WO2013129864A1 - Composition photosensible positive chimiquement amplifiée pour couche diélectrique organique hautement sensible, avec une excellente résistance à la chaleur, et procédé pour former une couche diélectrique l'employant - Google Patents

Composition photosensible positive chimiquement amplifiée pour couche diélectrique organique hautement sensible, avec une excellente résistance à la chaleur, et procédé pour former une couche diélectrique l'employant Download PDF

Info

Publication number
WO2013129864A1
WO2013129864A1 PCT/KR2013/001634 KR2013001634W WO2013129864A1 WO 2013129864 A1 WO2013129864 A1 WO 2013129864A1 KR 2013001634 W KR2013001634 W KR 2013001634W WO 2013129864 A1 WO2013129864 A1 WO 2013129864A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
insulating film
organic insulating
acid
formula
Prior art date
Application number
PCT/KR2013/001634
Other languages
English (en)
Korean (ko)
Inventor
이윤형
Original Assignee
Lee Yun Hyeong
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Lee Yun Hyeong filed Critical Lee Yun Hyeong
Publication of WO2013129864A1 publication Critical patent/WO2013129864A1/fr

Links

Images

Classifications

    • 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
    • G03F7/022—Quinonediazides
    • G03F7/023—Macromolecular quinonediazides; Macromolecular additives, e.g. binders
    • G03F7/0233—Macromolecular quinonediazides; Macromolecular additives, e.g. binders characterised by the polymeric binders or the macromolecular additives other than the macromolecular quinonediazides
    • 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
    • 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
    • G03F7/0045—Photosensitive materials with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors
    • 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
    • G03F7/039—Macromolecular compounds which are photodegradable, e.g. positive electron resists
    • 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
    • G03F7/039—Macromolecular compounds which are photodegradable, e.g. positive electron resists
    • G03F7/0392—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition
    • 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
    • G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
    • 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
    • G03F7/26—Processing photosensitive materials; Apparatus therefor
    • 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
    • G03F7/26—Processing photosensitive materials; Apparatus therefor
    • G03F7/40—Treatment after imagewise removal, e.g. baking

