WO2015182278A1 - 着色組成物、膜、カラーフィルタ、パターン形成方法、カラーフィルタの製造方法、固体撮像素子および赤外線センサ - Google Patents
着色組成物、膜、カラーフィルタ、パターン形成方法、カラーフィルタの製造方法、固体撮像素子および赤外線センサ Download PDFInfo
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Images
Classifications
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- H01L27/14—Devices consisting of a plurality of semiconductor or other solid-state components formed in or on a common substrate including semiconductor components sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation and specially adapted either for the conversion of the energy of such radiation into electrical energy or for the control of electrical energy by such radiation
- H01L27/144—Devices controlled by radiation
- H01L27/146—Imager structures
- H01L27/14601—Structural or functional details thereof
- H01L27/14625—Optical elements or arrangements associated with the device
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L27/00—Devices consisting of a plurality of semiconductor or other solid-state components formed in or on a common substrate
- H01L27/14—Devices consisting of a plurality of semiconductor or other solid-state components formed in or on a common substrate including semiconductor components sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation and specially adapted either for the conversion of the energy of such radiation into electrical energy or for the control of electrical energy by such radiation
- H01L27/144—Devices controlled by radiation
- H01L27/146—Imager structures
- H01L27/14643—Photodiode arrays; MOS imagers
- H01L27/14649—Infrared imagers
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L27/00—Devices consisting of a plurality of semiconductor or other solid-state components formed in or on a common substrate
- H01L27/14—Devices consisting of a plurality of semiconductor or other solid-state components formed in or on a common substrate including semiconductor components sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation and specially adapted either for the conversion of the energy of such radiation into electrical energy or for the control of electrical energy by such radiation
- H01L27/144—Devices controlled by radiation
- H01L27/146—Imager structures
- H01L27/14683—Processes or apparatus peculiar to the manufacture or treatment of these devices or parts thereof
- H01L27/14685—Process for coatings or optical elements
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/10—Esters
- C08F222/1006—Esters of polyhydric alcohols or polyhydric phenols
- C08F222/106—Esters of polycondensation macromers
Definitions
- the present invention relates to a coloring composition.
- the coloring composition preferably used for formation of a color filter.
- the present invention also relates to a pattern forming method using a colored composition and a method for producing a color filter.
- Color filters are indispensable components for solid-state image sensors and liquid crystal displays.
- color filters for solid-state imaging devices are required to improve color separation and color reproducibility.
- Such a color filter is formed with a plurality of colored regions. For example, it is formed with red, green, and blue colored regions (hereinafter also referred to as “colored patterns” or “colored pixels”).
- a coloring pattern first, in the first hue, a coloring composition having a colorant of red, green, or blue is applied, and is colored by performing exposure, development, and heat treatment as necessary. After the pattern is formed, the same coating, exposure, development, and heat treatment processes as necessary are repeated in the second hue and the third hue.
- Patent Document 1 discloses a resin black matrix having a maximum light transmittance of 1% or less in a wavelength range of 400 to 700 nm and an average light transmittance of 60% or more in a wavelength range of 850 to 3000 nm. .
- Sensing using near infrared rays is utilized in various applications.
- Near-infrared light has a longer wavelength than visible light, so it is difficult to scatter and can be used for distance measurement and three-dimensional measurement.
- near infrared rays are used for proximity sensors, motion sensors, and the like.
- near infrared rays are invisible to humans and animals, even if the subject is illuminated with a near infrared light source at night, the subject will not be noticed. It can also be used for shooting without stimulating.
- development of a color filter capable of transmitting near-infrared light with less visible light-derived noise is desired.
- a colored composition capable of forming a film capable of transmitting near-infrared rays with little visible light-derived noise is applied and cured to form a film. It was found that wrinkles are likely to occur on the surface. It was also found that wrinkles are likely to occur on the surface as the film thickness is increased.
- an object of the present invention is to provide a coloring composition that can transmit near infrared rays with less visible light-derived noise and can form a film with suppressed wrinkles. Moreover, it aims at providing the film
- the content of the polymerizable compound in the coloring composition, the ratio of the mass of the colorant and the mass of the polymerizable compound are adjusted to the predetermined ranges described later, respectively.
- the present invention is as follows. ⁇ 1> A coloring composition comprising a colorant, a polymerizable compound, and a resin, wherein a ratio P / M between the mass P of the colorant and the mass M of the polymerizable compound is 0.05 to 0.35.
- the content of the polymerizable compound in the total solid content of the colored composition is 25 to 65% by mass, the minimum absorbance A of the colored composition in the wavelength range of 400 nm to less than 580 nm, and the wavelength of 580 nm to 770 nm.
- the ratio A / B with the minimum absorbance B in the following range is 0.3 to 3, the minimum absorbance C in the wavelength range from 400 nm to 750 nm, and the maximum absorbance in the wavelength range from 850 nm to 1300 nm.
- the coloring composition whose ratio C / D with the value D is 5 or more.
- a coloring composition comprising a colorant and a polymerizable compound, wherein a ratio P / M between the mass P of the colorant and the mass M of the polymerizable compound is 0.05 to 0.35,
- the content of the polymerizable compound in the total solid content of the coloring composition is 25 to 65% by mass
- the colorant contains at least a yellow colorant and a blue colorant, and the mass ratio of the yellow colorant to the total amount of the colorant
- the yellow colorant / total colorant is 0.1 to 0.5
- the blue colorant / total colorant is 0.1 to 0.6, which is the mass ratio of the blue colorant to the total amount of colorant.
- the colorant further contains a red colorant and a purple colorant, and the red colorant / total colorant in a mass ratio of the red colorant to the total amount of the colorant is 0.1 to 0.5, yellow
- the yellow colorant / total colorant which is the mass ratio of the colorant to the total amount of colorant, is 0.1 to 0.4
- the blue colorant / total colorant which is the mass ratio of the blue colorant to the total amount of colorant, is 0.
- the colored composition according to ⁇ 3> wherein the purple colorant / total colorant, which is a mass ratio of the purple colorant to the total amount of the colorant, is 0.01 to 0.3.
- ⁇ 5> The colored composition according to any one of ⁇ 1> to ⁇ 4>, wherein the colorant includes a blue pigment, a red pigment, a yellow pigment, and a purple pigment.
- the polymerizable compound contains a polymerizable compound having an alkyleneoxy chain containing two or more alkyleneoxy groups as repeating units.
- the polymerizable compound is any one of ⁇ 1> to ⁇ 6>, wherein a value obtained by dividing the molecular weight value of the polymerizable compound by the number of polymerizable groups contained in the polymerizable compound is 100 to 300.
- the coloring composition as described in.
- ⁇ 8> When a film having a dried film thickness of 12.0 ⁇ m is formed, the maximum transmittance in the wavelength range of 400 to 780 nm is 15% or less, and the transmittance at a wavelength of 850 nm is 80% or more.
- ⁇ 9> The colored composition according to any one of ⁇ 1> to ⁇ 8>, wherein the viscosity at 25 ° C. is 100 to 150 mP ⁇ s.
- ⁇ 11> A color filter having the film according to ⁇ 10>.
- ⁇ 12> a step of applying the colored composition according to any one of ⁇ 1> to ⁇ 9> on a support to form a colored composition layer, a step of exposing the colored composition layer in a pattern, Forming a colored pattern by developing and removing an unexposed portion.
- a method for producing a color filter comprising the pattern forming method according to ⁇ 12>.
- ⁇ 14> A solid-state imaging device having the color filter according to ⁇ 11> or the color filter obtained by the method for producing a color filter according to ⁇ 13>.
- ⁇ 15> An infrared sensor having the color filter according to ⁇ 11> or the color filter obtained by the method for producing a color filter according to ⁇ 13>.
- the present invention it is possible to provide a coloring composition capable of transmitting a near infrared ray with less visible light-derived noise and capable of forming a film in which wrinkles are suppressed.
- membrane using this coloring composition, a color filter, the pattern formation method, the manufacturing method of a color filter, a solid-state image sensor, and an infrared sensor can be provided.
- the total solid content refers to the total mass of components excluding the solvent from the total composition of the colored composition.
- solid content means solid content in 25 degreeC.
- the viscosity refers to a viscosity at 25 ° C.
- 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).
- radiation means, for example, an emission line spectrum of a mercury lamp, far ultraviolet rays represented by an excimer laser, extreme ultraviolet rays (EUV light), X-rays, electron beams, and the like.
- light means actinic rays or radiation.
- exposure means not only exposure with a deep ultraviolet ray, an X-ray, EUV light, etc. represented by a mercury lamp and an excimer laser, but also drawing with a particle beam such as an electron beam or an ion beam unless otherwise specified. Are also included in the exposure.
- (meth) acrylate represents both and / or acrylate and methacrylate
- (meth) acryl represents both and / or acrylic and “(meth) acrylic”.
- Acryloyl represents both and / or acryloyl and methacryloyl.
- “monomer” and “monomer” are synonymous.
- “Monomer” is distinguished from “oligomer” and “polymer”, and refers to a compound having a weight average molecular weight of 2,000 or less.
- the polymerizable compound means a compound having a polymerizable functional group, and may be a monomer or a polymer.
- the polymerizable functional group refers to a group that participates in a polymerization reaction.
- Me in the chemical formula represents a methyl group
- Et represents an ethyl group
- Pr represents a propyl group
- Bu represents a butyl group
- Ph represents a phenyl group.
- the term “process” is not limited to an independent process, and is included in the term if the intended action of the process is achieved even when it cannot be clearly distinguished from other processes. It is.
- a weight average molecular weight and a number average molecular weight are defined as a polystyrene conversion value by gel permeation chromatography (GPC) measurement.
- the weight average molecular weight (Mw) and the number average molecular weight (Mn) are, for example, HLC-8220 (manufactured by Tosoh Corporation), and TSKgel Super AWM-H (manufactured by Tosoh Corporation, 6) as a column.
- 0.0 mm ID ⁇ 15.0 cm can be determined by using a 10 mmol / L lithium bromide NMP (N-methylpyrrolidinone) solution as the eluent.
- “Pigment” means an insoluble coloring compound that is difficult to dissolve in a solvent. Typically, it means a dye compound that exists in a dispersed state as particles in the composition.
- the pigment preferably has a solubility at 25 ° C. of 0.1 g / 100 g Solvent or less in both propylene glycol monomethyl ether acetate and water.
- a first aspect of the coloring composition of the present invention includes a coloring agent and a polymerizable compound, and a ratio P / M of the mass P of the coloring agent to the mass M of the polymerizable compound is 0.05 to 0.35.
- the content of the polymerizable compound in the total solid content of the colored composition is 25 to 65% by mass, the minimum absorbance A of the colored composition in the wavelength range of 400 nm to less than 580 nm, and the wavelength of 580 nm or more.
- the ratio A / B to the minimum absorbance B in the range of 770 nm or less is 0.3 to 3, the minimum absorbance C in the wavelength range of 400 nm to 750 nm, and the absorbance in the wavelength range of 850 nm to 1300 nm.
- the ratio C / D with the maximum value D is 5 or more.
- the absorbance ratio A / B described above is preferably 0.4 to 2.5, and more preferably 0.5 to 2. Further, the above-described absorbance ratio C / D is preferably 10 or more, and more preferably 50 or more.
- the absorbance ratios A / B and C / D of the coloring composition By setting the absorbance ratios A / B and C / D of the coloring composition within the above ranges, it is easy to form a film capable of transmitting near infrared rays with less visible light-derived noise.
- the means for achieving the absorbance is not particularly defined, it is preferable to obtain the absorbance by adjusting the type and content of each colorant.
- Other achievement means include, for example, combining materials that reflect a specific wavelength.
- the absorbance A ⁇ at a certain wavelength ⁇ is defined by the following equation (1).
- a ⁇ ⁇ log (T ⁇ ) (1)
- a ⁇ is the absorbance at wavelength ⁇
- T ⁇ is the transmittance at wavelength ⁇ .
- the absorbance value of the colored composition may be a value measured in the state of a solution, or may be a value of a film formed using the colored composition.
- a colored composition is applied onto a glass substrate by a method such as spin coating so that the film thickness after drying becomes a predetermined film thickness, and then a hot plate at 100 ° C. for 120 seconds. It is preferable to use a membrane prepared by drying with The film thickness of the film can be measured by using a stylus type surface shape measuring instrument (DEKTAK150 manufactured by ULVAC) for the substrate having the film.
- the absorbance can be measured using a conventionally known spectrophotometer.
- the measurement conditions for absorbance are not particularly limited.
- the measurement is preferably performed under conditions adjusted so that the minimum absorbance A in the wavelength range of 400 nm to less than 580 nm is 0.1 to 3.0.
- the measurement error can be further reduced.
- the method for adjusting the minimum absorbance A in the wavelength range of 400 nm or more and less than 580 nm to be 0.1 to 3.0 For example, when measuring the absorbance in a liquid state, a method of adjusting the optical path length of the sample cell can be mentioned. Moreover, when measuring a light absorbency in the state of a film
- the second embodiment of the coloring composition of the present invention comprises a colorant and a polymerizable compound, and the ratio P / M of the mass P of the colorant to the mass M of the polymerizable compound is 0.05 to 0. 35, the content of the polymerizable compound in the total solid content of the coloring composition is 25 to 65% by mass, and the coloring agent includes at least a yellow coloring agent and a blue coloring agent, and the coloring of the yellow coloring agent
- the yellow colorant / total colorant which is a mass ratio to the total amount of the colorant, is 0.1 to 0.5
- the blue colorant / total colorant which is the mass ratio of the blue colorant to the total amount of the colorant, is 0.1 to 0. .6.
- the colorant further includes a red colorant and a purple colorant
- the red colorant / total colorant in a mass ratio of the red colorant to the total amount of colorant is 0.1 to 0.5 (preferably 0.1 to 0.4), and the weight ratio of the yellow colorant to the total amount of the colorant is 0.1 to 0.4, and the blue colorant is based on the total amount of the colorant.
- the ratio of blue colorant / total colorant is 0.2 to 0.6
- the ratio of purple colorant / total colorant is 0.01 to 0.3. It is preferable.
