Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
  • C07C251/32—Oximes
  • C07C251/62—Oximes having oxygen atoms of oxyimino groups esterified
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
  • C07C251/32—Oximes
  • C07C251/62—Oximes having oxygen atoms of oxyimino groups esterified
  • C07C251/64—Oximes having oxygen atoms of oxyimino groups esterified by carboxylic acids
  • C07C251/66—Oximes having oxygen atoms of oxyimino groups esterified by carboxylic acids with the esterifying carboxyl groups bound to hydrogen atoms, to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings
• • G—PHYSICS
  • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
  • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
  • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
  • G03F7/004—Photosensitive materials
  • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
  • G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
• • G—PHYSICS
  • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
  • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
  • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
  • G03F7/004—Photosensitive materials
  • G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable

Definitions

• the present invention relates to an oxime ester compound, a photopolymerization initiator using the same, and more particularly, to a oxime ester having a novel structure useful for preparing a photosensitive resin composition that maintains high brightness, has excellent thermal stability, and has excellent solubility in an organic solvent. It relates to a compound and a photopolymerization initiator comprising the same.
• the photosensitive composition is obtained by adding a photopolymerization initiator to a binder resin and a polymerizable compound having an ethylenically unsaturated bond, and can be polymerized and cured by irradiating 365 to 435 nm light to the photosensitive composition. It is used for transparent or colored protective film of, and recently it is widely used in TV of flat panel display (FPD), among which LCD TV.
• FPD flat panel display
• the color filter is manufactured by the optical etching method using a phenomenon that the solubility is reduced by the polymerization reaction by light, and the photopolymerization initiator is applied to the color-sensitive photosensitive composition used in the color filter.
• the photosensitive resin composition As for the photosensitive resin composition, high production efficiency, photospeed, the sensitivity which can photopolymerize with minimum exposure, etc. are important, The most important factor which affects this is a photoinitiator.
• the color filter when the content of the color material increases, there is a problem that the sensitivity, developability, resolution, adhesion, etc. of the photosensitive resin composition are deteriorated, and not only the productivity is lowered, but also the precision and reliability required for the color filter can be obtained. It is known that it becomes impossible. That is, the color filter is required to have high sensitivity and high resolution at high concentration, and the photosensitive resin composition for black matrix is also required to be able to exhibit high sensitivity and high resolution under conditions of thin film and high light blocking property (high concentration).
• the present invention aims to solve the problems of the prior art as described above and the technical problems that have been requested from the past.
• the novel structure of the oxime ester compound, as described later has superior transparency and thermal stability as compared to the initiator of the prior art, and thus, negative photosensitive properties When applied to the resin composition has been confirmed that there is little brightness deterioration and change in the transparency of the resin and excellent in resolution, developability, adhesion, etc., and also excellent thermal stability, to complete the present invention.
• the present invention provides an oxime ester compound represented by the compound of formula (1).
• R 1 is a methyl or phenyl group
• R 2 and R 3 are each independently selected from hydrogen, methyl group, ethyl group, propyl group and butyl group,
• n is an integer from 1 to 4,
• n is an integer from 0 to 6
• n is 1
• m is an integer of 1-6.
• the present invention also provides a photopolymerization initiator comprising the oxime ester compound as an active ingredient.
• the present invention also provides a binder resin, a compound having an ethylenically unsaturated bond, and a photosensitive resin composition comprising the photopolymerization initiator.
• the oxime ester compound according to the present invention has excellent storage stability, polymerization does not occur in a storage state, and the polymerizable composition can be efficiently polymerized in a short time.
• it has excellent solubility in PGMEA (Propylene glycol monomethyl ether acetate) which is a solvent mainly used in color filters, so it is excellent in transparency and chemical resistance when applied as photoinitiator of photoresist composition, column spacer, LCD manufacturing process, When applied to overcoat, organic insulating film, color filter, and black mattress, there is little change in brightness of resin composition and transparency of resin, which can minimize the quality problems caused by this, and can prepare photopolymerization initiator and photosensitive composition with excellent thermal stability. have.