Definitions

  • the present invention relates to a chemically amplified positive photosensitive organic insulating film composition having excellent heat resistance and a method of forming an organic insulating film using the same. More particularly, in forming an organic insulating film such as a liquid crystal display device, sensitivity and resolution are higher than in the related art.
  • the chemically amplified positive photosensitive organic insulating film composition having excellent heat resistance properties such as maintaining the shape of the pattern by significantly improving the heat shrinkage and thermal flow of the coating film during the thermal process after the pattern formation and the same A method for forming an organic insulating film used.
  • an inorganic protective film such as silicon nitride (SiOx or SiNx) is conventionally used as a protective film for protecting and isolating a thin film transistor (TFT) circuit.
  • SiOx or SiNx silicon nitride
  • TFT thin film transistor
  • the organic insulating film applied at this time provides a photosensitive function to the insulating film itself, thereby enabling the formation of a fine pattern for providing interconnection passages between circuits without a separate process, and through this, a separate photo using a photoresist on a conventional inorganic insulating film.
  • the process can be reduced, resulting in higher productivity and cost savings, leading to increased use.
  • the organic insulating film is a photosensitive resin, which is a polymer compound in which the solubility in a specific solvent is changed by chemical reaction by light and electron beams.
  • the microprocessing of the circuit pattern is performed by the polarization of the polymer due to the photoreaction of the organic insulating film.
  • the organic insulating film material utilizes a change characteristic of solubility in a developer such as an aqueous alkali solution after exposure.
  • the organic insulating film is classified into a positive type and a negative type according to the solubility of the sensitized part.
  • the exposed part is dissolved by the developer due to the polarity change
  • the negative type photoresist the exposed part is not dissolved in the developer through the crosslinking reaction and the unexposed part is dissolved to form a pattern.
  • the positive type organic insulating film is advantageous in terms of working environment because there is no problem in the development of the developer, unlike the disadvantage of foreign matter generation when mixed with the alkaline developer in which the negative type organic insulating film is widely used in the existing mass production process. Since the swelling phenomenon of the portion not exposed to ultraviolet rays can be prevented, the resolution is improved. In addition, since the removal of the organic film after the formation of the organic film is easy, there is an advantage that the substrate recovery and reusability is greatly improved by removing the organic film during the generation of a defective panel during the process.
  • the positive type organic insulating film composition has been actively applied to a composition in which an acrylic polymer resin and a quinonediazide-based sensitizer (PAC) used as a representative binder resin are mixed.
  • PAC quinonediazide-based sensitizer
  • Sensitivity is mentioned as an important characteristic among the characteristics calculated
  • organic insulating film compositions using acrylic photosensitive resins and sensitizers which are conventionally used, often have low sensitivity due to their low transmittance to exposure ultraviolet rays. In many cases, the difference in solubility with the non-part is not so large that it does not have sufficient resolution.
  • PAC alkali-soluble resin and sensitizer
  • US Patent No. 4139391 discloses a photosensitive resin organic insulating film composition prepared by using a copolymer of an acrylic acid compound and an acrylate compound as a binder resin and an acrylate compound as a polyfunctional monomer.
  • the dissolution inhibiting ability is not high, so the difference in dissolution rate between the exposed portion and the non-exposed portion is not large enough, so that the development characteristics are not good, and thus it is difficult to obtain a fine pattern of 15 microns or less.
  • the conventional positive type organic insulating film not only satisfies the problem of sensitivity sufficiently, but also has a limitation in resolution to cope with miniaturization for higher integration.
  • the polarity change is removed by removing the protecting group of the polymer binder through an acid catalyst reaction using an acid generated through exposed light. Through this, a chemically amplified positive organic insulating film was introduced to make it soluble in a developer.
  • the acid-decomposable acetal protecting group used in the polymer binder has a small boiling point due to the small size of the product decomposed upon exposure, and has a high volatility to generate a large amount of vapor during exposure, thereby easily contaminating an expensive lens of the exposure machine.
  • the thickness of the film through volume shrinkage is relatively reduced due to the detachment and volatilization of the protecting group during exposure.
  • the present invention is to solve the above problems, unlike the prior art, a unit or an active energy ray or heat cross-linkable functional group containing an acid-decomposable protecting group having a cross-linking group (active-rays or heat) ( It comprises a unit having a cross-linking group) and does not include an acid-decomposable protecting group, comprising a polymer, a copolymer, or a mixture thereof containing at least one or more of the above unit as a binder resin
  • a chemically amplified positive photosensitive organic insulating film composition that not only significantly increases sensitivity but also significantly reduces pattern distortion and coating reduction due to thermal shrinkage and thermal flow that may occur in a post-thermal process. And to provide a method for forming an organic insulating film using the same.
  • An object of the present invention is to provide a photosensitive organic insulating film composition and a method of forming an organic insulating film using the same.
  • an active energy ray crosslinking or a thermal crosslinkable functional group is introduced into a unit including an acid decomposable protecting group or a unit including an acid decomposable protecting group, and the unit is at least one
  • the above-described polymer, copolymer or mixture thereof as binder resin, cross-linking between them by active energy ray or heat during the process leads to desorption of the acid-decomposable protecting group by heat even in the post-thermal process.
  • the chemically amplified positive photosensitive organic insulating film composition capable of suppressing thermal damage and thermal contraction of a pre-formed pattern to realize and maintain a high sensitivity and high resolution pattern and To provide a method of forming an organic insulating film using the same Do as an enemy.
  • the chemically amplified positive photosensitive organic insulating film composition comprising a binder resin, the binder resin by active energy rays or heat
  • a unit comprising an acid-decomposable protecting group having a cross-linking group or a unit having an active energy ray or heat cross-linking group and not containing an acid-decomposable protecting group. It is characterized in that it comprises a polymer, a copolymer, or a mixture thereof comprising at least one or more of the above unit together or separately.
  • the unit comprising an acid-decomposable protecting group having a cross-linking group (cross-linking group) by the active energy ray or heat is characterized in that consisting of at least one of the following formula (1-1 to 1-10).
