WO2020241536A1 - 樹脂組成物、膜、カラーフィルタ、固体撮像素子および画像表示装置 - Google Patents
樹脂組成物、膜、カラーフィルタ、固体撮像素子および画像表示装置 Download PDFInfo
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- WO2020241536A1 WO2020241536A1 PCT/JP2020/020441 JP2020020441W WO2020241536A1 WO 2020241536 A1 WO2020241536 A1 WO 2020241536A1 JP 2020020441 W JP2020020441 W JP 2020020441W WO 2020241536 A1 WO2020241536 A1 WO 2020241536A1
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- C08J2379/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2433/00—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers
- C08J2433/04—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers esters
- C08J2433/06—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers esters of esters containing only carbon, hydrogen, and oxygen, the oxygen atom being present only as part of the carboxyl radical
- C08J2433/10—Homopolymers or copolymers of methacrylic acid esters
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2433/00—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers
- C08J2433/04—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers esters
- C08J2433/14—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers esters of esters containing halogen, nitrogen, sulfur, or oxygen atoms in addition to the carboxy oxygen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2201/00—Properties
- C08L2201/10—Transparent films; Clear coatings; Transparent materials
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2203/00—Applications
- C08L2203/16—Applications used for films
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- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
Definitions
- the present invention relates to a resin composition containing a coloring material, a film, a color filter, a solid-state image sensor, and an image display device.
- a film containing a color material such as a color filter is used for the solid-state image sensor.
- a film containing a color material such as a color filter is manufactured by using a resin composition containing the color material, a resin, and a solvent.
- Patent Document 1 describes that a colored resin composition containing a predetermined polyimide precursor, a colorant, and a solvent is used to produce a colored film having excellent light-shielding property and insulating property.
- Patent Document 2 describes that a colored pattern is produced using a photosensitive composition containing a predetermined polysiloxane compound, a photoacid generator, a colorant, and a solvent.
- an object of the present invention is to provide a novel resin composition, a film, a color filter, a solid-state image sensor, and an image display device capable of expanding the process window of a process after manufacturing a film.
- the present invention provides: ⁇ 1> A resin composition containing a coloring material, a resin, and a solvent. When a film having a thickness of 0.60 ⁇ m was formed by heating at 200 ° C. for 30 minutes using the above resin composition, the thickness of the film after heat-treating the film at 300 ° C. for 5 hours in a nitrogen atmosphere. A resin composition having a thickness of 70% or more of the thickness of the film before heat treatment.
- the resin contains at least one resin A selected from a polyimide resin, a polybenzoxazole resin, an epoxy resin, a bismaleimide resin, a silicone resin, a polyarylate resin, a benzoxazine resin, and a precursor thereof.
- the resin composition according to 1> is not limited to 1>.
- ⁇ 3> The resin composition according to ⁇ 1>, wherein the resin A is at least one selected from a polyimide resin, a polybenzoxazole resin, and a precursor thereof.
- the resin A is applied to a glass substrate and heated at 100 ° C. for 120 seconds to form a film having a thickness of 0.60 ⁇ m, the minimum value of the transmittance of the film having a wavelength of 400 to 1100 nm is 70%.
- ⁇ 5> The resin composition according to any one of ⁇ 2> to ⁇ 4>, which contains 20% by mass or more of the resin A in the components obtained by removing the coloring material from the total solid content of the resin composition.
- ⁇ 6> The resin composition according to any one of ⁇ 2> to ⁇ 5>, wherein the resin contains a resin other than the resin A.
- ⁇ 12> The resin composition according to any one of ⁇ 1> to ⁇ 9>, wherein the coloring material contains at least one selected from a chromatic pigment and a near-infrared absorbing pigment.
- the coloring material contains at least one selected from a chromatic pigment and a near-infrared absorbing pigment.
- ⁇ 13> The resin composition according to any one of ⁇ 1> to ⁇ 12>, further containing a photopolymerization initiator.
- ⁇ 14> The resin composition according to ⁇ 13>, further comprising a polymerizable compound.
- ⁇ 15> When the resin composition is applied to a glass substrate and heated at 100 ° C. for 120 seconds to form a film having a film thickness of 0.6 ⁇ m, the film has a maximum transmittance at a wavelength of 400 to 1100 nm.
- ⁇ 19> A film obtained from the resin composition according to any one of ⁇ 1> to ⁇ 18>.
- ⁇ 20> A color filter containing the film according to ⁇ 19>.
- the present invention it is possible to provide a novel resin composition, a film, a color filter, a solid-state image sensor, and an image display device capable of expanding the process window of a process after manufacturing a film.
- the contents of the present invention will be described in detail below.
- "-" is used in the meaning of including the numerical values described before and after it as the lower limit value and the upper limit value.
- the notation not describing substitution and non-substituent also includes a group having a substituent (atomic group) as well as a group having no substituent (atomic group).
- the "alkyl group” includes not only an alkyl group having no substituent (unsubstituted alkyl group) but also an alkyl group having a substituent (substituted alkyl group).
- exposure includes not only exposure using light but also drawing using particle beams such as an electron beam and an ion beam, unless otherwise specified.
- the light used for exposure include the emission line spectrum of a mercury lamp, far ultraviolet rays typified by an excimer laser, extreme ultraviolet rays (EUV light), X-rays, active rays such as electron beams, or radiation.
- EUV light extreme ultraviolet rays
- active rays such as electron beams, or radiation.
- the (meth) allyl group represents both allyl and metharyl, or either, and "(meth) acrylate” represents both acrylate and methacrylate, or "(meth).
- “Acrylic” represents both acrylic and methacrylic, or either, and "(meth) acryloyl” represents both acryloyl and methacrylic, or either.
- the weight average molecular weight and the number average molecular weight are polystyrene-equivalent values measured by a GPC (gel permeation chromatography) method.
- the near infrared ray means light having a wavelength of 700 to 2500 nm.
- the total solid content means the total mass of all the components of the composition excluding the solvent.
- the term "process” does not only refer to an independent process, but even if it cannot be clearly distinguished from other processes, if the desired action of the process is achieved, the term is used. included.
- the resin composition of the present invention is a resin composition containing a coloring material, a resin, and a solvent.
- a film having a thickness of 0.60 ⁇ m was formed by heating at 200 ° C. for 30 minutes using the above resin composition, the thickness of the film after heat-treating the film at 300 ° C. for 5 hours in a nitrogen atmosphere. It is characterized in that it is 70% or more of the thickness of the film before the heat treatment.
- the film can be subjected to a process at a high temperature. It is possible to suppress film shrinkage after heat treatment. Therefore, the applicable range of the heating temperature in the process after manufacturing the film using the resin composition can be expanded to a higher temperature (for example, 300 ° C. or higher), and the process window of the process after manufacturing the film can be expanded. It can be expanded.
- the film on which the inorganic film is formed is heated to a high temperature of 300 ° C. or higher. Even when heated, it is possible to suppress the occurrence of cracks in the inorganic film. Therefore, the applicable range of the heating temperature in the step after forming the inorganic film on the film surface can be expanded to a higher temperature (for example, 300 ° C. or higher).
- the thickness of the film is preferably 70% or more, more preferably 80% or more, and further preferably 90% or more of the thickness of the film before the heat treatment.
- the thickness of the film after being heat-treated at 350 ° C. for 5 hours in a nitrogen atmosphere is preferably 70% or more, preferably 80% or more of the thickness of the film before the heat treatment. Is more preferable, and 90% or more is further preferable.
- the thickness of the film after being heat-treated at 400 ° C. for 5 hours in a nitrogen atmosphere is preferably 70% or more, preferably 80% or more of the thickness of the film before the heat treatment. Is more preferable, and 90% or more is further preferable.
- the above physical properties can be achieved by adjusting the type and content of the resin used.
- the resin composition of the present invention can be used for a color filter, a near-infrared transmission filter, a near-infrared cut filter, a black matrix, a light-shielding film, and the like.
- the color filter examples include a filter having colored pixels that transmit light of a specific wavelength, and at least one colored pixel selected from red pixels, blue pixels, green pixels, yellow pixels, cyan pixels, and magenta pixels. It is preferable that the filter has.
- the color filter can be formed by using a resin composition containing a chromatic color material.
- the near-infrared cut filter examples include a filter having a maximum absorption wavelength in the wavelength range of 700 to 1800 nm.
- the near-infrared cut filter is preferably a filter having a maximum absorption wavelength in the wavelength range of 700 to 1300 nm, and more preferably a filter having a wavelength in the wavelength range of 700 to 1100 nm.
- the transmittance of the near-infrared cut filter in the entire wavelength range of 400 to 650 nm is preferably 70% or more, more preferably 80% or more, and further preferably 90% or more. Further, the transmittance at at least one point in the wavelength range of 700 to 1800 nm is preferably 20% or less.
- the absorbance Amax / absorbance A550 which is the ratio of the absorbance Amax at the maximum absorption wavelength of the near-infrared cut filter to the absorbance A550 at a wavelength of 550 nm, is preferably 20 to 500, more preferably 50 to 500. , 70 to 450 is more preferable, and 100 to 400 is particularly preferable.
- the near-infrared cut filter can be formed by using a resin composition containing a near-infrared absorbing color material.
- a near-infrared ray transmitting filter is a filter that transmits at least a part of near infrared rays.
- the near-infrared transmitting filter may be a filter (transparent film) that transmits both visible light and near-infrared light, and is a filter that blocks at least a part of visible light and transmits at least a part of near-infrared light. May be good.
- the maximum value of the transmittance in the wavelength range of 400 to 640 nm is 20% or less (preferably 15% or less, more preferably 10% or less), and the transmittance in the wavelength range of 1100 to 1300 nm.
- a filter satisfying the spectral characteristics having a minimum value of 70% or more is preferably mentioned.
- the near-infrared transmission filter is preferably a filter that satisfies any of the following spectral characteristics (1) to (4).
- the maximum value of the transmittance in the wavelength range of 400 to 640 nm is 20% or less (preferably 15% or less, more preferably 10% or less), and the minimum value of the transmittance in the wavelength range of 800 to 1300 nm is.
- the maximum value of the transmittance in the wavelength range of 400 to 750 nm is 20% or less (preferably 15% or less, more preferably 10% or less), and the minimum value of the transmittance in the wavelength range of 900 to 1300 nm is.
- the maximum value of the transmittance in the wavelength range of 400 to 830 nm is 20% or less (preferably 15% or less, more preferably 10% or less), and the minimum value of the transmittance in the wavelength range of 1000 to 1300 nm is.
- the maximum value of the transmittance in the wavelength range of 400 to 950 nm is 20% or less (preferably 15% or less, more preferably 10% or less), and the minimum value of the transmittance in the wavelength range of 1100 to 1300 nm is.
- a filter that is 70% or more (preferably 75% or more, more preferably 80% or more).
- the resin composition of the present invention can be preferably used as a resin composition for a color filter. Specifically, it can be preferably used as a resin composition for forming pixels of a color filter, and more preferably as a resin composition for forming red or blue pixels of a color filter. Further, the resin composition of the present invention can be preferably used as a resin composition for forming pixels of a color filter used in a solid-state image sensor.
- the film When the resin composition of the present invention is applied to a glass substrate and heated at 100 ° C. for 120 seconds to form a film having a film thickness of 0.6 ⁇ m, the film has a maximum transmittance of 70 at a wavelength of 400 to 1100 nm. % Or more (preferably 75% or more, more preferably 80% or more, still more preferably 85% or more), and the minimum value is 30% or less (preferably 25% or less, more preferably 20% or less, still more preferably 15%). The following) is preferable.
- a resin composition capable of forming a film satisfying the above spectral characteristics can be particularly preferably used as a resin composition for forming a color filter, a near-infrared transmission filter or a near-infrared cut filter.
- the resin composition of the present invention is a resin composition for pattern formation by a photolithography method. According to this aspect, finely sized pixels can be easily formed. Therefore, it can be particularly preferably used as a resin composition for forming pixels of a color filter used in a solid-state image sensor.
- a resin composition containing a component having a polymerizable group for example, a resin having a polymerizable group or a polymerizable compound
- a photopolymerization initiator can be used as a resin composition for pattern formation in a photolithography method. It can be preferably used.
- the resin composition for pattern formation in the photolithography method preferably further contains an alkali-soluble resin.
- the resin composition of the present invention contains a coloring material.
- the coloring material include a white coloring material, a black coloring material, a chromatic coloring material, and a near-infrared absorbing coloring material.
- the white color material includes not only pure white color material but also a light gray color material close to white (for example, grayish white, light gray, etc.).
- the coloring material preferably contains at least one selected from a chromatic coloring material, a black coloring material, and a near-infrared absorbing coloring material, and at least one selected from the chromatic coloring material and the near-infrared absorbing coloring material. It is more preferable to include, and it is further preferable to include a chromatic coloring material.
- the coloring material preferably contains two or more kinds of chromatic color materials and a near-infrared absorbing color material, or preferably contains a black pigment and a near-infrared absorbing color material. According to this aspect, it can be preferably used as a resin composition for forming a near-infrared transmission filter.
- the coloring material examples include dyes and pigments, and pigments are preferable from the viewpoint of heat resistance.
- the pigment may be either an inorganic pigment or an organic pigment, but is preferably an organic pigment from the viewpoints of many color variations, ease of dispersion, safety and the like. Further, the pigment preferably contains at least one selected from a chromatic pigment and a near-infrared absorbing pigment, and more preferably contains a chromatic pigment.
- the pigment may contain at least one selected from phthalocyanine pigments, dioxazine pigments, quinacridone pigments, anthraquinone pigments, perylene pigments, azo pigments, diketopyrrolopyrrole pigments, pyrolopyrrolop pigments, isoindolin pigments and quinophthalone pigments. It is more preferable that it contains at least one selected from a phthalocyanine pigment, a diketopyrrolopyrrole pigment and a pyrolopyrrolop pigment, and even more preferably it contains a phthalocyanine pigment or a diketopyrrolopyrrole pigment.
- the phthalocyanine pigment has a phthalocyanine pigment having no central metal and copper or zinc as the central metal because it is easy to form a film whose spectral characteristics do not easily fluctuate even after heating to a high temperature (for example, 300 ° C. or higher). Phthalocyanine pigments are preferred.
- the coloring material contained in the resin composition easily forms a film whose spectral characteristics do not easily fluctuate even after being heated to a high temperature (for example, 300 ° C. or higher), and therefore red pigment, yellow pigment, blue pigment and infrared absorption. It is preferable to contain at least one selected from pigments, more preferably to contain at least one selected from red pigments and blue pigments, and even more preferably to include blue pigments.
- the coloring material contained in the resin composition preferably contains the pigment A showing the condition 1 shown below.
- the ratio of the pigment A in the total amount of the pigment contained in the resin composition is preferably 20 to 100% by mass, more preferably 30 to 100% by mass, and further preferably 40 to 100% by mass. ..
- A11 is the maximum value of the absorbance in the wavelength range of 400 to 1100 nm of the film before the heat treatment.
- A12 is the absorbance of the film after the heat treatment, which is the absorbance at the wavelength indicating the maximum value of the absorbance of the film before the heat treatment in the wavelength range of 400 to 1100 nm;
- Resin B-5 is a resin having the following structure, and the numerical values added to the main chain are molar ratios, the weight average molecular weight is 11000, and the acid value is 32 mgKOH / g.
- Pigment A that satisfies the above condition 1 includes C.I. I. Pigment Red 254, C.I. I. Pigment Red 264, Pigment Red 272, Pigment Red 122, Pigment Red 177, C.I. I. Pigment Blue 15: 3, C.I. I. Pigment Blue 15: 4, C.I. I. Pigment Blue 15: 6, C.I. I. Pigment Blue 16 and the like.
- the average primary particle size of the pigment is preferably 1 to 200 nm.
- the lower limit is preferably 5 nm or more, more preferably 10 nm or more.
- the upper limit is preferably 180 nm or less, more preferably 150 nm or less, and even more preferably 100 nm or less.
- the primary particle size of the pigment can be determined from a photograph obtained by observing the primary particles of the pigment with a transmission electron microscope. Specifically, the projected area of the primary particles of the pigment is obtained, and the corresponding circle-equivalent diameter is calculated as the primary particle diameter of the pigment.
- the average primary particle diameter in the present invention is an arithmetic mean value of the primary particle diameter for the primary particles of 400 pigments.
- the primary particles of the pigment refer to independent particles without aggregation.
- the chromatic color material examples include a color material having a maximum absorption wavelength in the wavelength range of 400 to 700 nm. For example, a yellow color material, an orange color material, a red color material, a green color material, a purple color material, a blue color material, and the like can be mentioned. From the viewpoint of heat resistance, the chromatic color material is preferably a pigment (chromatic pigment), more preferably a red pigment, a yellow pigment, and a blue pigment, and further preferably a red pigment and a blue pigment. Specific examples of the chromatic pigment include those shown below.
- C.I. is used as a red pigment because it is easy to form a film whose spectral characteristics do not easily change even after heating to a high temperature (for example, 300 ° C. or higher).
- I. Pigment Red 254, C.I. I. Pigment Red 264, Pigment Red 272, Pigment Red 122, Pigment Red 177 are preferable.
- a halogenated zinc phthalocyanine having an average of 10 to 14 halogen atoms in one molecule, an average of 8 to 12 bromine atoms, and an average of 2 to 5 chlorine atoms. Pigments can also be used. Specific examples include the compounds described in International Publication No. 2015/118720. Further, as a green pigment, a compound described in Chinese Patent Application No. 106909027, a phthalocyanine compound having a phosphate ester described in International Publication No. 2012/10395 as a ligand, and Japanese Patent Application Laid-Open No. 2019-008014. Phthalocyanine compounds and phthalocyanine compounds described in JP-A-2018-180023 can also be used.
- an aluminum phthalocyanine compound having a phosphorus atom can also be used. Specific examples include the compounds described in paragraphs 0022 to 0030 of JP2012-247591A and paragraph numbers 0047 of JP2011-157478A.
- the compounds described in JP-A-2017-201003 the compounds described in JP-A-2017-197719, and paragraph numbers 0011 to 0062 and 0137-0276 of JP-A-2017-171912.
- the quinophthalone compound described in Japanese Patent Application Laid-Open No. 2019-008014, the compound represented by the following formula (QP1), and the compound represented by the following formula (QP2) can also be used.
- X 1 to X 16 independently represent a hydrogen atom or a halogen atom, and Z 1 represents an alkylene group having 1 to 3 carbon atoms.
- Specific examples of the compound represented by the formula (QP1) include the compounds described in paragraph No. 0016 of Japanese Patent No. 6443711.
- Y 1 ⁇ Y 3 represents a halogen atom independently.
- n and m represent integers of 0 to 6, and p represents an integer of 0 to 5.
- N + m is 1 or more.
- Specific examples of the compound represented by the formula (QP2) include the compounds described in paragraphs 0047 to 0048 of Japanese Patent No. 6432077.
- the diketopyrrolopyrrole compound described in WO2012 / 102399, the diketopyrrolopyrrole compound described in WO2012 / 117965, the naphtholazo compound described in JP2012-229344A, and the like are used. You can also.
- red pigment a compound having a structure in which an aromatic ring group having an oxygen atom, a sulfur atom or a nitrogen atom bonded to the aromatic ring is bonded to a diketopyrrolopyrrole skeleton can also be used. It can.
- a compound represented by the formula (DPP1) is preferable, and a compound represented by the formula (DPP2) is more preferable.
- R 11 and R 13 independently represent a substituent
- R 12 and R 14 independently represent a hydrogen atom, an alkyl group, an aryl group or a heteroaryl group
- n 11 and n 13 are independent of each other.
- X 12 and X 14 independently represent an oxygen atom, a sulfur atom or a nitrogen atom
- m12 represents 1 and X.
- m12 represents 2 when X 14 is a nitrogen atom.
- Examples of the substituent represented by R 11 and R 13 include the group mentioned in Substituent T described later, which includes an alkyl group, an aryl group, a halogen atom, an acyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, and a heteroaryloxycarbonyl.
- Preferred specific examples include a group, an amide group, a cyano group, a nitro group, a trifluoromethyl group, a sulfoxide group, a sulfo group and the like.
- the chromatic dyes include pyrazole azo compounds, anilino azo compounds, triarylmethane compounds, anthraquinone compounds, anthrapyridone compounds, benzylidene compounds, oxonor compounds, pyrazorotriazole azo compounds, pyridone azo compounds, cyanine compounds, phenothiazine compounds, and pyropyrazole azomethine compounds.
- Two or more kinds of chromatic color materials may be used in combination. Further, when two or more kinds of chromatic color materials are used in combination, black may be formed by a combination of two or more kinds of chromatic color materials. Examples of such a combination include the following aspects (1) to (7).
- the resin composition of the present invention can be used as a near infrared transmission filter. It can be preferably used.
- An embodiment containing a red color material, a blue color material, a yellow color material, and a purple color material (3) An embodiment containing a red color material, a blue color material, a yellow color material, and a purple color material. (4) An embodiment containing a red color material, a blue color material, a yellow color material, a purple color material, and a green color material. (5) An embodiment containing a red color material, a blue color material, a yellow color material, and a green color material. (6) An embodiment containing a red color material, a blue color material, and a green color material. (7) An embodiment containing a yellow color material and a purple color material.
- White coloring materials include titanium oxide, strontium titanate, barium titanate, zinc oxide, magnesium oxide, zirconium oxide, aluminum oxide, barium sulfate, silica, talc, mica, aluminum hydroxide, calcium silicate, aluminum silicate, Examples thereof include hollow resin particles and inorganic pigments (white pigments) such as zinc sulfide.
- the white pigment is preferably particles having a titanium atom, and more preferably titanium oxide.
- the white pigment is preferably particles having a refractive index of 2.10 or more with respect to light having a wavelength of 589 nm. The above-mentioned refractive index is preferably 2.10 to 3.00, and more preferably 2.50 to 2.75.
- titanium oxide described in "Titanium Oxide Physical Properties and Applied Technology, by Manabu Kiyono, pp. 13-45, published on June 25, 1991, published by Gihodo Publishing" can also be used.
- the white pigment is not limited to a single inorganic substance, but particles compounded with other materials may be used. For example, particles having pores or other materials inside, particles in which a large number of inorganic particles are attached to core particles, core particles composed of core particles composed of polymer particles, and core and shell composite particles composed of a shell layer composed of inorganic nanoparticles are used. Is preferable.