• PGMEA Polylene glycol monomethyl ether acetate
• the present invention provides an oxime ester compound represented by the compound of formula (1).
• R 1 is a methyl or phenyl group
• R 2 and R 3 are each independently selected from hydrogen, methyl group, ethyl group, propyl group and butyl group,
• n is an integer from 1 to 4,
• n is an integer from 0 to 6
• n is 1
• m is an integer of 1-6.
• the oxime ester compound according to the present invention may be selected from the group consisting of the following compounds, but is not limited thereto.
• Oximes used as starting materials in the preparation of oxime ester compounds according to the invention can be prepared in standard chemistry textbooks (e.g., J. March, Advanced Organic chemistry, 4 th Edition, Wiley Interscience, 1992) or professional monographs (e.g. For example, SR Sandler & W. Karo.Organic functional group preparations, Vol. 3. Academic Press) can be obtained by various methods.
• the present invention provides a photopolymerization initiator comprising the oxime ester compound as an active ingredient.
• the photopolymerization initiator according to the present invention has higher sensitivity than conventional initiators, has excellent resolution, developability, adhesion, and the like, and has excellent solubility in PGMEA, a solvent mainly used in LCD manufacturing processes, It can be used in the entire industry for photocuring such as black matrix, column spacer, organic insulating film, overcoat, and the like.
• the present invention also provides a binder resin, a compound having an ethylenically unsaturated bond, and a photosensitive resin composition comprising the photopolymerization initiator.
• the addition amount of the said photoinitiator is not specifically limited, With respect to 100 weight part of said polymeric compound solids which have an ethylenically unsaturated bond, the oxime ester compound which concerns on this invention becomes like this. Preferably it is 1-50 weight part, More preferably, It may be included in 5 to 30 parts by weight.
• the compound having an ethylenically unsaturated bond is a compound used in a conventional photosensitive resin composition, for example, 2-hydroxy ethyl (meth) acrylate, 2-hydroxy propyl (meth) acrylate, cyclohexyl (meth) Acrylate, polyethylene glycol di (meth) acrylate, pentaerythritol tetra (meth) acrylate, pentaerythritol tri (meth) acrylate, trimethylolpropane tri (meth) acrylate, triethylene glycol (meth) acrylate, Various acrylic esters and methacrylic esters, such as dipentaerythritol acrylate, glycerol (meth) acrylate, melamine (meth) acrylate, and epoxy (meth) acrylate, (meth) acrylic acid, styrene, acrylonitrile, etc. are mentioned. Can be. Moreover, although bisphenol-A type
• the compound which has such an ethylenically unsaturated bond can be used individually or in mixture of 2 or more types.
• the compound may be used in a proportion of usually 5 to 60% by weight, preferably 10 to 50% by weight, based on the total solids weight of the negative photosensitive resin composition according to the present invention.
• the total weight of the photosensitive resin composition may be 0.001 to 50% by weight, preferably 0.1 to 7% by weight.
• the photopolymerization initiator in addition to the oxime ester compound of the present invention as the photopolymerization initiator, it is also possible to use other types of photopolymerization initiators as necessary, and synergistic effects can be achieved by using different types of photopolymerization initiators together. It can also be exercised.
• the negative photosensitive resin composition containing such a photoinitiator can be used as a highly sensitive material which decomposes considerably efficiently and generates radicals efficiently even without using a sensitizer for light irradiation in a specific wavelength range.
• the photoinitiator which can be used together with the oxime ester compound of this invention can use a conventionally well-known compound, As a preferable example, benzyl, benzoin ether, benzoin butyl ether, benzoin propylether, benzophenone, 3'-dimethyl 4-methoxybenzophenone, benzoylbenzoic acid, esterified product of benzoylbenzoic acid, 4-benzoyl-4'-methyldiphenylsulfide, benzyl dimethyl ketal, 2-butoxyethyl-4-methylaminobenzoate, chlorothioxanthone , Methyl thioxanthone, ethyl thioxanthone, isopropyl thioxanthone, dimethyl thioxanthone, diethyl thioxanthone, diisopropyl thioxanthone, dimethylaminomethylbenzoate, dimethylamin
• Such a photoinitiator can mix and use 2 or more types in arbitrary ratios as one type or as needed.