- the ratio of the yellow colorant and the blue colorant to the total amount of the colorant preferably the ratio of the yellow colorant, the blue colorant, the red colorant, and the purple colorant to the total amount of the colorant within the above ranges, it becomes visible. It is easy to form a film that can transmit near-infrared rays with little noise derived from light.
- the color composition of the first aspect wherein the absorbance ratio A / B is 0.3 to 3 and the absorbance ratio C / D is 5 or more, and the yellow colorant and the blue colorant
- the colored composition of the second embodiment contained in the above-described range can form a film that can transmit near infrared rays with little visible light-derived noise.
- the ratio P / M of the mass P of the colorant to the mass M of the polymerizable compound is 0.05 to 0.35, and polymerization in the total solid content of the colored composition is performed.
- the content of the active compound is 25 to 65% by mass, a film in which wrinkles are suppressed can be formed. The reason why such an effect is obtained is presumed to be as follows.
- a colored composition capable of forming a film capable of transmitting near-infrared rays with less visible light-derived noise has a low permeability to i-line and the like, and therefore tends to have a lower curability inside the film than the film surface. It is in. For this reason, since the film
- the ratio P / M between the mass P of the colorant and the mass M of the polymerizable compound is 0.05 to 0.35, and the content of the polymerizable compound in the total solid content of the colored composition is 25 to 65 mass%.
- the curability of the film surface and the inside of the film of the colored composition applied in the form of a film was almost uniform, and it is presumed that a film in which wrinkles were suppressed could be formed.
- each component of the coloring composition of the present invention will be described.
- the coloring composition of the present invention contains a colorant.
- the colorant may be a pigment or a dye. Preferably, it is a pigment because it has high resistance to heat and light.
- the colorant preferably has a pigment content of 95% by mass or more, more preferably 97% by mass or more, and still more preferably 99% by mass or more based on the total amount of the colorant. .
- the pigment is preferably an organic pigment, and examples thereof include the following. However, the present invention is not limited to these.
- 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, etc. (Orange pigment) C. I.
- black pigments such as carbon black (CI Pigment Black 7), titanium black, iron, Examples thereof include metal oxides such as cobalt, aluminum, cadmium, lead, copper, titanium, magnesium, chromium, zinc, and antimony, and composite oxides of the above metals.
- the well-known dye currently used for the color filter can be used.
- the chemical structure includes pyrazole azo, anilino azo, triphenyl methane, anthraquinone, anthrapyridone, benzylidene, oxonol, pyrazolotriazole azo, pyridone azo, cyanine, phenothiazine, pyrrolopyrazole azomethine, Xanthene, phthalocyanine, benzopyran, indigo, and pyromethene dyes can be used. Moreover, you may use the multimer of these dyes.
- an acid dye and / or a derivative thereof may be suitably used.
- direct dyes, basic dyes, mordant dyes, acid mordant dyes, azoic dyes, disperse dyes, oil-soluble dyes, food dyes, and / or derivatives thereof can also be used effectively.
- acid alizarin violet N acid black 1, 2, 24, 48, acid blue 1,7,9,15,18,23,25,27,29,40-45,62,70,74,80,83,86,87,90,92,103,112,113,120, 129, 138, 147, 158, 171, 182, 192, 243, 324: 1, acid chroma violet K, acid Fuchsin; acid green 1,3,5,9,16,25,27,50, acid orange 6, 7, 8, 10, 12, 50, 51, 52, 56, 63, 74, 95, acid red 1,4,8,14,17,18,26,27,29,31,34,35,37,42,44,50,51,52,57,66,73,80,87,88, 91, 92, 94, 97, 103, 111, 114, 129, 133, 134, 138, 143, 145, 150, 151, 158, 176,
- the acid dye derivatives described above are also preferably used.
- azo, xanthene and phthalocyanine acid dyes are also preferred.
- I. Solvent Blue 44, 38; C.I. I. Solvent orange 45; Rhodamine B, Rhodamine 110 and other acid dyes and derivatives of these dyes are also preferably used.
- the dye triarylmethane, anthraquinone, azomethine, benzylidene, oxonol, cyanine, phenothiazine, pyrrolopyrazole azomethine, xanthene, phthalocyanine, benzopyran, indigo, pyrazoleazo
- a colorant selected from anilinoazo, pyrazolotriazole azo, pyridone azo, and anthrapyridone pyromethene is preferable. Further, pigments and dyes may be used in combination.
- Bisbenzofuranone pigments can also be used.
- the bisbenzofuranone pigment include those described in JP-A-2012-528448, JP-A-2010-534726, JP-A-2012-515234, and the like.
- the azomethine pigment include those described in JP-A-1-170601, JP-A-2-34664, etc., and can be obtained, for example, as “Chromofine Black A1103” manufactured by Dainichi Seika Co., Ltd.
- the azo dye is not particularly limited, and preferred examples include compounds represented by the following formula (A-1).
- the colorant it is preferable to include at least a yellow colorant and a blue colorant, and it is more preferable to include a red colorant, a yellow colorant, a blue colorant, and a purple colorant.
- the colorant preferably contains a pigment, more preferably contains a yellow pigment and a blue pigment, and more preferably contains a red pigment, a yellow pigment, a blue pigment, and a purple pigment.
- red pigments include C.I. I. Pigment Red 254 is preferred.
- yellow pigments include C.I. I. Pigment Yellow 139 is preferred.
- the blue pigment include C.I. I. Pigment Blue 15: 6 is preferred.
- Purple pigments include, for example, C.I. I. Pigment Violet 23 is preferred.
- the colorant preferably contains at least one selected from bisbenzofuranone pigments, azomethine pigments, perylene pigments, and azo dyes. It is more preferable to contain one or more selected from pigments, azomethine pigments and perylene pigments.
- the mass ratio of the red colorant to the total amount of the colorant is 0.1 to 0.5 (more preferably 0.1 to 0.4), the mass ratio of the yellow colorant to the total amount of the colorant is 0.1 to 0.4, the mass ratio of the blue colorant to the total amount of the colorant is 0.2 to 0.6, and the purple color
- the mass ratio of the colorant to the total amount of the colorant is preferably 0.01 to 0.3.
- the mass ratio of the red colorant to the total amount of colorant is 0.3 to 0.5, the mass ratio of the yellow colorant to the total amount of colorant is 0.1 to 0.3, and the blue colorant is based on the total amount of colorant.
- the mass ratio is 0.3 to 0.5, and the mass ratio of the purple colorant to the total amount of the colorant is 0.01 to 0.2.
- the ratio A / B between the minimum value A of the absorbance in the wavelength range from 400 nm to less than 580 nm and the minimum value B in the wavelength range from 580 nm to 770 nm is 0.3 to 3
- a colored composition having a ratio C / D of 5 or more between the minimum absorbance C in the wavelength range of 400 nm to 750 nm and the maximum absorbance D in the wavelength range of 850 nm to 1300 nm can be obtained.
- the content of the colorant is preferably 1 to 60% by mass, more preferably 3 to 50% by mass, and more preferably 3 to 20% by mass based on the total solid content of the colored composition. % Is more preferable.
- Pigment dispersion when a pigment is used as the colorant, it is preferably used in the form of a pigment dispersion in which the pigment is dispersed together with a resin, an organic solvent, a pigment derivative and the like.
- the composition of the pigment dispersion and the method for preparing the pigment dispersion are described in detail below.
- the average particle diameter of the pigment is preferably 20 to 300 nm, more preferably 25 to 250 nm, and still more preferably 30 to 200 nm.
- the “average particle size” means the average particle size of secondary particles in which primary particles (single crystallites) of the pigment are aggregated.
- the average particle diameter of the pigment is obtained by observing with a scanning electron microscope (SEM) or a transmission electron microscope (TEM), measuring 100 particle sizes in a portion where the particles are not aggregated, and calculating an average value. be able to.
- the particle size distribution of the secondary particles of the pigment (hereinafter, simply referred to as “particle size distribution”) is 70% by mass or more, preferably 80% by mass, of secondary particles falling into (average particle size ⁇ 100) nm. % Or more is preferable.
- the particle size distribution is measured using the scattering intensity distribution.
- the pigment having the average particle size and particle size distribution described above is obtained by mixing and dispersing a commercially available pigment, preferably with a resin and an organic solvent, and using a pulverizer such as a bead mill or a roll mill while pulverizing. Can be prepared.
- the pigment thus obtained is usually in the form of a pigment dispersion.
- a fine and sized pigment it is preferable to use a fine and sized pigment. Refinement of the pigment is achieved by preparing a high-viscosity liquid composition together with the pigment, the organic solvent, and the water-soluble inorganic salts, and applying a stress and grinding using a wet pulverizer.
- a water-soluble organic solvent is preferable.
- the water-soluble organic solvent include methanol, ethanol, isopropanol, n-propanol, isobutanol, n-butanol, ethylene glycol, diethylene glycol, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, propylene glycol, propylene glycol monomethyl.
- examples include ether acetate.
- the amount of the water-soluble organic solvent used in the miniaturization step is preferably 50 to 300 parts by mass, more preferably 100 to 200 parts by mass with respect to 100 parts by mass of the pigment.
- other solvents include benzene, toluene, xylene, ethylbenzene, chlorobenzene, nitrobenzene, aniline, pyridine, quinoline, tetrahydrofuran, dioxane, ethyl acetate, isopropyl acetate, butyl acetate, hexane, heptane, octane, nonane, decane, and undecane.
- water-soluble inorganic salts used in the pigment refinement process examples include sodium chloride, potassium chloride, calcium chloride, barium chloride, sodium sulfate and the like.
- the amount of the water-soluble inorganic salt used in the miniaturization step is preferably 1 to 50 parts by mass, more preferably 1 to 10 parts by mass with respect to 1 part by mass of the pigment.
- the operating condition when the apparatus is a kneader is the rotational speed of the blade in the apparatus. Is preferably from 10 to 200 rpm, and a relatively large biaxial rotation ratio is preferable because of a high grinding effect.
- the operation time is preferably 1 to 8 hours together with the dry grinding time, and the internal temperature of the apparatus is preferably 50 to 150 ° C.
- the water-soluble inorganic salt as a grinding medium preferably has a grinding particle size of 5 to 50 ⁇ m, a sharp particle size distribution, and a spherical shape.
- Resins (dispersed resin) that can be used in the preparation of pigment dispersions include polymer dispersants [for example, resins having amine groups (polyamideamine and salts thereof), oligoimine resins, polycarboxylic acids and salts thereof, high molecular weight Unsaturated acid ester, modified polyurethane, modified polyester, modified poly (meth) acrylate, (meth) acrylic copolymer, naphthalenesulfonic acid formalin condensate], polyoxyethylene alkyl phosphate ester, polyoxyethylene alkyl amine, alkanol Surfactants such as amines can be mentioned.
- polymer dispersants for example, resins having amine groups (polyamideamine and salts thereof), oligoimine resins, polycarboxylic acids and salts thereof, high molecular weight Unsaturated acid ester, modified polyurethane, modified polyester, modified poly (meth) acrylate, (meth) acrylic copolymer, naphthal
- the polymer dispersant can be further classified into a linear polymer, a terminal-modified polymer, a graft polymer, and a block polymer from the structure thereof.
- the terminal-modified polymer having an anchor site to the pigment surface include a polymer having a phosphate group at the terminal described in JP-A-3-112992, JP-A-2003-533455, and the like.
- examples thereof include polymers having a sulfonic acid group at the terminal end described in JP-A-273191 and the like, and polymers having a partial skeleton of an organic dye and a heterocyclic ring described in JP-A-9-77994.
- polymers having two or more pigment surface anchor sites (acid groups, basic groups, organic dye partial skeletons, heterocycles, etc.) introduced at the polymer ends described in JP-A-2007-277514 are also available. It is preferable because of excellent dispersion stability.
- the graft polymer having an anchor site to the pigment surface include poly (lower alkyleneimine) described in JP-A-54-37082, JP-A-8-507960, JP-A-2009-258668, and the like.
- reaction product of polyester a reaction product of polyallylamine and polyester described in JP-A-9-169821 and the like, a macromonomer described in JP-A-10-339949, JP-A-2004-37986 and the like, Copolymers with nitrogen atom monomers, graft-type polymers having partial skeletons or heterocyclic rings of organic dyes described in JP-A-2003-238837, JP-A-2008-9426, JP-A-2008-81732, etc.
- a known macromonomer can be used as the macromonomer used when the graft polymer having an anchor site to the pigment surface is produced by radical polymerization.
- macromonomer AA-6 polymethyl methacrylate whose terminal group is a methacryloyl group
- AS-6 polystyrene whose terminal group is a methacryloyl group
- AN-6S terminal group is methacryloyl
- AB-6 polybutyl acrylate whose terminal group is a methacryloyl group
- Plaxel FM5 manufactured by Daicel Chemical Industries, Ltd.
- polyester macromonomer described in JP-A-2-272009 examples include a polyester-based macromonomer that is particularly excellent in flexibility and solvophilicity is particularly preferable from the viewpoint of dispersibility of the pigment, dispersion stability, and developability exhibited by the coloring composition using the pigment dispersion.
- a polyester macromonomer represented by a polyester macromonomer described in JP-A-2-272009 is most preferred.
- block type polymer having an anchor site to the pigment surface block type polymers described in JP-A Nos. 2003-49110 and 2009-52010 are preferable.
- a graft copolymer containing a structural unit represented by any one of the following formulas (1) to (4) can also be used.
- X 1 , X 2 , X 3 , X 4 and X 5 each independently represent a hydrogen atom or a monovalent organic group.
- a hydrogen atom or an alkyl group having 1 to 12 carbon atoms is preferable, a hydrogen atom or a methyl group is more preferable, and a methyl group is particularly preferable.
- W 1 , W 2 , W 3 , and W 4 each independently represent an oxygen atom or NH, preferably an oxygen atom.
- R 3 represents a branched or straight chain alkylene group (preferably having 1 to 10 carbon atoms, more preferably 2 or 3), and —CH 2 —CH (CH 3 ) from the viewpoint of dispersion stability.
- a group represented by — or a group represented by —CH (CH 3 ) —CH 2 — is preferred.
- Y 1 , Y 2 , Y 3 and Y 4 are each independently a divalent linking group and are not particularly limited in structure.
- the description of paragraph numbers 0025 to 0069 of JP2012-255128A can be referred to, and the above contents are incorporated in this specification.