- the core and shell composite particles composed of the core particles composed of the polymer particles and the shell layer composed of the inorganic nanoparticles for example, the description in paragraphs 0012 to 0042 of JP2015-047520 can be referred to. This content is incorporated herein by reference.
- Hollow inorganic particles can also be used as the white pigment.
- Hollow inorganic particles are inorganic particles having a structure having cavities inside, and refer to inorganic particles having cavities surrounded by an outer shell.
- Examples of the hollow inorganic particles include the hollow inorganic particles described in JP-A-2011-075786, International Publication No. 2013/061621, JP-A-2015-164881, and the like, and the contents thereof are incorporated in the present specification. Is done.
- Black color material The black color material is not particularly limited, and known materials can be used.
- inorganic pigments black pigments
- carbon black and titanium black being preferable, and titanium black being more preferable.
- Titanium black is black particles containing a titanium atom, and low-order titanium oxide or titanium oxynitride is preferable.
- the surface of titanium black can be modified as needed for the purpose of improving dispersibility and suppressing cohesiveness.
- Titanium black preferably has a small primary particle size and an average primary particle size of each particle. Specifically, the average primary particle size is preferably 10 to 45 nm. Titanium black can also be used as a dispersion. For example, a dispersion containing titanium black particles and silica particles and having a content ratio of Si atoms and Ti atoms in the dispersion adjusted to a range of 0.20 to 0.50 can be mentioned. Regarding the above dispersion, the description in paragraphs 0020 to 0105 of JP2012-169556A can be referred to, and the contents thereof are incorporated in the present specification.
- titanium black products examples include titanium black 10S, 12S, 13R, 13M, 13M-C, 13RN, 13MT (trade name: manufactured by Mitsubishi Materials Corporation), Tilak D ( Product name: Ako Kasei Co., Ltd.) and the like.
- an organic black color material such as a bisbenzofuranone compound, an azomethin compound, a perylene compound, or an azo compound
- a bisbenzofuranone compound include the compounds described in JP-A-2010-534726, JP-T-2012-515233, and JP-2012-515234.
- Irgaphor Black manufactured by BASF. It is available.
- the perylene compound include the compounds described in paragraphs 0016 to 0020 of JP-A-2017-226821, C.I. I. Pigment Black 31, 32 and the like can be mentioned.
- the azomethine compound include compounds described in JP-A-01-17601 and JP-A-02-0346664, and are available as, for example, "Chromofine Black A1103" manufactured by Dainichiseika.
- the near-infrared absorbing color material is preferably a pigment, more preferably an organic pigment. Further, the near-infrared absorbing color material preferably has a maximum absorption wavelength in a range of more than 700 nm and 1400 nm or less. Further, the maximum absorption wavelength of the near-infrared absorbing color material is preferably 1200 nm or less, more preferably 1000 nm or less, and further preferably 950 nm or less.
- the near-infrared absorbing color material preferably has A 550 / A max, which is the ratio of the absorbance A 550 at a wavelength of 550 nm to the absorbance A max at the maximum absorption wavelength, of 0.1 or less, preferably 0.05 or less. More preferably, it is more preferably 0.03 or less, and particularly preferably 0.02 or less.
- the lower limit is not particularly limited, but can be, for example, 0.0001 or more, or 0.0005 or more.
- the maximum absorption wavelength of the near-infrared absorbing color material and the value of the absorbance at each wavelength are values obtained from the absorption spectrum of the film formed by using the resin composition containing the near-infrared absorbing color material.
- the near-infrared absorbing coloring material is not particularly limited, but is pyrolopyrrole compound, cyanine compound, squarylium compound, phthalocyanine compound, naphthalocyanine compound, quaterylene compound, merocyanine compound, croconium compound, oxonor compound, iminium compound, dithiol compound, and tria.
- Examples thereof include reelmethane compounds, pyromethene compounds, azomethine compounds, anthraquinone compounds, dibenzofuranone compounds, and dithiolene metal complexes.
- Examples of the pyrrolopyrrole compound include the compounds described in paragraphs 0016 to 0058 of JP2009-263614, the compounds described in paragraphs 0037 to 0052 of JP2011-066731, and International Publication No. 2015/166783. Examples thereof include the compounds described in paragraphs 0010 to 0033.
- Examples of the squarylium compound include the compounds described in paragraphs 0044 to 0049 of JP2011-208101A, the compounds described in paragraphs 0060 to 0061 of Patent No. 6065169, and paragraph numbers 0040 of International Publication No. 2016/181987. , The compound described in JP-A-2015-176046, the compound described in paragraph number 0072 of International Publication No.
- JP2012-077153 the oxytitanium phthalocyanine described in JP2006-343631, and paragraphs 0013 to 0029 of JP2013-195480.
- vanadium phthalocyanine compound described in Japanese Patent No. 6081771.
- examples of the naphthalocyanine compound include the compounds described in paragraph No. 0093 of JP2012-077153.
- Examples of the dithiolene metal complex include the compounds described in Japanese Patent No. 5733804.
- Examples of the near-infrared absorbing color material include a squarylium compound described in JP-A-2017-197437, a squarylium compound described in JP-A-2017-025311, a squarylium compound described in International Publication No. 2016/154782, and a patent.
- Squalylium compound described in Japanese Patent No. 5884953 Squalylium compound described in Japanese Patent No. 6036689
- Squalylium compound described in Japanese Patent No. 5810604 Squalylium compound described in paragraph numbers 0090 to 0107 of International Publication No. 2017/213047.
- Amid-linked squarylium compound a compound having a pyrrolbis-type squarylium skeleton or a croconium skeleton described in JP-A-2017-141215, a dihydrocarbazolebis-type squarylium compound described in JP-A-2017-082029, JP-A-2017 Asymmetric compounds described in paragraphs 0027 to 0114 of Japanese Patent Application Laid-Open No. -068120, pyrrol ring-containing compounds (carbazole type) described in JP-A-2017-067963, phthalocyanine compounds described in Japanese Patent No. 6251530, etc. Can also be used.
- the content of the coloring material in the total solid content of the resin composition is preferably 5% by mass or more, more preferably 10% by mass or more, further preferably 15% by mass or more, and 20% by mass. The above is even more preferable.
- the upper limit is preferably 90% by mass or less, more preferably 80% by mass or less, and further preferably 70% by mass or less.
- the content of the pigment in the total solid content of the resin composition is preferably 5% by mass or more, more preferably 10% by mass or more, further preferably 15% by mass or more, and 20% by mass. % Or more is even more preferable.
- the upper limit is preferably 90% by mass or less, more preferably 80% by mass or less, and further preferably 70% by mass or less.
- the content of the dye in the coloring material is preferably 50% by mass or less, more preferably 40% by mass or less, and further preferably 30% by mass or less. Further, it is also preferable that the resin composition of the present invention does not substantially contain a dye because it is easy to more effectively suppress the change in film thickness when the obtained film is heated to a high temperature.
- the content of the dye in the total solid content of the resin composition of the present invention is preferably 0.1% by mass or less, preferably 0.05% by mass. The following is more preferable, and it is particularly preferable that the content is not contained.
- the resin composition of the present invention contains a resin.
- the resin is blended, for example, for the purpose of dispersing particles such as pigments in the resin composition and for the purpose of a binder.
- a resin mainly used for dispersing particles such as pigments is also referred to as a dispersant.
- such an application of the resin is an example, and it can be used for a purpose other than such an application.
- the resin contained in the resin composition of the present invention preferably contains an alkali-soluble resin.
- the alkali-soluble resin is preferably a resin having an acid group. Examples of the acid group include a phenolic hydroxy group, a carboxy group, a sulfo group, a phosphoric acid group, a phosphonic acid group and the like.
- the alkali-soluble resin may be the resin A described later, or may be a resin other than the resin A.
- the resin composition of the present invention contains at least one resin A selected from a polyimide resin, a polybenzoxazole resin, an epoxy resin, a bismaleimide resin, a silicone resin, a polyarylate resin, a benzoxazine resin and a precursor thereof. Is preferable. Further, a copolymer of (meth) acrylamide and styrene is also preferably used.
- the resin composition of the present invention contains the resin A, it is easy to form a film having excellent heat resistance, and it is easy to suppress film shrinkage and discoloration after heating.
- the resin A is preferably a polyimide resin, a precursor of a polyimide resin, a polybenzoxazole resin, a precursor of a polybenzoxazole resin, an epoxy resin, a bismaleimide resin, and a silicone resin, and has good heat resistance after heating.
- it is at least one selected from a polyimide resin, a polybenzoxazole resin and a precursor thereof, because the shrinkage of the polyimide resin is small, and it is a precursor of the polyimide resin and a precursor of the polybenzoxazole resin. More preferred.
- the minimum value of the transmittance of the film having a wavelength of 400 to 1100 nm is 70% or more. Is more preferable, 75% or more is more preferable, 80% or more is further preferable, and 85% or more is particularly preferable.
- the resin A having such spectral characteristics the spectral characteristics of the film formed by using the resin composition can be made more excellent.
- Polyimide precursor examples of the polyimide resin precursor (hereinafter, also referred to as a polyimide precursor) include those containing a structural unit represented by the following formula (PI-1).
- Ri 1 represents a divalent organic group
- Ri 5 represents a tetravalent organic group
- Ri 3 and Ri 4 independently represent a hydrogen atom or a monovalent organic group
- Xi 1 and Xi. 2 independently represent O or NRxi
- Rxi represents a hydrogen atom or a substituent.
- Ri 1 represents a divalent organic group.
- the divalent organic group include a linear or branched aliphatic hydrocarbon group, a cyclic aliphatic hydrocarbon group, an aromatic hydrocarbon group or a heterocyclic group, and a direct group having 2 to 20 carbon atoms.
- Ri 1 is preferably a diamine-derived group.
- Diamines are linear aliphatic hydrocarbon groups having 2 to 20 carbon atoms, branched aliphatic hydrocarbon groups having 3 to 20 carbon atoms, cyclic aliphatic hydrocarbon groups having 3 to 20 carbon atoms, or 6 to 6 carbon atoms.
- a compound containing 20 aromatic hydrocarbon groups is preferable, and a compound containing an aromatic hydrocarbon group having 6 to 20 carbon atoms is more preferable.
- Specific examples of the diamine include the compounds described in paragraphs 0024 to 0029 of WO 2017/209177, the contents of which are incorporated herein.
- Ri 1 is preferably represented by ⁇ Ar 0 ⁇ L 0 ⁇ Ar 0 ⁇ from the viewpoint of the flexibility of the obtained cured film.
- Ar 0 is independently an aromatic hydrocarbon group (preferably an aromatic hydrocarbon group having 6 to 22 carbon atoms, more preferably an aromatic hydrocarbon group of 6 to 18, and an aromatic hydrocarbon group of 6 to 10). Is particularly preferable), and a phenylene group is preferable.
- L 0 represents a single bond or a divalent linking group.
- - -, - more preferably a group selected from, -CH 2 - - S- and -SO 2, - O -, - S -, - SO 2 -, - C (CF 3) 2 -, And, it is more preferable that it is ⁇ C (CH 3 ) 2- .
- the tetravalent organic group represented by Ri 5, is preferably a group containing an aromatic ring, more preferably a group represented by the following formula (ri 5 -1) or formula (Ri 5 -2).
- Xi 10 represents a single bond or a divalent linking group.
- - -, - more preferably a group selected from, -CH 2 - - S- and -SO 2, - O -, - S -, - SO 2 -, - C (CF 3) 2 -, And, it is more preferable that it is ⁇ C (CH 3 ) 2- .
- tetravalent organic group represented by Ri 5 include a tetracarboxylic acid residue remaining after removing the acid dianhydride group from the tetracarboxylic dianhydride. Only one type of tetracarboxylic dianhydride may be used, or two or more types may be used. Specific examples of the tetracarboxylic dianhydride include the compounds described in paragraphs 0035 to 0037 of International Publication No. 2017/209177, the contents of which are incorporated herein.
- Ri 3 and Ri 4 independently represent a hydrogen atom or a monovalent organic group.
- the monovalent organic group include a polymerizable group, an acid-decomposable group, a hydrocarbon group, and a heterocyclic group.
- At least one of Ri 3 and Ri 4 is preferably a polymerizable group, and more preferably both are polymerizable groups.
- a polyimide precursor containing a polymerizable group is used, a film having better properties can be easily obtained.
- the resin composition of the present invention contains a photopolymerization initiator, it can be a resin composition having excellent pattern forming property in a photolithography method.
- the polymerizable group represented by Ri 3 and Ri 4 is preferably a radically polymerizable group.
- the radically polymerizable group is a group capable of a cross-linking reaction by the action of a radical, and a preferable example thereof is an ethylenically unsaturated bond-containing group.
- examples of the ethylenically unsaturated bond-containing group include a vinyl group, an allyl group, a (meth) acryloyl group, and a group represented by the following formula (III).
- R200 represents a hydrogen atom or a methyl group, with a methyl group being more preferred.
- R 201 is an alkylene group having 2 to 12 carbon atoms, -CH 2 CH (OH) CH 2- or a (poly) oxyalkylene group having 4 to 30 carbon atoms (the alkylene group has 1 carbon atom).
- ⁇ 12 is preferable, 1 to 6 is more preferable, 1 to 3 is particularly preferable; the number of repetitions is preferably 1 to 12, 1 to 6 is more preferable, and 1 to 3 is particularly preferable).
- the (poly) oxyalkylene group means an oxyalkylene group or a polyoxyalkylene group.
- R 201 examples include ethylene group, propylene group, trimethylene group, tetramethylene group, 1,2-butandyl group, 1,3-butandyl group, pentamethylene group, hexamethylene group, octamethylene group, dodecamethylene group. , -CH 2 CH (OH) CH 2-, and preferred are ethylene group, propylene group, trimethylene group, and -CH 2 CH (OH) CH 2- .
- R 200 is a methyl group and R 201 is an ethylene group.
- Examples of the acid-degradable group represented by Ri 3 and Ri 4 include a tertiary alkyl group and an acetal-type acid-degradable group.
- Examples of the tertiary alkyl group include a t-butyl group.
- Examples of the acetal-type acid-degradable group include a 1-alkoxyalkyl group, a 2-tetrahydrofuranyl group, and a 2-tetrahydropyranyl group.
- Examples of the hydrocarbon group represented by Ri 3 and Ri 4 include an alkyl group, an aryl group, and an arylalkyl group.
- the number of carbon atoms of the alkyl group is preferably 1 to 30, more preferably 1 to 15, and even more preferably 1 to 8.
- the alkyl group may be linear, branched or cyclic, preferably linear or branched.
- the aryl group preferably has 6 to 30 carbon atoms, more preferably 6 to 25 carbon atoms, and even more preferably 6 to 12 carbon atoms.
- the arylalkyl group preferably has 7 to 30 carbon atoms, more preferably 7 to 25 carbon atoms, and even more preferably 7 to 12 carbon atoms.
- the heterocyclic group represented by Ri 3 and Ri 4 may be a monocyclic ring or a condensed ring.
- the heterocyclic group is preferably a single ring or a condensed ring having 2 to 4 condensation numbers.
- the number of heteroatoms constituting the ring of the heterocyclic group is preferably 1 to 3.
- the hetero atom constituting the ring of the heterocyclic group is preferably a nitrogen atom, an oxygen atom or a sulfur atom.
- the number of carbon atoms constituting the ring of the heterocyclic group is preferably 3 to 30, more preferably 3 to 18, and even more preferably 3 to 12.
- the hydrocarbon group and heterocyclic group represented by Ri 3 and Ri 4 may have a substituent or may be unsubstituted.
- substituents include acid groups such as a hydroxy group, a carboxy group, a sulfo group, a phosphoric acid group and a phosphonic acid group; a group in which these acid groups are protected by an acid-degradable group; a polymerizable group and the like. ..
- the acid-degradable group and the polymerizable group in the group in which the acid groups are protected by the acid-degradable group have the same meanings as the above.
- Xi 1 and Xi 2 independently represent O or NRxi, and Rxi represents a hydrogen atom or a substituent.
- Rxi represents a hydrogen atom or a substituent.
- substituent represented by Rxi include an alkyl group, an aryl group, an alkoxy group, an aryloxy group, and an acyl group.
- Rxi is preferably a hydrogen atom. It is preferable that Xi 1 and Xi 2 are O.
- the structural unit represented by the formula (PI-1) may be one kind, but may be two or more kinds. Further, it may contain a structural isomer of a structural unit represented by the formula (PI-1). Further, the polyimide precursor may contain other types of structural units in addition to the structural units represented by the above formula (PI-1).
- polyimide precursor As one embodiment of the polyimide precursor, a polyimide precursor in which 50 mol% or more, more 70 mol% or more, particularly 90 mol% or more of all the structural units is the structural unit represented by the formula (PI-1) is used. Illustrated.
- Polyimide precursors are described in paragraphs 0015 to 0029 of JP2017-186530, paragraphs 0030 to 0036 of JP2019-023728, and paragraphs 0029 to 0035 of JP2019-045865. Polyimide precursors can also be used, the contents of which are incorporated herein by reference.
- the weight average molecular weight (Mw) of the polyimide precursor is preferably 2000 to 500000, more preferably 5000 to 100,000, and even more preferably 10000 to 50000.
- the number average molecular weight (Mn) is preferably 800 to 250,000, more preferably 2000 to 50000, and even more preferably 4000 to 25000.
- the degree of dispersion of the molecular weight of the polyimide precursor is preferably 1.5 to 3.5, more preferably 2 to 3.
- polyimide resin examples include those obtained by cyclizing a precursor of a polyimide resin (polyimide precursor). Examples of the polyimide precursor include those described above. Further, it is also preferable that the polyimide resin has at least one group selected from a carboxy group, a sulfo group, a phosphoric acid group, and a phosphonic acid group on at least one of the main chain and the side chain. According to this aspect, a polyimide resin having excellent solubility in an alkaline developer can be obtained.
- Polybenzoxazole precursor examples of the precursor of the polybenzoxazole resin (hereinafter, also referred to as the polybenzoxazole precursor) include those containing a structural unit represented by the following formula (PBO-1).
- Rb 1 represents a divalent organic group
- Rb 5 represents a tetravalent organic group
- Rb 3 and Rb 4 independently represent a hydrogen atom or a monovalent organic group.
- the divalent organic group represented by Rb 1 of the formula (PBO-1) includes a linear or branched aliphatic hydrocarbon group, a cyclic aliphatic hydrocarbon group, an aromatic hydrocarbon group or a heterocyclic group.
- the tetravalent organic group represented by Rb 5 of formula (PBO-1), is preferably a group containing an aromatic ring, represented by the above-mentioned formula (Ri 5 -1) or formula (Ri 5 -2) Groups are more preferred.
- Examples of the monovalent organic group represented by Rb 3 and Rb 4 of the formula (PBO-1) include a polymerizable group, an acid-degradable group, a hydrocarbon group, and a heterocyclic group. At least one of Rb 3 and Rb 4 is preferably a polymerizable group, and more preferably both are polymerizable groups. Details of the polymerizable group, the acid-degradable group, the hydrocarbon group, and the heterocyclic group are described in the section of the monovalent organic group represented by Ri 3 and Ri 4 of the formula (PI-1). The same applies to the preferred range. When a polybenzoxazole precursor containing a polymerizable group is used, a film having more excellent properties can be easily obtained. Further, when the resin composition of the present invention contains a photopolymerization initiator, it can be a resin composition having excellent pattern forming property in a photolithography method.
- the structural unit represented by the formula (PBO-1) may be one kind, but may be two or more kinds. Further, it may contain a structural isomer of a structural unit represented by the formula (PBO-1). Further, the polybenzoxazole precursor may contain other types of structural units in addition to the structural units represented by the above formula (PBO-1).
- the weight average molecular weight (Mw) of the polybenzoxazole precursor is preferably 2000 to 500,000, more preferably 5000 to 100,000, and even more preferably 10,000 to 50,000.
- the number average molecular weight (Mn) is preferably 800 to 250,000, more preferably 2000 to 50000, and even more preferably 4000 to 25000.
- the degree of dispersion of the molecular weight of the polybenzoxazole precursor is preferably 1.5 to 3.5, more preferably 2 to 3.
- polybenzoxazole resin examples include those obtained by cyclizing a precursor (polybenzoxazole precursor) of the polybenzoxazole resin.
- examples of the polybenzoxazole precursor include those described above.
- the polybenzoxazole resin has at least one group selected from a carboxy group, a sulfo group, a phosphoric acid group, and a phosphonic acid group in at least one of the main chain and the side chain. According to this aspect, a polybenzoxazole resin having excellent solubility in an alkaline developer can be obtained.
- epoxy resin a compound having two or more epoxy groups in one molecule is preferable.
- the number of epoxy groups in one molecule is preferably 2 to 10, more preferably 2 to 5, and particularly preferably 3.
- the epoxy resin is preferably a compound containing a benzene ring, and more preferably a compound having a diaryl structure, a triaryl structure or a tetraaryl structure.
- Re 1 represents a hydrogen atom, an alkyl group, an aryl group or a halogen atom, preferably a hydrogen atom, an alkyl group or a halogen atom, and more preferably a hydrogen atom or an alkyl group. It is preferably an alkyl group, more preferably an alkyl group.
- the alkyl group represented by Re 1 preferably has 1 to 30 carbon atoms, and more preferably 1 to 12 carbon atoms.
- the alkyl group may be linear, branched or cyclic, preferably linear or branched, more preferably linear.
- the alkyl group may have a substituent, but is preferably unsubstituted.
- the aryl group represented by Re 1 preferably has 6 to 30 carbon atoms, more preferably 6 to 25 carbon atoms, and even more preferably 6 to 12 carbon atoms.
- the alkyl group and aryl group represented by Re 1 may have a substituent, but are preferably unsubstituted.
- Examples of the halogen atom represented by Re 1 include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.
- Le 1 represents a single bond or a divalent linking group, and is preferably a divalent linking group.
- the divalent linking group includes an alkylene group, an arylene group, -O-, and -NR'-(R'may have a hydrogen atom, an alkyl group which may have a substituent, or a substituent. (Representing a good aryl group), -SO 2- , -CO-, -O-, -OCO-, -COO-, -S-, -SO- and a group composed of a combination thereof can be mentioned. Is preferable.
