 1 to Comparative Synthesis Example 3 Compounds synthesized in the UV-1800 UV-Vis Spectrometer was measured at the absorption wavelength (λ) is shown in Table 2 below. Synthesis Example 1 to Synthesis Example 5 and Comparative Synthesis Example 1 20 mg of the compound synthesized in Comparative Synthesis Example 3 was dissolved in Anone (Cyclohexanone) to make 20 g of a thick solution, and then diluted 0.1 g of the concentrated solution to 1 (^) to form a dilute solution of 0.001% by weight. After measuring the spectroscopy of the 0.001% by weight of the solution, the molar extinction coefficient was calculated from Equation 1 shown in Table 2 below.
[수학식 1]  [Equation 1]
A = eel  A = eel
(A: 최대 홉광도ᅳ e: 몰흡광계수, c: 몰농도 , 1: 광로 길이)  (A: maximum hop intensity ᅳ e: molar extinction coefficient, c: molar concentration, 1: optical path length)
[표 2] TABLE 2
Figure imgf000027_0001
상기 표 2로부터, 일 구현예에 따른 화합물인 합성예 1 내지 합성예 5의 화합물은 비교 합성예 1 내지 비교 합성예 3의 화합물과 달리, 시아노기를 포함하기 때문애, 최대 흡수 파장이 유사하더라도, 보다 우수한 착색력을 가짐을 확인할 수 있다. 이상 본 발명의 바람직한 실시예에 대하여 설명하였지만, 본 발명은 이에 한정되는 것이 아니고, 특허청구범위와 발명의 상세한 설명 및 첨부한 도면의 범위 안에서 여러 가지로 변형하여 실시하는 것이 가능하고, 이 또한 본 발명의 범위에 속하는 것은 당연하다.
Figure imgf000027_0001
From Table 2, the compounds of Synthesis Example 1 to Synthesis Example 5, which is a compound according to one embodiment, unlike the compounds of Comparative Synthesis Examples 1 to 3, because it contains a cyano group, even if the maximum absorption wavelength is similar It can be confirmed that it has more excellent coloring power. As mentioned above, although preferred embodiment of this invention was described, this invention is not limited to this, It is possible to variously deform and implement within the range of a claim, a detailed description of an invention, and an accompanying drawing. Naturally, it belongs to the scope of the invention.