- Specific examples of the graft copolymer include the following. Further, resins described in JP-A-2012-255128, paragraphs 0072 to 0094 can be used.
- an oligoimine resin containing a nitrogen atom in at least one of the main chain and the side chain can also be used.
- the oligoimine resin includes a repeating unit having a partial structure X having a functional group of pKa14 or less, a side chain containing a side chain Y having 40 to 10,000 atoms, and at least a main chain and a side chain.
- a resin having a basic nitrogen atom on one side is preferred.
- the basic nitrogen atom is not particularly limited as long as it is a basic nitrogen atom.
- the oligoimine resin includes, for example, a repeating unit represented by the following formula (I-1), a repeating unit represented by the formula (I-2), and / or a repeating unit represented by the formula (I-2a). And a resin containing a unit.
- R 1 and R 2 each independently represents a hydrogen atom, a halogen atom or an alkyl group (preferably having 1 to 6 carbon atoms).
- a independently represents an integer of 1 to 5; * Represents a connecting part between repeating units.
- R 8 and R 9 have the same meaning as R 1 .
- L is a single bond, an alkylene group (preferably having 1 to 6 carbon atoms), an alkenylene group (preferably having 2 to 6 carbon atoms), an arylene group (preferably having 6 to 24 carbon atoms), a heteroarylene group (having 1 to 6 carbon atoms).
- an imino group preferably having a carbon number of 0 to 6
- an ether group preferably having a carbon number of 0 to 6
- a thioether group preferably having a carbonyl group, or a combination group thereof.
- a single bond or —CR 5 R 6 —NR 7 — is preferable.
- R 5 R 6 each independently represents a hydrogen atom, a halogen atom, or an alkyl group (preferably having 1 to 6 carbon atoms).
- R 7 is a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.
- L a is a structural site to form a ring structure together with CR 8 CR 9 and N, be combined with the carbon atoms of CR 8 CR 9 is a structural site that form a non-aromatic heterocyclic ring having 3 to 7 carbon atoms preferable. More preferably, it is a structural part that forms a 5- to 7-membered non-aromatic heterocyclic ring by combining the carbon atom of CR 8 CR 9 and N (nitrogen atom), more preferably a 5-membered non-aromatic heterocyclic ring. It is a structural part to be formed and is particularly preferably a structural part to form pyrrolidine. This structural part may further have a substituent such as an alkyl group.
- X represents a group having a functional group of pKa14 or less.
- Y represents a side chain having 40 to 10,000 atoms.
- the resin oligoimine-based resin
- the resin further contains, as a copolymerization component, one or more selected from repeating units represented by formula (I-3), formula (I-4), and formula (I-5) You may do it.
- the resin contains such a repeating unit, the dispersion performance of the pigment can be further improved.
- R 1 , R 2 , R 8 , R 9 , L, La, a and * are as defined in the formulas (I-1), (I-2) and (I-2a).
- Ya represents a side chain having an anionic group having 40 to 10,000 atoms.
- the repeating unit represented by the formula (I-3) is reacted by adding an oligomer or polymer having a group that reacts with an amine to form a salt to a resin having a primary or secondary amino group in the main chain. Can be formed.
- oligoimine-based resin described above, the description of paragraph numbers 0102 to 0166 in JP 2012-255128 A can be referred to, and the above contents are incorporated in this specification. Specific examples of the oligoimine resin include the following. Also, resins described in paragraph numbers 0168 to 0174 of JP 2012-255128 A can be used.
- the resin is also available as a commercial product. Specific examples of such resins include “Disperbyk-101 (polyamidoamine phosphate), 107 (carboxylic acid ester), 110, 111 (copolymer containing an acid group) manufactured by BYK Chemie.
- DA-705, DA-725 “ Demol RN, N (Naphthalenesulfonic acid formalin polycondensate), MS, C, SN-B (aromatic sulfonic acid formalin polycondensate) ”manufactured by Kao Corporation,“ Homogenol L- 18 (polymer polycarboxylic acid) "," Emulgen 920, 930, 935, 985 ( "Reoxyethylene nonylphenyl ether)", “Acetamine 86 (stearylamine acetate)”, “Solsperse 5000 (phthalocyanine derivative), 22000 (azo pigment derivative), 13240 (polyesteramine), 3000, 17000” manufactured by Nippon Lubrizol Co., Ltd.
- Nonionic surfactants anionic surfactants such as “W004, W005, W017”, “EFKA-46, EFKA-47, EFKA-47EA, EFKA polymer 100, EFKA polymer 400, EFKA polymer manufactured by Morishita Sangyo Co., Ltd.
- Disperse Aid 6 Disperse Aid 8
- Disperse Aid 15 Disperse Aid 9100
- Polymer dispersants such as “ADEKA Pluronic L31, F38, L42, L44, L61, L64, F68, L72, P95, F77, P84, F87, P94, L101, P103, F108, L121, P manufactured by ADEKA Corporation -123 ",” Ionet S-20 "manufactured by Sanyo Kasei Co., Ltd., and the like.
- Alkali-soluble resins include (meth) acrylic acid copolymer, itaconic acid copolymer, crotonic acid copolymer, maleic acid copolymer, partially esterified maleic acid copolymer, etc., and carboxylic acid in the side chain.
- the acidic cellulose derivative include a resin having a hydroxyl group modified with an acid anhydride, and a (meth) acrylic acid copolymer is particularly preferable.
- An alkali-soluble resin containing is also preferred.
- the content of the resin (dispersion resin) in the pigment dispersion is preferably 1 to 100 parts by mass with respect to 100 parts by mass of the pigment.
- the upper limit is preferably 80 parts by mass or less, more preferably 70 parts by mass or less, and more preferably 60 parts by mass or less.
- the lower limit is preferably 5 parts by mass or more, and more preferably 10 parts by mass or more.
- the amount of pigment means the total amount of pigment contained in the total amount of colorant.
- the pigment dispersion preferably further contains a pigment derivative.
- the pigment derivative is a compound having a structure in which a part of the pigment is substituted with an acidic group, a basic group, a phthalimidomethyl group, or the like.
- the pigment derivative preferably contains a pigment derivative having an acidic group or a basic group from the viewpoint of dispersibility and dispersion stability.
- pigments for constituting the pigment derivative diketopyrrolopyrrole pigment, azo pigment, phthalocyanine pigment, anthraquinone pigment, quinacridone pigment, dioxazine pigment, perinone pigment, perylene pigment, thioindigo pigment, isoindolinone pigment, isoindolinone pigment, examples include quinophthalone pigments, selenium pigments, and metal complex pigments.
- a sulfonic acid group, a carboxylic acid group, and its quaternary ammonium salt are preferable, a carboxylic acid group and a sulfonic acid group are more preferable, and a sulfonic acid group is especially preferable.
- the basic group possessed by the pigment derivative is preferably an amino group, particularly preferably a tertiary amino group.
- a quinoline pigment derivative, a benzimidazolone pigment derivative and an isoindoline pigment derivative are preferable, and a quinoline pigment derivative and a benzimidazolone pigment derivative are particularly preferable.
- the content of the pigment derivative in the pigment dispersion is preferably 1 to 50% by mass, more preferably 3 to 30% by mass, based on the total mass of the pigment. Only one pigment derivative may be used, or two or more pigment derivatives may be used in combination.
- the pigment dispersion preferably contains an organic solvent.
- the organic solvent is selected depending on the solubility of each component contained in the pigment dispersion and the coating property when the pigment dispersion is applied to the coloring composition.
- esters, ethers, ketones, and aromatic hydrocarbons are used as the organic solvent.
- the organic solvent which can be contained in the coloring composition mentioned later.
- the content of the organic solvent in the pigment dispersion is preferably 50 to 95% by mass, more preferably 70 to 90% by mass.
- the coloring composition of the present invention contains a polymerizable compound.
- the polymerizable compound is a compound having a polymerizable group, and a known polymerizable compound that can be polymerized by a radical can be used.
- a group having an ethylenically unsaturated bond is preferable. Examples of the group having an ethylenically unsaturated bond include vinyl group, allyl group, methallyl group, acryloyl group, methacryloyl group, allyloxycarbonyl group, and methallyloxycarbonyl group.
- the polymerizable compound may be in any chemical form such as, for example, a monomer, a prepolymer (ie, a dimer, a trimer and an oligomer), or a mixture thereof and a multimer thereof.
- the polymerizable compound is preferably a compound having one or more polymerizable groups, and more preferably a compound having two or more polymerizable groups.
- a polyfunctional polymerizable compound having 4 or more functional groups having 4 or more polymerizable groups is preferable, and a polyfunctional polymerizable compound having 5 or more functional groups is more preferable.
- the molecular weight of the polymerizable compound is preferably 100 to 2000, more preferably 1000 to 2000.
- the value obtained by dividing the molecular weight value of the polymerizable compound by the number of polymerizable groups contained in the polymerizable compound is preferably 100 to 300, more preferably 200 to 300. According to this aspect, since the crosslinking density of the polymerizable compound is moderate, the generation of wrinkles can be more effectively suppressed.
- the molecular weight value of the polymerizable compound is a theoretical value obtained from the molecular structure when the polymerizable compound is a monomer, and means a weight average molecular weight when the polymerizable compound is an oligomer or a polymer.
- Polymerizable compound having an alkyleneoxy chain ⁇ Polymerizable compound having an alkyleneoxy chain ⁇ Polymerizable compound having an alkyleneoxy chain ⁇ Polymerizable compound having an alkyleneoxy chain ⁇ Polymerizable compound having an alkyleneoxy chain ⁇ Polymerizable compound having an alkyleneoxy chain ⁇ Polymerizable compound having an alkyleneoxy chain ⁇ Polymerizable compound having an alkyleneoxy chain ⁇ the polymerizable compound having an alkyleneoxy chain containing two or more alkyleneoxy groups as repeating units. Since the polymerizable compound having an alkyleneoxy chain has flexibility, the shrinkage of the film accompanying the curing of the polymerizable compound can be suppressed, and the generation of wrinkles on the film surface can be effectively suppressed.
- the number of repeating units of the alkyleneoxy group is preferably 2 to 30, more preferably 2 to 20, and still more preferably 5 to 15.
- the number of carbon atoms of the alkyleneoxy group is preferably 2 or more, more preferably 2 to 10, still more preferably 2 to 4, and particularly preferably 2.
- the alkyleneoxy group may be either linear or branched, but is preferably linear.
- the alkyleneoxy group is preferably unsubstituted. That is, the alkyleneoxy chain is preferably represented by “— ((CH 2 ) a —O) b —”.
- a is preferably 2 or more, more preferably 2 to 20.
- b is preferably 2 or more, more preferably 2 to 10.
- the polymerizable compound having an alkyleneoxy chain is preferably a polymerizable compound having an ethyleneoxy chain containing two or more ethyleneoxy groups as repeating units. Since the polymerizable compound having an ethyleneoxy chain is particularly excellent in flexibility, generation of wrinkles on the film surface can be more effectively suppressed.
- the polymerizable compound having an alkyleneoxy chain preferably has a cyclic structure. Adhesiveness improves by having a cyclic structure.
- the cyclic structure include an aromatic ring structure, an alicyclic structure, and a heterocyclic structure.
- a heterocyclic structure is preferred.
- the heterocyclic ring is preferably a 5-membered ring or a 6-membered ring.
- the heterocycle is preferably a single ring or a condensed ring, and more preferably a single ring. Examples of the hetero atom constituting the hetero ring include a nitrogen atom, an oxygen atom, and a sulfur atom, and a nitrogen atom is preferable.
- the number of heteroatoms is preferably 1 to 3, more preferably 2 to 3, and particularly preferably 3.
- the polymerizable compound having an alkyleneoxy chain preferably has a partial structure represented by the following general formula (1). * In the formula is a connecting hand.
- Examples of the polymerizable compound having the partial structure include a polymerizable compound represented by the following general formula (1a).
- X 1 ⁇ X 3 each independently represent a hydrogen atom or a polymerizable group, at least one of X 1 ⁇ X 3 represents a polymerizable group.
- the polymerizable group is preferably at least one selected from vinyl group, allyl group, methallyl group, acryloyl group, methacryloyl group, allyloxycarbonyl group, and methallyloxycarbonyl group.
- the plurality of X 1 to X 3 may be the same or different.
- L 1 represents a (1 + n1) -valent linking group
- L 2 represents a (1 + n2) -valent linking group
- L 3 represents a (1 + n3) -valent linking group
- L At least one of 1 to L 3 represents a linking group containing — ((CH 2 ) a —O) b —.
- a represents an integer of 2 or more
- b represents an integer of 2 or more.
- linking group represented by L 1 to L 3 for example, in the case of a divalent linking group, — ((CH 2 ) a —O) b —, — (CH 2 ) c —, —CO—, and — Examples thereof include a group formed by combining one or more selected from NH-.
- a represents an integer of 2 or more, preferably 2 to 10, more preferably 2 to 4, and still more preferably 2.
- b represents an integer of 2 or more, preferably 2 to 30, more preferably 2 to 20, and still more preferably 5 to 15.
- c represents an integer of 1 or more, preferably 1 to 30, more preferably 1 to 20, and still more preferably 1 to 10.
- the linking group represented by L 1 to L 3 is a trivalent or higher linking group, among the groups listed as examples of the divalent linking group described above, a group in which one or more hydrogen atoms have been removed can be used.
- n1 to n3 each independently represents an integer of 1 or more. 1 or 2 is preferred.
- polymerizable compound represented by the general formula (1a) include the following compounds.
- Examples of commercially available polymerizable compounds represented by the general formula (1a) include UA-7200 manufactured by Shin-Nakamura Chemical Co., Ltd.
- polymerizable compound having an alkyleneoxy chain for example, at least one selected from the group of compounds represented by the following general formula (Z-4) or (Z-5) can also be used.
- each E independently represents — ((CH 2 ) y CH 2 O) — or — ((CH 2 ) y CH (CH 3 ) O).
- — Each independently represents an integer of 0 to 10
- each X independently represents an acryloyl group, a methacryloyl group, a hydrogen atom, or a carboxyl group.
- the total number of acryloyl groups and methacryloyl groups is 3 or 4
- each m independently represents an integer of 0 to 10
- at least one of m represents an integer of 2 to 10
- the sum of each m is an integer from 2 to 40.