- the alkylene group preferably has 1 to 30 carbon atoms, and more preferably 1 to 12 carbon atoms.
- the alkylene group is preferably linear or branched, more preferably branched.
- the weight average molecular weight (Mw) of the epoxy resin is preferably 100 to 10000, more preferably 500 to 5000, and even more preferably 1000 to 3000.
- the epoxy equivalent of the epoxy resin is within the above range, both the heat resistance of the cured film and the mechanical strength can be achieved at a high level.
- the compound represented by the formula (EP-1) include 1- [4- (1-hydroxy-1-methyl-ethyl) -phenyl] etanone and phenols (unsubstituted or having 1 to 12 carbon atoms).
- Phenol resin and epihalohydrin at least one selected from epichlorohydrin and epibromohydrin obtained by reaction with an alkyl group, an alkoxy group having 1 to 12 carbon atoms, and phenols having a halogen atom as a substituent). Examples thereof include a compound obtained as a main component by the reaction with.
- epoxy resins include VG-3101M80 (manufactured by Printec Co., Ltd.), NC-6000, NC-6300 (manufactured by Nippon Kayaku Co., Ltd.), Denacol EX-611 (manufactured by Nagase ChemteX Corporation, etc.). Be done.
- bismaleimide resin examples include compounds represented by the following formula (BM-1).
- Rbm 1 to Rbm 4 independently represent a hydrogen atom or a substituent, and Lbm 1 represents a divalent linking group.
- Examples of the substituent represented by Rbm 1 to Rbm 4 include a halogen atom, an alkyl group, an aryl group, and a heterocyclic group.
- the divalent linking group represented by Lbm1 includes an alkylene group, an arylene group, -O-, and -NR'-(R'has a hydrogen atom, an alkyl group which may have a substituent, or a substituent. (Representing an aryl group which may be), -SO 2- , -CO-, -O-, -OCO-, -COO-, -S-, -SO-, and a group composed of a combination thereof can be mentioned. ..
- bismaleimide resin examples include compounds having the following structures.
- bismaleimide resins include HR3030, 3032, 3070 (above, manufactured by Brintech), BMI-1000, BMI-2000 (above, manufactured by Daiwa Kasei Kogyo Co., Ltd.), Sanfel BM-G (Sanshin Kagaku). (Made by Kogyo Co., Ltd.) and the like.
- silicone resin examples thereof include resins having repeating units containing a siloxane bond.
- the repeating unit containing a siloxane bond may be contained in the main chain or the side chain.
- the silicone resin include epoxy-modified silicone resin, polyester-modified silicone resin, alkyd-modified silicone resin, urethane-modified silicone resin, acrylic-modified silicone resin, and the like, and these can be preferably used. Of these, epoxy-modified silicone resins and polyester-modified silicone resins are preferable because the heat resistance of the cured film can be more easily improved.
- the weight average molecular weight (Mw) of the silicone resin is preferably 500 to 1,000,000, more preferably 1,000 to 100,000, and even more preferably 2000 to 20000.
- the silicone resin includes a reaction product of a compound having a hydroxy group and an epoxy group and a silsesquioxane compound containing an epoxy group and an alkoxy group.
- the silicone resin of this embodiment preferably has an epoxy group.
- the epoxy equivalent of the silicone resin of this embodiment is preferably 150 to 500 g / eq. Further, in the silicone resin of this embodiment, the ratio of the number of moles of the epoxy group derived from the compound having a hydroxy group and the epoxy group to the number of moles of the epoxy group derived from the silsesquioxane compound containing the epoxy group and the alkoxy group.
- the silicone resin of this embodiment has an alkoxy group.
- the amount of the alkoxy group contained in the silicone resin is preferably 150 to 3000 g / eq.
- Examples of the compound having a hydroxy group and an epoxy group include a bisphenol A type epoxy resin, a bisphenol F type epoxy resin, a bisphenol type epoxy resin such as a bisphenol S type epoxy resin, and a hydrogenated bisphenol type in which the benzene ring of the epoxy resin is nuclear-hydrated.
- Examples thereof include epoxy resin, phenol novolac type epoxy resin, cresol novolac type epoxy resin, biphenol type epoxy resin, naphthalene type epoxy resin and the like.
- the average number of hydroxy groups contained in the compound having a hydroxy group and an epoxy group is preferably 0.3 to 5.
- Examples of the silsesquioxane compound containing an epoxy group and an alkoxy group include a compound obtained by hydrolyzing and condensing a compound represented by the following formula (Si-1). Rs 1 Si (ORs 2 ) 3 ... (Si-1) (In the formula, Rs 1 represents a hydrocarbon group having an epoxy group and having 3 to 8 carbon atoms, and Rs 2 represents a hydrogen atom or a hydrocarbon group having 1 to 4 carbon atoms.)
- Specific examples of the compound represented by the formula (Si-1) include glycids such as 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropyltriethoxysilane, and 3-glycidoxypropyltripropoxysilane.
- trialkylalkoxysilanes such as trimethylmethoxysilane, trimethylethoxysilane, triethylmethoxysilane, triethylethoxysilane, triphenylmethoxysilane, and triphenylethoxysilane.
- Alkoxysilanes alkyltrialkoxysilanes such as methyltrimethoxysilane, methyltriethoxysilane, ethyltrimethoxysilane, ethyltriethoxysilane, phenyltrimethoxysilane, phenyltriethoxysilane; tetramethoxysilane, tetraethoxysilane, tetra Tetraalkoxysilanes such as propoxysilane and tetrabutoxysilane, tetraalkoxytitaniums such as tetramethoxytitanium, tetraethoxytitanium, tetrapropoxytitanium and tetrabutoxytitanium; Metal alkoxy groups containing no epoxy group such as zirconium may be further used in combination.
- the total number of the number and the number of moles of the metal alkoxides) is preferably 2.5 to 3.5, and more preferably 2.7 to 3.2.
- An epoxy group and an alkoxy group are contained by hydrolyzing and condensing a compound represented by the formula (Si-1) or a mixture of the compound represented by the formula (Si-1) and the above metal alkoxides.
- a silsesquioxane compound is obtained.
- the compound represented by the formula (Si-1) and the alkoxy group contained in the above metal alkoxides become silanol groups, and alcohol is by-produced.
- the amount of water required for the hydrolysis reaction is (the number of moles of water used for the hydrolysis reaction) / (the total number of moles of each alkoxy group contained in the compound represented by the formula (Si-1) and the metal alkoxides). Is preferably 0.2 to 1, more preferably 0.3 to 0.7.
- a compound having a hydroxy group and an epoxy group and a compound having a hydroxy group and an epoxy group are used.
- the ratio of the compound having a hydroxy group and an epoxy group to the silsesquioxane compound containing an epoxy group and an alkoxy group is preferably 20 to 800 with respect to 100 parts by mass of the compound having a hydroxy group and an epoxy group. , 50-500, more preferably.
- silicone resin examples include compounds having the following structures.
- silicone resin products examples include KR-5230, RK-5234, KR-5235 (above, manufactured by Shin-Etsu Silicone Co., Ltd.), compocerans E103A, E103D, E203 (above, manufactured by Arakawa Chemical Industry Co., Ltd.) and the like.
- the resin composition of the present invention can further contain a resin other than the above-mentioned resin A.
- a resin other than the above-mentioned resin A When other resins are further contained, it is also possible to impart appropriate flexibility to the film obtained by using the resin composition. Therefore, when an inorganic film or the like is formed on the surface of a film obtained by using the resin composition of the present invention, it is also effective that cracks or the like occur in the inorganic film even if the laminate is exposed to a high temperature. It can also be suppressed. Further, when resolving by photolithography using the resin composition of the present invention, the resolvability can be further improved by containing a resin having alkali developability other than the above-mentioned resin A.
- the weight average molecular weight (Mw) of the other resin is preferably 3000 to 2000000.
- the upper limit is more preferably 1,000,000 or less, still more preferably 500,000 or less.
- the lower limit is more preferably 4000 or more, and even more preferably 5000 or more.
- Examples of other resins include (meth) acrylic resin, polyimine resin, polyether resin, polyolefin resin, cyclic olefin resin, polyester resin, styrene resin, etc., and (meth) acrylic resin and polyimine resin are preferable, and (meth) Acrylic resin is more preferable.
- the resin described in JP-A-2017-032685, the resin described in JP-A-2017-075248, and the resin described in JP-A-066240 can also be used.
- the other resin it is preferable to use a resin having an acid group.
- the developability of the resin composition can be further improved.
- the acid group include a phenolic hydroxy group, a carboxy group, a sulfo group, a phosphoric acid group, a phosphonic acid group and the like, and a carboxy group is preferable.
- the resin having an acid group can be used as, for example, an alkali-soluble resin.
- the resin having an acid group preferably contains a repeating unit having an acid group in the side chain, and more preferably contains 1 to 70 mol% of the repeating unit having an acid group in the side chain in all the repeating units of the resin.
- the upper limit of the content of the repeating unit having an acid group in the side chain is preferably 50 mol% or less, and more preferably 40 mol% or less.
- the lower limit of the content of the repeating unit having an acid group in the side chain is preferably 2 mol% or more, and more preferably 5 mol% or more.
- the acid value of the resin having an acid group is preferably 200 mgKOH / g or less, more preferably 150 mgKOH / g or less, further preferably 120 mgKOH / g or less, and particularly preferably 100 mgKOH / g or less.
- the acid value of the resin having an acid group is preferably 5 mgKOH / g or more, more preferably 10 mgKOH / g or more, and even more preferably 20 mgKOH / g or more.
- the resin having an acid group further has an ethylenically unsaturated bond-containing group.
- the ethylenically unsaturated bond-containing group include a vinyl group, an allyl group, a (meth) acryloyl group, and the like, preferably an allyl group and a (meth) acryloyl group, and more preferably a (meth) acryloyl group.
- the resin having an ethylenically unsaturated bond-containing group preferably contains a repeating unit having an ethylenically unsaturated bond-containing group in the side chain, and the repeating unit having an ethylenically unsaturated bond-containing group in the side chain is the whole resin. More preferably, it contains 5-80 mol% in the repeating unit.
- the upper limit of the content of the repeating unit having an ethylenically unsaturated bond-containing group in the side chain is preferably 60 mol% or less, and more preferably 40 mol% or less.
- the lower limit of the content of the repeating unit having an ethylenically unsaturated bond-containing group in the side chain is preferably 10 mol% or more, and more preferably 15 mol% or more.
- the other resin is a monomer component containing a compound represented by the following formula (ED1) and / or a compound represented by the following formula (ED2) (hereinafter, these compounds may be referred to as "ether dimer”). It is also preferable to include the derived repeating unit.
- R 1 and R 2 each independently represent a hydrocarbon group having 1 to 25 carbon atoms which may have a hydrogen atom or a substituent.
- R represents a hydrogen atom or an organic group having 1 to 30 carbon atoms.
- paragraph number 0317 of JP2013-209760A can be referred to, and this content is incorporated in the present specification.
- the other resin contains a repeating unit derived from the compound represented by the following formula (X).
- R 1 represents a hydrogen atom or a methyl group
- R 2 represents an alkylene group having 2 to 10 carbon atoms
- R 3 represents a hydrogen atom or a benzene ring and may contain 1 to 20 carbon atoms.
- n represents an integer from 1 to 15.
- Examples of the resin having an acid group include a resin having the following structure.
- Me represents a methyl group.
- the resin composition of the present invention may also contain a resin as a dispersant.
- the dispersant include an acidic dispersant (acidic resin) and a basic dispersant (basic resin).
- the acidic dispersant (acidic resin) represents a resin in which the amount of acid groups is larger than the amount of basic groups.
- the acidic dispersant (acidic resin) is preferably a resin in which the amount of acid groups accounts for 70 mol% or more when the total amount of the amount of acid groups and the amount of basic groups is 100 mol%, and is substantially an acid. A resin consisting only of groups is more preferable.
- the acid group of the acidic dispersant (acidic resin) is preferably a carboxy group.
- the acid value of the acidic dispersant (acidic resin) is preferably 40 to 105 mgKOH / g, more preferably 50 to 105 mgKOH / g, and even more preferably 60 to 105 mgKOH / g.
- the basic dispersant (basic resin) represents a resin in which the amount of basic groups is larger than the amount of acid groups.
- the basic dispersant (basic resin) is preferably a resin in which the amount of basic groups exceeds 50 mol% when the total amount of the amount of acid groups and the amount of basic groups is 100 mol%.
- the basic group contained in the basic dispersant is preferably an amino group.
- the resin used as the dispersant preferably contains a repeating unit having an acid group.
- the resin used as the dispersant is also preferably a graft resin.
- the graft resin include the resins described in paragraphs 0025 to 0094 of JP2012-255128, the contents of which are incorporated in the present specification.
- the resin used as the dispersant is preferably a polyimine-based dispersant (polyimine resin) containing a nitrogen atom in at least one of the main chain and the side chain.
- the polyimine-based dispersant has a main chain having a partial structure having a functional group of pKa14 or less, a side chain having 40 to 10,000 atoms, and a basic nitrogen atom in at least one of the main chain and the side chain.
- the resin to have is preferable.
- the basic nitrogen atom is not particularly limited as long as it is a nitrogen atom exhibiting basicity. Examples of the polyimine-based dispersant include the resins described in paragraphs 0102 to 0166 of JP2012-255128A, the contents of which are incorporated in the present specification.
- the resin used as the dispersant is also preferably a resin having a structure in which a plurality of polymer chains are bonded to the core portion.
- a resin include dendrimers (including star-shaped polymers).
- specific examples of the dendrimer include polymer compounds C-1 to C-31 described in paragraphs 0196 to 0209 of JP2013-043962.
- the resin described in the above-mentioned resin A section or the resin described in the section of other resins can also be used as the dispersant.
- the dispersant is also available as a commercially available product, and specific examples thereof include DISPERBYK series manufactured by BYK Chemie (for example, DISPERBYK-111, 161 etc.) and Solspace series manufactured by Lubrizol (for example, Solspire 36000). And so on. Further, the pigment dispersant described in paragraphs 0041 to 0130 of JP2014-130338A can also be used, and the contents thereof are incorporated in the present specification.
- the resin described as the dispersant can also be used for purposes other than the dispersant.
- it can also be used as a binder.
- the content of the resin in the total solid content of the resin composition is preferably 10 to 95% by mass.
- the lower limit is more preferably 20% by mass or more, further preferably 30% by mass or more.
- the upper limit is more preferably 90% by mass or less, further preferably 85% by mass or less.
- the content of the above-mentioned resin A in the total solid content of the resin composition is preferably 5 to 95% by mass.
- the lower limit is preferably 10% by mass or more, more preferably 20% by mass or more.
- the upper limit is preferably 90% by mass or less, more preferably 85% by mass or less.
- the resin A is contained in an amount of 20% by mass or more, more preferably 30% by mass or more, and further preferably 40% by mass or more in the component obtained by removing the coloring material from the total solid content of the resin composition.
- the upper limit can be 100% by mass, 90% by mass or less, or 85% by mass or less.
- the total content of the coloring material and the above-mentioned resin A in the total solid content of the resin composition is preferably 25 to 100% by mass.
- the lower limit is more preferably 30% by mass or more, further preferably 40% by mass or more.
- the upper limit is more preferably 90% by mass or less, further preferably 80% by mass or less.
- the ratio of the coloring material to the above-mentioned resin A in the total solid content of the resin composition is preferably 3 to 1500 parts by mass of the resin A with respect to 100 parts by mass of the coloring material.
- the lower limit is preferably 5 parts by mass or more, and more preferably 10 parts by mass or more.
- the upper limit is preferably 1000 parts by mass or less, and more preferably 500 parts by mass or less.
- the content of the above-mentioned other resin is preferably 230 parts by mass or less, more preferably 200 parts by mass or less, and 150 parts by mass with respect to 100 parts by mass of the above-mentioned resin A.
- the lower limit may be 0 parts by mass, 5 parts by mass or more, or 10 parts by mass or more.
- the resin composition does not substantially contain the other resins described above. According to this aspect, it is easy to form a film having more excellent heat resistance.
- the case where the other resin is substantially not contained means that the content of the other resin in the total solid content of the resin composition is 0.1% by mass or less, and is 0.05% by mass or less. It is preferable, and it is more preferable that it is not contained.
- the resin composition of the present invention contains a solvent.
- an organic solvent is preferable.
- the organic solvent is basically not particularly limited as long as it satisfies the solubility of each component and the coatability of the resin composition.
- the organic solvent include ester-based solvents, ketone-based solvents, alcohol-based solvents, amide-based solvents, ether-based solvents, hydrocarbon-based solvents and the like.
- paragraph number 0223 of WO 2015/166779 can be referred to, the contents of which are incorporated herein by reference.
- an ester solvent substituted with a cyclic alkyl group and a ketone solvent substituted with a cyclic alkyl group can also be preferably used.
- organic solvent examples include polyethylene glycol monomethyl ether, dichloromethane, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, ethyl cellosolve acetate, ethyl lactate, diethylene glycol dimethyl ether, butyl acetate, methyl 3-methoxypropionate, 2 -Heptanone, cyclohexanone, cyclohexyl acetate, cyclopentanone, ethyl carbitol acetate, butyl carbitol acetate, propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, 3-methoxy-N, N-dimethylpropanamide, 3-butoxy-N , N-Dimethylpropanamide, gamma butyrolactone, N-methyl-2-pyrrolidone and the like.
- aromatic hydrocarbons (benzene, toluene, xylene, ethylbenzene, etc.) as organic solvents may need to be reduced for environmental reasons (for example, 50 mass ppm (parts) with respect to the total amount of organic solvent. Per million) or less, 10 mass ppm or less, or 1 mass ppm or less).
- an organic solvent having a low metal content it is preferable to use an organic solvent having a low metal content, and the metal content of the organic solvent is preferably, for example, 10 mass ppb (parts per parts) or less. If necessary, an organic solvent at the mass ppt (parts per trillion) level may be used, and such an organic solvent is provided by, for example, Toyo Synthetic Co., Ltd. (The Chemical Daily, November 13, 2015).
- Examples of the method for removing impurities such as metals from the organic solvent include distillation (molecular distillation, thin film distillation, etc.) and filtration using a filter.
- the filter pore diameter of the filter used for filtration is preferably 10 ⁇ m or less, more preferably 5 ⁇ m or less, and even more preferably 3 ⁇ m or less.
- the filter material is preferably polytetrafluoroethylene, polyethylene or nylon.
- the organic solvent may contain isomers (compounds having the same number of atoms but different structures). Further, only one kind of isomer may be contained, or a plurality of kinds may be contained.
- the content of peroxide in the organic solvent is preferably 0.8 mmol / L or less, and more preferably substantially free of peroxide.
- the content of the organic solvent in the resin composition is preferably 10 to 95% by mass, more preferably 20 to 90% by mass, and even more preferably 30 to 90% by mass.
- the resin composition of the present invention can contain a pigment derivative.
- the pigment derivative include compounds having a structure in which a part of the chromophore is replaced with an acid group, a basic group or a phthalimide methyl group.
- the chromogens constituting the pigment derivative include quinoline skeleton, benzoimidazolone skeleton, diketopyrrolopyrrole skeleton, azo skeleton, phthalocyanine skeleton, anthracinone skeleton, quinacridone skeleton, dioxazine skeleton, perinone skeleton, perylene skeleton, thioindigo skeleton, and iso.
- the azo skeleton and the benzoimidazolone skeleton are more preferred.
- the acid group contained in the pigment derivative a sulfo group and a carboxy group are preferable, and a sulfo group is more preferable.
- the basic group contained in the pigment derivative an amino group is preferable, and a tertiary amino group is more preferable.
- a pigment derivative having excellent visible transparency (hereinafter, also referred to as a transparent pigment derivative) can be used.
- the maximum value of the molar extinction coefficient in the wavelength region of 400 ⁇ 700 nm of the transparent pigment derivative (.epsilon.max) is that it is preferable, 1000L ⁇ mol -1 ⁇ cm -1 or less is not more than 3000L ⁇ mol -1 ⁇ cm -1 Is more preferable, and 100 L ⁇ mol -1 ⁇ cm -1 or less is further preferable.
- the lower limit of ⁇ max is, for example, 1 L ⁇ mol -1 ⁇ cm -1 or more, and may be 10 L ⁇ mol -1 ⁇ cm -1 or more.
- pigment derivative examples include Japanese Patent Application Laid-Open No. 56-118462, Japanese Patent Application Laid-Open No. 63-264674, Japanese Patent Application Laid-Open No. 01-2170777, Japanese Patent Application Laid-Open No. 03-09961 Japanese Patent Application Laid-Open No. 03-153780, Japanese Patent Application Laid-Open No. 03-405662, Japanese Patent Application Laid-Open No. 04-285669, Japanese Patent Application Laid-Open No. 06-145546, Japanese Patent Application Laid-Open No. 06-212808, Japanese Patent Application Laid-Open No. 06-240158, Japanese Patent Application Laid-Open No. 10-030063, Japanese Patent Application Laid-Open No.
- the content of the pigment derivative is preferably 1 to 30 parts by mass, more preferably 3 to 20 parts by mass with respect to 100 parts by mass of the pigment. Only one kind of pigment derivative may be used, or two or more kinds may be used in combination.
- the resin composition of the present invention can contain a polymerizable compound.
- the polymerizable compound is preferably, for example, a compound having an ethylenically unsaturated bond-containing group.
- Examples of the ethylenically unsaturated bond-containing group include a vinyl group, a (meth) allyl group, and a (meth) acryloyl group.
- the polymerizable compound used in the present invention is preferably a radically polymerizable compound.
- the polymerizable compound may be in any chemical form such as a monomer, a prepolymer, or an oligomer, but a monomer is preferable.
- the molecular weight of the polymerizable compound is preferably 100 to 3000.
- the upper limit is more preferably 2000 or less, and even more preferably 1500 or less.
- the lower limit is more preferably 150 or more, and even more preferably 250 or more.
