WO2016204337A1 - 신규한 지용성 화합물, 이를 포함하는 감광성 수지 조성물 및 컬러필터 - Google Patents

신규한 지용성 화합물, 이를 포함하는 감광성 수지 조성물 및 컬러필터 Download PDF

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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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substituted
group
unsubstituted
fat
soluble compound
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PCT/KR2015/008104
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English (en)
French (fr)
Korean (ko)
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최은정
박채원
신명엽
정의수
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삼성에스디아이 주식회사
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Priority to CN201580080997.9A priority Critical patent/CN107801394A/zh
Publication of WO2016204337A1 publication Critical patent/WO2016204337A1/ko

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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D213/00Heterocyclic 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
    • C07D213/02Heterocyclic 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
    • C07D213/04Heterocyclic 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
    • C07D213/60Heterocyclic 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
    • C07D213/78Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/84Nitriles
    • C07D213/85Nitriles in position 3
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C213/00Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
    • C07C213/06Preparation 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D213/00Heterocyclic 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
    • C07D213/02Heterocyclic 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
    • C07D213/04Heterocyclic 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D239/00Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24Heterocyclic 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
    • C07D239/28Heterocyclic 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
    • C07D239/46Two or more oxygen, sulphur or nitrogen atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D239/00Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24Heterocyclic 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
    • C07D239/28Heterocyclic 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
    • C07D239/46Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/60Three or more oxygen or sulfur atoms
    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03FPHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004Photosensitive 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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  • General Physics & Mathematics (AREA)
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  • Materials For Photolithography (AREA)
  • Optical Filters (AREA)
PCT/KR2015/008104 2015-06-19 2015-08-03 신규한 지용성 화합물, 이를 포함하는 감광성 수지 조성물 및 컬러필터 WO2016204337A1 (ko)

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Citations (4)

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Publication number Priority date Publication date Assignee Title
GB1349727A (en) * 1971-05-25 1974-04-10 Bayer Ag Azo dyestuffs
US4250089A (en) * 1975-04-12 1981-02-10 Bayer Aktiengesellschaft Process for diazotizing aromatic amines
JPS6044556A (ja) * 1983-08-22 1985-03-09 Nippon Kayaku Co Ltd 水不溶性モノアゾ化合物及びそれを用いる染色法
JPH05142863A (ja) * 1991-11-18 1993-06-11 Ricoh Co Ltd 電子写真用トナー

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Publication number Priority date Publication date Assignee Title
DE2163378A1 (de) * 1971-12-21 1973-06-28 Bayer Ag Azofarbstoffe
DE2340569C2 (de) * 1973-08-10 1982-12-02 Bayer Ag, 5090 Leverkusen Azofarbstoffe
JP2012208474A (ja) 2011-03-14 2012-10-25 Jsr Corp カラーフィルタ用着色組成物、カラーフィルタ及び表示素子

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Publication number Priority date Publication date Assignee Title
GB1349727A (en) * 1971-05-25 1974-04-10 Bayer Ag Azo dyestuffs
US4250089A (en) * 1975-04-12 1981-02-10 Bayer Aktiengesellschaft Process for diazotizing aromatic amines
JPS6044556A (ja) * 1983-08-22 1985-03-09 Nippon Kayaku Co Ltd 水不溶性モノアゾ化合物及びそれを用いる染色法
JPH05142863A (ja) * 1991-11-18 1993-06-11 Ricoh Co Ltd 電子写真用トナー

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DATABASE CHEMICAL ABSTRACT 13 June 2007 (2007-06-13), retrieved from STN Database accession no. 937171-54-5 *
DATABASE CHEMICAL ABSTRACT 23 October 2008 (2008-10-23), retrieved from STN Database accession no. 1065123-41-2 *
DATABASE CHEMICAL ABSTRACT 23 October 2008 (2008-10-23), retrieved from STN Database accession no. 1065123-42-3 *
DATABASE CHEMICAL ABSTRACT 23 October 2008 (2008-10-23), retrieved from STN Database accession no. 1065123-65-0 *
DATABASE Chemical Abstract retrieved from STN Database accession no. 1065123-68-3 *

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