  • R1 is a chain or cyclic aliphatic group, or an aromatic group
  • R2 is a chain or cyclic alkyl group
  • R3 is a hydrogen group or a chain alkyl group
  • R4 is a hydrogen group Or a chain alkyl group
  • R5 and R6 are hydrogen or a chain alkyl group
  • R7 is absent or a chain or cyclic alkyl group.
  • m is 0 or 1 and n ⁇ 0.
  • X is an alkoxy group (-ORx), a hydroxyl group (-OH), a thiol group (-SH), or a carboxy group (-) containing or not containing silicone as a functional group crosslinked by active energy rays or heat.
  • the average molecular weight of the polymer or copolymer constituting the binder resin is 2,000 to 200,000, the dispersion degree is characterized in that 1 to 10.
  • the unit comprising an acid-decomposable protecting group having no active energy ray crosslinkable or thermal crosslinkable functional group is characterized in that consisting of at least one of the formulas (2) to (5).
  • G is a unit corresponding to a parent including an acid-decomposable protecting group represented by Chemical Formulas 1-1 to 1-10
  • Y is an aryl group, a chained or cyclic aliphatic group, Either a chain or cyclic ester group or a chain or cyclic ether group.
  • R8 is a hydrogen group, a chain alkyl group or a cyclic alkyl group
  • R9 is a chain or cyclic alkyl group, or a chain or cyclic alkene group
  • R10 is a hydrogen group, a chain It is a type
  • the dissolution inhibitor is an alkali-soluble phenol compound or a fluorene-based compound containing at least one phenol group, an alkali-soluble compound containing at least one carboxylic acid group or at least one
  • An acid-decomposable protecting group is included in at least one of the alkali-soluble compounds including a benzoic acid group, and in the dissolution inhibitor, the acid-decomposable protecting group is any one of the acid-decomposable protecting groups represented by Chemical Formulas 1-1 to 1-10. Or an acid-decomposable protecting group having no X as the active energy ray crosslinkable or thermal crosslinkable functional group in Chemical Formulas 1-1 to 1-10.
  • the photoacid generator is made of at least one of an onium salt compound, a halogen-containing compound, a sulfone compound, a sulfonic acid ester compound or a triazine-based compound, based on 100 parts by weight of the binder resin, It is characterized by including 0.1 to 10 parts by weight.
  • a radical generator or an amine generator or an acid generator by an active energy ray or heat is further included to promote the binding reaction between the active energy ray crosslinkable and the thermal crosslinkable functional groups. And it is characterized in that it comprises 0.01 to 10 parts by weight based on 100 parts by weight of the binder resin.
  • PAC sensitizer
  • quinonediazide quinonediazide
  • additive is a thermal crosslinking agent, a thermal stabilizer, a photocuring accelerator, a surfactant, a base quencher ( base quencher), an anti-halation agent, an adhesion aid, a light stabilizer or an antifoaming agent.
  • the thermal crosslinking agent is made of a compound containing at least one of urea resin, melamine resin, isocyanate group, epoxy group, oxetane group, acrylate group, vinyl group, aryl group, hydroxy group or mercapto group
  • the heat stabilizer is characterized by consisting of at least one of a phenolic, lactone-based, amine-based, phosphorus-based or sulfur-based compound.
  • the light stabilizer characterized in that consisting of at least one of benzotriazole-based, triazine-based, benzophenone-based, hindered amino ether-based or hindered amine-based compound, wherein the adhesion aid, isocyanate group, amino group, urea group, alkyl group ,
  • An alkoxy silane compound comprising at least one of an epoxy group, an acrylate group, a vinyl group or a mercapto group.
  • the base quencher is a nitrogen-containing organic compound, the nitrogen-containing organic compound is characterized in that consisting of at least one of the primary amine, secondary amine, tertiary amine or amide (amide) compound.
  • the organic insulating film composition is formed on a substrate of a display device, a source / drain or silicon nitride layer formed on the substrate. Applying; Pre-bake the organic insulating film composition; Selectively exposing the organic insulating film composition and then developing the organic insulating film composition to form a pattern; And forming an insulating protective film by exposing the organic insulating film composition to full surface exposure and heat treatment (cure bake).
  • a post-bake process may be added between exposure and development.
  • the chemically amplified positive photosensitive organic insulating film composition of the present invention and a method of forming an organic insulating film using the same unlike the conventional method, it includes an acid-decomposable protecting group having a cross-linking group by active energy rays or heat. It comprises a unit or a unit having an active energy ray or heat cross-linking group (cross-linking group) and does not include an acid-decomposable protecting group, a polymer containing at least one or more of the unit together or separately In the form of coalescing or a mixture thereof, not only the sensitivity and resolution are significantly increased, but also the reduction of the film and the reduction of the film with the shape of the pattern after the thermal process can be significantly reduced. have.
  • FIG. 1 is a cross-sectional view showing a unit cell device of a TFT-LCD having a high opening ratio to which the chemically amplified positive photosensitive organic insulating film composition of the present invention is applied.
  • Figure 2a is a cross-sectional photograph by an electron microscope (SEM) of the organic insulating film pattern before and after the cure bake to evaluate the heat resistance according to the composition of Example 1 of the present invention
  • Figure 2b is a cross-sectional photograph by an electron microscope (SEM) of the organic insulating film pattern before and after the cure bake to evaluate the heat resistance according to the composition of Example 2 of the present invention
  • Figure 2c is a cross-sectional photograph by an electron microscope (SEM) of the organic insulating film pattern before and after the cure bake to evaluate the heat resistance according to the composition of Comparative Example 1 of the present invention
  • Figure 2d is a cross-sectional photograph by an electron microscope (SEM) of the organic insulating film pattern before and after the cure bake to evaluate the heat resistance according to the composition of Comparative Example 2 of the present invention
  • the chemically amplified positive photosensitive high-sensitivity organic insulating film composition having excellent heat resistance includes a binder resin, and the binder resin includes an acid-decomposable protecting group having a cross-linking group by active energy rays or heat. It comprises a unit or a unit having an active energy ray or heat cross-linking group (cross-linking group) and does not include an acid-decomposable protecting group, a polymer containing at least one or more of the unit together or separately It is characterized by including a coalescence, or a mixture thereof.
  • the unit means a minimum unit constituting the (co) polymer, including a monomer, and corresponds to a mother linked to an acid-decomposable protecting group or an active energy ray or a thermal crosslinking group. It is defined as containing any substance that is used.
  • the unit including an acid-decomposable protecting group having a cross-linking group (cross-linking group) by the active energy ray or heat is characterized in that consisting of at least one of the formula (1-1) to 1-10.