- the polymerizable compound is preferably a compound containing 3 or more ethylenically unsaturated bond-containing groups, more preferably a compound containing 3 to 15 ethylenically unsaturated bond-containing groups, and an ethylenically unsaturated bond. It is more preferable that the compound contains 3 to 6 containing groups. Further, the polymerizable compound is preferably a (meth) acrylate compound having 3 to 15 functionalities, and more preferably a (meth) acrylate compound having 3 to 6 functionalities.
- polymerizable compound examples include paragraph numbers 0905 to 0108 of JP2009-288705A, paragraphs 0227 of JP2013-209760A, paragraphs 0254 to 0257 of JP2008-292970, and JP-A.
- Examples include the compounds described in the publication, the contents of which are incorporated herein.
- dipentaerythritol triacrylate (commercially available KAYARAD D-330; manufactured by Nippon Kayaku Co., Ltd.), dipentaerythritol tetraacrylate (commercially available KAYARAD D-320; Nihon Kayaku Co., Ltd.) ), Dipentaerythritol penta (meth) acrylate (commercially available KAYARAD D-310; manufactured by Nippon Kayaku Co., Ltd.), dipentaerythritol hexa (meth) acrylate (commercially available KAYARAD DPHA; Nippon Kayaku) NK ester A-DPH-12E manufactured by Shin-Nakamura Chemical Industry Co., Ltd., and a structure in which these (meth) acryloyl groups are bonded via ethylene glycol and / or propylene glycol residues.
- trimethylolpropane tri (meth) acrylate trimethylolpropane propyleneoxy-modified tri (meth) acrylate, trimethylolpropane ethyleneoxy-modified tri (meth) acrylate, and isocyanurate ethyleneoxy-modified tri (meth) acrylate.
- a trifunctional (meth) acrylate compound such as pentaerythritol trimethylolpropane (meth) acrylate.
- Commercially available trifunctional (meth) acrylate compounds include Aronix M-309, M-310, M-321, M-350, M-360, M-313, M-315, M-306, and M-305.
- M-303, M-452, M-450 manufactured by Toa Synthetic Co., Ltd.
- NK ester A9300, A-GLY-9E, A-GLY-20E, A-TMM-3, A-TMM-3L, A -TMM-3LM-N, A-TMPT, TMPT manufactured by Shin Nakamura Chemical Industry Co., Ltd.
- KAYARAD GPO-303, TMPTA, THE-330, TPA-330, PET-30 (manufactured by Nippon Kayaku Co., Ltd.) And so on.
- a compound having an acid group can also be used.
- the polymerizable compound in the unexposed portion can be easily removed during development, and the generation of development residue can be suppressed.
- the acid group include a carboxy group, a sulfo group, a phosphoric acid group and the like, and a carboxy group is preferable.
- Examples of commercially available products of the polymerizable compound having an acid group include Aronix M-305, M-510, M-520, and Aronix TO-2349 (manufactured by Toagosei Co., Ltd.).
- the preferable acid value of the polymerizable compound having an acid group is 0.1 to 40 mgKOH / g, and more preferably 5 to 30 mgKOH / g.
- the acid value of the polymerizable compound is 0.1 mgKOH / g or more, the solubility in a developing solution is good, and when it is 40 mgKOH / g or less, it is advantageous in production and handling.
- the polymerizable compound is a compound having a caprolactone structure.
- Polymerizable compounds having a caprolactone structure are commercially available from Nippon Kayaku Co., Ltd. as the KAYARAD DPCA series, and examples thereof include DPCA-20, DPCA-30, DPCA-60, and DPCA-120.
- a polymerizable compound having an alkyleneoxy group can also be used.
- a polymerizable compound having an ethyleneoxy group and / or a propyleneoxy group is preferable, a polymerizable compound having an ethyleneoxy group is more preferable, and 3 to 3 having 4 to 20 ethyleneoxy groups.
- a hexafunctional (meth) acrylate compound is more preferred.
- Commercially available products of the polymerizable compound having an alkyleneoxy group include SR-494, which is a tetrafunctional (meth) acrylate having four ethyleneoxy groups manufactured by Sartomer, and a trifunctional (meth) having three isobutyleneoxy groups. Examples thereof include KAYARAD TPA-330, which is an acrylate.
- a polymerizable compound having a fluorene skeleton can also be used.
- examples of commercially available products of the polymerizable compound having a fluorene skeleton include Ogsol EA-0200 and EA-0300 (manufactured by Osaka Gas Chemical Co., Ltd., a (meth) acrylate monomer having a fluorene skeleton).
- the polymerizable compound it is also preferable to use a compound that does not substantially contain an environmentally regulated substance such as toluene.
- an environmentally regulated substance such as toluene.
- commercially available products of such compounds include KAYARAD DPHA LT and KAYARAD DPEA-12 LT (manufactured by Nippon Kayaku Co., Ltd.).
- Examples of the polymerizable compound include urethane acrylates as described in JP-A-48-041708, JP-A-51-0371993, JP-A-02-032293, and JP-A-02-016765.
- Urethane compounds having an ethylene oxide-based skeleton described in Japanese Patent Publication No. 58-049860, Japanese Patent Publication No. 56-017654, Japanese Patent Publication No. 62-039417, and Japanese Patent Publication No. 62-039418 are also suitable.
- a polymerizable compound having an amino structure or a sulfide structure in the molecule described in JP-A-63-277653, JP-A-63-260909, and JP-A-01-105238.
- the polymerizable compounds are UA-7200 (manufactured by Shin Nakamura Chemical Industry Co., Ltd.), DPHA-40H (manufactured by Nippon Kayaku Co., Ltd.), UA-306H, UA-306T, UA-306I, AH-600, Commercially available products such as T-600, AI-600, and LINK-202UA (manufactured by Kyoeisha Chemical Co., Ltd.) can also be used.
- the content of the polymerizable compound in the total solid content of the resin composition is preferably 0.1 to 50% by mass.
- the lower limit is more preferably 0.5% by mass or more, and further preferably 1% by mass or more.
- the upper limit is more preferably 45% by mass or less, and further preferably 40% by mass or less.
- the polymerizable compound may be used alone or in combination of two or more.
- the resin composition of the present invention can contain a photopolymerization initiator.
- the photopolymerization initiator is not particularly limited and may be appropriately selected from known photopolymerization initiators. For example, a compound having photosensitivity to light rays in the ultraviolet region to the visible region is preferable.
- the photopolymerization initiator is preferably a photoradical polymerization initiator.
- the photopolymerization initiator examples include halogenated hydrocarbon derivatives (for example, compounds having a triazine skeleton, compounds having an oxadiazole skeleton, compounds having an imidazole skeleton, etc.), acylphosphine compounds, hexaarylbiimidazole, oxime compounds, and organic compounds.
- halogenated hydrocarbon derivatives for example, compounds having a triazine skeleton, compounds having an oxadiazole skeleton, compounds having an imidazole skeleton, etc.
- acylphosphine compounds examples include peroxides, thio compounds, ketone compounds, aromatic onium salts, ⁇ -hydroxyketone compounds, and ⁇ -aminoketone compounds.
- the photopolymerization initiator is a trihalomethyltriazine compound, a biimidazole compound, a benzyl dimethyl ketal compound, an ⁇ -hydroxyketone compound, an ⁇ -aminoketone compound, an acylphosphine compound, a phosphine oxide compound, a metallocene compound, or an oxime compound.
- Triarylimidazole dimer onium compound, benzothiazole compound, benzophenone compound, acetophenone compound, cyclopentadiene-benzene-iron complex, halomethyloxaziazole compound and 3-aryl substituted coumarin compound, preferably biimidazole compound,
- a compound selected from an oxime compound, an ⁇ -hydroxyketone compound, an ⁇ -aminoketone compound, and an acylphosphine compound is more preferable, and an oxime compound is further preferable.
- the photopolymerization initiator include compounds described in paragraphs 0065 to 0111 of JP-A-2014-130173 and JP-A-6301489, the contents of which are incorporated in the present specification.
- biimidazole compound examples include 2,2-bis (2-chlorophenyl) -4,4', 5,5'-tetraphenylbiimidazole and 2,2'-bis (o-chlorophenyl) -4,4', 5 , 5-Tetrakiss (3,4,5-trimethoxyphenyl) -1,2'-biimidazole, 2,2'-bis (2,3-dichlorophenyl) -4,4', 5,5'-tetraphenyl Examples thereof include biimidazole and 2,2'-bis (o-chlorophenyl) -4,4,5,5'-tetraphenyl-1,2'-biimidazole.
- ⁇ -hydroxyketone compounds include Omnirad 184, Omnirad 1173, Omnirad 2959, Omnirad 127 (all manufactured by IGM Resins BV), Irgacure 184, Irgacure 1173, Irgacare 1173, Irgacure29. (Made by the company) and so on.
- Commercially available ⁇ -aminoketone compounds include Omnirad 907, Omnirad 369, Omnirad 369E, Omnirad 379EG (above, IGM Resins BV), Irgacare 907, Irgacare 369, Irgacure 369, Irgacure 369, Irgacure 369, Irgar (Made) and so on.
- acylphosphine compounds examples include Omnirad 819, Omnirad TPO (above, manufactured by IGM Resins BV), Irgacure 819, Irgacure TPO (above, manufactured by BASF) and the like.
- Examples of the oxime compound include the compounds described in JP-A-2001-233842, the compounds described in JP-A-2000-080068, and the compounds described in JP-A-2006-342166.
- oxime compound examples include 3-benzoyloxyiminobutane-2-one, 3-acetoxyiminobutane-2-one, 3-propionyloxyiminobutane-2-one, 2-acetoxyiminopentane-3-one, 2-acetoxyimino-1-phenylpropane-1-one, 2-benzoyloxyimino-1-phenylpropane-1-one, 3- (4-toluenesulfonyloxy) iminobutane-2-one, and 2-ethoxycarbonyloxy Examples thereof include imino-1-phenylpropane-1-one.
- An oxime compound having a fluorene ring can also be used as the photopolymerization initiator.
- Specific examples of the oxime compound having a fluorene ring include the compounds described in JP-A-2014-137466.
- an oxime compound having a skeleton in which at least one benzene ring of the carbazole ring is a naphthalene ring can also be used.
- Specific examples of such an oxime compound include the compounds described in International Publication No. 2013/083505.
- An oxime compound having a fluorine atom can also be used as the photopolymerization initiator.
- Specific examples of the oxime compound having a fluorine atom are described in the compounds described in JP-A-2010-262028, compounds 24, 36-40 described in JP-A-2014-500852, and JP-A-2013-164471. Compound (C-3) and the like.
- An oxime compound having a nitro group can be used as the photopolymerization initiator.
- the oxime compound having a nitro group is also preferably a dimer.
- Specific examples of the oxime compound having a nitro group include the compounds described in paragraphs 0031 to 0047 of JP2013-114249A and paragraphs 0008-0012 and 0070-0079 of JP2014-137466. Examples thereof include the compound described in paragraphs 0007 to 0025 of Japanese Patent No. 4223071, ADEKA ARKULS NCI-831 (manufactured by ADEKA Corporation).
- An oxime compound having a benzofuran skeleton can also be used as the photopolymerization initiator.
- Specific examples include OE-01 to OE-75 described in International Publication No. 2015/036910.
- the oxime compound is preferably a compound having a maximum absorption wavelength in the wavelength range of 350 to 500 nm, and more preferably a compound having a maximum absorption wavelength in the wavelength range of 360 to 480 nm.
- the molar extinction coefficient of the oxime compound at a wavelength of 365 nm or a wavelength of 405 nm is preferably high, more preferably 1000 to 300,000, further preferably 2000 to 300,000, and more preferably 5000 to 200,000 from the viewpoint of sensitivity. It is particularly preferable to have.
- the molar extinction coefficient of a compound can be measured using a known method. For example, it is preferable to measure at a concentration of 0.01 g / L using ethyl acetate with a spectrophotometer (Cary-5 spectrophotometer manufactured by Varian).
- a bifunctional or trifunctional or higher functional photoradical polymerization initiator may be used as the photopolymerization initiator.
- a photoradical polymerization initiator two or more radicals are generated from one molecule of the photoradical polymerization initiator, so that good sensitivity can be obtained.
- the crystallinity is lowered, the solubility in a solvent or the like is improved, the precipitation is less likely to occur with time, and the stability of the resin composition with time can be improved.
- Specific examples of the bifunctional or trifunctional or higher functional photo-radical polymerization initiators include JP-A-2010-527339, JP-A-2011-524436, International Publication No.
- the content of the photopolymerization initiator in the total solid content of the resin composition is preferably 0.1 to 30% by mass.
- the lower limit is preferably 0.5% by mass or more, and more preferably 1% by mass or more.
- the upper limit is preferably 20% by mass or less, more preferably 15% by mass or less. Only one type of photopolymerization initiator may be used, or two or more types may be used.
- the resin composition of the present invention can contain a silane coupling agent.
- the silane coupling agent means a silane compound having a hydrolyzable group and other functional groups.
- the hydrolyzable group refers to a substituent that is directly linked to a silicon atom and can form a siloxane bond by at least one of a hydrolysis reaction and a condensation reaction.
- the hydrolyzable group include a halogen atom, an alkoxy group, an acyloxy group and the like, and an alkoxy group is preferable. That is, the silane coupling agent is preferably a compound having an alkoxysilyl group.
- Examples of the functional group other than the hydrolyzable group include a vinyl group, a (meth) allyl group, a (meth) acryloyl group, a mercapto group, an epoxy group, an oxetanyl group, an amino group, a ureido group, a sulfide group and an isocyanate group.
- a phenyl group and the like preferably an amino group, a (meth) acryloyl group and an epoxy group.
- Specific examples of the silane coupling agent include the compounds described in paragraphs 0018 to 0036 of JP2009-288703A and the compounds described in paragraphs 0056 to 0066 of JP2009-242604A. The contents of are incorporated herein by reference.
- the content of the silane coupling agent in the total solid content of the resin composition is preferably 0.1 to 5% by mass.
- the upper limit is preferably 3% by mass or less, and more preferably 2% by mass or less.
- the lower limit is preferably 0.5% by mass or more, and more preferably 1% by mass or more.
- the silane coupling agent may be only one kind or two or more kinds.
- the resin composition of the present invention may further contain a curing accelerator for the purpose of accelerating the reaction of the resin or the polymerizable compound and lowering the curing temperature.
- the curing accelerator is a methylol-based compound (for example, a compound exemplified as a cross-linking agent in paragraph No. 0246 of JP-A-2015-034963), amines, a phosphonium salt, an amidin salt, an amide compound (for example, JP-A-2015).
- cyanate compound for example, Japanese Patent Application Laid-Open No. 2012-150180.
- alkoxysilane compound for example, alkoxysilane compound having an epoxy group described in JP-A-2011-253504
- onium salt compound eg, JP-A-2015-034963
- a compound exemplified as an acid generator in 0216, a compound described in JP-A-2009-180949) and the like can also be used.
- the content of the curing accelerator is preferably 0.3 to 8.9% by mass, preferably 0.8 to 6.4% by mass, based on the total solid content of the resin composition. More preferably by mass.
- the resin composition of the present invention can contain a polymerization inhibitor.
- the polymerization inhibitor include hydroquinone, p-methoxyphenol, di-tert-butyl-p-cresol, pyrogallol, tert-butylcatechol, benzoquinone, quaternary-4'-thiobis (3-methyl-6-tert-butylphenol), and the like. Examples thereof include 2,2'-methylenebis (4-methyl-6-t-butylphenol) and N-nitrosophenylhydroxyamine salts (ammonium salt, primary cerium salt, etc.). Of these, p-methoxyphenol is preferable.
- the content of the polymerization inhibitor in the total solid content of the resin composition is preferably 0.0001 to 5% by mass.
- the resin composition of the present invention can contain a surfactant.
- a surfactant various surfactants such as a fluorine-based surfactant, a nonionic surfactant, a cationic surfactant, an anionic surfactant, and a silicon-based surfactant can be used.
- the surfactant the surfactant described in paragraph Nos. 0238 to 0245 of International Publication No. 2015/166779 is mentioned, and the content thereof is incorporated in the present specification.
- the surfactant is preferably a fluorine-based surfactant.
- a fluorine-based surfactant in the resin composition, the liquid characteristics (particularly, fluidity) can be further improved, and the liquid saving property can be further improved. It is also possible to form a film having a small thickness unevenness.
- the fluorine content in the fluorine-based surfactant is preferably 3 to 40% by mass, more preferably 5 to 30% by mass, and particularly preferably 7 to 25% by mass.
- a fluorine-based surfactant having a fluorine content within this range is effective in terms of uniformity of coating film thickness and liquid saving property, and has good solubility in a resin composition.
- fluorine-based surfactant examples include the surfactants described in paragraphs 0060 to 0064 of Japanese Patent Application Laid-Open No. 2014-041318 (paragraphs 0060 to 0064 of the corresponding International Publication No. 2014/017669) and the like, JP-A-2011- The surfactants described in paragraphs 0117 to 0132 of the Publication No. 132503 are mentioned and their contents are incorporated herein by reference.
- fluorine-based surfactants include, for example, Megafuck F171, F172, F173, F176, F177, F141, F142, F143, F144, R30, F437, F475, F479, F482, F554, F780, EXP, MFS.
- the fluorine-based surfactant it is also preferable to use a polymer of a fluorine atom-containing vinyl ether compound having a fluorinated alkyl group or a fluorinated alkylene ether group and a hydrophilic vinyl ether compound.
- a fluorine-based surfactant the description in JP-A-2016-216602 can be referred to, and the content thereof is incorporated in the present specification.
- the fluorine-based surfactant a block polymer can also be used.
- the fluorine-based surfactant has a repeating unit derived from a (meth) acrylate compound having a fluorine atom and 2 or more (preferably 5 or more) alkyleneoxy groups (preferably ethyleneoxy groups and propyleneoxy groups) (meth).
- a fluorine-containing polymer compound containing a repeating unit derived from an acrylate compound can also be preferably used.
- the following compounds are also exemplified as the fluorine-based surfactant used in the present invention.
- the weight average molecular weight of the above compounds is preferably 3000-50000, for example 14000.
- % indicating the ratio of the repeating unit is mol%.
- a fluorine-based surfactant a fluorine-containing polymer having an ethylenically unsaturated bond-containing group in the side chain can also be used.
- the compounds described in paragraphs 0050 to 0090 and paragraph numbers 0289 to 0295 of JP2010-164965 for example, Megafuck RS-101, RS-102, RS-718K manufactured by DIC Corporation. , RS-72-K and the like.
- the fluorine-based surfactant the compounds described in paragraphs 0015 to 0158 of JP2015-117327A can also be used.
- the content of the surfactant in the total solid content of the resin composition is preferably 0.001% by mass to 5.0% by mass, more preferably 0.005 to 3.0% by mass.
- the surfactant may be only one kind or two or more kinds. In the case of two or more types, the total amount is preferably in the above range.
- the resin composition of the present invention can contain an ultraviolet absorber.
- an ultraviolet absorber a conjugated diene compound, an aminodiene compound, a salicylate compound, a benzophenone compound, a benzotriazole compound, an acrylonitrile compound, a hydroxyphenyltriazine compound, an indol compound, a triazine compound and the like can be used.
- paragraph numbers 0052 to 0072 of JP2012-208374A paragraph numbers 0317 to 0334 of JP2013-066814, and paragraphs 0061 to 0080 of JP2016-162946. It can be taken into consideration and these contents are incorporated herein by reference.
- Examples of commercially available ultraviolet absorbers include UV-503 (manufactured by Daito Kagaku Co., Ltd.).
- Examples of the benzotriazole compound include the MYUA series made by Miyoshi Oil & Fat Co., Ltd. (The Chemical Daily, February 1, 2016).
- the ultraviolet absorber the compounds described in paragraphs 0049 to 0059 of Japanese Patent No. 6268967 can also be used.
- the content of the ultraviolet absorber in the total solid content of the resin composition is preferably 0.01 to 10% by mass, more preferably 0.01 to 5% by mass. Only one kind of ultraviolet absorber may be used, or two or more kinds may be used. When two or more types are used, the total amount is preferably in the above range.
- the resin composition of the present invention can contain an antioxidant.
- the antioxidant include phenol compounds, phosphite ester compounds, thioether compounds and the like.
- the phenol compound any phenol compound known as a phenolic antioxidant can be used.
- Preferred phenolic compounds include hindered phenolic compounds.
- a compound having a substituent at a site (ortho position) adjacent to the phenolic hydroxy group is preferable.
- a substituted or unsubstituted alkyl group having 1 to 22 carbon atoms is preferable.
- the antioxidant a compound having a phenol group and a phosphite ester group in the same molecule is also preferable.
- a phosphorus-based antioxidant can also be preferably used.
- the content of the antioxidant in the total solid content of the resin composition is preferably 0.01 to 20% by mass, more preferably 0.3 to 15% by mass. Only one type of antioxidant may be used, or two or more types may be used. When two or more types are used, the total amount is preferably in the above range.
- the resin composition of the present invention if necessary, sensitizers, fillers, thermosetting accelerators, plasticizers and other auxiliaries (eg, conductive particles, fillers, defoamers, flame retardants, leveling). Agents, peeling accelerators, fragrances, surface tension modifiers, chain transfer agents, etc.) may be included. By appropriately containing these components, properties such as film physical properties can be adjusted. These components are described in, for example, paragraph No. 0183 and subsequent paragraphs of JP2012-003225A (paragraph number 0237 of the corresponding US Patent Application Publication No. 2013/0034812), paragraphs of JP-A-2008-250074. The descriptions of Nos. 0101 to 0104, 0107 to 0109, etc.
- the resin composition may contain a latent antioxidant, if necessary.
- the latent antioxidant is a compound in which the site that functions as an antioxidant is protected by a protecting group, and is heated at 100 to 250 ° C. or at 80 to 200 ° C. in the presence of an acid / base catalyst. This includes compounds in which the protecting group is eliminated and functions as an antioxidant.
- Examples of the latent antioxidant include compounds described in International Publication No. 2014/021023, International Publication No. 2017/030005, and JP-A-2017-008219.
- Examples of commercially available products include ADEKA ARKULS GPA-5001 (manufactured by ADEKA Corporation) and the like. Further, as described in JP-A-2018-155881, C.I. I. Pigment Yellow 129 may be added for the purpose of improving weather resistance.
- the resin composition of the present invention may contain a metal oxide in order to adjust the refractive index of the obtained film.