• the photopolymerization initiator may be usually used in the range of 0.5 to 30% by weight, preferably 1 to 20% by weight, based on the total solids weight of the negative photosensitive resin composition according to the present invention.
• the total weight of the photosensitive resin composition may be 0.01 to 10% by weight, preferably 0.1 to 7% by weight.
• binder resin a copolymer of a compound having an unsaturated carboxyl group and other monomers copolymerizable therewith may be used.
• the compound having an unsaturated carboxyl group can be used without limitation so long as it is a carboxylic acid compound having an unsaturated double bond which can be polymerized.
• monocarboxylic acids such as acrylic acid, methacrylic acid, and crotonic acid
• Dicarboxylic acids such as fumaric acid, mesaconic acid and itaconic acid
• Anhydrides of the dicarboxylic acids and mono (meth) acrylates of polymers having a carboxyl group and a hydroxyl group at both terminals, such as ⁇ -carboxypolycaprolactone mono (meth) acrylate, monomethylmaleic acid, isoprenesulfonic acid, styrenesulfonic acid, 5-norbornene-2 -Carboxylic acid, mono-2-((meth) acryloyloxy) ethylphthalate, mono-2-((meth) acryloyloxy) ethylsuccinate or mixtures thereof, and
• Aromatic vinyl compounds such as styrene, (alpha) -methylstyrene, and vinyltoluene; Methyl acrylate, methyl methacrylate, ethyl acrylate, ethyl methacrylate, butyl acrylate, butyl methacrylate, 2-hydroxyethyl acrylate, 2-hydroxyethyl methacrylate, benzyl acrylate, benzyl methacrylate Unsaturated carboxylate compounds such as acrylates; Unsaturated aminoalkyl carboxylate compounds such as aminoethyl acrylate; Unsaturated glycidyl carboxylate compounds such as glycidyl methacrylate; Vinyl carboxylate compounds such as vinyl acetate and vinyl propionate; Vinyl cyanide compounds such as
• the binder resin may be an acrylic polymer or an acrylic polymer having an acrylic unsaturated bond in the side chain.
• the binder resin may be a cardo-based resin represented by the following general formula (2) generally used in the black matrix field.
• Q is a tetravalent organic group
• z is an integer of 1 or more indicating a repeating unit.
• the cardo resin is preferably bis (4-hydroxyphenyl) sulfone, bis (4-hydroxy-3,5-dimethylphenyl) sulfone and bis (4-hydroxy-3,5-dichlorophenyl) sulfone , Bis (4-hydroxyphenyl) hexafluoropropane, bis (4-hydroxy-3,5-dimethylphenyl) hexafluoropropane and bis (4-hydroxy-3,5-dichlorophenyl) hexafluoro Propane, bis (4-hydroxyphenyl) dimethylsilane, bis (4-hydroxy-3,5-dimethylphenyl) dimethylsilane and bis (4-hydroxy-3,5-dichlorophenyl) dimethylsilane, bis (4 -Hydroxyphenyl) methane, bis (4-hydroxy-3,5-dichlorofetyl) methane and bis (4-hydroxy-3,5-dibromophenyl) methane, 2,
• the weight average molecular weight (Mw) of the binder resin may be 2,000 to 1,000,000, preferably 3,000 to 400,000. If the average molecular weight is 2,000 or less or 400,000 or more, the sensitivity and developability may be deteriorated.
• the binder resin may be included in the present invention 5 to 60% by weight, preferably 10 to 40% by weight based on the total weight of the solid content of the photosensitive resin composition. If the binder resin is within the content range, it is possible to form a pattern, and the resolution and the residual film ratio may be improved, but when it is out of this range, the resolution and the residual film ratio may decrease, which is not preferable.