  • the unit having a cross-linking group (cross-linking group) by the active energy ray or heat and does not include an acid-decomposable protecting group is an alkoxy group (-OR x ), a hydroxyl group (-or without a silicon) OH), cyclic ethers including thiol group (-SH), carboxyl group (-COOH), phosphate group (-PO (OH) x ), furanyl, oxetane and epoxy group, At least among monomers which can form a (co) polymer having at least one functional group among an aryl group, a vinyl group, an acryl group, an isocyanate group, a urea group, a melamine group, an imide, or an amide group It is characterized by consisting of one.
  • the organic insulating layer forms a pattern and It remains after the thermal process and functions as an insulation and protective film of the wiring, and it is very effective in improving the sensitivity, residual film ratio, resolution and volatilization control, which are required for the organic insulating film, and at the same time, it can maintain the shape of the pattern after the thermal process. In addition to showing heat resistance, it was confirmed that the shape of the pattern can be controlled by controlling the desired level of thermal flow.
  • the binder resin is a unit comprising an acid-decomposable protecting group having a cross-linking group by active energy rays or heat of Formulas 1-1 to 1-10, or Formulas 1-1 to 1-10. 1 comprising a unit having an active energy ray or a cross-linking functional group cross-linked by heat and not including an acid-decomposable protecting group, wherein the unit includes at least one kind together or separately It may be formed in a form distributed in at least a polymer or copolymer, or may be made by simply mixing the (co) polymers.
  • the average molecular weight of the binder resin is preferably 2,000 to 200,000, more preferably 5,000 to 30,000 is effective.
  • the dispersion degree of the binder resin is preferably 1 to 10, more preferably 1.1 to 5.0 is effective. If it is out of the range of the optimum average molecular weight and dispersion degree, there is a problem that the characteristics of the organic insulating film is significantly lowered or the economy is inferior.
  • the organic insulating film composition of the present invention a unit including an acid-decomposable protecting group that does not have an active energy ray crosslinking or a thermal crosslinkable functional group represented by X, or an acid-decomposable protecting group without having an active energy ray crosslinking or a thermal crosslinking functional group. It is preferable to further include a polymer or copolymer comprising a unit which does not contain, the average molecular weight of the polymer or copolymer that does not include the unit is 2,000 to 100,000, more preferably 5,000 to 30,000, Dispersion is 1-20, More preferably, it is 1.1-5.
  • the (co) polymer composed of units having no such crosslinkable functional groups effectively mixes with the binder resin, thereby improving optical properties such as transmittance of the residual pattern coating film, and also serves to control the mechanical strength at a desired level. .
  • the organic insulating film composition of the present invention further comprises a dissolution inhibitor, wherein the dissolution inhibitor is an alkali-soluble phenolic compound or a fluorene-based compound containing at least one phenol group, at least one carr It is preferable that an acid-decomposable protecting group is contained in at least one of an alkali-soluble compound containing an acidic group or an alkali-soluble compound containing at least one benzoic acid group.
  • the acid-decomposable protecting group is any one of the acid-decomposable protecting groups represented by Formulas 1-1 to 1-10, or X, which is an active energy ray crosslinking or thermal crosslinking functional group in Formulas 1-1 to 1-10. It is preferable that it is either of the acid-decomposable protecting groups which do not have.
  • Such a dissolution inhibitor is effectively mixed with the binder resin, thereby improving the sensitivity and resolution, and serves to facilitate pattern formation.
  • the molecular weight of the dissolution inhibitor is preferably 5,000 or less in the case of a monomolecular structure, and 5,000 to 30,000 in the case of the polymer structure.
  • the binder resin of the present invention exhibits sufficient dissolution inhibiting ability to the developer in the non-exposed portion while using a minimum amount of an acid-decomposable protecting group, which may occur in the residual organic pattern film during or after the exposure process.
  • the amount of volatilized vapor can be significantly reduced, and the exposed portion is deprotected at a very high rate by the catalytic reaction by the action of acid triggered from the photo acid generator (PAG) in the exposure process, so that the solubility in the developer is rapidly increased.
  • PAG photo acid generator
  • the residual organic film pattern formed after the development process is crosslinked with each other by the activation energy or heat between the crosslinkable functional groups in the (co) polymer constituting the binder resin and has a net structure, whereby a high glass transition temperature (Tg) value is obtained. It is possible to form a high heat-resistant coating film having a. This results in controlling the thermal flow of the pattern due to heat generated between post-processes, maintaining the high resolution by preserving the shape of the pattern, and controlling the shrinkage due to heat to maintain a stable thickness of the coating. There is an advantage. In particular, when appropriately adjusting the shape of the pattern to a desired shape by appropriately using the flow by heat, it is possible to implement a pattern having a specific shape by changing the content and type of the crosslinkable functional group.
  • the performance can be maximized.
  • any photoacid generator may be used as long as it is capable of generating an acid when exposed to live radiation and does not degrade optical properties such as protective film formation and transmittance, but preferably at a wavelength of 250 nm to 400 nm. It is effective to use a material having an appropriate light absorption and capable of maintaining the excellent transmittance and transparent color of the organic insulating film in the visible light region of 400 nm or more.
  • the photoacid generator consists of at least one of an onium salt compound, a halogen-containing compound, a sulfone compound, a sulfonic acid ester compound, or a triazine-based compound.
  • the onium compound is effective to use an iodonium salt, a forest sulfonium salt, a phosphonium salt, a diazonium salt, an ammonium salt or a pyridinium salt, and the halogen-containing compound is a haloalkyl group-containing hydrocarbon compound or a haloalkyl group-containing heterocyclic compound. It is effective to use.
  • ⁇ -ketosulfone, ⁇ -sulfonylsulfone or ⁇ -diazo compounds thereof is alkyl sulfonic acid ester, haloalkyl sulfonic acid ester, aryl sulfonic acid ester, imino sulfo. It is effective to use nate or amide sulfonate.
  • the content of the photoacid generator it is preferable to include 0.1 to 10 parts by weight, more preferably 1 to 5 parts by weight with respect to 100 parts by weight of the binder resin. If it is less than 0.1 part by weight, it is difficult to realize sensitivity at a sufficient speed due to the limitation of the amount of acid generated during exposure, and if it exceeds 10 parts by weight, problems of decrease in permeability and discoloration of the coating film may occur.
  • a free-radical generator or base generator or acid generator by active energy rays or heat when exposed to active energy rays or heat, free radicals or salts or It is possible to use any material as long as it generates an acid and acts as a catalyst for inducing crosslinking reactions smoothly in the crosslinking functional period, and does not degrade optical properties such as protective film formation and permeability. It is effective to use a material that can maintain the excellent transmittance and transparent color of the organic insulating film in the visible light region of 400nm or more.