- the total number of acryloyl groups and methacryloyl groups is 5 or 6, and each n independently represents an integer of 0 to 10, and at least one of n represents an integer of 2 to 10 And the sum of each n is an integer from 2 to 60.
- m is preferably an integer of 0 to 6, and more preferably an integer of 0 to 4.
- the total of each m is preferably an integer of 2 to 40, more preferably an integer of 2 to 16, and particularly preferably an integer of 4 to 8.
- n is preferably an integer of 0 to 6, and more preferably an integer of 0 to 4.
- the total of each n is preferably an integer of 3 to 60, more preferably an integer of 3 to 24, and particularly preferably an integer of 6 to 12.
- — ((CH 2 ) y CH 2 O) — or — ((CH 2 ) y CH (CH 3 ) O) — represents oxygen
- a form in which the end on the atom side is bonded to X is preferred.
- the compounds represented by formula (Z-4) or formula (Z-5) may be used alone or in combination of two or more.
- a form in which all six Xs are acryloyl groups is preferable.
- the compound represented by the general formula (Z-4) or (Z-5) is a ring-opening addition of ethylene oxide or propylene oxide to pentaerythritol or dipentaerythritol, which is a conventionally known process. It can be synthesized from a step of bonding a ring-opening skeleton by a reaction and a step of introducing a (meth) acryloyl group by reacting, for example, (meth) acryloyl chloride with a terminal hydroxyl group of the ring-opening skeleton. Each step is a well-known step, and a person skilled in the art can easily synthesize a compound represented by the general formula (Z-4) or the general formula (Z-5).
- pentaerythritol derivatives and / or dipentaerythritol derivatives are more preferable.
- Specific examples include compounds represented by the following formulas (a) to (f) (hereinafter also referred to as “exemplary compounds (a) to (f)”).
- exemplary compounds (a), (f) b), (e) and (f) are preferred.
- Examples of commercially available polymerizable compounds represented by the general formulas (Z-4) and (Z-5) include SR-494, a tetrafunctional acrylate having four ethyleneoxy chains manufactured by Sartomer, Nippon Kayaku Examples thereof include DPCA-60, which is a hexafunctional acrylate having six pentyleneoxy chains, and TPA-330, which is a trifunctional acrylate having three isobutyleneoxy chains.
- the polymerizable compound used in the colored composition of the present invention preferably contains 50-100% by mass of the above-mentioned polymerizable compound having an alkyleneoxy chain, based on the total amount of the polymerizable compound, and 80-100% by mass. Is more preferable, and 95 to 100% by mass is still more preferable, and it is particularly preferable that it is composed only of a polymerizable compound having an alkyleneoxy chain.
- the colored composition of the present invention may contain a polymerizable compound other than the polymerizable compound having an alkyleneoxy chain (hereinafter referred to as “other polymerizable compound”).
- a polymerizable compound other than the polymerizable compound having an alkyleneoxy chain hereinafter referred to as “other polymerizable compound”.
- a conventionally well-known polymeric compound can be used.
- unsaturated carboxylic acids for example, acrylic acid, methacrylic acid, itaconic acid, crotonic acid, isocrotonic acid, maleic acid, etc.
- esters thereof, amides, and multimers thereof can be mentioned.
- an ester of an unsaturated carboxylic acid and an aliphatic polyhydric alcohol compound, an amide of an unsaturated carboxylic acid and an aliphatic polyhydric amine compound, and a multimer thereof can be used.
- addition reaction products of monofunctional or polyfunctional isocyanates or epoxies with unsaturated carboxylic acid esters or amides having a nucleophilic substituent such as hydroxyl group, amino group, mercapto group, monofunctional or polyfunctional can also be used.
- an addition reaction product of an unsaturated carboxylic acid ester or amide having an electrophilic substituent such as an isocyanate group or an epoxy group with a monofunctional or polyfunctional alcohol, amine or thiol, and further a halogen group A substitution reaction product of an unsaturated carboxylic acid ester or amide having a detachable substituent such as a tosyloxy group and a monofunctional or polyfunctional alcohol, amine or thiol can also be used.
- a compound group in which the unsaturated carboxylic acid is replaced with an unsaturated phosphonic acid, a vinylbenzene derivative such as styrene, vinyl ether, allyl ether or the like As these specific compounds, the compounds described in paragraphs [0095] to [0108] of JP-A-2009-288705 can also be used in the present invention.
- a compound having an ethylenically unsaturated group having a boiling point of 100 ° C. or higher under normal pressure, which has at least one addition-polymerizable ethylene group can be used.
- Examples include monofunctional (meth) acrylates such as polyethylene glycol mono (meth) acrylate, polypropylene glycol mono (meth) acrylate, and phenoxyethyl (meth) acrylate; polyethylene glycol di (meth) acrylate, trimethylolethanetri ( (Meth) acrylate, neopentyl glycol di (meth) acrylate, pentaerythritol tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, dipentaerythritol penta (meth) acrylate, dipentaerythritol hexa (meth) acrylate, hexanediol ( (Meth) acrylate, trimethylolpropane tri (acryloyloxypropyl) ether, tri (acryloyloxyethyl) isocyanurate
- a polyfunctional alcohol such as glycerin or
- Urethane (meth) acrylates as described in each publication, polyester acrylates and epoxy resins described in JP-A-48-64183, JP-B-49-43191, JP-B-52-30490 And polyfunctional acrylates and methacrylates such as epoxy acrylates which are reaction products of (meth) acrylic acid and mixtures thereof.
- a polyfunctional (meth) acrylate obtained by reacting a polyfunctional carboxylic acid with a compound having a cyclic ether group such as glycidyl (meth) acrylate and an ethylenically unsaturated group can also be used.
- a cardo resin for example, having a fluorene ring and having two or more functional ethylenically unsaturated groups. Compound
- a cardo resin for example, having a fluorene ring and having two or more functional ethylenically unsaturated groups. Compound
- a compound having a boiling point of 100 ° C. or higher under normal pressure and having at least one addition-polymerizable ethylenically unsaturated group is disclosed in paragraph No. of JP-A-2008-292970.
- the compounds described in ⁇ 0254> to ⁇ 0257> can also be used.
- polymerizable compounds represented by the following general formulas (MO-1) to (MO-5) can be used as the polymerizable compound.
- T is an alkyleneoxy group
- the terminal on the carbon atom side is bonded to R.
- n is 0 to 14 and m is 1 to 8.
- a plurality of R and T present in one molecule may be the same or different.
- at least one of a plurality of Rs is —OC ( ⁇ O) CH ⁇ CH 2 or —OC ( ⁇ O) C (CH 3 ) ⁇
- the group represented by CH 2 is represented.
- the polymerizable compounds represented by the general formulas (MO-1) to (MO-5) the compounds described in paragraph numbers 0248 to 0251 of JP-A-2007-26979 are disclosed in the present invention. Can also be suitably used.
- dipentaerythritol triacrylate (KAYARAD D-330 as a commercial product; manufactured by Nippon Kayaku Co., Ltd.), dipentaerythritol tetraacrylate (as a commercial product, KAYARAD D-320; Nippon Kayaku) Yakuhin Co., Ltd.), dipentaerythritol penta (meth) acrylate (commercially available product KAYARAD D-310; manufactured by Nippon Kayaku Co., Ltd.), dipentaerythritol hexa (meth) acrylate (commercially available product KAYARAD DPHA; Nippon Kayaku) Yakuhin Co., Ltd.), ethyleneoxy-modified dipentaerythritol hexaacrylate (commercially available A-DPH-12E; Shin-Nakamura Chemical Co., Ltd.) and their (meth) acryloyl groups are ethylene glycol and propylene glycol
- polymerizable compound 2- (meth) acryloyloxyethyl caproate acid phosphate (PM-20 manufactured by Nippon Kayaku Co., Ltd. as a commercial product), urethane acrylate (Shin Nakamura Chemical Co., Ltd. as a commercial product)
- Preferable examples include U-6LPA, pentaerythritol tri, and tetraacrylate (M-303, M-305, M-306, M-450, M-452, etc., manufactured by Toagosei Co., Ltd.).
- polymerizable compounds having a caprolactone structure can be used as other polymerizable compounds.
- the polymerizable compound having a caprolactone structure is not particularly limited as long as it has a caprolactone structure in the molecule, and examples thereof include trimethylolethane, ditrimethylolethane, trimethylolpropane, ditrimethylolpropane, pentaerythritol, diester.
- ⁇ -caprolactone modified polyfunctional (meth) obtained by esterifying polyhydric alcohol such as pentaerythritol, tripentaerythritol, glycerin, diglycerol, trimethylol melamine, (meth) acrylic acid and ⁇ -caprolactone Mention may be made of acrylates.
- a polymerizable compound having a caprolactone structure represented by the following general formula (Z-1) is preferable.
- R 1 represents a hydrogen atom or a methyl group
- m represents 1 or 2
- “*” represents a bond
- R 1 represents a hydrogen atom or a methyl group
- “*” represents a bond
- the content of the polymerizable compound is preferably 25 to 65% by mass, more preferably 25 to 60% by mass, and further preferably 25 to 50% by mass based on the total solid content of the colored composition. If content of a polymeric compound is the said range, it will be easy to form a film
- the ratio P / M between the mass P of the colorant contained in the colored composition and the mass M of the polymerizable compound contained in the colored composition is preferably 0.05 to 0.35. 0.1 to 0.35 is more preferable.
- the curability of the coloring composition applied in the form of a film can be made substantially uniform on the film surface and inside the film, and the generation of wrinkles can be more effectively suppressed.
- the generation of residues during pattern formation can be suppressed.
- the coloring composition of the present invention may contain a polyfunctional thiol compound having two or more mercapto groups in the molecule for the purpose of promoting the reaction of the polymerizable compound.
- the polyfunctional thiol compound is preferably a secondary alkanethiol, and particularly preferably a compound having a structure represented by the following general formula (I).
- n represents an integer of 2 to 4
- L represents a divalent to tetravalent linking group.
- the linking group L is preferably an aliphatic group having 2 to 12 carbon atoms, particularly preferably n is 2 and L is an alkylene group having 2 to 12 carbon atoms.
- Specific examples of the polyfunctional thiol compound include compounds represented by the following structural formulas (II) to (IV), and a compound represented by the structural formula (II) is particularly preferable. These polyfunctional thiol compounds can be used alone or in combination.
- the blending amount of the polyfunctional thiol compound in the coloring composition is preferably 0.3 to 8.9% by mass, and more preferably 0.8 to 6.4% by mass based on the total solid content excluding the solvent.
- the polyfunctional thiol compound may contain only 1 type, and may contain 2 or more types. When two or more types are included, the total amount is preferably within the above range.
- the polyfunctional thiol compound may be added for the purpose of improving stability, odor, resolution, developability, adhesion and the like.
- the coloring composition of the present invention contains a resin.
- resin does not include “polymerizable compound”.
- the resin preferably has a hydroxyl group. By having a hydroxyl group, the adhesion to the substrate can be improved.
- the resin content is preferably 10 to 80% by mass, more preferably 20 to 70% by mass, and still more preferably 30 to 60% by mass of the total solid content of the colored composition.
- the ratio M / B between the mass M of the polymerizable compound contained in the colored composition and the mass B of the mass polymerizable compound of the resin contained in the colored composition is 0.4-3.
- the curability of the coloring composition applied in the form of a film can be made substantially uniform on the film surface and inside the film, and the generation of wrinkles can be more effectively suppressed.
- the resin include the dispersion resins described above and alkali-soluble resins described below. Hereinafter, the alkali-soluble resin will be described.
- the coloring composition of this invention can contain alkali-soluble resin as resin. By containing an alkali-soluble resin, developability and pattern formability are improved.
- the molecular weight of the alkali-soluble resin is not particularly defined, but the weight average molecular weight (Mw) is preferably 5,000 to 100,000.
- the number average molecular weight (Mn) is preferably 1,000 to 20,000.
- the alkali-soluble resin may be a linear organic polymer, and has at least one alkali-soluble polymer in a molecule (preferably a molecule having an acrylic copolymer or a styrene copolymer as a main chain). It can be suitably selected from alkali-soluble resins having groups to promote.
- the alkali-soluble resin will be described.
- the alkali-soluble resin is preferably a polyhydroxystyrene resin, a polysiloxane resin, an acrylic resin, an acrylamide resin, or an acrylic / acrylamide copolymer resin from the viewpoint of heat resistance.
- Acrylic resins, acrylamide resins, and acrylic / acrylamide copolymer resins are preferred.
- Examples of the group that promotes alkali solubility (hereinafter also referred to as an acid group) include a carboxyl group, a phosphoric acid group, a sulfonic acid group, and a phenolic hydroxyl group. What can be developed is preferable, and (meth) acrylic acid is particularly preferable. These acid groups may be used alone or in combination of two or more.
- a known radical polymerization method can be applied.
- Polymerization conditions such as temperature, pressure, type and amount of radical initiator, type of solvent, etc. when producing an alkali-soluble resin by radical polymerization can be easily set by those skilled in the art, and experimental conditions are determined. It can also be done.
- the alkali-soluble resin a polymer having a carboxylic acid in the side chain is preferable, and a methacrylic acid copolymer, an acrylic acid copolymer, an itaconic acid copolymer, a crotonic acid copolymer, a maleic acid copolymer, and a partial esterification are used.
- a methacrylic acid copolymer, an acrylic acid copolymer, an itaconic acid copolymer, a crotonic acid copolymer, a maleic acid copolymer, and a partial esterification are used.
- examples thereof include maleic acid copolymers, alkali-soluble phenol resins such as novolak type resins, acidic cellulose derivatives having a carboxylic acid in the side chain, and polymers having hydroxyl groups added with acid anhydrides.
- a copolymer of (meth) acrylic acid and another monomer copolymerizable therewith is suitable as the alkali-soluble resin.
- examples of other monomers copolymerizable with (meth) acrylic acid include alkyl (meth) acrylates, aryl (meth) acrylates, and vinyl compounds.