• the photosensitive resin composition according to the present invention includes, as necessary, a thermal polymerization inhibitor such as p-anisole, hydroquinone, pyrocatechol, tertiary butylcatechol, phenothiazine; Plasticizers; Adhesion promoters; Ordinary additives, such as filler, can be added.
• a thermal polymerization inhibitor such as p-anisole, hydroquinone, pyrocatechol, tertiary butylcatechol, phenothiazine
• Plasticizers such as p-anisole, hydroquinone, pyrocatechol, tertiary butylcatechol, phenothiazine
• Plasticizers such as p-anisole, hydroquinone, pyrocatechol, tertiary butylcatechol, phenothiazine
• Adhesion promoters such as filler
• the photosensitive resin composition according to the present invention may further include one or more selected from a colorant, an inorganic compound, a dispersant, and a silane coupling agent.
• the photosensitive resin composition of this invention can contain a coloring material further.
• a pigment, dye, a natural pigment, etc. are mentioned as said color material, These color materials can be used individually or in mixture of 2 or more types.
• pigment it is a nitroso compound, for example; Nitro compounds; Azo compounds; Diazo compounds; Xanthene compound; Quinoline compounds; Anthraquinone compounds; Coumarin compounds; Phthalocyanine compounds; Isoindolinone compounds; Isoindolin compounds; Quinacridone compounds; Anthrone compounds; Perinone compound; Perylene compounds; Diketopyrrolopyrrole compounds; Thioindigo compounds; Dioxazine compounds; Triphenylmethane compound; Quinophthalone compounds; Naphthalenetetracarboxylic acid; Metal complex compounds of azo dyes and cyanine dyes; Lake pigments; Carbon black such as carbon black obtained by a furnace method, a channel method or a thermal method, or carbon black such as acetylene black, Ketjen black or lamp black; Adjusting or coating the carbon black with an epoxy resin, adsorbing 20 to 200 mg / g of the resin by dispersing the carbon black with a resin in
• content of the said color material may be 50-350 weight part more preferably 100-250 weight part with respect to 100 weight part of polymeric compounds which have the said ethylenically unsaturated bond.
• the amount of the colorant is included in an amount greater than or less than a preferred range for expressing a desired color, it is not preferable because a negative photosensitive resin composition having an appropriate color intended by the present invention cannot be obtained.
• the photosensitive resin composition which concerns on this invention can also contain an inorganic compound.
• the inorganic compound include a composite metal oxide pigment, carbon black, black lower titanium oxynitride, titanium oxide, barium sulfate, zinc oxide, lead sulfate, yellow lead, Bengala, ultramarine blue, and blue wire.
• Metal oxides such as chromium oxide, antimony white, iron black, podium, zinc sulfide, cadmium yellow, cadmium red, zinc, manganese violet, cobalt violet, barium sulfate, magnesium carbonate, metal sulfide, sulfate, metal hydroxide, metal carbonate, etc. But it is not limited thereto.
• the content of the inorganic compound is preferably 0.1 to 1000 parts by weight, preferably 10 to 800 parts by weight, based on 100 parts by weight of the polymerizable compound having the ethylenically unsaturated bond. have.
• distributes a coloring material and / or an inorganic compound can be added to the photosensitive resin composition of this invention.
• the dispersant is not limited as long as it can disperse and stabilize a colorant or an inorganic compound, and a commercially available dispersant, for example, BYK series manufactured by BIC Chemistry Co., may be used.
• a polymer dispersant comprising a polyester, polyether, or polyurethane having a basic functional group, a basic functional group having a nitrogen atom, a functional group having a nitrogen atom is an amine, and / or a quaternary salt thereof, and has an amine value of 1 to 100 mgKOH. / g is preferably used.
• a silane coupling agent may be added to the photosensitive resin composition of the present invention in order to improve the adhesion between the glass substrate and the photosensitive resin film.
• a silane coupling agent containing vinylalkoxy, vinyl trimethoxy silane, vinyl triethoxy silane, vinyl tris ( ⁇ -methoxy ethoxy) silane and the like can be used.