  • the additive is preferably made of at least one of a thermal crosslinking agent, a thermal stabilizer, a photocuring accelerator, a surfactant, a base quencher, an antihalation agent, an adhesion aid, an optical stabilizer or an antifoaming agent.
  • the thermal crosslinking agent may be formed between the binder resin and the thermal crosslinking agent, in addition to inducing a crosslinking reaction between the crosslinkable functional groups included in the (co) polymer constituting the binder resin through a post-exposure heat treatment process when forming the organic insulating film.
  • the thermal stabilizer is used to suppress discoloration and decrease in permeability due to heat generated during the subsequent process or during the reliability conditions of the device, and at least one of a phenolic, lactone-based, amine-based, phosphorus-based or sulfur-based compound. It is most preferred in the present invention that it consists of one.
  • the light stabilizer is used to maximize the light resistance of the organic insulating film composition, and the type of light stabilizer having such characteristics is not particularly limited, but benzotriazole-based, triazine-based, benzophenone-based, hindered amino ether-based or Use of at least one of the hindered amine compounds is most effective in the present invention.
  • the photocuring accelerator may be any material capable of promoting acid generation during exposure, and the adhesion assistant may include at least one of a socyanate group, an epoxy group, an acrylate group, a vinyl group, or a mercapto group. It is preferable that it consists of an alkoxy silane compound.
  • the base quencher serves to control the diffusion of the generated acid, and it is preferable to use a nitrogen-containing organic compound which does not change the basicity, more preferably a primary amine, a secondary amine, a tertiary amine or an amide compound. It is most effective to consist of at least one of.
  • the surfactant is used to improve the coating properties and thickness uniformity by improving the wetting properties (wetting) of the substrate and the organic insulating film composition
  • the type is not particularly limited, but preferably polyoxy lauryl ether , Polyoxyethylene stearyl ether, polyoxyethylene oleyl ether, polyoxyethylene octyl phenol ether, polyoxyethylene nonyl phenol ether or polyethylene glycol dilaurate and the like. It is preferable to use content of these surfactant at 3 weight part or less with respect to 100 weight part of positive type organic insulating film compositions of this invention.
  • photocuring accelerators In addition, generally used photocuring accelerators, antihalation agents (leveling agents), antifoaming agents, and the like can be used. If necessary, various other additives can be used to improve desired properties in addition to the additives listed above.
  • an organic solvent may be used for the organic insulating film composition, and the organic solvent may preferably be at least one of an alcohol, acetate, ether, glycol, ketone, or carbonate organic solvent.
  • the use of propylene glycol methyl ether acetate (PGMEA) is most effective because of excellent coating properties and excellent film thickness uniformity of the organic insulating film on a large glass substrate.
  • the organic insulating film composition is coated on a substrate, a source / drain or silicon nitride layer formed on the substrate of the display device. (S10), pre-bake the organic insulating film composition (S20), selectively exposing and developing the organic insulating film composition to form a pattern (S30) and the organic insulating film composition on the entire surface. And forming an insulating protective film by exposure and heat treatment (cure bake) (S40).
  • the substrate glass or transparent plastic resins commonly used in flat panel displays (FPDs) such as liquid crystal displays (TFT-LCDs) and OLEDs are mainly used, but are not particularly limited according to the characteristics of the display apparatus used.
  • the organic insulating film is formed on an ITO metal film used as an anode in an OLED, on an EL layer of each RGB color, or on a metal film constituting a gate electrode on a substrate such as glass, thereby protecting and insulating. Can be used for purposes.
  • the method of coating the organic insulating film composition on the substrate or the like may include a coating method using a slit nozzle such as a spray coating method, a roll coating method, a discharge nozzle type coating method, a rotary coating method such as a central dropping spin method, There are an extrusion coating method and a bar coating method, and two or more coating methods can be combined and coated.
  • the applied film thickness varies depending on the coating method, the solid content concentration of the composition, the viscosity, and the like, but is usually applied so as to have a film thickness of 0.5 to 10 ⁇ m after drying.
  • the solvent is volatilized by applying vacuum, infrared rays, or heat to obtain a non-flowable coating film after forming the coating film.
  • Heating conditions vary depending on the type and composition of each component, but in the case of hot plate heating, it is heated to 60 to 130 ° C. for 30 to 300 seconds, and to 60 to 150 ° C. when using a hot oven. It is common to heat for 30 to 1,000 seconds.
  • the selective exposure process may be excimer laser, far ultraviolet, ultraviolet light, visible light, electron beam, X-ray or g-ray (wavelength 436nm), i-ray (wavelength 365nm), h-ray (wavelength 405nm) or mixed rays thereof. Is carried out while investigating.
  • the exposure may be performed by contact, porximity, projection exposure, or the like.
  • the step of performing the entire surface exposure and annealing (annealing) of the organic insulating film composition is performed.
  • the thermal crosslinking agent is applied to the composition of the organic insulating film composition of the present invention for the high temperature firing.
  • the heat treatment step is performed for 30 minutes to 2 hours under a temperature of 150 °C to 250 °C using a heating apparatus such as a hot plate or oven. After the heat treatment, a completely cross-cured pattern is obtained.
  • the organic insulating film thus formed is, as shown in the display device of FIG. 1, the semiconductor layer 40, the source 51 made of the substrate 10, the gate electrode 20, the gate insulating film 30, silicon nitride, or the like.
  • the laminated structure consisting of the drain 52 and the protective film 60 it is used for the gate insulating film 30 or the protective film 60.
  • a (co) polymer represented by the following Chemical Formula 6 to be used as the binder resin of the organic insulating film composition was synthesized / prepared. And, based on 100 parts by weight of the organic solvent (PGMEA), 35.20 parts by weight of a binder resin using the (co) polymer represented by the formula (6) below, 1.76 parts by weight of N-hydroxynaphthalimide triflate as a photoacid generator, triethylamine as base (triethylamine) 0.20 parts by weight, azo amide radical thermal initiator VAm-110 (Wako) 0.53 parts by weight, 1.06 parts by weight of gamma-Glycidoxypropyltrimethoxysilane as adhesion aid, 2,5-Bis (1,1- as polymerization inhibitor) 0.18 parts by weight of dimethylbuthyl) hydroquinone and 0.14 parts by weight of surfactant F-475 (Dainippon Ink & Chemicals) are completely dissolved for coating properties.
  • TMAH tetramethylammonium hydroxide
  • the entire surface of the patterned organic film was exposed to UV light at an exposure dose of 500 mJ / cm 2 to 700 mJ / cm 2 , and the thickness and pattern shape of the coating film formed through a 30 minute cure bake process at 230 ° C. oven were measured.