- alkyl (meth) acrylate and aryl (meth) acrylate methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, butyl (meth) acrylate, isobutyl (meth) acrylate, pentyl (meth) acrylate,
- vinyl compounds such as hexyl (meth) acrylate, octyl (meth) acrylate, phenyl (meth) acrylate, benzyl (meth) acrylate, tolyl (meth) acrylate, naphthyl (meth) acrylate, cyclohexyl (meth) acrylate, styrene, ⁇ -methylstyrene, vinyltoluene, glycidyl methacrylate, acrylonitrile, vinyl acetate, N-vinylpyrrolidone, tetrahydrofurfury
- the alkali-soluble phenol resin can be suitably used when the colored composition is a positive composition.
- the alkali-soluble phenol resin include novolak resins and vinyl polymers.
- the novolak resin include those obtained by condensing phenols and aldehydes in the presence of an acid catalyst.
- the phenols include phenol, cresol, ethylphenol, butylphenol, xylenol, phenylphenol, catechol, resorcinol, pyrogallol, naphthol, and bisphenol A.
- aldehydes examples include formaldehyde, paraformaldehyde, acetaldehyde, propionaldehyde, benzaldehyde, and the like. Phenols and aldehydes can be used alone or in combination of two or more.
- Specific examples of the novolak resin include, for example, a condensation product of metacresol, paracresol, or a mixture thereof and formalin.
- the molecular weight distribution of the novolak resin may be adjusted using a means such as fractionation.
- an alkali-soluble resin having a polymerizable group may be used.
- the polymerizable group include an allyl group, a methallyl group, and a (meth) acryloyl group.
- an alkali-soluble resin having a polymerizable group an alkali-soluble resin containing a polymerizable group in a side chain is useful.
- alkali-soluble resin containing a polymerizable group a compound containing a polymerizable group such as a (meth) acryloyl group and a carboxyl group is obtained by previously reacting an isocyanate group with a hydroxyl group, leaving one unreacted isocyanate group.
- alkali-soluble resins obtained by treatment examples include NR series (manufactured by Mitsubishi Rayon Co., Ltd.), Photomer 6173 (produced by COOH containing polyurethane acrylic oligomer. 106 (all manufactured by Osaka Organic Chemical Industry Co., Ltd.), Cyclomer P series, Plaxel CF200 series (all manufactured by Daicel Chemical Industries, Ltd.), Ebecryl 3800 (manufactured by Daicel UC Corporation) and the like.
- Alkali-soluble resins include benzyl (meth) acrylate / (meth) acrylic acid copolymer, benzyl (meth) acrylate / (meth) acrylic acid / 2-hydroxyethyl (meth) acrylate copolymer, benzyl (meth) acrylate / Multi-component copolymers composed of (meth) acrylic acid / other monomers can be preferably used.
- the alkali-soluble resin is a compound represented by the following general formula (ED) and / or a compound represented by the following general formula (ED2) (hereinafter, these compounds may be referred to as “ether dimers”).
- ED general formula
- ether dimers a compound represented by the following general formula (ED2)
- R 1 and R 2 each independently represent a hydrogen atom or a hydrocarbon group having 1 to 25 carbon atoms which may have a substituent.
- R represents a hydrogen atom or an organic group having 1 to 30 carbon atoms.
- ED2 the description in JP 2010-168539 A can be referred to.
- the hydrocarbon group represented by R 1 and R 2 is preferably a hydrocarbon group having 1 to 25 carbon atoms.
- the hydrocarbon group may have a substituent.
- the hydrocarbon group is not particularly limited. For example, straight chain such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, t-butyl, t-amyl, stearyl, lauryl, 2-ethylhexyl, etc.
- An aryl group such as phenyl; an alicyclic group such as cyclohexyl, t-butylcyclohexyl, dicyclopentadienyl, tricyclodecanyl, isobornyl, adamantyl, 2-methyl-2-adamantyl; And alkyl groups substituted with alkoxy such as 1-methoxyethyl and 1-ethoxyethyl; alkyl groups substituted with aryl groups such as benzyl; and the like.
- an acid such as methyl, ethyl, cyclohexyl, benzyl or the like, or a primary or secondary carbon hydrocarbon group which is difficult to be removed by heat is preferable from the viewpoint of heat resistance.
- ether dimers include, for example, dimethyl-2,2 ′-[oxybis (methylene)] bis-2-propenoate, diethyl-2,2 ′-[oxybis (methylene)] bis-2-propenoate, di ( n-propyl) -2,2 ′-[oxybis (methylene)] bis-2-propenoate, di (isopropyl) -2,2 ′-[oxybis (methylene)] bis-2-propenoate, di (n-butyl) -2,2 '-[oxybis (methylene)] bis-2-propenoate, di (isobutyl) -2,2'-[oxybis (methylene)] bis-2-propenoate, di (t-butyl) -2,2 '-[Oxybis (methylene)] bis-2-propenoate, di (t-amyl) -2,2'-[oxybis (methylene)] bis-2-propenoe Di (stearyl)
- dimethyl-2,2 ′-[oxybis (methylene)] bis-2-propenoate, diethyl-2,2 ′-[oxybis (methylene)] bis-2-propenoate, dicyclohexyl-2,2′- [Oxybis (methylene)] bis-2-propenoate and dibenzyl-2,2 ′-[oxybis (methylene)] bis-2-propenoate are preferred.
- These ether dimers may be only one kind or two or more kinds.
- the content of the ether dimer in the monomer component is not particularly limited, but is preferably 2 to 60% by mass, more preferably 5 to 55% by mass, and still more preferably 5 to 50% by mass.
- the resin (a) may be a copolymer obtained by copolymerizing other monomers together with the ether dimer.
- ether dimer dimer examples include, for example, a monomer for introducing an acid group, a monomer for introducing a radical polymerizable double bond, and an epoxy group. Monomers and other copolymerizable monomers other than these may be mentioned. Only 1 type may be used for such a monomer and it may use 2 or more types. With respect to the other monomers described above, for example, the description in JP-A-2004-300204, 0016 to 0022 can be referred to, and these contents are incorporated in this specification.
- the weight average molecular weight (Mw) of the resin (a) is not particularly limited, but is preferably 5,000 to 200,000 from the viewpoint of the viscosity of the colored composition and the heat resistance of the film formed of the colored composition. More preferably from 5,000 to 100,000, and even more preferably from 5,000 to 20,000.
- the acid value is preferably 30 to 500 mgKOH / g, more preferably 50 to 400 mgKOH / g.
- the resin (a) can be easily obtained by polymerizing a monomer containing an ether dimer. At this time, the cyclization reaction of the ether dimer proceeds simultaneously with the polymerization to form a tetrahydropyran ring structure.
- combination of resin (a) Although conventionally well-known various polymerization methods can be employ
- the resin (a) can be synthesized according to the synthesis method of the resin (a) described in JP-A-2004-300204.
- the exemplary compound of resin (a) is shown, this invention is not limited to these.
- the composition ratio of the exemplary compounds shown below is mol%.
- alkali-soluble resin a resin containing a structural unit derived from an ethylenically unsaturated monomer represented by the following formula (X) can also be used.
- 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 which may contain a benzene ring.
- n represents an integer of 1 to 15.
- the alkylene group of R 2 preferably has 2 to 3 carbon atoms.
- the carbon number of the alkyl group of R 3 is preferably 1-10.
- the alkyl group of R 3 may contain a benzene ring.
- Examples of the alkyl group containing a benzene ring represented by R 3 include a benzyl group and a 2-phenyl (iso) propyl group.
- Specific examples of the resin containing a structural unit derived from the ethylenically unsaturated monomer represented by the above formula (X) include resins described in JP2012-247591A and JP2013-24934A Etc.
- the acid value of the alkali-soluble resin is preferably 30 to 500 mgKOH / g.
- the lower limit is preferably 50 mgKOH / g or more, and more preferably 70 mgKOH / g or more.
- the upper limit is preferably 400 mgKOH / g or less, more preferably 200 mgKOH / g or less, still more preferably 150 mgKOH / g or less, and most preferably 120 mgKOH / g or less.
- the content of the alkali-soluble resin is preferably 10 to 80% by mass, more preferably 20 to 70% by mass, and still more preferably 30 to 60% by mass with respect to the total solid content of the coloring composition.
- the coloring composition of the present invention preferably contains a photopolymerization initiator.
- the photopolymerization initiator is not particularly limited as long as it has the ability to initiate polymerization of a polymerizable compound, and can be appropriately selected from known photopolymerization initiators. For example, those having photosensitivity to visible light from the ultraviolet region are preferable. Further, it may be a photopolymerization initiator that generates an active radical by causing some action with a photoexcited sensitizer, and is a photopolymerization initiator that initiates cationic polymerization according to the type of the polymerizable compound. May be.
- photopolymerization initiator examples include halogenated hydrocarbon derivatives (for example, those having a triazine skeleton, those having an oxadiazole skeleton, etc.), acylphosphine compounds such as acylphosphine oxide, hexaarylbiimidazole, and oxime derivatives.
- halogenated hydrocarbon derivatives for example, those having a triazine skeleton, those having an oxadiazole skeleton, etc.
- acylphosphine compounds such as acylphosphine oxide, hexaarylbiimidazole, and oxime derivatives.
- Oxime compounds such as organic peroxides, thio compounds, ketone compounds (eg, benzophenone, 2-methylbenzophenone, 4,4′-bis (diethylamino) benzophenone, 2-methyl-1- [4- (methylthio) phenyl] -2-morpholino-1-propanone, benzoin, benzoin methyl ether, acridone, N-methylacridone, 2-benzyl-dimethylamino-1- (4-morpholinophenyl) -1-butanone), aromatic onium salts, Ketoxime ether, Mino acetophenone compounds, such as hydroxy acetophenone. Among these, oxime compounds are preferable.
- halogenated hydrocarbon compounds having a triazine skeleton examples include those described in Wakabayashi et al., Bull. Chem. Soc. Japan, 42, 2924 (1969), a compound described in British Patent No. 1388492, a compound described in JP-A-53-133428, a compound described in German Patent No. 3337024, F.I. C. J. Schaefer et al. Org. Chem. 29, 1527 (1964), compounds described in JP-A-62-258241, compounds described in JP-A-5-281728, compounds described in JP-A-5-34920, US Pat. No. 4,221,976 Examples thereof include compounds described in the specification (for example, compounds having an oxadiazole skeleton).
- photopolymerization initiators other than those mentioned above, polyhalogen compounds (for example, 9-phenylacridine, 1,7-bis (9,9′-acridinyl) heptane, etc.), N-phenylglycine, etc.
- polyhalogen compounds for example, 9-phenylacridine, 1,7-bis (9,9′-acridinyl) heptane, etc.
- N-phenylglycine etc.
- acylphosphine oxides for example, bis (2,4 , 6-Trimethylbenzoyl) -phenylphos Zinc oxide, bis (2,6-dimethoxybenzoyl) -2,4,4-trimethyl-pentylphenylphosphine oxide, Lucirin TPO, etc.
- metallocenes for example, bis ( ⁇ 5-2,4-cyclopentadien-1-yl)- Bis (2,6-difluoro-3- (1H-pyrrol-1-yl) -phenyl) titanium, ⁇ 5-cyclopentadienyl- ⁇ 6-cumenyl-iron (1 +)-hexafluorophosphate (1-), etc.
- Examples thereof include compounds described in JP-A-53-133428, JP-B-57-1819, JP-A-57-60
- hydroxyacetophenone compounds As the photopolymerization initiator, hydroxyacetophenone compounds, aminoacetophenone compounds, and acylphosphine compounds can also be suitably used. More specifically, for example, aminoacetophenone initiators described in JP-A-10-291969 and acylphosphine oxide initiators described in Japanese Patent No. 4225898 can also be used.
- hydroxyacetophenone-based initiator IRGACURE-184, DAROCUR-1173, IRGACURE-500, IRGACURE-2959, IRGACURE-127 (trade names: all manufactured by BASF) can be used.
- aminoacetophenone-based initiator commercially available products IRGACURE-907, IRGACURE-369, and IRGACURE-379 (trade names: all manufactured by BASF) can be used.
- aminoacetophenone-based initiator compounds described in JP-A-2009-191179 whose absorption wavelength is matched with a long wave light source of 365 nm or 405 nm can also be used.
- acylphosphine initiator commercially available products such as IRGACURE-819 and DAROCUR-TPO (trade names: both manufactured by BASF) can be used.
- the photopolymerization initiator include oxime compounds.
- the pattern property dependency also referred to as “PCD dependency”
- PCD Post Coating Delay
- Specific examples of the oxime compound include compounds described in JP-A No. 2001-233842, compounds described in JP-A No. 2000-80068, and compounds described in JP-A No. 2006-342166.
- Examples of the oxime compound suitably used as the photopolymerization initiator include 3-benzoyloxyiminobutan-2-one, 3-acetoxyiminobutan-2-one, 3-propionyloxyiminobutan-2-one, 2 -Acetoxyiminopentan-3-one, 2-acetoxyimino-1-phenylpropan-1-one, 2-benzoyloxyimino-1-phenylpropan-1-one, 3- (4-toluenesulfonyloxy) iminobutane- Examples include 2-one and 2-ethoxycarbonyloxyimino-1-phenylpropan-1-one.
- oxime compounds include J.M. C. S. Perkin II (1979) pp. 1653-1660, J.A. C. S. Perkin II (1979) pp. 156-162, Journal of Photopolymer Science and Technology (1995) pp. 202-232, compounds described in JP-A No. 2000-66385, compounds described in JP-A Nos. 2000-80068, JP-T 2004-534797, JP-A No. 2006-342166, and the like.
- oxime compounds other than those described above compounds described in JP-A-2009-519904 in which oxime is linked to the N-position of carbazole, compounds described in US Pat. No. 7,626,957 in which a hetero substituent is introduced into the benzophenone moiety, A compound described in Japanese Patent Application Laid-Open No. 2010-15025 and US Patent Publication No. 2009-292039 in which a nitro group is introduced at the dye moiety, a ketoxime compound described in International Patent Publication No. 2009-131189, the triazine skeleton and the oxime skeleton are the same A compound described in US Pat. No.
- the oxime compound is preferably a compound represented by the following general formula (OX-1).
- the oxime N—O bond may be an (E) oxime compound, a (Z) oxime compound, or a mixture of (E) and (Z) isomers. .