• silane coupling agent containing (meth) acryloxy, 3-methacryloxy propyl methyl dimethoxy silane, 3-methacryloxy propyl methyl diethoxy silane, 3-methacryloxy propyl trimethoxy silane, 3-methacryl Roxy propyl triethoxy silane, 3-acryloxy propyl trimethoxy silane, 3-acryloxy propyl methyl dimethoxy silane and the like
• Their addition ratio may be 0.01 to 2% by weight, more preferably 0.05 to 0.5% by weight based on the total weight of the negative photosensitive resin composition solids.
• a solvent may be used in the photosensitive resin composition of the present invention as necessary for viscosity control, and specific examples include ethylene such as ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, and ethylene glycol monobutyl ether.
• Diethylene glycol dialkyl ethers such as glycol monoalkyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol dipropyl ether, diethylene glycol dibutyl ether, methyl cellosolve acetate, and ethyl cell
• Alkylene glycol alkyl ether acetates such as ethylene glycol alkyl ether acetates such as rosolve acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate, methoxy butyl acetate, methoxy Alkoxyalkyl acetates such as acetylacetate, aromatic hydrocarbons such as benzene, toluene, xylene, mesitylene, ketones such as methyl ethyl ketone, acetone, methyl amyl ketone,
• the solvent may preferably be an organic solvent having a boiling point of 100 ° C. to 200 ° C. among the solvents exemplified above in terms of applicability and dryness, and may include alkylene glycol alkyl ether acetates, ketones, and ethyl 3-ethoxypropionate. Ester, such as methyl methoxy propionate, may be used more preferably, and especially propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, cyclohexanone, 3-ethoxy propionate, 3-methoxy propionate, etc. This may be more preferably used.
• a solvent can be used individually or in combination of 2 or more types.
• the resin liquid can have a viscosity that can be applied to the substrate, and may be generally included in 10 to 95% by weight, preferably 20 to 80% by weight based on the total weight of the photosensitive resin composition. have.
• a certain amount of other additives such as a chain transfer agent, a sensitizer, a surfactant, an antioxidant, and a stabilizer may be added to the photosensitive resin composition according to the present invention within a range that does not impair the physical properties of the resin composition.
• the amount of such additives to be added may be adjusted by those skilled in the art.
• a color filter, a black matrix, a column spacer, an organic insulating film, an overcoat, etc. can be manufactured.
• the present invention may provide a color filter including the photosensitive resin composition.
• the negative photosensitive resin composition used in such a color filter is, for example, pigment blue, which represents blue, 15: 6, based on the total weight of solids, 20 to 30% by weight, preferably 23 to 27% by weight, for example For example, it may represent blue, including 25% by weight.
• the black matrix containing the said photosensitive resin composition may include, for example, 10% by weight to 15% by weight, preferably 11% to 13% by weight, for example about 12.4% by weight, based on the total weight of solid carbon black. It may include black.
• the manufacturing method of the color filter and black matrix of this invention apply
• coating method such as a rotary coating, a flexible coating, and a roll coating, on a support body. It forms, exposes the said layer through a predetermined
• curing the formed coloring pattern by heating and / or exposure can be included as needed.
• a color filter having a desired color can be produced by repeating the image forming step (and curing step, if necessary) by the desired number of colors.
• light or radiation used at this time particularly ultraviolet rays such as g-ray, h-ray and i-ray can be preferably used.
• CMOS complementary metal oxide semiconductor
• a primer layer may be formed on these supports as necessary to improve adhesion to the top layer, to prevent diffusion of materials, or to planarize the surface of the support.
• any can be used.
• a combination of various organic solvents and an alkaline aqueous solution can be used.
• said organic solvent the organic solvent mentioned above used for preparation of the dye-containing negative curable resin composition of this invention is mentioned.