  • a is 0.35, b is 0.30, c is 0.10, d is 0.10, e is 0.10, f is 0.05.
  • the (co) polymers represented by the following Chemical Formulas 7 and 8 were synthesized and prepared in the same manner as in Example 1, except that they were mixed in a weight ratio of 70:30 after synthesis / manufacturing, and used as binder resin of the organic insulating film composition.
  • a is 0.40
  • b is 0.15
  • c is 0.40
  • d is 0.05
  • x is 0.45
  • y is 0.30
  • z is 0.10
  • w is 0.15.
  • a is 0.35, b is 0.40, c is 0.10, d is 0.05, e is 0.10.
  • the (co) polymers represented by the following Chemical Formulas 10 and 11 were mixed in a weight ratio of 60:40 after synthesis / manufacturing, respectively, and were used in the same manner as in Example 1 except that they were used as the binder resin of the organic insulating film composition.
  • a is 0.35
  • b is 0.45
  • c is 0.10
  • d is 0.10
  • x is 0.35
  • y is 0.30
  • z is 0.25
  • w is 0.10.
  • Example 1 except that the (co) polymer represented by the following formula (12), formula (13), and formula (14) was mixed in a weight ratio of 35:25:40 after synthesis / manufacturing, respectively, and used as a binder resin of the organic insulating film composition. It was carried out according to the case.
  • a is 0.35
  • b is 0.45
  • c is 0.10
  • d is 0.10
  • x is 0.35
  • y is 0.45
  • z is 0.10
  • w is 0.10
  • p is 0.20 in Formula 14
  • q is 0.30
  • r is 0.30
  • s is 0.20.
  • a is 0.30, b is 0.45, c is 0.10, d is 0.10, e is 0.05, and in Formula 16, x is 0.35, y is 0.45, z is 0.10, w is 0.10.
  • a is 0.35
  • b is 0.45
  • c is 0.10
  • d is 0.10.
  • a is 0.25
  • b is 0.25
  • c is 0.50
  • x is 0.25
  • y is 0.30
  • z is 0.20
  • w is 0.25.
  • the (co) polymers represented by the following Chemical Formulas 21 and 22 were synthesized and prepared in the same manner as in Example 1 except that they were mixed in a weight ratio of 65:35 after synthesis / manufacturing and used as binder resins of the organic insulating film composition.
  • a is 0.20
  • b is 0.30
  • c is 0.10
  • d is 0.40
  • x is 0.50
  • y is 0.20
  • z is 0.10
  • w is 0.20.
  • the (co) polymers represented by the following Chemical Formulas 23 and 24 were respectively synthesized in a weight ratio of 65:35 after synthesis / manufacturing, and further mixed with a thermal crosslinking agent represented by the following Chemical Formula 25 to be used as a binder resin of the organic insulating film composition. It was carried out according to the case of Example 1 except that.
  • a is 0.33, b is 0.50, c is 0.17, in Formula 24 x is 0.50, y is 0.20, z is 0.10, w is 0.20.
  • the (co) polymers represented by the following Chemical Formulas 26 and 27 were synthesized and synthesized in a weight ratio of 65:35, respectively, and were used in the same manner as in Example 1 except that they were used as the binder resin of the organic insulating film composition.
  • a is 0.35
  • b is 0.15
  • c is 0.30
  • d is 0.10
  • e is 0.10
  • x is 0.40
  • y is 0.20
  • z is 0.20
  • w is 0.20.
  • the (co) polymers represented by the formulas (28) and (29) below were mixed in a weight ratio of 50:50 after synthesis / manufacturing, respectively, and were carried out in the same manner as in Example 1 except that they were used as the binder resin of the organic insulating film composition.
  • a is 0.30, b is 0.25, c is 0.30, d is 0.15, in Formula 29 x is 0.25, y is 0.35, z is 0.20, w is 0.20.
  • the (co) polymers represented by the following Chemical Formulas 30 and 31 were mixed in a weight ratio of 55:45 after synthesis / manufacturing, respectively, and were carried out in the same manner as in Example 1 except that they were used as the binder resin of the organic insulating film composition.
  • a is 0.30, b is 0.25, c is 0.30, d is 0.15, in Formula 31 x is 0.20, y is 0.35, z is 0.25, w is 0.10, u is 0.10.
  • a is 0.25, b is 0.40, c is 0.10, d is 0.10, e is 0.05, f is 0.10.
  • a is 0.30
  • b is 0.45
  • c is 0.15
  • d is 0.10
  • x is 0.05
  • y is 0.30
  • z is 0.30
  • w is 0.35.
  • a is 0.35
  • b is 0.20
  • c is 0.30
  • d is 0.10
  • e is 0.05.
  • Appropriate exposure dose (Eop), residual film rate after development, residual film rate after cure bake, taper angle, resolution, and total light transmittance for measuring sensitivity using patterns formed by the examples and comparative examples Were respectively measured by the following method.
  • the thickness of the coating organic film before development and the pattern thickness of the residual organic film after development were measured, and the residual film ratio after development was calculated using the following equation.
  • the residual film ratio after the development is derived by a formula of (pattern thickness of the residual organic film after development) / (thickness of the coating film before development) ⁇ 100 (%).
  • the residual organic film was left in an additional 230 ° C. oven for 30 minutes to undergo a cure bake process, and the pattern thickness of the residual organic film was measured.
  • the residual film rate after cure bake was calculated using the following equation.
  • the residual film ratio after the cure bake is derived by a formula of (pattern thickness of the residual organic film after cure bake) / (thickness of the coating film before development) ⁇ 100 (%).
  • the heat resistance of the pattern is derived through the measurement of the inclination (taper angle) of the lower part of the pattern representing the shape of the pattern as shown in FIGS. 2A to 2D.
  • the pattern width (CD) that can be finely formed without distortion or peel-off of the pattern was measured.
  • the light transmittance at 450 nm was measured using a UV-Visible-Spectrometer and PDA UV-Vis Spectro (Scinco).
  • Table 1 below shows the appropriate exposure amount (Eop), the residual film rate after development, the residual film rate after cure bake, the taper angle, resolution, and the like of the thin film coated according to Examples 1 to 13. The evaluation results for the light transmittance are shown.
  • Example 1 Example Proper exposure amount (mJ / cm2) Post-development rate (%) Retention rate after cure bake (%) Taper angle (degree) Resolution ( ⁇ m) Light transmittance (%)
  • Example 1 45 99.3% 84.6% 51 ⁇ 3 94.29
  • Example 2 35 98.8% 81.7% 45 ⁇ 3 95.26
  • Example 3 40 99.6% 83.9% 54 ⁇ 3 95.49
  • Example 4 40 99.2% 85.8% 56 ⁇ 3 94.76
  • Example 5 35 98.6% 86.3% 53 ⁇ 3 95.02
  • Example 6 50 99.4% 85.6% 55 ⁇ 3 95.58
  • Example 7 40 99.4% 85.6% 52 ⁇ 3 96.05
  • Example 8 55 99.1% 80.9% 45 ⁇ 4 94.78
  • Example 9 50 98.2% 78.8% 42 ⁇ 4 94.54
  • Example 10 50 99.2% 79.1% 46 ⁇ 4 93.35
  • Example 11 40 98.2% 77.7% 43
  • the pattern according to the embodiment of the present invention has excellent sensitivity with an exposure dose in the range of 35 to 55 mJ / cm 2, and is excellent in resolution and light transmittance.
  • Comparative Example 1 chemically amplified organic insulating film having an acid-decomposable protecting group having a chain structure
  • Comparative Example 2 positive organic insulating film using a conventional quinonediazide-based photosensitive compound
  • active energy ray-crosslinking or thermal cross-linking functional groups By introducing active energy ray-crosslinking or thermal cross-linking functional groups into acid-decomposable protecting groups, they induce mutual molecular bonds, thereby significantly lowering the volatility of the deprotecting group itself, and thereby by-products that may arise from deprotecting groups of the binder resin by heat.
  • the concentration of can ultimately be kept low, thereby suppressing volume shrinkage and pattern deformation of the coating film.
  • the glass transition temperature (Tg) is significantly increased to have excellent heat resistance to control the thermal flow characteristics.