- R and B each independently represent a monovalent substituent
- A represents a divalent organic group
- Ar represents an aryl group.
- the monovalent substituent represented by R is preferably a monovalent nonmetallic atomic group.
- the monovalent nonmetallic atomic group include an alkyl group, an aryl group, an acyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, a heterocyclic group, an alkylthiocarbonyl group, and an arylthiocarbonyl group. These groups may have one or more substituents.
- the substituent examples include a halogen atom, an aryloxy group, an alkoxycarbonyl group or an aryloxycarbonyl group, an acyloxy group, an acyl group, an alkyl group, and an aryl group.
- the monovalent substituent represented by B is preferably an aryl group, a heterocyclic group, an arylcarbonyl group, or a heterocyclic carbonyl group. These groups may have one or more substituents. Examples of the substituent include the above-described substituents.
- the divalent organic group represented by A is preferably an alkylene group having 1 to 12 carbon atoms, a cycloalkylene group, or an alkynylene group. These groups may have one or more substituents. Examples of the substituent include the above-described substituents.
- the oxime compound has an absorption maximum wavelength in a wavelength region of 350 nm to 500 nm, preferably has an absorption maximum wavelength in a wavelength region of 360 nm to 480 nm, and particularly preferably has a high absorbance at 365 nm and 405 nm. .
- the molar extinction coefficient at 365 nm or 405 nm of the oxime compound is preferably from 1,000 to 300,000, more preferably from 2,000 to 300,000, more preferably from 5,000 to 200, from the viewpoint of sensitivity. Is particularly preferred.
- a known method can be used for the molar extinction coefficient of the compound. Specifically, for example, it is preferable to measure at a concentration of 0.01 g / L using ethyl acetate with an ultraviolet-visible spectrophotometer (Carry-5 spectrophotometer manufactured by Varian).
- the content of the photopolymerization initiator is preferably 0.1 to 20% by mass, more preferably 0.5 to 10% by mass, and particularly preferably 1 to 8% by mass with respect to the total solid content of the coloring composition. Within this range, good sensitivity and pattern formability can be obtained.
- a photoinitiator may use only 1 type and may use it in combination of 2 or more type. When using 2 or more types in combination, the total content is preferably in the above range.
- the coloring composition of the present invention can contain an ultraviolet absorber.
- the ultraviolet absorber is preferably a compound having an extinction coefficient per 1 g at a wavelength of 365 nm of more than 100 and an extinction coefficient per 1 g at a wavelength of 400 nm or more. If the extinction coefficient per gram at a wavelength of 365 nm exceeds 100, an excellent ultraviolet absorption effect can be obtained even with a small amount. In addition, if the extinction coefficient per gram at a wavelength of 400 nm or more is 10 or less, the influence on device spectroscopy in the visible region can be reduced.
- the extinction coefficient is a value measured with an ultraviolet-visible spectrophotometer (Varian, Carry-5 spectrophotometer) at a concentration of 0.01 g / L using ethyl acetate.
- the ultraviolet absorber a compound represented by the following general formula (I) which is a conjugated diene compound is preferable.
- this conjugated diene compound is used, fluctuations in development performance after exposure, especially when low-illuminance exposure is performed, can be suppressed, and exposure illuminance dependence related to pattern formability such as pattern line width, film thickness, and spectral spectrum can be reduced. It can suppress more effectively.
- R 1 and R 2 each independently represent a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, or an aryl group having 6 to 20 carbon atoms, and R 1 and R 2 May be the same as or different from each other. However, R 1 and R 2 do not represent a hydrogen atom at the same time.
- R 3 and R 4 represent an electron withdrawing group.
- the electron-withdrawing group is preferably an electron-withdrawing group having a Hammett's substituent constant ⁇ p value (hereinafter simply referred to as “ ⁇ p value”) of 0.20 or more and 1.0 or less, and the ⁇ p value is 0.30.
- ⁇ p value Hammett's substituent constant
- Hammett's rule was found in 1935 by L. L. in order to quantitatively discuss the effect of substituents on the reaction or equilibrium of benzene derivatives.
- Substituent constants obtained by Hammett's rule include a ⁇ p value and a ⁇ m value, and these values are described in many general books.
- R 3 is preferably a group selected from a cyano group, —COOR 5 , —CONHR 5 , —COR 5 , and —SO 2 R 5 .
- R 4 is preferably a group selected from a cyano group, —COOR 6 , —CONHR 6 , —COR 6 , and —SO 2 R 6 .
- R 5 and R 6 each independently represents an alkyl group having 1 to 20 carbon atoms or an aryl group having 6 to 20 carbon atoms.
- R 3 and R 4 may combine with each other to form a ring.
- At least one of R 1 , R 2 , R 3 , and R 4 may be in the form of a polymer derived from a monomer bonded to a vinyl group via a linking group. Moreover, the copolymer with another monomer may be sufficient.
- the colored composition of the present invention may or may not contain an ultraviolet absorber, but when it is contained, the content of the ultraviolet absorber is 0.01 to from the total solid content of the colored composition of the present invention. 10% by mass is preferable, and 0.01 to 5% by mass is more preferable. If the content of the ultraviolet absorber is in the above range, the sensitivity is good, and furthermore, a fine pattern shape (in particular, a rectangle) can be finely formed. Only one type of ultraviolet absorber may be used, or two or more types may be used in combination. When using 2 or more types in combination, the total content is preferably in the above range.
- the ratio (D / B) between the mass (D) of the photopolymerization initiator and the mass (B) of the ultraviolet absorber is 0. .25 to 1.25 is preferable, 0.3 to 1.1 is more preferable, and a range of 0.4 to 1.0 is particularly preferable. If the above-mentioned ratio is within the above range, the sensitivity is good, and furthermore, a fine pattern shape (in particular, a rectangle) can be finely formed.
- the coloring composition of the present invention can contain an organic solvent.
- the organic solvent is basically not particularly limited as long as the solubility of each component and the coating property of the coloring composition are satisfied, but particularly the solubility of an ultraviolet absorber, an alkali-soluble resin, etc., the coating property of the coloring composition, It is preferable to select in consideration of safety.
- esters include ethyl acetate, n-butyl acetate, isobutyl acetate, cyclohexyl acetate, amyl formate, isoamyl acetate, isobutyl acetate, butyl propionate, isopropyl butyrate, ethyl butyrate, butyl butyrate, methyl lactate, ethyl lactate, oxy Alkyl acetates (eg, methyl oxyacetate, ethyl oxyacetate, butyl oxyacetate (eg, methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate)), 3-oxypropionic acid alkyl esters (For example, methyl 3-oxypropionate, ethyl 3-oxypropionate, etc.
- 2-oxypropionic acid alkyl esters eg, methyl 2-oxypropionate, ethyl 2-oxypropionate, propyl 2-oxypropionate, etc.
- ethers include diethylene glycol dimethyl ether, tetrahydrofuran, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, methyl cellosolve acetate, ethyl cellosolve acetate, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, propylene glycol monomethyl ether, propylene glycol Monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate, etc.
- ketones include methyl ethyl ketone, cyclopentanone, cyclohexanone, 2-heptanone, 3-heptanone, and the like
- aromatic hydrocarbons include toluene and xylene.
- An organic solvent may be used individually by 1 type, and may be used in combination of 2 or more type.
- organic solvents particularly preferred are methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, ethyl cellosolve acetate, ethyl lactate, diethylene glycol dimethyl ether, butyl acetate, methyl 3-methoxypropionate,
- a mixed solution composed of two or more selected from heptanone, cyclohexanone, ethyl carbitol acetate, butyl carbitol acetate, propylene glycol methyl ether, and propylene glycol methyl ether acetate.
- the amount of the organic solvent contained in the coloring composition is preferably 10 to 90% by mass, more preferably 20 to 80% by mass, still more preferably 25 to 75% by mass, and more preferably 45 to 65% with respect to the total amount of the coloring composition. Mass% is particularly preferred.
- the colored composition of the present invention may contain a sensitizer for the purpose of improving the radical generation efficiency of the photopolymerization initiator and increasing the photosensitive wavelength.
- the sensitizer include sensitizers having an absorption wavelength in the wavelength region of 300 nm to 450 nm.
- the sensitizer is preferably one that sensitizes the photopolymerization initiator by an electron transfer mechanism or an energy transfer mechanism.
- sensitizer examples include polynuclear aromatics such as phenanthrene, anthracene, pyrene, perylene, triphenylene, 9,10-dialkoxyanthracene, xanthene such as fluorescein, eosin, erythrosin, rhodamine B, and rose bengal.
- polynuclear aromatics such as phenanthrene, anthracene, pyrene, perylene, triphenylene, 9,10-dialkoxyanthracene, xanthene such as fluorescein, eosin, erythrosin, rhodamine B, and rose bengal.
- Thioxanthones cyanines, merocyanines, phthalocyanines, thiazines such as thionine, methylene blue, toluidine blue, acridines, anthraquinones, squaryliums, coumarins, phenothiazines, phenazines, styrylbenzenes, azo compounds , Diphenylmethane, triphenylmethane, distyrylbenzenes, carbazoles, porphyrins, spiro compounds, quinacridone, indigo, styryl, pyrylium compounds, pyromethene compounds, pyra Rotoriazoru compounds, benzothiazole compounds, barbituric acid derivatives, thiobarbituric acid derivatives, acetophenone, benzophenone, aromatic ketone compounds such as Michler's ketone, and heterocyclic compounds such as N- aryl oxazolidinone and the
- the content of the sensitizer in the coloring composition is preferably 0.1 to 20% by mass in terms of solid content from the viewpoint of light absorption efficiency in the deep part and initiation decomposition efficiency, and preferably 0.5 to 15%.
- the mass% is more preferable.
- a sensitizer may be used individually by 1 type and may use 2 or more types together. When using 2 or more types together, it is preferable that a total amount is the said range.
- Chain transfer agent Depending on the photopolymerization initiator used, it is preferable to add a chain transfer agent to the colored composition of the present invention.
- chain transfer agents include N, N-dialkylaminobenzoic acid alkyl esters and thiol compounds.
- thiol compounds include 2-mercaptobenzothiazole, 2-mercapto-1-phenylbenzimidazole, and 3-mercaptopropion.
- An acid etc. can be used individually or in mixture of 2 or more types.
- the colored composition in the present invention may contain a polymerization inhibitor in order to prevent unnecessary thermal polymerization of the polymerizable compound during the production or storage of the colored composition.
- Polymerization inhibitors include hydroquinone, p-methoxyphenol, di-t-butyl-p-cresol, pyrogallol, t-butylcatechol, benzoquinone, 4,4′-thiobis (3-methyl-6-t-butylphenol), 2,2′-methylenebis (4-methyl-6-t-butylphenol), N-nitrosophenylhydroxyamine primary cerium salt and the like. Of these, p-methoxyphenol is preferred.
- the addition amount of the polymerization inhibitor is preferably 0.01 to 5% by mass relative to the mass of the colored composition.
- the coloring composition of the present invention may contain a substrate adhesion agent for the purpose of improving the substrate adhesion.
- a substrate adhesion agent it is preferable to use a silane coupling agent, a titanate coupling agent, or an aluminum coupling agent.
- silane coupling agents include ⁇ -methacryloxypropyltrimethoxysilane, ⁇ -methacryloxypropyltriethoxysilane, ⁇ -acryloxypropyltrimethoxysilane, ⁇ -acryloxypropyltriethoxysilane, and ⁇ -mercaptopropyl.
- Examples include trimethoxysilane, ⁇ -aminopropyltriethoxysilane, and phenyltrimethoxysilane.
- ⁇ -methacryloxypropyltrimethoxysilane is preferable as the substrate adhesive.
- the content of the substrate adhesion agent is from 0.1 to 30 masses based on the total solid content of the colored composition from the viewpoint of leaving no residue in the unexposed area when the colored composition is exposed and developed. %, More preferably 0.5 to 20% by mass, and particularly preferably 1 to 10% by mass.
- the coloring composition of this invention may contain various surfactant from a viewpoint of improving applicability
- various surfactants such as a fluorine-based surfactant, a nonionic surfactant, a cationic surfactant, an anionic surfactant, and a silicone-based surfactant can be used.
- the liquid properties (particularly fluidity) when prepared as a coating liquid are further improved, and the uniformity of coating thickness and liquid-saving property can be further improved. it can. That is, when a film is formed using a coating liquid to which a coloring composition containing a fluorosurfactant is applied, the interfacial tension between the surface to be coated and the coating liquid is reduced, and the wettability to the surface to be coated is reduced. Is improved, and the coating property to the coated surface is improved. For this reason, it is possible to more suitably form a film having a uniform thickness with small thickness unevenness.
- the fluorine-containing surfactant preferably has a fluorine content of 3 to 40% by mass, more preferably 5 to 30% by mass, and still more 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 properties, and has good solubility in the composition.
- fluorosurfactant examples include Megafac F171, F172, F173, F176, F176, F177, F141, F142, F143, F144, R30, F437, F475, F479, F482, F554, F780, F780, F781 (above DIC Corporation), Florard FC430, FC431, FC171 (above, Sumitomo 3M Limited), Surflon S-382, SC-101, SC-103, SC-104, SC-105, SC1068, SC-381, SC-383, S393, KH-40 (above, manufactured by Asahi Glass Co., Ltd.) and the like.
- nonionic surfactants include glycerol, trimethylolpropane, trimethylolethane, and ethoxylates and propoxylates thereof (for example, glycerol propoxylate, glycerin ethoxylate, etc.), polyoxyethylene lauryl ether, polyoxyethylene Stearyl ether, polyoxyethylene oleyl ether, polyoxyethylene octylphenyl ether, polyoxyethylene nonylphenyl ether, polyethylene glycol dilaurate, polyethylene glycol distearate, sorbitan fatty acid ester (Pluronic L10, L31, L61, L62 manufactured by BASF, 10R5, 17R2, 25R2, Tetronic 304, 701, 704, 901, 904, 150R1), Rusupasu 20000 (manufactured by Nippon Lubrizol Corporation), and the like.