Claims

【청구의 범위】  [Range of request]
【청구항 1】  [Claim 1]
하기 화학식 1로 표시되는 지용성 화합물:  A fat-soluble compound represented by Formula 1 below:
1]  One]
Figure imgf000028_0001
Figure imgf000028_0001
상기 화학식 1에서,  In Chemical Formula 1,
R1은 시아노기이고, R 1 is a cyano group,
R2는 치환또는 비치환된 C1 내지 C20 알킬기， 치환 또는 비치환된 C2 내 C20 알킬렌기 또는 치환 또는 비치환된 C6 내지 C20 아릴기이고, R 2 is a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C2 alkylene group in C2 or a substituted or unsubstituted C6 to C20 aryl group,
n은 2 내지 5의 정수이고 , m은 0 내지 5의 정수이고, 단, 2≤n+m≤5이고， A는 치환또는 비치환된 C6 내지 C20 방향족 헤테로 고리 또는 치환 또는 비치환된 C3 내지 C20 지환족 헤테로 고리이다.  n is an integer from 2 to 5, m is an integer from 0 to 5, provided that 2 ≦ n + m ≦ 5, A is a substituted or unsubstituted C6 to C20 aromatic hetero ring or a substituted or unsubstituted C3 to C20 alicyclic hetero ring.
【청구힝- 2】 [Billing Hing-2]
제 1항에 있어서, ' The method of claim 1 wherein '
상기 방향족 헤테로 고리 및 지환족 헤테로 고리는 상기 고리 내에 하기 화학식 2로 표시되는 구조를 적어도 하나 이상 포함하는 지용성 화합물,  The aromatic hetero ring and alicyclic hetero ring is a fat-soluble compound containing at least one structure represented by the following formula (2) in the ring,
[화학식 2] [Formula 2 ]
o  o
^ᅳ L  ^ ᅳ L
【청구항 3】 [Claim 3]
제 1항에 있어서，  The method of claim 1,
상기 방향족 헤테로 고리는 하기 화학식 3으로 표시되는 지용성 화합물: [화학식 3] 상기 화학식 3에서, The aromatic hetero ring is a fat-soluble compound represented by Formula 3 below: In Chemical Formula 3,
R3은 수소 원자, 치환또는 비치환된 C1 내지 C20 알킬기 또는 치환 또는 비치환된 C6 내지 C20 아릴기이고, 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,
R4 내지 R0은 각각 독립적으로, 수소 원지ᅵ, 시아노기, 히드톡시기, 치환 또는 비치환된 C1 내지 C20 알킬기 또는 치환 또는 비치환된 C6 내지 C20 아릴기이다. R 4 to R 0 are each independently a hydrogen base l , cyano group, hydroxy group, substituted or unsubstituted C1 to C20 alkyl group, or substituted or unsubstituted C6 to C20 aryl group.
【청구항 4】 [Claim 4]
제 3항에 있어서,  The method of claim 3, wherein
상기 R3은 치환 또는 비치환된 C1 내지 C20 알킬기 또는 치환 또는 비치환된 C6 내지 C20 아릴기이고, R 3 is a substituted or unsubstituted C1 to C20 alkyl group or a substituted or unsubstituted C6 to C20 aryl group,
상기 R4는 시아노기이고, R 4 is a cyano group,
상기 R5는 치환 또는 비치환된 C1 내지 C20 알킬기 또는 치환또는 비치환된 C6 내지 C20 아릴기이고, R 5 is a substituted or unsubstituted C1 to C20 alkyl group or a substituted or unsubstituted C6 to C20 aryl group,
싱-기 Rfi는 히드록시기인 지용성 화합물. Singh-group R fi is a fat-soluble compound which is a hydroxyl group.
【청구항 5】 [Claim 5]
제 1항에 있어서,  The method of claim 1,
싱-기 지환족 헤테로 고리는 히-기 화학식 4로 표시되는 지용성 화합물:  The sing-group alicyclic hetero ring is a fat-soluble compound represented by the hi-group formula:
Figure imgf000029_0001
Figure imgf000029_0001
상기 화학식 4에서,  In Chemical Formula 4,
R7 및 R8은 각각 득립적으로 수소 원지ᅳ， 치환 또는 비치환된 C1 내지 C20 알킬기 또는 치환 또는 비치환된 C6 내지 C20 아릴기이디-. R 7 and R 8 are each independently hydrogenated, substituted or unsubstituted C1 to C20 alkyl group, or substituted or unsubstituted C6 to C20 aryl groupidi-.
【청구항 6】 [Claim 6]
제 1항에 있어서,  The method of claim 1,
상기 화학식 1로 표시되는 지용성 화합물은 하기 화학식 5 내지 화학식 9로 표시되는 화합물 중 어느 하나로 표시되는 지용성 화합물.
Figure imgf000030_0001
제 1항에 있어서, The fat-soluble compound represented by Formula 1 is a fat-soluble compound represented by any one of the compounds represented by the following formula (5).
Figure imgf000030_0001
The method of claim 1,
상기 지용성 화합물은 황색 염료인 지용성 화합물. 【청구항 8】  The fat soluble compound is a yellow dye. [Claim 8]
저 1 1힝' 내지 제 7항 증 어느 한 항의 지용성 화합물을 포함하는 감광성 수지 조성물.  A photosensitive resin composition comprising the fat-soluble compound of any one of Claims 1 to 7.
【청구항 9】 [Claim 9]
저 ] 8항에 있어서,  According to claim 8,
상기 감광성 수지 조성물은 알칼리 가용성 수지, 광중합성 화합물 s 광중합 개시제 및 용매를 더 포함하는 감광성 수지 조성물. The photosensitive resin composition further comprises an alkali-soluble resin, a photopolymerizable compound s photopolymerization initiator and a solvent.
【청구힝ᅳ 10] [10 claim]
제 9항애 있어서,  The method of claim 9,
상기 감광성 수지 조성물은 안료를 더 포함하는 감광성 수지 조성물. 【청구항 1 1】  The photosensitive resin composition further comprises a pigment. [Claim 1 11]
제 8항의 감광성 수지 조성물을 이용하여 제조되는 컬러필터.  The color filter manufactured using the photosensitive resin composition of Claim 8.
【청구항 121 [Claim 121]
제 1 1항에 있어서,  The method of claim 1,
상기 컬러필터는 녹색 컬러필터 또는 적색 컬러필터인 컬러필터.  The color filter is a green color filter or a red color filter.
PCT/KR2015/008104 2015-06-19 2015-08-03 Novel oil-soluble compound, photosensitive resin composition containing same, and color filter WO2016204337A1 (en)

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