Landscapes

  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Materials For Photolithography (AREA)
  • Engineering & Computer Science (AREA)
  • Architecture (AREA)
  • Structural Engineering (AREA)

Abstract

La présente invention concerne une composition photosensible positive chimiquement amplifiée pour couche diélectrique organique hautement sensible, présentant une excellente résistance à la chaleur, et un procédé pour former une couche diélectrique l'employant. La composition photosensible positive chimiquement amplifiée pour couche diélectrique organique hautement sensible contient une résine lieuse, la résine lieuse comprenant un monomère ayant un groupe de réticulation par rayonnement d'énergie active ou chaleur et contenant un groupe protecteur labile aux acides, ou un monomère ayant un groupe de réticulation par rayonnement d'énergie active ou chaleur mais ne contenant pas de groupe protecteur labile aux acides, la résine lieuse comprenant au moins un type des monomères ou chacun des monomères. Selon la présente invention, un monomère contenant un groupe protecteur labile aux acides ou ayant un groupe de réticulation par rayonnement d'énergie active ou chaleur qui n'est pas un groupe protecteur labile aux acides dans une structure moléculaire, est formé sous la forme d'un polymère, d'un copolymère ou d'un mélange de ceux-ci, qui est conventionnellement différent, et il est donc possible de maintenir une excellente sensibilité et une excellente résolution, de réduire notablement le dégagement de vapeurs volatiles pendant l'exposition, et de maintenir la forme d'un modèle dans une fourchette désirée de pente (angle aigu) en inhibant la déformation du modèle due au thermorétrécissement ou à un flux thermique d'un film dans un procédé thermique après formation du modèle.
PCT/KR2013/001634 2012-02-29 2013-02-28 Composition photosensible positive chimiquement amplifiée pour couche diélectrique organique hautement sensible, avec une excellente résistance à la chaleur, et procédé pour former une couche diélectrique l'employant WO2013129864A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR1020120020756A KR20130099338A (ko) 2012-02-29 2012-02-29 내열성이 우수한 화학증폭형 포지티브 감광형 고감도 유기절연막 조성물 및 이를 이용한 유기절연막의 형성방법
KR10-2012-0020756 2012-02-29

Publications (1)

Publication Number Publication Date
WO2013129864A1 true WO2013129864A1 (fr) 2013-09-06

Family

ID=49082988

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/KR2013/001634 WO2013129864A1 (fr) 2012-02-29 2013-02-28 Composition photosensible positive chimiquement amplifiée pour couche diélectrique organique hautement sensible, avec une excellente résistance à la chaleur, et procédé pour former une couche diélectrique l'employant

Country Status (3)

Country Link
KR (1) KR20130099338A (fr)
TW (1) TW201337463A (fr)
WO (1) WO2013129864A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20160147155A1 (en) * 2013-08-01 2016-05-26 Fujifilm Corporation Pattern formation method, active light-sensitive or radiation-sensitive resin composition, resist film, production method for electronic device using same, and electronic device

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR101694698B1 (ko) 2014-03-20 2017-01-10 동우 화인켐 주식회사 감광성 수지 조성물
JP6667361B2 (ja) * 2016-05-06 2020-03-18 東京応化工業株式会社 化学増幅型ポジ型感光性樹脂組成物
KR102687295B1 (ko) * 2016-12-26 2024-07-22 엘지디스플레이 주식회사 고굴절 화합물과 이를 포함하는 절연막, 광 추출 필름, 유기발광 소자 및 유기발광 장치
US20210198468A1 (en) * 2019-12-31 2021-07-01 Taiwan Semiconductor Manufacturing Co., Ltd. Photoresist composition and method of manufacturing a semiconductor device
KR20230045952A (ko) * 2021-09-29 2023-04-05 주식회사 동진쎄미켐 포토레지스트 하층막 형성용 고분자 화합물, 이를 포함하는 euv용 포토레지스트 하층막 조성물, euv용 포토레지스트 하층막의 제조방법 및 포토레지스트 막 패턴의 형성 방법