- the metal oxide include TiO 2 , ZrO 2 , Al 2 O 3 , SiO 2 and the like.
- the primary particle size of the metal oxide is preferably 1 to 100 nm, more preferably 3 to 70 nm, and even more preferably 5 to 50 nm.
- the metal oxide may have a core-shell structure. Further, in this case, the core portion may be hollow.
- the resin composition of the present invention may contain a light resistance improving agent.
- the light resistance improving agent include the compounds described in paragraphs 0036 to 0037 of JP-A-2017-198787, the compounds described in paragraphs 0029 to 0034 of JP-A-2017-146350, and JP-A-2017-129774.
- the resin composition of the present invention preferably has a free metal content of 100 ppm or less, more preferably 50 ppm or less, and further preferably 10 ppm or less, which is not bonded or coordinated with a pigment or the like. , It is particularly preferable that it is not substantially contained.
- stabilization of pigment dispersibility agglomeration suppression
- improvement of spectral characteristics due to improvement of dispersibility agglomeration suppression
- stabilization of curable components suppression of conductivity fluctuation due to elution of metal atoms / metal ions
- Effects such as improvement of characteristics can be expected.
- the types of free metals include Na, K, Ca, Sc, Ti, Mn, Cu, Zn, Fe, Cr, Co, Mg, Al, Sn, Zr, Ga, Ge, Ag, Au, Pt, and the like.
- examples thereof include Cs, Ni, Cd, Pb and Bi.
- the resin composition of the present invention preferably has a content of free halogen that is not bonded or coordinated with a pigment or the like of 100 ppm or less, more preferably 50 ppm or less, and more preferably 10 ppm or less. More preferably, it is particularly preferably not contained substantially.
- halogens include F, Cl, Br, I and their anions.
- the method for reducing free metals and halogens in the resin composition include methods such as washing with ion-exchanged water, filtration, ultrafiltration, and purification with an ion-exchange resin.
- the resin composition of the present invention does not substantially contain a terephthalic acid ester.
- substantially free means that the content of the terephthalic acid ester is 1000 mass ppb or less in the total amount of the resin composition, and more preferably 100 mass ppb or less. It is particularly preferred to be zero.
- the storage container for the resin composition of the present invention is not particularly limited, and a known storage container can be used.
- a storage container a multi-layer bottle in which the inner wall of the container is composed of 6 types and 6 layers of resin and a bottle in which 6 types of resin are composed of 7 layers are used for the purpose of suppressing impurities from being mixed into raw materials and resin compositions. It is also preferable to use. Examples of such a container include the container described in Japanese Patent Application Laid-Open No. 2015-123351.
- the inner wall of the container is preferably made of glass or stainless steel for the purpose of preventing metal elution from the inner wall of the container, improving the storage stability of the resin composition, and suppressing deterioration of the components.
- the resin composition of the present invention can be prepared by mixing the above-mentioned components.
- all the components may be simultaneously dissolved and / or dispersed in an organic solvent to prepare the resin composition, or if necessary, two or more solutions or dispersions of each component may be appropriately prepared. However, these may be mixed at the time of use (at the time of application) to prepare a resin composition.
- the mechanical force used for dispersing the pigment includes compression, squeezing, impact, shearing, cavitation and the like.
- Specific examples of these processes include bead mills, sand mills, roll mills, ball mills, paint shakers, microfluidizers, high speed impellers, sand grinders, flow jet mixers, high pressure wet atomization, ultrasonic dispersion and the like.
- the process and disperser for dispersing pigments are "Dispersion Technology Complete Works, Published by Information Organization Co., Ltd., July 15, 2005" and "Dispersion technology centered on suspension (solid / liquid dispersion system) and industrial. Practical application The process and disperser described in Paragraph No. 0022 of Japanese Patent Application Laid-Open No.
- the particles may be miniaturized in the salt milling step.
- the materials, equipment, processing conditions, etc. used in the salt milling step for example, the descriptions in JP-A-2015-194521 and JP-A-2012-046629 can be referred to.
- any filter that has been conventionally used for filtration or the like can be used without particular limitation.
- fluororesin such as polytetrafluoroethylene (PTFE), polyamide resin such as nylon (for example, nylon-6, nylon-6,6), and polyolefin resin such as polyethylene and polypropylene (PP) (high density, ultrahigh molecular weight).
- PTFE polytetrafluoroethylene
- nylon nylon-6, nylon-6,6
- PP polypropylene
- a filter using a material such as (including a polyolefin resin) can be mentioned.
- polypropylene including high-density polypropylene
- nylon are preferable.
- the pore size of the filter is preferably 0.01 to 7.0 ⁇ m, more preferably 0.01 to 3.0 ⁇ m, and even more preferably 0.05 to 0.5 ⁇ m. If the pore size of the filter is within the above range, fine foreign matter can be removed more reliably.
- the nominal value of the filter manufacturer can be referred to.
- various filters provided by Nippon Pole Co., Ltd. (DFA4201NIEY, etc.), Advantech Toyo Co., Ltd., Nippon Entegris Co., Ltd. (formerly Nippon Microlith Co., Ltd.), KITZ Microfilter Co., Ltd., etc. can be used.
- fibrous filter medium examples include polypropylene fiber, nylon fiber, glass fiber and the like.
- examples of commercially available products include SBP type series (SBP008, etc.), TPR type series (TPR002, TPR005, etc.), and SHPX type series (SHPX003, etc.) manufactured by Loki Techno Co., Ltd.
- filters for example, a first filter and a second filter
- the filtration with each filter may be performed only once or twice or more.
- filters having different pore diameters may be combined within the above-mentioned range.
- the filtration with the first filter may be performed only on the dispersion liquid, and after mixing the other components, the filtration with the second filter may be performed.
- the film of the present invention is a film obtained from the above-mentioned resin composition of the present invention.
- the film of the present invention can be used for a color filter, a near-infrared transmission filter, a near-infrared cut filter, a black matrix, a light-shielding film, and the like.
- it can be preferably used as a coloring layer of a color filter.
- the film thickness of the film of the present invention can be appropriately adjusted according to the purpose.
- the film thickness is preferably 20 ⁇ m or less, more preferably 10 ⁇ m or less, and even more preferably 5 ⁇ m or less.
- the lower limit of the film thickness is preferably 0.1 ⁇ m or more, more preferably 0.2 ⁇ m or more, and further preferably 0.3 ⁇ m or more.
- the thickness of the film of the present invention after heat treatment at 300 ° C. for 5 hours in a nitrogen atmosphere is preferably 70% or more, preferably 80% or more of the thickness of the film before heat treatment. More preferably, it is more preferably 90% or more.
- the thickness of the film after being heat-treated at 350 ° C. for 5 hours in a nitrogen atmosphere is preferably 70% or more, preferably 80% or more of the thickness of the film before the heat treatment. Is more preferable, and 90% or more is further preferable.
- the thickness of the film after being heat-treated at 400 ° C. for 5 hours in a nitrogen atmosphere is preferably 70% or more, preferably 80% or more of the thickness of the film before the heat treatment. Is more preferable, and 90% or more is further preferable.
- the film of the present invention has a maximum transmittance of 70% or more (preferably 75% or more, more preferably 80% or more, still more preferably 85% or more) and a minimum value of 30% or less (preferably 75% or more, more preferably 85% or more) at a wavelength of 400 to 1100 nm. It is preferably 25% or less, more preferably 20% or less, still more preferably 15% or less).
- the film of the present invention can be produced through the steps of applying the above-mentioned resin composition of the present invention onto a support.
- the film manufacturing method of the present invention preferably further includes a step of forming a pattern (pixel).
- Examples of the pattern (pixel) forming method include a photolithography method and a dry etching method, and the photolithography method is preferable.
- Pattern formation by the photolithography method includes a step of forming a resin composition layer on a support using the resin composition of the present invention, a step of exposing the resin composition layer in a pattern, and a step of exposing the resin composition layer in a pattern. It is preferable to include a step of developing and removing the exposed portion to form a pattern (pixel). If necessary, a step of baking the resin composition layer (pre-baking step) and a step of baking the developed pattern (pixels) (post-baking step) may be provided.
- the resin composition layer of the present invention is used to form the resin composition layer on the support.
- the support is not particularly limited and may be appropriately selected depending on the intended use.
- a glass substrate, a silicon substrate, and the like can be mentioned, and a silicon substrate is preferable.
- a charge coupling element (CCD), a complementary metal oxide semiconductor (CMOS), a transparent conductive film, or the like may be formed on the silicon substrate.
- CMOS complementary metal oxide semiconductor
- a black matrix that separates each pixel may be formed on the silicon substrate.
- the silicon substrate may be provided with an undercoat layer for improving the adhesion with the upper layer, preventing the diffusion of substances, or flattening the surface of the substrate.
- a known method can be used as a method for applying the resin composition.
- a dropping method drop casting
- a slit coating method for example, a spray method; a roll coating method; a rotary coating method (spin coating); a casting coating method; a slit and spin method; a pre-wet method (for example, JP-A-2009-145395).
- Methods described in the publication Inkjet (for example, on-demand method, piezo method, thermal method), ejection system printing such as nozzle jet, flexographic printing, screen printing, gravure printing, reverse offset printing, metal mask printing, etc.
- Various printing methods; transfer method using a mold or the like; nanoimprint method and the like can be mentioned.
- the method of application to an inkjet is not particularly limited, and for example, the method shown in "Expandable / Usable Inkjet-Infinite Possibilities Seen in Patents-, Published in February 2005, Sumi Betechno Research" (especially from page 115). (Page 133), and the methods described in JP-A-2003-262716, JP-A-2003-185831, JP-A-2003-261827, JP-A-2012-126830, JP-A-2006-169325, and the like. Can be mentioned. Further, as a method for applying the resin composition, the methods described in International Publication No. 2017/030174 and International Publication No. 2017/018419 can also be used, and these contents are incorporated in the present specification.
- the resin composition layer formed on the support may be dried (prebaked).
- prebaking may not be performed.
- the prebaking temperature is preferably 150 ° C. or lower, more preferably 120 ° C. or lower, and even more preferably 110 ° C. or lower.
- the lower limit can be, for example, 50 ° C. or higher, or 80 ° C. or higher.
- the prebaking time is preferably 10 to 300 seconds, more preferably 40 to 250 seconds, and even more preferably 80 to 220 seconds. Pre-baking can be performed on a hot plate, an oven, or the like.
- the resin composition layer is exposed in a pattern (exposure step).
- the resin composition layer can be exposed in a pattern by exposing the resin composition layer through a mask having a predetermined mask pattern using a stepper exposure machine, a scanner exposure machine, or the like. As a result, the exposed portion can be cured.
- Examples of radiation (light) that can be used for exposure include g-line and i-line. Further, light having a wavelength of 300 nm or less (preferably light having a wavelength of 180 to 300 nm) can also be used. Examples of the light having a wavelength of 300 nm or less include KrF line (wavelength 248 nm), ArF line (wavelength 193 nm), and KrF line (wavelength 248 nm) is preferable. Further, a long wave light source having a diameter of 300 nm or more can also be used.
- pulse exposure is an exposure method of a method in which light irradiation and pause are repeated in a short cycle (for example, millisecond level or less).
- the pulse width is preferably 100 nanoseconds (ns) or less, more preferably 50 nanoseconds or less, and even more preferably 30 nanoseconds or less.
- the lower limit of the pulse width is not particularly limited, but may be 1 femtosecond (fs) or more, and may be 10 femtoseconds or more.
- the frequency is preferably 1 kHz or higher, more preferably 2 kHz or higher, and even more preferably 4 kHz or higher.
- the upper limit of the frequency is preferably 50 kHz or less, more preferably 20 kHz or less, and further preferably 10 kHz or less.
- Maximum instantaneous intensity is preferably at 50000000W / m 2 or more, more preferably 100000000W / m 2 or more, more preferably 200000000W / m 2 or more.
- the upper limit of the maximum instantaneous intensity is preferably at 1000000000W / m 2 or less, more preferably 800000000W / m 2 or less, further preferably 500000000W / m 2 or less.
- the pulse width is the time during which light is irradiated in the pulse period.
- the frequency is the number of pulse cycles per second.
- the maximum instantaneous illuminance is the average illuminance within the time during which the light is irradiated in the pulse period.
- the pulse cycle is a cycle in which light irradiation and pause in pulse exposure are one cycle.
- Irradiation dose for example, preferably 0.03 ⁇ 2.5J / cm 2, more preferably 0.05 ⁇ 1.0J / cm 2.
- the oxygen concentration at the time of exposure can be appropriately selected, and in addition to the operation in the atmosphere, for example, in a low oxygen atmosphere having an oxygen concentration of 19% by volume or less (for example, 15% by volume, 5% by volume, or substantially). It may be exposed in an oxygen-free environment) or in a high oxygen atmosphere (for example, 22% by volume, 30% by volume, or 50% by volume) in which the oxygen concentration exceeds 21% by volume.
- the exposure illuminance can be set as appropriate, and is usually selected from the range of 1000 W / m 2 to 100,000 W / m 2 (for example, 5000 W / m 2 , 15,000 W / m 2 , or 35,000 W / m 2 ). Can be done. Oxygen concentration and exposure illuminance may appropriately combined conditions, for example, illuminance 10000 W / m 2 at an oxygen concentration of 10 vol%, oxygen concentration of 35 vol% can be such illuminance 20000W / m 2.
- the unexposed portion of the resin composition layer is developed and removed to form a pattern (pixel).
- the unexposed portion of the resin composition layer can be developed and removed using a developing solution.
- the resin composition layer of the unexposed portion in the exposure step is eluted in the developing solution, and only the photocured portion remains.
- the temperature of the developing solution is preferably, for example, 20 to 30 ° C.
- the development time is preferably 20 to 180 seconds. Further, in order to improve the residue removability, the steps of shaking off the developing solution every 60 seconds and further supplying a new developing solution may be repeated several times.
- Examples of the developing solution include organic solvents and alkaline developing solutions, and alkaline developing solutions are preferably used.
- the alkaline developer an alkaline aqueous solution (alkaline developer) obtained by diluting an alkaline agent with pure water is preferable.
- the alkaline agent include ammonia, ethylamine, diethylamine, dimethylethanolamine, diglycolamine, diethanolamine, hydroxyamine, ethylenediamine, tetramethylammonium hydroxide, tetraethylammonium hydroxide, tetrapropylammonium hydroxide, and tetrabutylammonium hydroxide.
- Ethyltrimethylammonium hydroxide Ethyltrimethylammonium hydroxide, benzyltrimethylammonium hydroxide, dimethylbis (2-hydroxyethyl) ammonium hydroxide, choline, pyrrole, piperidine, 1,8-diazabicyclo [5.4.0] -7-undecene and other organic substances.
- alkaline compounds examples include alkaline compounds and inorganic alkaline compounds such as sodium hydroxide, potassium hydroxide, sodium carbonate, sodium hydrogencarbonate, sodium silicate and sodium metasilicate.
- the alkaline agent a compound having a large molecular weight is preferable in terms of environment and safety.
- the concentration of the alkaline agent in the alkaline aqueous solution is preferably 0.001 to 10% by mass, more preferably 0.01 to 1% by mass.
- the developer may further contain a surfactant.
- the surfactant include the above-mentioned surfactants, and nonionic surfactants are preferable.
- the developer may be once produced as a concentrated solution and diluted to a concentration required for use.
- the dilution ratio is not particularly limited, but can be set in the range of, for example, 1.5 to 100 times. It is also preferable to wash (rinse) with pure water after development.
- the rinsing is performed by supplying the rinsing liquid to the developed resin composition layer while rotating the support on which the developed resin composition layer is formed. It is also preferable to move the nozzle for discharging the rinse liquid from the central portion of the support to the peripheral edge of the support. At this time, when moving the nozzle from the central portion of the support to the peripheral portion, the nozzle may be moved while gradually reducing the moving speed. By rinsing in this way, in-plane variation of rinsing can be suppressed. Further, the same effect can be obtained by gradually reducing the rotation speed of the support while moving the nozzle from the central portion to the peripheral portion of the support.
- Additional exposure treatment and post-baking are post-development curing treatments to complete the curing.
- the heating temperature in the post-bake is, for example, preferably 100 to 240 ° C, more preferably 200 to 240 ° C.
- Post-baking can be performed on the developed film in a continuous or batch manner by using a heating means such as a hot plate, a convection oven (hot air circulation dryer), or a high frequency heater so as to meet the above conditions. ..
- the light used for the exposure is preferably light having a wavelength of 400 nm or less. Further, the additional exposure process may be performed by the method described in Korean Patent Publication No. 10-2017-0122130.
- Pattern formation by the dry etching method includes a step of forming a resin composition layer on a support using the resin composition of the present invention and curing the entire resin composition layer to form a cured product layer.
- the color filter of the present invention has the above-mentioned film of the present invention. More preferably, it has the film of the present invention as a pixel of a color filter.
- the color filter of the present invention can be used for a solid-state image sensor such as a CCD (charge-coupled device) or CMOS (complementary metal oxide semiconductor), an image display device, or the like.
- the film thickness of the film of the present invention can be appropriately adjusted according to the purpose.
- the film thickness is preferably 20 ⁇ m or less, more preferably 10 ⁇ m or less, and even more preferably 5 ⁇ m or less.
- the lower limit of the film thickness is preferably 0.1 ⁇ m or more, more preferably 0.2 ⁇ m or more, and further preferably 0.3 ⁇ m or more.
- the color filter of the present invention preferably has a pixel width of 0.5 to 20.0 ⁇ m.
- the lower limit is preferably 1.0 ⁇ m or more, and more preferably 2.0 ⁇ m or more.
- the upper limit is preferably 15.0 ⁇ m or less, and more preferably 10.0 ⁇ m or less.
- the Young's modulus of the pixel is preferably 0.5 to 20 GPa, more preferably 2.5 to 15 GPa.
- each pixel included in the color filter of the present invention has high flatness.
- the surface roughness Ra of the pixel is preferably 100 nm or less, more preferably 40 nm or less, and further preferably 15 nm or less.
- the lower limit is not specified, but it is preferably 0.1 nm or more, for example.
- the surface roughness of the pixels can be measured using, for example, AFM (Atomic Force Microscope) Measurement 3100 manufactured by Veeco.
- the contact angle of water on the pixel can be appropriately set to a preferable value, but is typically in the range of 50 to 110 °.
- the contact angle can be measured using, for example, a contact angle meter CV-DT ⁇ A type (manufactured by Kyowa Interface Science Co., Ltd.). Further, it is preferable that the volume resistance value of the pixel is high. Specifically, it is preferred that the volume resistivity value of the pixel is 10 9 ⁇ ⁇ cm or more, and more preferably 10 11 ⁇ ⁇ cm or more. The upper limit is not specified, but it is preferably 10 14 ⁇ ⁇ cm or less, for example.
- the volume resistance value of the pixel can be measured using an ultra-high resistance meter 5410 (manufactured by Advantest).
- the color filter of the present invention may be provided with a protective layer on the surface of the film of the present invention.
- a protective layer By providing the protective layer, various functions such as oxygen blocking, low reflection, hydrophobicization, and shielding of light of a specific wavelength (ultraviolet rays, near infrared rays, etc.) can be imparted.
- the thickness of the protective layer is preferably 0.01 to 10 ⁇ m, more preferably 0.1 to 5 ⁇ m.
- Examples of the method for forming the protective layer include a method of applying a resin composition for forming a protective layer dissolved in an organic solvent to form the protective layer, a chemical vapor deposition method, a method of attaching the molded resin with an adhesive, and the like.
- the components constituting the protective layer include (meth) acrylic resin, en-thiol resin, polycarbonate resin, polyether resin, polyarylate resin, polysulfone resin, polyethersulfone resin, polyphenylene resin, polyarylene ether phosphine oxide resin, and polyimide.
- Resin polyamideimide resin, polyolefin resin, cyclic olefin resin, polyester resin, styrene resin, polyol resin, polyvinylidene chloride resin, melamine resin, urethane resin, aramid resin, polyamide resin, alkyd resin, epoxy resin, modified silicone resin, fluorine Examples thereof include resins, polycarbonate resins, polyacrylonitrile resins, cellulose resins, Si, C, W, Al 2 O 3 , Mo, SiO 2 , and Si 2 N 4, and two or more of these components may be contained.
- the protective layer preferably contains a polyol resin, SiO 2 , and Si 2 N 4 .
- the protective layer preferably contains a (meth) acrylic resin and a fluororesin.
- the protective layer forming resin composition When the protective layer forming resin composition is applied to form the protective layer, known methods such as a spin coating method, a casting method, a screen printing method, and an inkjet method are used as the coating method of the protective layer forming resin composition. Can be used.
- a known organic solvent for example, propylene glycol 1-monomethyl ether 2-acetate, cyclopentanone, ethyl lactate, etc.
- the protective layer is formed by a chemical vapor deposition method
- the chemical vapor deposition method is a known chemical vapor deposition method (thermochemical vapor deposition method, plasma chemical vapor deposition method, photochemical vapor deposition method). Can be used.
- the protective layer may be an additive such as organic / inorganic fine particles, an absorber of light of a specific wavelength (for example, ultraviolet rays, near infrared rays, etc.), a refractive index adjuster, an antioxidant, an adhesive, a surfactant, etc., if necessary. May be contained.
- organic / inorganic fine particles include polymer fine particles (for example, silicone resin fine particles, polystyrene fine particles, melamine resin fine particles), titanium oxide, zinc oxide, zirconium oxide, indium oxide, aluminum oxide, titanium nitride, and titanium oxynitride. , Magnesium fluoride, hollow silica, silica, calcium carbonate, barium sulfate and the like.
- a known absorbent can be used as the light absorber of a specific wavelength.
- the content of these additives can be adjusted as appropriate, but is preferably 0.1 to 70% by mass, more preferably 1 to 60% by mass, based on the total mass of the protective layer
- the protective layer described in paragraphs 0073 to 0092 of JP-A-2017-151176 can also be used.
- the color filter may have a structure in which each colored pixel is embedded in a space partitioned by a partition wall, for example, in a grid pattern.
- the solid-state image sensor of the present invention has the above-mentioned film of the present invention.
- the configuration of the solid-state image sensor of the present invention is not particularly limited as long as it includes the film of the present invention and functions as a solid-state image sensor, and examples thereof include the following configurations.