- cationic surfactant examples include phthalocyanine derivatives (trade name: EFKA-745, manufactured by Morishita Sangyo Co., Ltd.), organosiloxane polymer KP341 (manufactured by Shin-Etsu Chemical Co., Ltd.), (meth) acrylic acid ( Co) polymer polyflow no. 75, no. 90, no. 95 (manufactured by Kyoeisha Chemical Co., Ltd.) and W001 (manufactured by Yusho Co., Ltd.).
- phthalocyanine derivatives trade name: EFKA-745, manufactured by Morishita Sangyo Co., Ltd.
- organosiloxane polymer KP341 manufactured by Shin-Etsu Chemical Co., Ltd.
- (meth) acrylic acid ( Co) polymer polyflow no. 75, no. 90, no. 95 manufactured by Kyoeisha Chemical Co., Ltd.
- W001 manufactured by Yusho Co., Ltd.
- anionic surfactants include W004, W005, W017 (manufactured by Yusho Co., Ltd.) and the like.
- silicone-based surfactants include Torre Silicone DC3PA, Torre Silicone SH7PA, Torre Silicone DC11PA, Torresilicone SH21PA, Torree Silicone SH28PA, Torree Silicone SH29PA, Torree Silicone SH30PA, Torree Silicone SH8400 (above, Toray Dow Corning Co., Ltd.) )), TSF-4440, TSF-4300, TSF-4445, TSF-4460, TSF-4442 (above, manufactured by Momentive Performance Materials), KP341, KF6001, KF6002 (above, manufactured by Shin-Etsu Silicone Co., Ltd.) , BYK307, BYK323, BYK330 (above, manufactured by BYK Chemie) and the like.
- the content of the surfactant is preferably 0.001 to 2.0% by mass, and more preferably 0.005 to 1.0% by mass with respect to the total mass of the coloring composition.
- the coloring composition according to the present invention comprises, as necessary, a thermal polymerization initiator; a thermal polymerization component, a plasticizer such as an epoxy compound or dioctyl phthalate; a developability improver such as a low molecular weight organic carboxylic acid; another filler; Various additives such as an agent; an aggregation inhibitor;
- a coloring composition can be prepared by mixing each component mentioned above.
- the components constituting the colored composition may be combined at once, or may be sequentially added after each component is dissolved or dispersed in a solvent.
- a colored composition may be prepared by dissolving or dispersing all components in a solvent at the same time, and if necessary, each component is appropriately used as two or more solutions or dispersions at the time of use (application) May be mixed to prepare a composition.
- any filter can be used without any particular limitation as long as it is a filter that has been used for filtration.
- filter materials include: fluorine resins such as polytetrafluoroethylene (PTFE); polyamide resins such as nylon-6 and nylon-6, 6; polyolefin resins such as polyethylene and polypropylene (PP) (high density, super Including high molecular weight); Among these materials, polypropylene (including high density polypropylene) is preferable.
- the pore size of the filter is not particularly limited, but is preferably 0.01 to 7.0 ⁇ m, more preferably 0.01 to 2.5 ⁇ m, and still more preferably 0.01 to 2.0 ⁇ m.
- the pore size of the filter can refer to the nominal value of the filter manufacturer.
- a commercially available filter for example, it can be selected from various filters provided by Nippon Pole Co., Ltd., Advantech Toyo Co., Ltd., Japan Entegris Co., Ltd. (formerly Japan Microlith Co., Ltd.) or KITZ Micro Filter Co., Ltd. .
- two or more types of filters may be used in combination. For example, it is possible to first perform filtration using a first filter and then perform filtration using a second filter having a hole diameter different from that of the first filter. At that time, the filtering by the first filter and the filtering by the second filter may be performed only once or twice or more, respectively.
- the second filter a filter formed of the same material as the first filter described above can be used.
- the colored composition of the present invention has a viscosity at 25 ° C. of preferably 1 to 200 mPa ⁇ s, more preferably 50 to 200 mPa ⁇ s, and particularly preferably 100 to 150 mPa ⁇ s.
- the viscosity of the colored composition at 25 ° C. is preferably 1 to 50 mPa ⁇ s, more preferably 1 to 20 mPa ⁇ s when a film (color filter) having a film thickness of 0.1 to 2 ⁇ m is formed. 1 to 15 mPa ⁇ s is more preferable.
- the viscosity at 25 ° C. of the colored composition is preferably 50 to 200 mPa ⁇ s, more preferably 50 to 150 mPa ⁇ s, and more preferably 100 to 150 mPa ⁇ s is particularly preferable.
- the viscosity can be measured, for example, using a viscometer RE85L (rotor: 1 ° 34 ′ ⁇ R24 measurement range 0.6 to 1200 mPa ⁇ s) manufactured by Toki Sangyo Co., Ltd., with the temperature adjusted to 25 ° C. .
- the colored composition of the present invention has a light transmittance in the thickness direction of a film when a film having a thickness of 12.0 ⁇ m after drying is formed, and has a maximum transmittance in a wavelength range of 400 to 780 nm.
- the value is preferably 15% or less
- the transmittance at a wavelength of 850 nm is preferably 80% or more.
- the maximum value of transmittance in the wavelength range of 400 to 780 nm is preferably 15% or less, more preferably 10% or less, and particularly preferably 5% or less.
- the transmittance at a wavelength of 850 nm is preferably 80% or more, more preferably 85% or more, and particularly preferably 90% or more.
- the minimum transmittance in the wavelength range of 850 to 1300 nm is preferably 80% or more, more preferably 85% or more, and particularly preferably 90% or more.
- a film which is one embodiment of the present invention is described.
- the film is formed by curing the above-described coloring composition of the present invention.
- Such a film is preferably used for a color filter.
- the maximum value of light transmittance in the thickness direction of the film is preferably 15% or less in the wavelength range of 400 to 780 nm, and the minimum value in the wavelength range of 850 to 1300 nm is preferably 80% or more.
- the spectral characteristics of the film transmittance was measured in a wavelength range of 300 to 1300 nm using a spectrophotometer (ref. Glass substrate) of an ultraviolet-visible near-infrared spectrophotometer (U-4100 manufactured by Hitachi High-Technologies Corporation). Value.
- the film thickness is not particularly limited, but is preferably 0.1 to 20 ⁇ m, more preferably 0.5 to 15 ⁇ m, and particularly preferably 3 to 15 ⁇ m.
- the film having the above spectral characteristics has a tendency that wrinkles are more likely to occur on the film surface as the film thickness increases. When it is large, the effect of the present invention is remarkably obtained.
- the pattern forming method includes a step of applying a colored composition on a support to form a colored composition layer, a step of exposing the colored composition layer in a pattern, and developing and removing unexposed portions to form a colored pattern. Forming.
- a pattern forming method is used for manufacturing a colored layer of a color filter.
- a method for manufacturing a color filter including a pattern forming method is also disclosed.
- each process in a pattern formation method is demonstrated in detail through the manufacturing method of the color filter for solid-state image sensors, this invention is not limited to this method.
- the color filter for the solid-state imaging device may be simply referred to as “color filter”.
- the colored composition layer is formed by applying the colored composition of the present invention on the support.
- a substrate for a solid-state imaging device in which an imaging device (light receiving device) such as a CCD or CMOS is provided on a substrate (for example, a silicon substrate), a silicon substrate, a non-alkali glass substrate, a soda glass substrate, Examples include a Pyrex (registered trademark) glass substrate, a quartz glass substrate, and those obtained by attaching a transparent conductive film thereto. In some cases, a black matrix for isolating each pixel is formed on these substrates. Further, an undercoat layer may be provided on these supports, if necessary, in order to improve adhesion to the upper layer, prevent diffusion of substances, or flatten the substrate surface.
- Examples of the application method of the coloring composition of the present invention on the support include various coating methods such as slit coating, ink jet method, spin coating, spin coating, roll coating, and screen printing.
- Drying (pre-baking) of the colored composition layer coated on the support can be performed at a temperature of 50 to 140 ° C. for 10 to 300 seconds using a hot plate, oven or the like.
- the thickness of the colored composition layer after drying is preferably 0.55 to 30 ⁇ m, more preferably 0.60 to 25 ⁇ m, still more preferably 0.70 to 20 ⁇ m, and particularly preferably 0.80 ⁇ m to 15 ⁇ m. .
- Exposure Step the colored composition layer is subjected to pattern exposure through a mask having a predetermined mask pattern, for example, using an exposure apparatus such as a stepper. Thereby, a cured film is obtained.
- Radiation (light) that can be used for exposure is preferably ultraviolet rays such as g-line and i-line, and i-line is more preferably used.
- Irradiation dose (exposure dose) is preferably 30 ⁇ 1500mJ / cm 2, more preferably 50 ⁇ 1000mJ / cm 2, particularly preferably 80 ⁇ 500mJ / cm 2.
- a development step is performed to elute the uncured portion after exposure into the developer and leave the photocured portion.
- the development method may be any of a dip method, a shower method, a spray method, a paddle method, etc., and a swing method, a spin method, an ultrasonic method, or the like may be combined with these. Unevenness of development can be prevented by pre-wetting the surface to be developed with water or the like before touching the developer.
- the developer an organic alkali developer that does not damage the underlying circuit or the like is desirable.
- the development temperature is preferably 20 to 30 ° C.
- the development time is preferably 20 to 90 seconds.
- the developer preferably contains an alkaline agent.
- the alkaline agent include ammonia water, ethylamine, diethylamine, dimethylethanolamine, tetramethylammonium hydroxide, tetraethylammonium hydroxide, tetrabutylammonium hydroxide, benzyltrimethylammonium hydroxide, choline, pyrrole, piperidine, 1,8.
- -Organic alkaline compounds such as -diazabicyclo- [5,4,0] -7-undecene, and inorganic compounds such as sodium hydroxide, potassium hydroxide, sodium hydrogen carbonate, potassium hydrogen carbonate and the like.
- an alkaline aqueous solution obtained by diluting the above-mentioned alkaline agent with pure water so as to be 0.001 to 10% by mass, preferably 0.01 to 1% by mass is preferably used.
- a developer composed of such an alkaline aqueous solution it is generally preferable that after development, the excess developer is washed and removed by rinsing with pure water, followed by drying.
- Post-baking is a heat treatment after development for complete curing, and usually a heat curing treatment at 100 ° C. to 270 ° C. is performed.
- Post-baking can be carried out continuously or batchwise using a heating means such as a hot plate, a convection oven (hot air circulation dryer), a high-frequency heater, etc., so that the film after development is in the above-mentioned condition. .
- the irradiation time is preferably 10 to 180 seconds, more preferably 30 to 60 seconds.
- post-exposure is preferably performed first.
- a color filter is manufactured by performing each process demonstrated above.
- the color filter may be configured with only the colored pixels using the film exhibiting the specific spectral characteristics described above, or the colored pixels using the film exhibiting the specific spectral characteristics, and red, green, blue, magenta, You may comprise the color filter which has colored pixels, such as yellow, cyan, black, and colorless.
- a colored pixel using a film exhibiting a specific spectral characteristic is configured with a color filter together with a pixel of another color, a colored pixel using a film exhibiting a specific spectral characteristic may be provided first or later. Also good.
- the colored composition in the present invention can be easily washed and removed using a known cleaning liquid even when it adheres to, for example, a nozzle of a coating apparatus discharge section, a piping section of a coating apparatus, or the inside of a coating apparatus.
- the surfactant described above may be added to the cleaning liquid as a surfactant that the coloring composition may contain.
- the color filter can be suitably mounted on a solid-state imaging device such as a CCD image sensor, a CMOS image sensor, an organic CMOS image sensor, or a CIGS image sensor. In particular, it is suitable to be mounted on a high-resolution solid-state imaging device exceeding 1 million pixels.
- the color filter can be disposed, for example, between a light receiving portion of each pixel constituting the CCD image sensor and a microlens for collecting light.
- a solid-state image sensor which is one embodiment of the present invention includes a color filter for a solid-state image sensor.
- the configuration of the solid-state imaging device is a configuration provided with the color filter that is one embodiment of the present invention as the color filter for the solid-state imaging device, and is not particularly limited as long as the configuration functions as a solid-state imaging device. The following configurations are listed.
- the solid-state imaging device has a transfer electrode made of a plurality of photodiodes and polysilicon constituting a light receiving area of a solid-state imaging device (CCD image sensor, CMOS image sensor, etc.) on a support. It has a light-shielding film made of tungsten or the like that is open only on the light-receiving part of the photodiode, and a device protective film made of silicon nitride or the like formed on the light-shielding film so as to cover the entire surface of the light-shielding film and the photodiode light-receiving part.
- the solid-state image sensor color filter is provided on the device protective film.
- a configuration having a condensing means for example, a microlens, etc., the same shall apply hereinafter
- a condensing means for example, a microlens, etc., the same shall apply hereinafter
- a condensing means on the device protective film and under the color filter for the solid-state imaging device (on the side close to the support), or a condensing means on the color filter The structure etc. which have these may be sufficient.
- An infrared sensor that is one embodiment of the present invention includes a color filter.
- the configuration of the infrared sensor is a configuration provided with the color filter that is one embodiment of the present invention, and is not particularly limited as long as it is a configuration that functions as an infrared sensor.
- An infrared sensor has a transfer electrode made of a plurality of photodiodes and polysilicon constituting a light receiving area of a solid-state imaging device (CCD sensor, CMOS sensor, organic CMOS sensor, etc.) on a substrate. It has a light-shielding film made of tungsten or the like that is open only on the light-receiving part of the photodiode, and a device protective film made of silicon nitride or the like formed on the light-shielding film so as to cover the entire surface of the light-shielding film and the photodiode light-receiving part. The device has a color filter on the device protective film.
- the device has a condensing means (for example, a microlens, etc., the same shall apply hereinafter) under the color filter (on the side close to the substrate) on the device protective film, or a constitution having the condensing means on the color filter. There may be.
- a condensing means for example, a microlens, etc., the same shall apply hereinafter
- the organic CMOS sensor includes a thin panchromatic photosensitive organic photoelectric conversion film as a photoelectric conversion layer and a CMOS signal readout substrate, and the organic material plays a role of capturing light and converting it into an electric signal.
- This is a two-layer hybrid structure in which an inorganic material plays a role of taking out a signal to the outside.
- the aperture ratio can be 100% with respect to incident light.
- the organic photoelectric conversion film is a structure-free continuous film that can be laid on a CMOS signal reading substrate, and therefore does not require an expensive fine processing process and is suitable for pixel miniaturization.