• alkaline aqueous solution examples include sodium hydroxide, potassium hydroxide, sodium carbonate, sodium silicate, sodium metasilicate, ammonia water, ethylamine, diethylamine, dimethylethanolamine, tetramethylammonium hydroxide, tetraethylammonium hydroxide, Alkaline compounds such as choline, pyrrole, piperidine, and 1,8-diazabicyclo- [5.4.0] -7-undecene are dissolved in a concentration of 0.001 to 10% by mass, preferably 0.01 to 1% by mass. Alkaline aqueous solution can be used. Moreover, when using the developing solution which consists of such alkaline aqueous solution, it can generally wash
• One or more such color filters, black matrices, or column spacers may be usefully included in a liquid crystal display or a solid state image pickup device.
• the liquid crystal display device may be manufactured in the order of, for example, a backlight, a polarizing film, a display electrode, a liquid crystal, an alignment film, a common electrode, a color filter of the present invention, a polarizing film, and the like.
• the solid-state imaging device may be manufactured by, for example, forming a color filter layer of the present invention on a silicon wafer on which a transfer electrode and a photodiode are formed, followed by laminating micro lenses.
• the following compound 8 was synthesized using the precursor obtained by reacting n-propylbromide with Fluorene by applying the method described in Example 1.
• Pyrolysis temperature was measured using PerkinElmer TGA (Pyris1) (10 ° C./10 min, N 2 ).
• the degree of dissolution in 20 ° C. 20 g of PGMEA was evaluated.
• a blue negative photosensitive resin composition was prepared in the same manner as in Preparation Example 1, except that the photopolymerization initiator such as Compound 8 (Comparative Example 1) and Compound 9 (Comparative Example 2) was used instead of Compounds 1 to 7. .
• the sensitivity was evaluated by making the minimum irradiation exposure amount which the film thickness after image development become 80% or more of the film thickness of the coating film as a required minimum exposure amount.
• the blue negative photosensitive resin composition prepared by using the compounds of Examples 1 to 7 according to Preparation Example 1 has high physical properties such as high sensitivity and excellent adhesiveness.
• a black negative photosensitive resin composition was prepared in the same manner as in Preparation Example 3, except that Comparative Example Compound 8-9 was used as the photopolymerization initiator instead of Example Compound 1-7.
• Equal 40 mJ / cm 2 This means the width of the pattern generated when the light is exposed and developed, and the wider the line width, the higher the sensitivity.
• the black negative photosensitive resin composition including the photoinitiators of Example Compounds 1 to 7 according to the present invention has excellent physical properties such as excellent adhesion and developability.
• Example 5 Preparation of Transparent Negative Photosensitive Resin Composition Using Example Compounds 1 to 7 (for Insulating Film)
• alkali developable resin (B) and 24.0 g of alkali developable resin (C) dipentaerythritol penta, 41 g of hexaacrylate, 1 to 72.0 g of photopolymerization initiator compound and 0.2 g of a surfactant were added thereto, followed by stirring.
• PGMEA was added so that solid content concentration might be 20% weight, and the transparent negative photosensitive resin composition was obtained.
• the ratio of the film thickness before exposure to the film thickness after exposure and development is defined as the residual film ratio.
• the minimum pattern size was defined as the resolution.
• the transparent negative photosensitive resin composition including the photoinitiators of the compounds 1 to 7 prepared according to Preparation Example 5 has excellent physical properties such as excellent resolution and developability.
• the oxime ester compound according to the present invention has excellent storage stability, polymerization does not occur in a storage state, and the polymerizable composition can be efficiently polymerized in a short time.
• it has excellent solubility in PGMEA (Propylene glycol monomethyl ether acetate) which is a solvent mainly used in color filters, so it is excellent in transparency and chemical resistance when applied as photoinitiator of photoresist composition, column spacer, LCD manufacturing process, When applied to overcoat, organic insulating film, color filter, and black mattress, there is little change in brightness of resin composition and transparency of resin, which can minimize the quality problems caused by this, and can prepare photopolymerization initiator and photosensitive composition with excellent thermal stability. have.
• PGMEA Polylene glycol monomethyl ether acetate

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