- a solid-state image sensor CCD (charge-coupled device) image sensor, CMOS (complementary metal oxide semiconductor) image sensor, etc.
- a transfer electrode made of polysilicon or the like.
- the color filter may have a structure in which each colored pixel is embedded in a space partitioned by a partition wall, for example, in a grid pattern.
- the partition wall preferably has a lower refractive index than each colored pixel. Examples of an imaging apparatus having such a structure are described in JP2012-227478A, Japanese Patent Application Laid-Open No. 2014-179757, International Publication No. 2018/043654, and US Patent Application Publication No.
- the image pickup device provided with the solid-state image pickup device of the present invention can be used not only for digital cameras and electronic devices having an image pickup function (mobile phones and the like), but also for in-vehicle cameras and surveillance cameras.
- the image display device of the present invention has the above-mentioned film of the present invention.
- the image display device include a liquid crystal display device and an organic electroluminescence display device.
- the liquid crystal display device is described in, for example, “Next Generation Liquid Crystal Display Technology (edited by Tatsuo Uchida, Kogyo Chosakai Co., Ltd., published in 1994)”.
- the liquid crystal display device to which the present invention can be applied is not particularly limited, and for example, it can be applied to various types of liquid crystal display devices described in the above-mentioned "next-generation liquid crystal display technology".
- the acid value of the sample represents the mass of potassium hydroxide required to neutralize the acidic component per 1 g of solid content.
- A 56.11 ⁇ Vs ⁇ 0.5 ⁇ f / w
- Vs Amount of 0.1 mol / L sodium hydroxide aqueous solution required for titration (mL)
- f Titer of 0.1 mol / L sodium hydroxide aqueous solution
- w Mass of sample (g) (in terms of solid content)
- a mixed solution containing the raw materials listed in the table below is mixed and dispersed for 3 hours using a bead mill (zirconia beads 0.3 mm diameter), and then a high pressure disperser with a decompression mechanism NANO-3000-10 (manufactured by Nippon BEE Co., Ltd.) ) was used to carry out dispersion treatment at a flow rate of 500 g / min under a pressure of 2000 kg / cm 3 . This dispersion treatment was repeated 10 times to obtain each dispersion.
- the unit of numerical values shown in the above table is parts by mass.
- PR254 C.I. I. Pigment Red 254 (red pigment, diketopyrrolopyrrole pigment)
- PR264 C.I. I. Pigment Red 264 (red pigment, diketopyrrolopyrrole pigment)
- PB16 C.I. I.
- Pigment Blue 16 blue pigment, phthalocyanine pigment
- PY139 C.I. I. Pigment Yellow 139 (yellow pigment, isoindoline pigment)
- PcAl Aluminum phthalocyanine (blue pigment, compound with the following structure)
- IR pigment A compound having the following structure (near-infrared absorbing pigment, in the structural formula, Me represents a methyl group and Ph represents a phenyl group).
- C.I. I. Pigment Blue 16 is a pigment that satisfies the following condition 1.
- Condition 1) A composition containing 6% by mass of a pigment, 10% by mass of resin B-5, and 84% by mass of propylene glycol monomethyl ether acetate was used and heated at 200 ° C. for 30 minutes to a thickness of 0.60 ⁇ m. When the film was formed and heat-treated at 300 ° C.
- ... (10) ⁇ A10 is the rate of change in the absorbance of the film after heat treatment.
- A11 is the maximum value of the absorbance in the wavelength range of 400 to 1100 nm of the film before the heat treatment.
- A12 is the absorbance of the film after the heat treatment, which is the absorbance at the wavelength indicating the maximum value of the absorbance of the film before the heat treatment in the wavelength range of 400 to 1100 nm;
- Resin B-5 is a resin having the following structure, and the numerical values added to the main chain are molar ratios, the weight average molecular weight is 11000, and the acid value is 32 mgKOH / g.
- (Pigment derivative) Derivative 1 Compound with the following structure
- Derivative 2 A compound having the following structure (in the structural formula, Me represents a methyl group and Ph represents a phenyl group).
- B-1 Resin having the following structure ((meth) acrylic resin, the numerical value added to the main chain is the molar ratio, and the numerical value added to the side chain is the number of repeating units.
- B-2 Resin having the following structure (weight average molecular weight 12000, acid value 195.4 mgKOH / g, amine value 0 mgKOH / g, the numerical values added to the main chain represent the molar ratio of the repeating unit).
- B-3 Resin having the following structure ((meth) acrylic resin, the numerical value added to the main chain is the molar ratio.
- Weight average molecular weight 14000, acid value 79.3 mgKOH / g) B-4 Resin having the following structure ((meth) acrylic resin, the numerical value added to the main chain is the molar ratio, and the numerical value added to the side chain is the number of repeating units.
- Weight average molecular weight 24000, acid value 52. 5 mgKOH / g) B-5 Resin having the following structure ((meth) acrylic resin, the numerical value added to the main chain is the molar ratio.
- Weight average molecular weight 11000, acid value 32 mgKOH / g) B-14 Resin having the following structure ((meth) acrylic resin, the numerical value added to the main chain is the molar ratio, and the numerical value added to the side chain is the number of repeating units.
- Weight average molecular weight 21000, acid value 77 mgKOH / g) B-15 Resin having the following structure (polyimine resin, the numerical value added to the main chain is the molar ratio, and the numerical value added to the side chain is the number of repeating units.
- MT-150A trade name: manufactured by TAYCA CORPORATION
- silica particles AEROPERL registered trademark
- Ebonic manufactured by Ebonic
- a uniform aqueous mixture was obtained.
- This aqueous solution is filled in a quartz container, heated to 920 ° C. in an oxygen atmosphere using a small rotary kiln (manufactured by Motoyama Co., Ltd.), the atmosphere is replaced with nitrogen, and ammonia gas is added at 100 mL / min at the same temperature for 5 hours.
- Nitriding reduction treatment was carried out by flowing.
- the recovered powder was pulverized in a mortar to obtain a powdery titanium black A-1 [disperse containing titanium black particles and Si atoms] having a specific surface area of 73 m 2 / g containing Si atoms.
- composition 1 The components shown in the following composition 1 were mixed for 15 minutes using a stirrer (Eurostar manufactured by IKA) to obtain a dispersion a.
- Composition 1 -Titanium black A-1 obtained as described above ... 25 parts by mass-Propylene glycol monomethyl ether acetate 30% by mass solution of resin B-16 ... 25 parts by mass-Propylene glycol monomethyl ether acetate (PGMEA) (solvent) ... 50 parts by mass
- the obtained dispersion a was subjected to a dispersion treatment using an Ultra Apex Mill UAM015 manufactured by Kotobuki Kogyo Co., Ltd. under the following conditions, and a titanium black dispersion liquid (solid content concentration 50% by mass, titanium black content) was carried out. 25% by mass) was obtained.
- ⁇ Manufacturing of resin composition The following raw materials were mixed to prepare a resin composition.
- the unit of the numerical value in the column of the amount of addition described in the table below is a mass part.
- the ratio of the pigment in the total solid content of the resin composition, the ratio of the pigment in the total solid content of the resin composition, and the ratio of the resin A in the components excluding the pigment from the total solid content of the resin composition are also described.
- Dye 1 Xanthene dye Rhodamine 6G (manufactured by Tokyo Chemical Industry Co., Ltd.)
- B-5 Resin B-5 described above
- B-7 Resin having the following structure (polybenzoxazole precursor, weight average molecular weight 21000, solid content 100%)
- B-8 Resin having the following structure (polyimide precursor, weight average molecular weight 24000, solid content 100%)
- B-9 Polyester-modified silicone resin (KR-5230: manufactured by Shinetsu Silicone Co., Ltd., solid content 60%)
- B-10 Resin with the following structure (epoxy resin, Techmore VG3101M80, manufactured by Printec, solid content 80.1%)
- B-11 Bismaleimide resin (HR3070: manufactured by Printec, 100% solid content)
- B-12 Resin with the following structure (epoxy-modified silicone resin, component E103D, manufactured by Arakawa Chemical Industry Co., Ltd., solid content 49%)
- B-13 Epoxy resin (Denacol EX-611, manufactured by Nagase ChemteX Corporation)
- the transmittance of the film having a wavelength of 400 to 1100 nm was increased.
- the minimum value was 70% or more.
- (Surfactant) E-1 A compound having the following structure (weight average molecular weight 14000,% value indicating the ratio of repeating units is mol%, fluorine-based surfactant)
- ⁇ Evaluation> (Membrane contraction rate)
- the resin composition is applied onto a glass substrate by spin coating, dried (prebaked) at 100 ° C. for 120 seconds using a hot plate, and then heated (post-baked) at 200 ° C. for 30 minutes using an oven to have a thickness of 0. A .60 ⁇ m film was produced.
- the film thickness was appropriately adjusted to be 0.60 ⁇ m according to the rotation speed and sequence of spin coating.
- the film thickness is measured by scraping a part of the film to expose the surface of the glass substrate and measuring the step between the glass substrate surface and the coating film (the film thickness of the coating film) using a stylus type profilometer (DectakXT, manufactured by BRUKER). did.
- the film thickness was measured after the substrate temperature was set to room temperature (22 ° C.) in a laboratory where the temperature and humidity were controlled to 22 ⁇ 5 ° C. and 60 ⁇ 20%.
- the obtained film was heat-treated at 300 ° C. for 5 hours in a nitrogen atmosphere, and the film thickness was measured again.
- the measurement was carried out after the substrate temperature was set to room temperature (22 ° C.) in a laboratory in which the temperature and humidity were controlled to 22 ⁇ 5 ° C. and 60 ⁇ 20% in the same manner as described above.
- the membrane shrinkage rate was calculated by the following formula.
- Membrane contraction rate (%) (T 1 / T 0 ) x 100
- T 1 Film thickness after heat treatment at 300 ° C. for 5 hours in a nitrogen atmosphere
- the resin composition is applied onto a glass substrate by spin coating, dried (prebaked) at 100 ° C. for 120 seconds using a hot plate, and then heated (post-baked) at 200 ° C. for 30 minutes using an oven to have a thickness of 0. A .60 ⁇ m film was produced.
- SiO 2 was laminated at 200 nm on the surface of the obtained film by a sputtering method to form an inorganic film.
- the film on which the inorganic film was formed was heat-treated at 300 ° C. for 5 hours in a nitrogen atmosphere. The surface of the inorganic film after the heat treatment was observed with an optical microscope to evaluate the presence or absence of cracks.
- the resin compositions of Examples had a film shrinkage rate of 70% or more. Therefore, as compared with the resin composition of Comparative Example 1, it was possible to expand the process window of the process after manufacturing the film. Further, when the resin composition of the example was used, no crack was generated in the inorganic film in the evaluation of cracks.
- Example 100 Pattern formation by photolithography method
- the resin composition of Example 10 was applied on a silicon wafer by spin coating on a glass substrate, and dried (pre-baked) at 100 ° C. for 120 seconds using a hot plate. Later, it was heated (post-baked) at 200 ° C. for 30 minutes using an oven to form a resin composition layer having a thickness of 0.60 ⁇ m.
- i-line stepper exposure apparatus FPA-3000i5 + (Canon, Inc.) via a mask pattern in which square pixels having a side of 1.1 ⁇ m are arranged in a region of 4 mm ⁇ 3 mm on the substrate, respectively.