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2003064134A (ja) * 2001-06-15 2003-03-05 Shin Etsu Chem Co Ltd 高分子化合物、レジスト材料、及びパターン形成方法
KR20110085924A (ko) * 2010-01-20 2011-07-27 후지필름 가부시키가이샤 경화막의 제조 방법, 감광성 수지 조성물, 경화 막, 유기 ｅｌ 표시 장치, 및 액정 표시 장치
KR20110095168A (ko) * 2010-02-16 2011-08-24 신에쓰 가가꾸 고교 가부시끼가이샤 화학 증폭 포지티브형 레지스트 조성물 및 패턴 형성 방법
KR20110135752A (ko) * 2010-06-11 2011-12-19 삼성전자주식회사 프로브 어레이 제조용 포토레지스트 조성물 및 이를 이용한 프로브 어레이의 제조 방법
KR20120106086A (ko) * 2011-03-17 2012-09-26 이윤형 화학증폭형 포지티브 감광형 유기절연막 조성물 및 이를 이용한 유기절연막의 형성방법

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2003064134A (ja) * 2001-06-15 2003-03-05 Shin Etsu Chem Co Ltd 高分子化合物、レジスト材料、及びパターン形成方法
KR20110085924A (ko) * 2010-01-20 2011-07-27 후지필름 가부시키가이샤 경화막의 제조 방법, 감광성 수지 조성물, 경화 막, 유기 ｅｌ 표시 장치, 및 액정 표시 장치
KR20110095168A (ko) * 2010-02-16 2011-08-24 신에쓰 가가꾸 고교 가부시끼가이샤 화학 증폭 포지티브형 레지스트 조성물 및 패턴 형성 방법
KR20110135752A (ko) * 2010-06-11 2011-12-19 삼성전자주식회사 프로브 어레이 제조용 포토레지스트 조성물 및 이를 이용한 프로브 어레이의 제조 방법
KR20120106086A (ko) * 2011-03-17 2012-09-26 이윤형 화학증폭형 포지티브 감광형 유기절연막 조성물 및 이를 이용한 유기절연막의 형성방법

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20160147155A1 (en) * 2013-08-01 2016-05-26 Fujifilm Corporation Pattern formation method, active light-sensitive or radiation-sensitive resin composition, resist film, production method for electronic device using same, and electronic device
US9829796B2 (en) * 2013-08-01 2017-11-28 Fujifilm Corporation Pattern formation method, active light-sensitive or radiation-sensitive resin composition, resist film, production method for electronic device using same, and electronic device

Also Published As

Publication number Publication date
KR20130099338A (ko) 2013-09-06
TW201337463A (zh) 2013-09-16

Similar Documents

Publication Publication Date Title
WO2012125009A2 (fr) Composition photosensible positive chimiquement amplifiée pour film isolant organique et procédé l'utilisant pour former un film isolant organique
WO2017057813A1 (fr) Résine liante et composition de résine photosensible contenant cette dernière
WO2013129864A1 (fr) Composition photosensible positive chimiquement amplifiée pour couche diélectrique organique hautement sensible, avec une excellente résistance à la chaleur, et procédé pour former une couche diélectrique l'employant
WO2017119645A1 (fr) Capteur tactile à pellicule et son procédé de fabrication
WO2015108386A1 (fr) Nouveau composé de β-ester d'oxime fluorène, amorceur de photopolymérisation comprenant ce composé et composition de résine photosensible
WO2016043558A1 (fr) Agent générateur de photo-acide
WO2018159975A1 (fr) Composé de résine polymère et composition de résine photosensible pour masque noir comprenant celui-ci
WO2019245172A1 (fr) Composition de résine photosensible positive amplifiée chimiquement servant à améliorer un profil de motif
WO2017119764A1 (fr) Capteur tactile à film et procédé de production associé
WO2023027360A1 (fr) Composition de résine photosensible positive amplifiée chimiquement pour améliorer le profil et la résolution de motif
WO2015160229A1 (fr) Copolymère de polysilsesquioxane et composition de résine photosensible le contenant
WO2020111522A1 (fr) Composition de résine photosensible, film et dispositif électronique
WO2012064074A1 (fr) Composition de résine photosensible, et film isolant diélectrique et dispositif électronique l'employant
WO2017039235A1 (fr) Composition de résine photosensible négative « i-line » ayant une excellente résistance à la gravure
WO2010038978A2 (fr) Composition de résine photopolymère
WO2012046917A1 (fr) Polymère à base de (méth)acrylate et composition de résine photosensible incluant ledit polymère
WO2021080267A1 (fr) Copolymère de polysiloxane, procédé de production associé et composition de résine le contenant
WO2021125821A1 (fr) Composé, résine liante, composition de résine photosensible de type négatif et dispositif d'affichage comprenant un masque noir formé en faisant appel à ceux-ci
WO2022055149A1 (fr) Composition pour résine photosensible semi-conductrice et procédé de formation de motif l'utilisant
WO2014193165A1 (fr) Composition de résine photosensible permettant de former un espaceur et espaceur préparé à partir de celle-ci
WO2018034460A1 (fr) Composition de résine photosensible et film durci préparé à partir de celle-ci
WO2017078267A1 (fr) Composition de résine photosensible et film durci préparé à partir de cette dernière
WO2019074262A1 (fr) Résine liante et composition de résine photosensible ou solution de revêtement la contenant
WO2023022452A1 (fr) Composition de résine photosensible et dispositif d'affichage
WO2024085292A1 (fr) Composition de résine photosensible positive chimiquement amplifiée pour améliorer le profil de motif et améliorer l'adhérence

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 13755249

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 13755249

Country of ref document: EP

Kind code of ref document: A1