- the silicon wafer on which the resin composition layer after exposure is formed is placed on a horizontal rotary table of a spin shower developer (DW-30 type, manufactured by Chemitronics Co., Ltd.), and a developer (CD) is placed. -2000, paddle developed at 23 ° C. for 60 seconds using Fujifilm Electronics Materials Co., Ltd.
- the silicon wafer was rotated at a rotation speed of 50 r. p. m. While rotating with, pure water was supplied from above the center of rotation in a shower shape from the ejection nozzle to perform a rinse treatment, and then spray-dried to form a pattern (pixel).
- the produced patterned silicon wafer was divided into two, and one of them was heat-treated at 300 ° C. for 5 hours in a nitrogen atmosphere (hereinafter referred to as a substrate before heat treatment at 300 ° C. and a substrate after heat treatment at 300 ° C.).
- a substrate before heat treatment at 300 ° C. and a substrate after heat treatment at 300 ° C. a nitrogen atmosphere
- the cross section of the resist pattern formed on the substrate before the heat treatment at 300 ° C. and the substrate after the heat treatment at 300 ° C. was evaluated by a scanning electron microscope (SEM), the resist pattern formed on the substrate after the heat treatment at 300 ° C.
- the height of the resist pattern was 71% of the height of the resist pattern formed on the substrate before heat treatment at 300 ° C.
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Abstract
Description
<1> 色材と、樹脂と、溶剤と、を含む樹脂組成物であって、
上記樹脂組成物を用いて、200℃で30分加熱して厚さ0.60μmの膜を形成した際に、上記膜を窒素雰囲気下にて300℃で5時間加熱処理した後の膜の厚さが、加熱処理前の膜の厚さの70%以上である、樹脂組成物。
<2> 上記樹脂は、ポリイミド樹脂、ポリベンゾオキサゾール樹脂、エポキシ樹脂、ビスマレイミド樹脂、シリコーン樹脂、ポリアリレート樹脂、ベンゾオキサジン樹脂およびそれらの前駆体から選ばれる少なくとも1種の樹脂Aを含む、<1>に記載の樹脂組成物。
<3> 上記樹脂Aは、ポリイミド樹脂、ポリベンゾオキサゾール樹脂およびそれらの前駆体から選ばれる少なくとも1種である、<1>に記載の樹脂組成物。
<4> 上記樹脂Aは、ガラス基板に塗布し100℃で120秒加熱して厚さ0.60μmの膜を形成した際に、上記膜の波長400~1100nmの透過率の最小値が70%以上である、<2>または<3>に記載の樹脂組成物。
<5> 上記樹脂組成物の全固形分から色材を除いた成分中に、上記樹脂Aを20質量%以上含む、<2>~<4>のいずれか1つに記載の樹脂組成物。
<6> 上記樹脂は、上記樹脂A以外の他の樹脂を含む、<2>~<5>のいずれか1つに記載の樹脂組成物。
<7> 上記他の樹脂が(メタ)アクリル樹脂である、<6>に記載の樹脂組成物。
<8> 上記他の樹脂の含有量が上記樹脂Aの100質量部に対して230質量部以下である、<6>または<7>に記載の樹脂組成物。
<9> 上記樹脂は、アルカリ可溶性樹脂を含む、<1>~<8>のいずれか1つに記載の樹脂組成物。
<10> 上記色材が、有彩色色材、黒色色材、及び近赤外線吸収色材から選ばれる少なくとも1種である、<1>~<9>のいずれか1つに記載の樹脂組成物。
<11> 上記色材が、2種以上の有彩色色材と近赤外線吸収色材とを含むか、あるいは、黒色顔料と近赤外線吸収色材とを含む、<1>~<9>のいずれか1つに記載の樹脂組成物。
<12> 上記色材が有彩色顔料および近赤外線吸収顔料から選ばれる少なくとも1種を含む、<1>~<9>のいずれか1つに記載の樹脂組成物。
<13> さらに、光重合開始剤を含む、<1>~<12>のいずれか1つに記載の樹脂組成物。
<14> さらに、重合性化合物を含む、<13>に記載の樹脂組成物。
<15> 上記樹脂組成物は、ガラス基板に塗布し100℃で120秒加熱して膜厚0.6μmの膜を形成した際に、上記膜は、波長400~1100nmの透過率の最大値が70%以上で、最小値が30%以下である、<1>~<14>のいずれか1つに記載の樹脂組成物。
<16> フォトリソグラフィ法でのパターン形成用である、<9>、<13>または<14>のいずれか1つに記載の樹脂組成物。
<17> カラーフィルタの画素形成用である、<1>~<16>のいずれか1つに記載の樹脂組成物。
<18> 固体撮像素子用である、<1>~<17>のいずれか1つに記載の樹脂組成物。
<19> <1>~<18>のいずれか1つに記載の樹脂組成物から得られる膜。
<20> <19>に記載の膜を含むカラーフィルタ。
<21> <19>に記載の膜を含む固体撮像素子。
<22> <19>に記載の膜を含む画像表示装置。
本明細書において、「~」とはその前後に記載される数値を下限値および上限値として含む意味で使用される。
本明細書における基(原子団)の表記において、置換および無置換を記していない表記は、置換基を有さない基(原子団)と共に置換基を有する基(原子団)をも包含する。例えば、「アルキル基」とは、置換基を有さないアルキル基(無置換アルキル基)のみならず、置換基を有するアルキル基(置換アルキル基)をも包含する。
本明細書において「露光」とは、特に断らない限り、光を用いた露光のみならず、電子線、イオンビーム等の粒子線を用いた描画も露光に含める。また、露光に用いられる光としては、水銀灯の輝線スペクトル、エキシマレーザに代表される遠紫外線、極紫外線(EUV光)、X線、電子線等の活性光線または放射線が挙げられる。
本明細書において、(メタ)アリル基は、アリルおよびメタリルの双方、または、いずれかを表し、「(メタ)アクリレート」は、アクリレートおよびメタクリレートの双方、または、いずれかを表し、「(メタ)アクリル」は、アクリルおよびメタクリルの双方、または、いずれかを表し、「(メタ)アクリロイル」は、アクリロイルおよびメタクリロイルの双方、または、いずれかを表す。
本明細書において、重量平均分子量および数平均分子量は、GPC(ゲルパーミエーションクロマトグラフィ)法により測定したポリスチレン換算値である。
本明細書において、近赤外線とは、波長700~2500nmの光をいう。
本明細書において、全固形分とは、組成物の全成分から溶剤を除いた成分の総質量をいう。
本明細書において「工程」との語は独立した工程だけを指すのではなく、他の工程と明確に区別できない場合であってもその工程の所期の作用が達成されれば、本用語に含まれる。
本発明の樹脂組成物は、色材と、樹脂と、溶剤と、を含む樹脂組成物であって、
上記樹脂組成物を用いて、200℃で30分加熱して厚さ0.60μmの膜を形成した際に、上記膜を窒素雰囲気下にて300℃で5時間加熱処理した後の膜の厚さが、加熱処理前の膜の厚さの70%以上であることを特徴とする。
また、上記膜を窒素雰囲気下にて350℃で5時間加熱処理した後の膜の厚さは、加熱処理前の膜の厚さの70%以上であることが好ましく、80%以上であることがより好ましく、90%以上であることが更に好ましい。
また、上記膜を窒素雰囲気下にて400℃で5時間加熱処理した後の膜の厚さは、加熱処理前の膜の厚さの70%以上であることが好ましく、80%以上であることがより好ましく、90%以上であることが更に好ましい。
(1):波長400~640nmの範囲における透過率の最大値が20%以下(好ましくは15%以下、より好ましくは10%以下)であり、波長800~1300nmの範囲における透過率の最小値が70%以上(好ましくは75%以上、より好ましくは80%以上)であるフィルタ。
(2):波長400~750nmの範囲における透過率の最大値が20%以下(好ましくは15%以下、より好ましくは10%以下)であり、波長900~1300nmの範囲における透過率の最小値が70%以上(好ましくは75%以上、より好ましくは80%以上)であるフィルタ。
(3):波長400~830nmの範囲における透過率の最大値が20%以下(好ましくは15%以下、より好ましくは10%以下)であり、波長1000~1300nmの範囲における透過率の最小値が70%以上(好ましくは75%以上、より好ましくは80%以上)であるフィルタ。
(4):波長400~950nmの範囲における透過率の最大値が20%以下(好ましくは15%以下、より好ましくは10%以下)であり、波長1100~1300nmの範囲における透過率の最小値が70%以上(好ましくは75%以上、より好ましくは80%以上)であるフィルタ。
本発明の樹脂組成物は、色材を含有する。色材としては白色色材、黒色色材、有彩色色材、近赤外線吸収色材が挙げられる。なお、本発明において、白色色材は純白色のみならず、白に近い明るい灰色(例えば灰白色、薄灰色など)の色材を含む。また、色材は、有彩色色材、黒色色材、及び近赤外線吸収色材から選ばれる少なくとも1種を含むことが好ましく、有彩色色材及び近赤外線吸収色材から選ばれる少なくとも1種を含むことがより好ましく、有彩色色材を含むことが更に好ましい。また、色材は、2種以上の有彩色色材と近赤外線吸収色材とを含むか、あるいは、黒色顔料と近赤外線吸収色材とを含むことも好ましい。この態様によれば、近赤外線透過フィルタ形成用の樹脂組成物として好ましく用いることができる。
顔料Aを6質量%と、樹脂B-5を10質量%と、プロピレングリコールモノメチルエーテルアセテートを84質量%含む組成物を用いて、200℃で30分加熱して厚さ0.60μmの膜を形成した際に、上記膜を窒素雰囲気下にて300℃で5時間加熱処理したとき、加熱処理後の膜の下記式(10)で表される吸光度の変化率ΔA10が50%以下である;
ΔA10=|100-(A12/A11)×100| ・・・(10)
ΔA10は、加熱処理後の膜の吸光度の変化率であり、
A11は、加熱処理前の膜の波長400~1100nmの範囲における吸光度の最大値であり、
A12は、加熱処理後の膜の吸光度であって、加熱処理前の膜の波長400~1100nmの範囲における吸光度の最大値を示す波長での吸光度である;
樹脂B-5は、下記構造の樹脂であって、主鎖に付記した数値はモル比であり、重量平均分子量は11000であり、酸価は32mgKOH/gである。
有彩色色材としては、波長400~700nmの範囲に極大吸収波長を有する色材が挙げられる。例えば、黄色色材、オレンジ色色材、赤色色材、緑色色材、紫色色材、青色色材などが挙げれる。耐熱性の観点から有彩色色材は、顔料(有彩色顔料)であることが好ましく、赤色顔料、黄色顔料、及び青色顔料がより好ましく、赤色顔料及び青色顔料が更に好ましい。有彩色顔料の具体例としては、例えば、以下に示すものが挙げられる。
C.I.Pigment Orange 2,5,13,16,17:1,31,34,36,38,43,46,48,49,51,52,55,59,60,61,62,64,71,73等(以上、オレンジ色顔料)、
C.I.Pigment Red 1,2,3,4,5,6,7,9,10,14,17,22,23,31,38,41,48:1,48:2,48:3,48:4,49,49:1,49:2,52:1,52:2,53:1,57:1,60:1,63:1,66,67,81:1,81:2,81:3,83,88,90,105,112,119,122,123,144,146,149,150,155,166,168,169,170,171,172,175,176,177,178,179,184,185,187,188,190,200,202,206,207,208,209,210,216,220,224,226,242,246,254,255,264,270,272,279,294(キサンテン系、Organo Ultramarine、Bluish Red),295(モノアゾ系),296(ジアゾ系)等(以上、赤色顔料)、
C.I.Pigment Green 7,10,36,37,58,59,62,63等(以上、緑色顔料)、
C.I.Pigment Violet 1,19,23,27,32,37,42,60(トリアリールメタン系),61(キサンテン系)等(以上、紫色顔料)、
C.I.Pigment Blue 1,2,15,15:1,15:2,15:3,15:4,15:6,16,22,29,60,64,66,79,80,87(モノアゾ系),88(メチン系)等(以上、青色顔料)。
(1)赤色色材と青色色材とを含有する態様。
(2)赤色色材と青色色材と黄色色材とを含有する態様。
(3)赤色色材と青色色材と黄色色材と紫色色材とを含有する態様。
(4)赤色色材と青色色材と黄色色材と紫色色材と緑色色材とを含有する態様。
(5)赤色色材と青色色材と黄色色材と緑色色材とを含有する態様。
(6)赤色色材と青色色材と緑色色材とを含有する態様。
(7)黄色色材と紫色色材とを含有する態様。
白色色材としては、酸化チタン、チタン酸ストロンチウム、チタン酸バリウム、酸化亜鉛、酸化マグネシウム、酸化ジルコニウム、酸化アルミニウム、硫酸バリウム、シリカ、タルク、マイカ、水酸化アルミニウム、ケイ酸カルシウム、ケイ酸アルミニウム、中空樹脂粒子、硫化亜鉛などの無機顔料(白色顔料)が挙げられる。白色顔料は、チタン原子を有する粒子が好ましく、酸化チタンがより好ましい。また、白色顔料は、波長589nmの光に対する屈折率が2.10以上の粒子であることが好ましい。前述の屈折率は、2.10~3.00であることが好ましく、2.50~2.75であることがより好ましい。
黒色色材としては特に限定されず、公知のものを用いることができる。例えば、カーボンブラック、チタンブラック、グラファイト等の無機顔料(黒色顔料)が挙げられ、カーボンブラック、チタンブラックが好ましく、チタンブラックがより好ましい。チタンブラックとは、チタン原子を含有する黒色粒子であり、低次酸化チタンや酸窒化チタンが好ましい。チタンブラックは、分散性向上、凝集性抑制などの目的で必要に応じ、表面を修飾することが可能である。例えば、酸化珪素、酸化チタン、酸化ゲルマニウム、酸化アルミニウム、酸化マグネシウム、又は、酸化ジルコニウムでチタンブラックの表面を被覆することが可能である。また、特開2007-302836号公報に表されるような撥水性物質での処理も可能である。黒色顔料として、カラーインデックス(C.I.)Pigment Black 1,7等が挙げられる。チタンブラックは、個々の粒子の一次粒子径及び平均一次粒子径のいずれもが小さいことが好ましい。具体的には、平均一次粒子径が10~45nmであることが好ましい。チタンブラックは、分散物として用いることもできる。例えば、チタンブラック粒子とシリカ粒子とを含み、分散物中のSi原子とTi原子との含有比が0.20~0.50の範囲に調整した分散物などが挙げられる。上記分散物については、特開2012-169556号公報の段落0020~0105の記載を参酌でき、この内容は本明細書に組み込まれる。チタンブラックの市販品の例としては、チタンブラック10S、12S、13R、13M、13M-C、13R-N、13M-T(商品名:三菱マテリアル(株)製)、ティラック(Tilack)D(商品名:赤穂化成(株)製)などが挙げられる。
近赤外線吸収色材は、顔料であることが好ましく、有機顔料であることがより好ましい。また、近赤外線吸収色材は、波長700nmを超え1400nm以下の範囲に極大吸収波長を有することが好ましい。また、近赤外線吸収色材の極大吸収波長は、1200nm以下であることが好ましく、1000nm以下であることがより好ましく、950nm以下であることが更に好ましい。また、近赤外線吸収色材は、波長550nmにおける吸光度A550と極大吸収波長における吸光度Amaxとの比であるA550/Amaxが0.1以下であることが好ましく、0.05以下であることがより好ましく、0.03以下であることが更に好ましく、0.02以下であることが特に好ましい。下限は、特に限定はないが、例えば、0.0001以上とすることができ、0.0005以上とすることもできる。上述の吸光度の比が上記範囲であれば、可視透明性および近赤外線遮蔽性に優れた近赤外線吸収色材とすることができる。なお、本発明において、近赤外線吸収色材の極大吸収波長および各波長における吸光度の値は、近赤外線吸収色材を含む樹脂組成物を用いて形成した膜の吸収スペクトルから求めた値である。
また、樹脂組成物の全固形分中における顔料の含有量は5質量%以上であることが好ましく、10質量%以上であることがより好ましく、15質量%以上であることが更に好ましく、20質量%以上であることがより一層好ましい。上限は90質量%以下であることが好ましく、80質量%以下であることがより好ましく、70質量%以下であることが更に好ましい。
また、色材中における染料の含有量は50質量%以下であることが好ましく、40質量%以下であることがより好ましく、30質量%以下であることが更に好ましい。
また、本発明の樹脂組成物は、得られる膜を高温に加熱した際の膜厚変化をより効果的に抑制しやすいという理由から染料を実質的に含有しないことも好ましい。本発明の樹脂組成物が染料を実質的に含まない場合、本発明の樹脂組成物の全固形分中における染料の含有量が0.1質量%以下であることが好ましく、0.05質量%以下であることがより好ましく、含有しないことが特に好ましい。
本発明の樹脂組成物は、樹脂を含有する。樹脂は、例えば、顔料などの粒子を樹脂組成物中で分散させる用途やバインダーの用途で配合される。なお、主に顔料などの粒子を分散させるために用いられる樹脂を分散剤ともいう。ただし、樹脂のこのような用途は一例であって、このような用途以外の目的で使用することもできる。
本発明の樹脂組成物は、ポリイミド樹脂、ポリベンゾオキサゾール樹脂、エポキシ樹脂、ビスマレイミド樹脂、シリコーン樹脂、ポリアリレート樹脂、ベンゾオキサジン樹脂およびそれらの前駆体から選ばれる少なくとも1種の樹脂Aを含むことが好ましい。また、(メタ)アクリルアミドとスチレンの共重合体も好適に用いられる。本発明の樹脂組成物が樹脂Aを含むことにより、耐熱性に優れた膜を形成しやすく、加熱後の膜収縮や変色などをより抑制しやすい。また、加熱に伴う黄変も生じにくい膜を形成しやすいので、例えば、本発明の樹脂組成物を用いて、カラーフィルタにおける青色の画素形成を形成した場合においては、青色画素の加熱に伴う黄変も抑制でき、加熱も分光特性の変動を効果的に抑制できる。さらには、樹脂組成物を用いて得られる膜の表面に無機膜などを形成した際において、この無機膜が表面に形成された膜を300℃以上の高温に加熱しても、無機膜にクラックなどが生じることもより効果的に抑制することもできる。特に、樹脂組成物の全固形分から色材を除いた成分中に、樹脂Aを20質量%以上含む場合においては、このような効果が顕著に得られる。樹脂Aは、ポリイミド樹脂、ポリイミド樹脂の前駆体、ポリベンゾオキサゾール樹脂、ポリベンゾオキサゾール樹脂の前駆体、エポキシ樹脂、ビスマレイミド樹脂およびシリコーン樹脂であることが好ましく、耐熱性が良好であり、加熱後の収縮が少ないという理由から、ポリイミド樹脂、ポリベンゾオキサゾール樹脂およびそれらの前駆体から選ばれる少なくとも1種であることがより好ましく、ポリイミド樹脂の前駆体、ポリベンゾオキサゾール樹脂の前駆体であることが更に好ましい。
ポリイミド樹脂の前駆体(以下、ポリイミド前駆体ともいう)としては下記式(PI-1)で表される構成単位を含むものが挙げられる。
式(III)において、R201は、炭素数2~12のアルキレン基、-CH2CH(OH)CH2-または炭素数4~30の(ポリ)オキシアルキレン基(アルキレン基としては炭素数1~12が好ましく、1~6がより好ましく、1~3が特に好ましい;繰り返し数は1~12が好ましく、1~6がより好ましく、1~3が特に好ましい)を表す。なお、(ポリ)オキシアルキレン基とは、オキシアルキレン基またはポリオキシアルキレン基を意味する。好適なR201の例は、エチレン基、プロピレン基、トリメチレン基、テトラメチレン基、1,2-ブタンジイル基、1,3-ブタンジイル基、ペンタメチレン基、ヘキサメチレン基、オクタメチレン基、ドデカメチレン基、-CH2CH(OH)CH2-が挙げられ、エチレン基、プロピレン基、トリメチレン基、-CH2CH(OH)CH2-が好ましい。
特に好ましくは、R200がメチル基で、R201がエチレン基である。
ポリイミド前駆体の分子量の分散度は、1.5~3.5が好ましく、2~3がより好ましい。
ポリイミド樹脂としては、ポリイミド樹脂の前駆体(ポリイミド前駆体)を環化して得られたものなどが挙げられる。ポリイミド前駆体としては上述したものが挙げられる。また、ポリイミド樹脂は、主鎖および側鎖の少なくとも一方に、カルボキシ基、スルホ基、リン酸基、およびホスホン酸基から選ばれる少なくとも1種の基を有するものであることも好ましい。この態様によれば、アルカリ現像液に対する溶解性に優れたポリイミド樹脂とすることができる。
ポリベンゾオキサゾール樹脂の前駆体(以下、ポリベンゾオキサゾール前駆体ともいう)としては下記式(PBO-1)で表される構成単位を含むものが挙げられる。
ポリベンゾオキサゾール前駆体の分子量の分散度は、1.5~3.5が好ましく、2~3がより好ましい。
ポリベンゾオキサゾール樹脂としては、ポリベンゾオキサゾール樹脂の前駆体(ポリベンゾオキサゾール前駆体)を環化して得られたものなどが挙げられる。ポリベンゾオキサゾール前駆体としては上述したものが挙げられる。また、ポリベンゾオキサゾール樹脂は、主鎖および側鎖の少なくとも一方に、カルボキシ基、スルホ基、リン酸基、およびホスホン酸基から選ばれる少なくとも1種の基を有するものであることも好ましい。この態様によれば、アルカリ現像液に対する溶解性に優れたポリベンゾオキサゾール樹脂とすることができる。
エポキシ樹脂としては、1分子内にエポキシ基を2つ以上有する化合物が好ましい。エポキシ基は、1分子内に2~10個が好ましく、2~5個がより好ましく、3個が特に好ましい。エポキシ樹脂は、ベンゼン環を含む化合物であることが好ましく、ジアリール構造、トリアリール構造またはテトラアリール構造を有する化合物であることがより好ましい。
Re1が表すアルキル基の炭素数は1~30が好ましく、1~12がより好ましい。アルキル基は、直鎖、分岐、環状のいずれでもよく、直鎖または分岐が好ましく、直鎖がより好ましい。アルキル基は、置換基を有していてもよいが、無置換であることが好ましい。
Re1が表すアリール基の炭素数は、6~30が好ましく、6~25がより好ましく、6~12が更に好ましい。Re1が表すアルキル基およびアリール基は、置換基を有していてもよいが、無置換であることが好ましい。
Re1が表すハロゲン原子としては、フッ素原子、塩素原子、臭素原子及びヨウ素原子が挙げられる。
アルキレン基の炭素数は、1~30が好ましく、1~12がより好ましい。アルキレン基は、直鎖または分岐であることが好ましく、分岐であることがより好ましい。
シロキサン結合を含む繰り返し単位を有する樹脂が挙げられる。シリコーン樹脂において、シロキサン結合を含む繰り返し単位は、主鎖に含まれていてもよく、側鎖に含まれていてもよい。シリコーン樹脂としては、エポキシ変性シリコーン樹脂、ポリエステル変性シリコーン樹脂、アルキッド変性シリコーン樹脂、ウレタン変性シリコーン樹脂、アクリル変性シリコーン樹脂などが挙げられ、これらを好ましく用いることができる。なかでも、硬化膜の耐熱性をより向上させやすいという理由からエポキシ変性シリコーン樹脂、ポリエステル変性シリコーン樹脂が好ましい。
この実施形態のシリコーン樹脂は、エポキシ基を有していることが好ましい。また、この実施形態のシリコーン樹脂のエポキシ当量は150~500g/eqであることが好ましい。また、この実施形態のシリコーン樹脂は、ヒドロキシ基およびエポキシ基を有する化合物由来のエポキシ基のモル数と、エポキシ基およびアルコキシ基を含有するシルセスキオキサン化合物由来のエポキシ基のモル数との比率((ヒドロキシ基およびエポキシ基を有する化合物由来のエポキシ基のモル数)/(エポキシ基およびアルコキシ基を含有するシルセスキオキサン化合物由来のエポキシ基のモル数)が0.1~3であることが好ましい。
また、この実施形態のシリコーン樹脂は、アルコキシ基を有していることも好ましい。シリコーン樹脂中に含まれるアルコキシ基の量は150~3000g/eqであることが好ましい。
Rs1Si(ORs2)3 ・・・(Si-1)
(式中、Rs1はエポキシ基を有する炭素数3~8の炭化水素基を表し、Rs2は水素原子または炭素数1~4の炭化水素基を表す。)
本発明の樹脂組成物は、上述した樹脂A以外の樹脂を更に含有することができる。他の樹脂を更に含む場合においては、樹脂組成物を用いて得られる膜に適度な柔軟性を付与することもできる。このため、本発明の樹脂組成物を用いて得られる膜の表面に無機膜などを形成した際において、この積層体が高温に晒されても、無機膜にクラックなどが生じることも効果的に抑制することもできる。また、本発明の樹脂組成物を用いてフォトリソグラフィによる解像を行う場合、上述した樹脂A以外のアルカリ現像性を有する樹脂を含有することで、解像性をより向上することもできる。
本発明の樹脂組成物は、分散剤としての樹脂を含むこともできる。分散剤は、酸性分散剤(酸性樹脂)、塩基性分散剤(塩基性樹脂)が挙げられる。ここで、酸性分散剤(酸性樹脂)とは、酸基の量が塩基性基の量よりも多い樹脂を表す。酸性分散剤(酸性樹脂)は、酸基の量と塩基性基の量の合計量を100モル%としたときに、酸基の量が70モル%以上を占める樹脂が好ましく、実質的に酸基のみからなる樹脂がより好ましい。酸性分散剤(酸性樹脂)が有する酸基は、カルボキシ基が好ましい。酸性分散剤(酸性樹脂)の酸価は、40~105mgKOH/gが好ましく、50~105mgKOH/gがより好ましく、60~105mgKOH/gがさらに好ましい。また、塩基性分散剤(塩基性樹脂)とは、塩基性基の量が酸基の量よりも多い樹脂を表す。塩基性分散剤(塩基性樹脂)は、酸基の量と塩基性基の量の合計量を100モル%としたときに、塩基性基の量が50モル%を超える樹脂が好ましい。塩基性分散剤が有する塩基性基は、アミノ基であることが好ましい。
また、樹脂組成物の全固形分中における上述した樹脂Aの含有量は、5~95質量%が好ましい。下限は、10質量%以上が好ましく、20質量%以上がより好ましい。上限は、90質量%以下が好ましく、85質量%以下がより好ましい。
また、樹脂組成物の全固形分中における色材と上述した樹脂Aの合計の含有量は、25~100質量%が好ましい。下限は、30質量%以上がより好ましく、40質量%以上がさらに好ましい。上限は、90質量%以下がより好ましく、80質量%以下がさらに好ましい。
また、樹脂組成物の全固形分中における色材と上述した樹脂Aとの比率は、色材100質量部に対して樹脂Aが3~1500質量部であることが好ましい。下限は、5質量部以上であることが好ましく、10質量部以上であることがより好ましい。上限は、1000質量部以下であることが好ましく、500質量部以下であることがより好ましい。
本発明の樹脂組成物は、溶剤を含有する。溶剤としては有機溶剤が好ましい。有機溶剤としては、各成分の溶解性や樹脂組成物の塗布性を満足すれば基本的には特に制限はない。有機溶剤としては、エステル系溶剤、ケトン系溶剤、アルコール系溶剤、アミド系溶剤、エーテル系溶剤、炭化水素系溶剤などが挙げられる。これらの詳細については、国際公開第2015/166779号の段落番号0223を参酌でき、この内容は本明細書に組み込まれる。また、環状アルキル基が置換したエステル系溶剤、環状アルキル基が置換したケトン系溶剤を好ましく用いることもできる。有機溶剤の具体例としては、ポリエチレングリコールモノメチルエーテル、ジクロロメタン、3-エトキシプロピオン酸メチル、3-エトキシプロピオン酸エチル、エチルセロソルブアセテート、乳酸エチル、ジエチレングリコールジメチルエーテル、酢酸ブチル、3-メトキシプロピオン酸メチル、2-ヘプタノン、シクロヘキサノン、酢酸シクロヘキシル、シクロペンタノン、エチルカルビトールアセテート、ブチルカルビトールアセテート、プロピレングリコールモノメチルエーテル、プロピレングリコールモノメチルエーテルアセテート、3-メトキシ-N,N-ジメチルプロパンアミド、3-ブトキシ-N,N-ジメチルプロパンアミド、ガンマブチロラクトン、N-メチル-2-ピロリドンなどが挙げられる。ただし有機溶剤としての芳香族炭化水素類(ベンゼン、トルエン、キシレン、エチルベンゼン等)は、環境面等の理由により低減したほうがよい場合がある(例えば、有機溶剤全量に対して、50質量ppm(parts per million)以下とすることもでき、10質量ppm以下とすることもでき、1質量ppm以下とすることもできる)。
本発明の樹脂組成物は顔料誘導体を含有することができる。顔料誘導体としては、発色団の一部分を、酸基、塩基性基またはフタルイミドメチル基で置換した構造を有する化合物が挙げられる。顔料誘導体を構成する発色団としては、キノリン骨格、ベンゾイミダゾロン骨格、ジケトピロロピロール骨格、アゾ骨格、フタロシアニン骨格、アンスラキノン骨格、キナクリドン骨格、ジオキサジン骨格、ペリノン骨格、ペリレン骨格、チオインジゴ骨格、イソインドリン骨格、イソインドリノン骨格、キノフタロン骨格、スレン骨格、金属錯体系骨格等が挙げられ、キノリン骨格、ベンゾイミダゾロン骨格、ジケトピロロピロール骨格、アゾ骨格、キノフタロン骨格、イソインドリン骨格およびフタロシアニン骨格が好ましく、アゾ骨格およびベンゾイミダゾロン骨格がより好ましい。顔料誘導体が有する酸基としては、スルホ基、カルボキシ基が好ましく、スルホ基がより好ましい。顔料誘導体が有する塩基性基としては、アミノ基が好ましく、三級アミノ基がより好ましい。
本発明の樹脂組成物は、重合性化合物を含有することができる。重合性化合物は、例えば、エチレン性不飽和結合含有基を有する化合物であることが好ましい。エチレン性不飽和結合含有基としては、ビニル基、(メタ)アリル基、(メタ)アクリロイル基などが挙げられる。本発明で用いられる重合性化合物は、ラジカル重合性化合物であることが好ましい。
本発明の樹脂組成物は光重合開始剤を含むことができる。光重合開始剤としては、特に制限はなく、公知の光重合開始剤の中から適宜選択することができる。例えば、紫外線領域から可視領域の光線に対して感光性を有する化合物が好ましい。光重合開始剤は光ラジカル重合開始剤であることが好ましい
本発明の樹脂組成物は、シランカップリング剤を含有することができる。本発明において、シランカップリング剤は、加水分解性基とそれ以外の官能基とを有するシラン化合物を意味する。また、加水分解性基とは、ケイ素原子に直結し、加水分解反応及び縮合反応の少なくともいずれかによってシロキサン結合を生じ得る置換基をいう。加水分解性基としては、例えば、ハロゲン原子、アルコキシ基、アシルオキシ基などが挙げられ、アルコキシ基が好ましい。すなわち、シランカップリング剤は、アルコキシシリル基を有する化合物が好ましい。また、加水分解性基以外の官能基としては、例えば、ビニル基、(メタ)アリル基、(メタ)アクリロイル基、メルカプト基、エポキシ基、オキセタニル基、アミノ基、ウレイド基、スルフィド基、イソシアネート基、フェニル基などが挙げられ、アミノ基、(メタ)アクリロイル基およびエポキシ基が好ましい。シランカップリング剤の具体例としては、特開2009-288703号公報の段落番号0018~0036に記載の化合物、特開2009-242604号公報の段落番号0056~0066に記載の化合物が挙げられ、これらの内容は本明細書に組み込まれる。
本発明の樹脂組成物は、樹脂や重合性化合物の反応を促進させたり、硬化温度を下げる目的で、硬化促進剤をさらに含有することができる。硬化促進剤は、メチロール系化合物(例えば特開2015-034963号公報の段落番号0246において、架橋剤として例示されている化合物)、アミン類、ホスホニウム塩、アミジン塩、アミド化合物(以上、例えば特開2013-041165号公報の段落番号0186に記載の硬化剤)、塩基発生剤(例えば、特開2014-055114号公報に記載のイオン性化合物)、シアネート化合物(例えば、特開2012-150180号公報の段落番号0071に記載の化合物)、アルコキシシラン化合物(例えば、特開2011-253054号公報に記載のエポキシ基を有するアルコキシシラン化合物)、オニウム塩化合物(例えば、特開2015-034963号公報の段落番号0216に酸発生剤として例示されている化合物、特開2009-180949号公報に記載の化合物)などを用いることもできる。
本発明の樹脂組成物は、重合禁止剤を含有することができる。重合禁止剤としては、ハイドロキノン、p-メトキシフェノール、ジ-tert-ブチル-p-クレゾール、ピロガロール、tert-ブチルカテコール、ベンゾキノン、4,4’-チオビス(3-メチル-6-tert-ブチルフェノール)、2,2’-メチレンビス(4-メチル-6-t-ブチルフェノール)、N-ニトロソフェニルヒドロキシアミン塩(アンモニウム塩、第一セリウム塩等)が挙げられる。中でも、p-メトキシフェノールが好ましい。樹脂組成物の全固形分中における重合禁止剤の含有量は、0.0001~5質量%が好ましい。
本発明の樹脂組成物は、界面活性剤を含有することができる。界面活性剤としては、フッ素系界面活性剤、ノニオン性界面活性剤、カチオン性界面活性剤、アニオン性界面活性剤、シリコン系界面活性剤などの各種界面活性剤を使用することができる。界面活性剤については、国際公開第2015/166779号の段落番号0238~0245に記載された界面活性剤が挙げられ、この内容は本明細書に組み込まれる。
本発明の樹脂組成物は、紫外線吸収剤を含有することができる。紫外線吸収剤は、共役ジエン化合物、アミノジエン化合物、サリシレート化合物、ベンゾフェノン化合物、ベンゾトリアゾール化合物、アクリロニトリル化合物、ヒドロキシフェニルトリアジン化合物、インドール化合物、トリアジン化合物などを用いることができる。これらの詳細については、特開2012-208374号公報の段落番号0052~0072、特開2013-068814号公報の段落番号0317~0334、特開2016-162946号公報の段落番号0061~0080の記載を参酌でき、これらの内容は本明細書に組み込まれる。紫外線吸収剤の市販品としては、例えば、UV-503(大東化学(株)製)などが挙げられる。また、ベンゾトリアゾール化合物としては、ミヨシ油脂製のMYUAシリーズ(化学工業日報、2016年2月1日)が挙げられる。また、紫外線吸収剤は、特許第6268967号公報の段落番号0049~0059に記載された化合物を用いることもできる。樹脂組成物の全固形分中における紫外線吸収剤の含有量は、0.01~10質量%が好ましく、0.01~5質量%がより好ましい。紫外線吸収剤は1種のみを用いてもよく、2種以上を用いてもよい。2種以上を用いる場合は、合計量が上記範囲となることが好ましい。
本発明の樹脂組成物は、酸化防止剤を含有することができる。酸化防止剤としては、フェノール化合物、亜リン酸エステル化合物、チオエーテル化合物などが挙げられる。フェノール化合物としては、フェノール系酸化防止剤として知られる任意のフェノール化合物を使用することができる。好ましいフェノール化合物としては、ヒンダードフェノール化合物が挙げられる。フェノール性ヒドロキシ基に隣接する部位(オルト位)に置換基を有する化合物が好ましい。前述の置換基としては炭素数1~22の置換又は無置換のアルキル基が好ましい。また、酸化防止剤は、同一分子内にフェノール基と亜リン酸エステル基を有する化合物も好ましい。また、酸化防止剤は、リン系酸化防止剤も好適に使用することができる。樹脂組成物の全固形分中における酸化防止剤の含有量は、0.01~20質量%であることが好ましく、0.3~15質量%であることがより好ましい。酸化防止剤は1種のみを用いてもよく、2種以上を用いてもよい。2種以上を用いる場合は、合計量が上記範囲となることが好ましい。
本発明の樹脂組成物は、必要に応じて、増感剤、フィラー、熱硬化促進剤、可塑剤及びその他の助剤類(例えば、導電性粒子、充填剤、消泡剤、難燃剤、レベリング剤、剥離促進剤、香料、表面張力調整剤、連鎖移動剤など)を含有してもよい。これらの成分を適宜含有させることにより、膜物性などの性質を調整することができる。これらの成分は、例えば、特開2012-003225号公報の段落番号0183以降(対応する米国特許出願公開第2013/0034812号明細書の段落番号0237)の記載、特開2008-250074号公報の段落番号0101~0104、0107~0109等の記載を参酌でき、これらの内容は本明細書に組み込まれる。また、樹脂組成物は、必要に応じて、潜在酸化防止剤を含有してもよい。潜在酸化防止剤としては、酸化防止剤として機能する部位が保護基で保護された化合物であって、100~250℃で加熱するか、又は酸/塩基触媒存在下で80~200℃で加熱することにより保護基が脱離して酸化防止剤として機能する化合物が挙げられる。潜在酸化防止剤としては、国際公開第2014/021023号、国際公開第2017/030005号、特開2017-008219号公報に記載された化合物が挙げられる。市販品としては、アデカアークルズGPA-5001((株)ADEKA製)等が挙げられる。また、特開2018-155881号公報に記載されているように、C.I.ピグメントイエロー129を耐候性改良の目的で添加しても良い。
本発明の樹脂組成物の収容容器としては、特に限定はなく、公知の収容容器を用いることができる。また、収容容器として、原材料や樹脂組成物中への不純物混入を抑制することを目的に、容器内壁を6種6層の樹脂で構成する多層ボトルや6種の樹脂を7層構造にしたボトルを使用することも好ましい。このような容器としては例えば特開2015-123351号公報に記載の容器が挙げられる。また、容器内壁は、容器内壁からの金属溶出を防ぎ、樹脂組成物の保存安定性を高めたり、成分変質を抑制するなど目的で、ガラス製やステンレス製などにすることも好ましい。
本発明の樹脂組成物は、前述の成分を混合して調製できる。樹脂組成物の調製に際しては、全成分を同時に有機溶剤に溶解および/または分散して樹脂組成物を調製してもよいし、必要に応じて、各成分を適宜2つ以上の溶液または分散液としておいて、使用時(塗布時)にこれらを混合して樹脂組成物を調製してもよい。
本発明の膜は、上述した本発明の樹脂組成物から得られる膜である。本発明の膜は、カラーフィルタ、近赤外線透過フィルタ、近赤外線カットフィルタ、ブラックマトリクス、遮光膜などに用いることができる。例えば、カラーフィルタの着色層として好ましく用いることができる。
また、上記膜を窒素雰囲気下にて350℃で5時間加熱処理した後の膜の厚さは、加熱処理前の膜の厚さの70%以上であることが好ましく、80%以上であることがより好ましく、90%以上であることが更に好ましい。
また、上記膜を窒素雰囲気下にて400℃で5時間加熱処理した後の膜の厚さは、加熱処理前の膜の厚さの70%以上であることが好ましく、80%以上であることがより好ましく、90%以上であることが更に好ましい。
本発明の膜は、上述した本発明の樹脂組成物を支持体上に塗布する工程を経て製造できる。本発明の膜の製造方法においては、更にパターン(画素)を形成する工程を含むことが好ましい。パターン(画素)の形成方法としては、フォトリソグラフィ法およびドライエッチング法が挙げられ、フォトリソグラフィ法が好ましい。
まず、フォトリソグラフィ法によりパターンを形成して膜を製造する場合について説明する。フォトリソグラフィ法によるパターン形成は、本発明の樹脂組成物を用いて支持体上に樹脂組成物層を形成する工程と、樹脂組成物層をパターン状に露光する工程と、樹脂組成物層の未露光部を現像除去してパターン(画素)を形成する工程と、を含むことが好ましい。必要に応じて、樹脂組成物層をベークする工程(プリベーク工程)、および、現像されたパターン(画素)をベークする工程(ポストベーク工程)を設けてもよい。
ドライエッチング法でのパターン形成は、本発明の樹脂組成物を用いて支持体上に樹脂組成物層を形成し、この樹脂組成物層の全体を硬化させて硬化物層を形成する工程と、この硬化物層上にフォトレジスト層を形成する工程と、フォトレジスト層をパターン状に露光したのち、現像してレジストパターンを形成する工程と、このレジストパターンをマスクとして硬化物層に対してエッチングガスを用いてドライエッチングする工程と、を含むことが好ましい。フォトレジスト層の形成においては、更にプリベーク処理を施すことが好ましい。特に、フォトレジスト層の形成プロセスとしては、露光後の加熱処理、現像後の加熱処理(ポストベーク処理)を実施する形態が望ましい。ドライエッチング法でのパターン形成については、特開2013-064993号公報の段落番号0010~0067の記載を参酌でき、この内容は本明細書に組み込まれる。
本発明のカラーフィルタは、上述した本発明の膜を有する。より好ましくは、カラーフィルタの画素として、本発明の膜を有する。本発明のカラーフィルタは、CCD(電荷結合素子)やCMOS(相補型金属酸化膜半導体)などの固体撮像素子や画像表示装置などに用いることができる。
本発明の固体撮像素子は、上述した本発明の膜を有する。本発明の固体撮像素子の構成としては、本発明の膜を備え、固体撮像素子として機能する構成であれば特に限定はないが、例えば、以下のような構成が挙げられる。
本発明の画像表示装置は、上述した本発明の膜を有する。画像表示装置としては、液晶表示装置や有機エレクトロルミネッセンス表示装置などが挙げられる。画像表示装置の定義や各画像表示装置の詳細については、例えば「電子ディスプレイデバイス(佐々木昭夫著、(株)工業調査会、1990年発行)」、「ディスプレイデバイス(伊吹順章著、産業図書(株)平成元年発行)」などに記載されている。また、液晶表示装置については、例えば「次世代液晶ディスプレイ技術(内田龍男編集、(株)工業調査会、1994年発行)」に記載されている。本発明が適用できる液晶表示装置に特に制限はなく、例えば、上記の「次世代液晶ディスプレイ技術」に記載されている色々な方式の液晶表示装置に適用できる。
試料の重量平均分子量は、ゲルパーミエーションクロマトグラフィ(GPC)により、以下の条件で測定した。
カラムの種類:TOSOH TSKgel Super HZM-Hと、TOSOH TSKgel Super HZ4000と、TOSOH TSKgel Super HZ2000とを連結したカラム
展開溶媒:テトラヒドロフラン
カラム温度:40℃
流量(サンプル注入量):1.0μL(サンプル濃度:0.1質量%)
装置名:東ソー製 HLC-8220GPC
検出器:RI(屈折率)検出器
検量線ベース樹脂:ポリスチレン樹脂
試料の酸価は、固形分1gあたりの酸性成分を中和するのに要する水酸化カリウムの質量を表したものである。試料の酸価は次のようにして測定した。すなわち、測定試料をテトラヒドロフラン/水=9/1(質量比)混合溶媒に溶解し、得られた溶液を、電位差滴定装置(商品名:AT-510、京都電子工業製)を用いて、25℃にて、0.1mol/L水酸化ナトリウム水溶液で中和滴定した。滴定pH曲線の変曲点を滴定終点として、次式により酸価を算出した。
A=56.11×Vs×0.5×f/w
A:酸価(mgKOH/g)
Vs:滴定に要した0.1mol/L水酸化ナトリウム水溶液の使用量(mL)
f:0.1mol/L水酸化ナトリウム水溶液の力価
w:試料の質量(g)(固形分換算)
下記表に記載の原料を混合した混合液をビーズミル(ジルコニアビーズ0.3mm径)を用いて3時間混合および分散した後さらに減圧機構付き高圧分散機NANO-3000-10(日本ビーイーイー(株)製)を用いて、2000kg/cm3の圧力下で流量500g/minとして分散処理を行った。この分散処理を10回繰り返して各分散液を得た。
(色材)
PR254 : C.I.Pigment Red 254(赤色顔料、ジケトピロロピロール顔料)
PR264 : C.I.Pigment Red 264(赤色顔料、ジケトピロロピロール顔料)
PB15:4 : C.I.Pigment Blue 15:4(青色顔料、フタロシアニン顔料)
PB15:6 : C.I.Pigment Blue 15:6(青色顔料、フタロシアニン顔料)
PB16 : C.I.Pigment Blue 16(青色顔料、フタロシアニン顔料)
PY139 : C.I.Pigment Yellow 139(黄色顔料、イソインドリン顔料)
PcAl : アルミニウムフタロシアニン(青色顔料、下記構造の化合物)
条件1)
顔料を6質量%と、樹脂B-5を10質量%と、プロピレングリコールモノメチルエーテルアセテートを84質量%と、を含む組成物を用いて、200℃で30分加熱して厚さ0.60μmの膜を形成した際に、上記膜を窒素雰囲気下にて300℃で5時間熱処理したとき、加熱処理後の膜の下記式(10)で表される吸光度の変化率ΔA10が50%以下である;
ΔA10=|100-(A12/A11)×100| ・・・(10)
ΔA10は、加熱処理後の膜の吸光度の変化率であり、
A11は、加熱処理前の膜の波長400~1100nmの範囲における吸光度の最大値であり、
A12は、加熱処理後の膜の吸光度であって、加熱処理前の膜の波長400~1100nmの範囲における吸光度の最大値を示す波長での吸光度である;
樹脂B-5は、下記構造の樹脂であって、主鎖に付記した数値はモル比であり、重量平均分子量は11000であり、酸価は32mgKOH/gである。
B-1:下記構造の樹脂((メタ)アクリル樹脂、主鎖に付記した数値はモル比であり、側鎖に付記した数値は繰り返し単位の数である。重量平均分子量20000、酸価77mgKOH/g)
S-1:プロピレングリコールモノメチルエーテルアセテート
S-2:プロピレングリコールモノメチルエーテル
S-3:シクロヘキサノン
平均粒径15nmの酸化チタンMT-150A(商品名:テイカ(株)製)を100g、BET表面積300m2/gのシリカ粒子AEROPERL(登録商標)300/30(エボニック製)を25g、及び、分散剤Disperbyk190(商品名:ビックケミー社製)を100g秤量し、イオン電気交換水71gを加えてKURABO製MAZERSTAR KK-400Wを使用して、公転回転数1360rpm、自転回転数1047rpmにて20分間処理することにより均一な混合物水溶液を得た。この水溶液を石英容器に充填し、小型ロータリーキルン(株式会社モトヤマ製)を用いて酸素雰囲気中で920℃に加熱した後、窒素で雰囲気を置換し、同温度でアンモニアガスを100mL/minで5時間流すことにより窒化還元処理を実施した。終了後回収した粉末を乳鉢で粉砕し、Si原子を含み、粉末状の比表面積73m2/gのチタンブラックA-1〔チタンブラック粒子及びSi原子を含む被分散体〕を得た。
間混合して分散物aを得た。
(組成1)
・上記のようにして得られたチタンブラックA-1 ・・・25質量部
・樹脂B-16のプロピレングリコールモノメチルエーテルアセテート30質量%溶液
・・・25質量部
・プロピレングリコールモノメチルエーテルアセテート(PGMEA)(溶剤)
・・・50質量部
(分散条件)
・ビーズ径:直径0.05mm
・ビーズ充填率:75体積%
・ミル周速:8m/秒
・分散処理する混合液量:500g
・循環流量(ポンプ供給量):13kg/hour
・処理液温度:25~30℃
・冷却水:水道水
・ビーズミル環状通路内容積:0.15L
・パス回数:90パス
下記の原料を混合して樹脂組成物を調製した。下記表に記載の添加量の欄の数値の単位は質量部である。樹脂組成物の全固形分、樹脂組成物の全固形分中の顔料の比率、樹脂組成物の全固形分から顔料を除いた成分中における樹脂Aの比率についても併せて記す。
分散液R1、R2、B1、B2、B3、B4、Y1、BK、IR、チタンブラック分散液:上述した分散液R1、R2、B1、B2、B3、B4、Y1、BK、IR、チタンブラック分散液
染料1:キサンテン系染料ローダミン6G(東京化成工業社製)
B-5:上述した樹脂B-5
B-7:下記構造の樹脂(ポリベンゾオキサゾール前駆体、重量平均分子量21000、固形分100%)
B-10:下記構造の樹脂(エポキシ樹脂、TechmoreVG3101M80、プリンテック社製、固形分80.1%)
B-12:下記構造の樹脂(エポキシ変性シリコーン樹脂、コンポセランE103D、荒川化学工業(株)製、固形分49%)
S-1:プロピレングリコールモノメチルエーテルアセテート
S-4:ガンマブチロラクトン
S-5:N-メチル-2-ピロリドン
(膜収縮率)
樹脂組成物をガラス基板上にスピンコートで塗布し、ホットプレートを用いて100℃で120秒乾燥(プリベーク)した後に、オーブンを用いて200℃で30分加熱(ポストベーク)して厚さ0.60μmの膜を製造した。膜厚はスピン塗布の回転数およびシーケンスにより0.60μmとなるように適宜調整した。膜厚は、膜の一部を削ってガラス基板表面を露出し、ガラス基板表面と塗布膜の段差(塗布膜の膜厚)を触針式段差計(DektakXT、BRUKER社製)を用いて測定した。膜厚測定は、温湿度を22±5℃、60±20%に管理した実験室で、基板温度を室温(22℃)にしてから測定した。得られた膜を窒素雰囲気下にて300℃で5時間加熱処理し、再度膜厚測定した。測定は上記同様、温湿度を22±5℃、60±20%に管理した実験室で、基板温度を室温(22℃)にしてから測定した。下記式により膜収縮率を求めた。
膜収縮率(%)=(T1/T0)×100
T0:製造直後の膜の膜厚(=0.60μm)
T1:窒素雰囲気下にて300℃で5時間加熱処理した後の膜厚
樹脂組成物をガラス基板上にスピンコートで塗布し、ホットプレートを用いて100℃で120秒乾燥(プリベーク)した後に、オーブンを用いて200℃で30分加熱(ポストベーク)して厚さ0.60μmの膜を製造した。
次いで、得られた膜の表面に、スパッタ法によりSiO2を200nm積層して無機膜を形成した。この、無機膜が表面に形成された膜を、窒素雰囲気下にて300℃で5時間加熱処理した。加熱処理後の無機膜の表面を光学顕微鏡で観察し、クラックの有無を評価した。
シリコンウエハ上に、実施例10の樹脂組成物をガラス基板上にスピンコートで塗布し、ホットプレートを用いて100℃で120秒乾燥(プリベーク)した後に、オーブンを用いて200℃で30分加熱(ポストベーク)して厚さ0.60μmの樹脂組成物層を形成した。
次いで、この樹脂組成物層に対して、一辺1.1μmの正方ピクセルがそれぞれ基板上の4mm×3mmの領域に配列されたマスクパターンを介して、i線ステッパー露光装置FPA-3000i5+(Canon(株)製)を使用して波長365nmの光を500mJ/cm2の露光量で照射して露光した。
次いで、露光後の樹脂組成物層が形成されているシリコンウエハを、スピン・シャワー現像機(DW-30型、(株)ケミトロニクス製)の水平回転テーブル上に載置し、現像液(CD-2000、富士フイルムエレクトロニクスマテリアルズ(株)製)を用い、23℃で60秒間パドル現像した。次いで、シリコンウエハを回転数50r.p.m.で回転させつつ、その回転中心の上方より純水を噴出ノズルからシャワー状に供給してリンス処理を行ない、その後スプレー乾燥してパターン(画素)を形成した。
Claims (22)
- 色材と、樹脂と、溶剤と、を含む樹脂組成物であって、
前記樹脂組成物を用いて、200℃で30分加熱して厚さ0.60μmの膜を形成した際に、前記膜を窒素雰囲気下にて300℃で5時間加熱処理した後の膜の厚さが、加熱処理前の膜の厚さの70%以上である、樹脂組成物。 - 前記樹脂は、ポリイミド樹脂、ポリベンゾオキサゾール樹脂、エポキシ樹脂、ビスマレイミド樹脂、シリコーン樹脂、ポリアリレート樹脂、ベンゾオキサジン樹脂およびそれらの前駆体から選ばれる少なくとも1種の樹脂Aを含む、請求項1に記載の樹脂組成物。
- 前記樹脂Aは、ポリイミド樹脂、ポリベンゾオキサゾール樹脂およびそれらの前駆体から選ばれる少なくとも1種である、請求項1に記載の樹脂組成物。
- 前記樹脂Aは、ガラス基板に塗布し100℃で120秒加熱して厚さ0.60μmの膜を形成した際に、前記膜の波長400~1100nmの透過率の最小値が70%以上である、請求項2または3に記載の樹脂組成物。
- 前記樹脂組成物の全固形分から色材を除いた成分中に、前記樹脂Aを20質量%以上含む、請求項2~4のいずれか1項に記載の樹脂組成物。
- 前記樹脂は、前記樹脂A以外の他の樹脂を含む、請求項2~5のいずれか1項に記載の樹脂組成物。
- 前記他の樹脂が(メタ)アクリル樹脂である、請求項6に記載の樹脂組成物。
- 前記他の樹脂の含有量が前記樹脂Aの100質量部に対して230質量部以下である、請求項6または7に記載の樹脂組成物。
- 前記樹脂は、アルカリ可溶性樹脂を含む、請求項1~8のいずれか1項に記載の樹脂組成物。
- 前記色材が、有彩色色材、黒色色材、及び近赤外線吸収色材から選ばれる少なくとも1種である、請求項1~9のいずれか1項に記載の樹脂組成物。
- 前記色材が、2種以上の有彩色色材と近赤外線吸収色材とを含むか、あるいは、黒色顔料と近赤外線吸収色材とを含む、請求項1~9のいずれか1項に記載の樹脂組成物。
- 前記色材が有彩色顔料および近赤外線吸収顔料から選ばれる少なくとも1種を含む、請求項1~9のいずれか1項に記載の樹脂組成物。
- さらに、光重合開始剤を含む、請求項1~12のいずれか1項に記載の樹脂組成物。
- さらに、重合性化合物を含む、請求項13に記載の樹脂組成物。
- 前記樹脂組成物は、ガラス基板に塗布し100℃で120秒加熱して膜厚0.6μmの膜を形成した際に、前記膜は、波長400~1100nmの透過率の最大値が70%以上で、最小値が30%以下である、請求項1~14のいずれか1項に記載の樹脂組成物。
- フォトリソグラフィ法でのパターン形成用である、請求項9、13または14のいずれか1項に記載の樹脂組成物。
- カラーフィルタの画素形成用である、請求項1~16のいずれか1項に記載の樹脂組成物。
- 固体撮像素子用である、請求項1~17のいずれか1項に記載の樹脂組成物。
- 請求項1~18のいずれか1項に記載の樹脂組成物から得られる膜。
- 請求項19に記載の膜を含むカラーフィルタ。
- 請求項19に記載の膜を含む固体撮像素子。
- 請求項19に記載の膜を含む画像表示装置。
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