- the infrared sensor 100 includes a solid-state image sensor 110.
- a near-infrared absorption filter 111 and a color filter 112 are provided in an imaging region provided on the solid-state imaging device 110.
- the near-infrared absorption filter 111 transmits light in the visible light region (for example, light having a wavelength of 300 to 700 nm) and light in the infrared region (for example, light having a wavelength of 800 to 1300 nm, preferably light having a wavelength of 900 to 1300 nm, More preferably, it is configured to shield light having a wavelength of 1000 to 1300 nm.
- the color filter 112 is formed with pixels that transmit and absorb light of a specific wavelength in the visible light region. For example, red (R), green (G), and blue (B) pixels are formed.
- a region 114 where the near infrared absorption filter 111 is not formed is provided between the near infrared transmission filter 113 and the solid-state imaging device 110.
- a resin layer for example, a transparent resin layer
- the near-infrared transmission filter 113 is a filter that has a visible light shielding property and transmits infrared rays having a specific wavelength, and is configured by the color filter having the specific spectral characteristics described above.
- the near infrared transmission filter 113 preferably blocks light having a wavelength of 400 to 780 nm and transmits light having a wavelength of 850 to 1300 nm.
- a microlens 115 is disposed on the incident light hv side of the color filter 112 and the near-infrared transmission filter 113.
- a planarization layer 116 is formed so as to cover the microlens 115.
- the resin layer is disposed in the region 114, but the infrared transmission filter 113 may be formed in the region 114. That is, the infrared transmission filter 113 may be formed on the solid-state image sensor 110.
- FIG. 1 the embodiment shown in FIG.
- the thickness of the color filter 112 and the thickness of the infrared transmission filter 113 are the same, but the thickness of both may be different.
- the color filter 112 is provided closer to the incident light h ⁇ than the near-infrared absorption filter 111.
- the order of the near-infrared absorption filter 111 and the color filter 112 is changed.
- the near-infrared absorption filter 111 may be provided on the incident light h ⁇ side with respect to the color filter 112.
- the near-infrared absorption filter 111 and the color filter 112 are stacked adjacent to each other.
- both filters are not necessarily adjacent to each other, and another layer is provided between them. May be. According to this infrared sensor, since image information can be captured simultaneously, motion sensing or the like that recognizes a target whose motion is to be detected is possible. Furthermore, since distance information can be acquired, an image including 3D information can be taken.
- FIG. 2 is a functional block diagram of the imaging apparatus.
- the imaging device emits infrared light, the lens optical system 1, the solid-state imaging device 10, the signal processing unit 20, the signal switching unit 30, the control unit 40, the signal storage unit 50, the light emission control unit 60, and the like.
- Infrared LED 70 of the light emitting element and image output units 80 and 81 are provided.
- the infrared sensor 100 described above can be used as the solid-state imaging device 10.
- the configuration other than the solid-state imaging device 10 and the lens optical system 1 may be formed entirely or partially on the same semiconductor substrate.
- paragraphs 0032 to 0036 of JP 2011-233983 A can be referred to, and the contents thereof are incorporated in the present specification.
- pigment dispersion B-2 A mixed solution having the following composition was mixed and dispersed for 3 hours using a zirconia bead having a diameter of 0.3 mm in a bead mill (high pressure disperser NANO-3000-10 with a pressure reducing mechanism (manufactured by Nippon BEE Co., Ltd.)). Thus, a pigment dispersion B-2 was prepared. -12.8 parts of mixed pigment consisting of blue pigment (CI Pigment Blue 15: 6) and purple pigment (CI Pigment Violet 23)-Dispersant: BYK-111 2.0 parts by BYK-Alkali Soluble resin 1 3.2 parts Organic solvent: Cyclohexanone 31.0 parts Organic solvent: PGMEA 51.0 parts
- Example 1 (Preparation of coloring composition) The following components were mixed to prepare the coloring composition of Example 1.
- -Pigment dispersion B-1 (see Table 1 below for the mass ratio of each pigment) 11.2 parts-Pigment dispersion B-2 (See Table 1 below for the mass ratio of each pigment) 9.1 parts-below 40 mass% PGMEA solution of alkali-soluble resin 1 54.2 parts ⁇
- the following polymerizable compound 1 13.6 parts ⁇
- the following photopolymerization initiator 1 2.0 parts ⁇
- Surfactant 1 Megafac F-781F manufactured by DIC Corporation 0.42 part of 10% by weight PGMEA solution 0.41 part of the following UV absorber 1
- Polymerization inhibitor 0.01 part of p-methoxyphenol Organic solvent 1: 9.2 parts of PGMEA
- Examples 2 to 8, Comparative Examples 1 to 4 In the preparation of the colored composition of Example 1, the pigment dispersion, alkali-soluble resin, polymerizable compound, photopolymerization initiator, and organic solvent were changed to those shown in Table 2 below and in amounts (parts by mass) (pigment dispersion). For the mass ratio of each pigment in the liquid, see Table 1. Also, in Table 2, it means that those without numerical values are not used.), Colored compositions of Examples 2 to 8 and Comparative Examples 1 to 4 was prepared.
- Each pigment ratio in Table 1 is the ratio (in terms of mass) of each pigment in the total pigment.
- alkali-soluble resin 1 is a value (part by mass) in a 40% by mass PGMEA solution.
- alkali-soluble resin 2 is a value (mass part) in a 40 mass% PGMEA solution.
- Surfactant 1 is a value (parts by mass) in a 10% by mass PGMEA solution.
- Alkali-soluble resin 1 following structure (ratio in repeating unit is molar ratio)
- Alkali-soluble resin 2 the following structure (ratio in repeating units is molar ratio)
- Photopolymerization initiator 1 structure shown below
- Photopolymerization initiator 2 Structure shown below Ultraviolet absorber 1: The following structure
- the colored composition was applied to a glass substrate so that the film thickness after post-baking was 12 ⁇ m, and a colored layer was formed on the glass substrate.
- the colored composition is spin-coated on a glass substrate, dried on a hot plate at 100 ° C. for 120 seconds, dried, and further heat-treated (post-baked) for 300 seconds using a hot plate at 200 ° C. Went.
- the minimum value and the transmittance at a wavelength of 850 nm were measured.
- the coloring composition is applied onto a silicon wafer using a spin coater so that the film thickness after drying is 12 ⁇ m, and heat-treated (prebaked) for 120 seconds using a hot plate at 100 ° C. to form a coating film did.
- an i-line stepper exposure apparatus FPA-3000i5 + manufactured by Canon Inc.
- exposure was performed at an optimal exposure amount using a photomask on which a square pixel pattern of 1.4 ⁇ m square was formed.
- the optimum exposure dose was determined on the basis of the exposure dose for resolving the square pixel pattern by increasing 50 mJ / cm 2 from 50 to 750 mJ / cm 2 .
- the silicon wafer on which the exposed coating film is formed is placed on a horizontal rotary table of a spin shower developing machine (DW-30 type, manufactured by Chemitronics), and CD-2060 (Fuji Film Electronics Co., Ltd.). Paddle development was performed at 23 ° C. for 60 seconds using Materials Co., Ltd. to form a colored pattern on the silicon wafer.
- the silicon wafer on which the colored pattern was formed was rinsed with pure water and then spray-dried.
- a heat treatment post-bake was performed for 300 seconds using a 200 ° C. hot plate to obtain silicon wafers having colored patterns as color filters of Examples 1 to 8 and Comparative Examples 1 to 4, respectively.
- the surface of the color filter was measured with an AFM (atomic force microscope), and the surface roughness (Ra) was obtained by calculation.
- Variation in transmittance is less than 1% 2: Variation in transmittance is 1% or more and less than 5% 1: Variation in transmittance is 5% or more [adhesion]
- the state after development of the coating film in the production of the color filter was observed with an optical microscope, and the number of peeled square pixel patterns was counted. 3: No peeling of the pattern is observed 2: Less than 10 peeling of the pattern 1: 10 or more peeling of the pattern
- lens optical system 10: solid-state imaging device
- 20 signal processing unit
- 30 signal switching unit
- 40 control unit
- 50 signal storage unit
- 60 light emission control unit
- 70 infrared LED
- 80 81
- Image output unit 100: Infrared sensor
- 110 Solid-state imaging device
- 111 Near-infrared absorption filter
- 112 Color filter
- 113 Near-infrared transmission filter
- 114 Region
- 115 Micro lens
- 116 Flattening layer
- H ⁇ incident light
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Abstract
Description
近赤外線は可視光に比べて波長が長いので散乱しにくく、距離計測や、3次元計測などにも活用可能である。このような近赤外線の特徴を利用して、近赤外線は、近接センサや、モーションセンサ等に使用されている。また、近赤外線は人間や動物などの目に見えないので、夜間に被写体を近赤外線光源で照らしても被写体に気付かれることがなく、夜行性の野生動物を撮影する用途や防犯用途として、相手を刺激せずに撮影することにも使用可能である。
このように、可視光由来のノイズが少ない状態で近赤外線を透過可能なカラーフィルタの開発が望まれている。
<1> 着色剤と重合性化合物と樹脂とを含む着色組成物であって、着色剤の質量Pと、重合性化合物の質量Mとの比率P/Mが、0.05~0.35であり、着色組成物の全固形分中における重合性化合物の含有量が25~65質量%であり、着色組成物の、波長400nm以上580nm未満の範囲における吸光度の最小値Aと、波長580nm以上770nm以下の範囲における吸光度の最小値Bとの比率A/Bが0.3~3であり、波長400nm以上750nm以下の範囲における吸光度の最小値Cと、波長850nm以上1300nm以下の範囲における吸光度の最大値Dとの比率C/Dが5以上である、着色組成物。
<2> 重合性化合物の質量Mと、樹脂の質量Bとの比率M/Bが、0.4~3.0である、<1>に記載の着色組成物。
<3> 着色剤と重合性化合物とを含む着色組成物であって、着色剤の質量Pと、重合性化合物の質量Mとの比率P/Mが、0.05~0.35であり、着色組成物の全固形分中における重合性化合物の含有量が25~65質量%であり、着色剤は、黄色着色剤と青色着色剤とを少なくとも含み、黄色着色剤の着色剤全量に対する質量比である黄色着色剤/全着色剤が0.1~0.5であり、青色着色剤の着色剤全量に対する質量比である青色着色剤/全着色剤が0.1~0.6である、着色組成物。
<4> 着色剤は、更に赤色着色剤と紫色着色剤とを含み、赤色着色剤の着色剤全量に対する質量比である赤色着色剤/全着色剤が0.1~0.5であり、黄色着色剤の着色剤全量に対する質量比である黄色着色剤/全着色剤が0.1~0.4であり、青色着色剤の着色剤全量に対する質量比である青色着色剤/全着色剤が0.2~0.6であり、紫色着色剤の着色剤全量に対する質量比である紫色着色剤/全着色剤が0.01~0.3である、<3>に記載の着色組成物。
<5> 着色剤は、青色顔料と赤色顔料と黄色顔料と紫色顔料とを含む、<1>~<4>のいずれかに記載の着色組成物。
<6> 重合性化合物は、アルキレンオキシ基を繰り返し単位として2以上含むアルキレンオキシ鎖を有する重合性化合物を含有する、<1>~<5>のいずれかに記載の着色組成物。
<7> 重合性化合物は、重合性化合物の分子量の値を、重合性化合物中に含まれる重合性基の数で割った値が100~300である、<1>~<6>のいずれかに記載の着色組成物。
<8> 乾燥後の膜厚が12.0μmの膜を形成した際に、波長400~780nmの範囲における透過率の最大値が15%以下であり、波長850nmの透過率が80%以上である<1>~<7>のいずれかに記載の着色組成物。
<9> 25℃における粘度が100~150mP・sである、<1>~<8>のいずれかに記載の着色組成物。
<10> <1>~<9>のいずれかに記載の着色組成物を硬化してなる膜。
<11> <10>に記載の膜を有するカラーフィルタ。
<12> <1>~<9>のいずれかに記載の着色組成物を支持体上に適用して着色組成物層を形成する工程と、着色組成物層をパターン状に露光する工程と、未露光部を現像除去して着色パターンを形成する工程とを含むパターン形成方法。
<13> <12>に記載のパターン形成方法を含む、カラーフィルタの製造方法。
<14> <11>に記載のカラーフィルタまたは<13>に記載のカラーフィルタの製造方法により得られたカラーフィルタを有する固体撮像素子。
<15> <11>に記載のカラーフィルタまたは<13>に記載のカラーフィルタの製造方法により得られたカラーフィルタを有する赤外線センサ。
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、置換基を有さないものと共に置換基を有するものをも包含するものである。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)をも包含するものである。
本明細書において、「放射線」とは、例えば、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、電子線等を意味する。
本明細書において、「光」とは、活性光線または放射線を意味する。
本明細書において、「露光」とは、特に断らない限り、水銀灯、エキシマレーザに代表される遠紫外線、X線、EUV光などによる露光のみならず、電子線、イオンビーム等の粒子線による描画も露光に含める。
本明細書において、「(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、「単量体」と「モノマー」とは同義である。また、「単量体」は、「オリゴマー」および「ポリマー」と区別され、重量平均分子量が2,000以下の化合物をいう。
本明細書において、重合性化合物とは、重合性官能基を有する化合物のことをいい、単量体であっても、ポリマーであってもよい。重合性官能基とは、重合反応に関与する基を言う。
本明細書において、化学式中のMeはメチル基を、Etはエチル基を、Prはプロピル基を、Buはブチル基を、Phはフェニル基をそれぞれ示す。
本明細書において、「工程」との語は、独立した工程だけではなく、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。
本明細書において、重量平均分子量および数平均分子量は、ゲルパーミエーションクロマトグラフィー(GPC)測定によるポリスチレン換算値として定義される。本明細書において、重量平均分子量(Mw)および数平均分子量(Mn)は、例えば、HLC-8220(東ソー(株)製)を用い、カラムとしてTSKgel Super AWM―H(東ソー(株)製、6.0mmID×15.0cm)を、溶離液として10mmol/L リチウムブロミドNMP(N-メチルピロリジノン)溶液を用いることによって求めることができる。
「顔料」は、溶剤に溶解しにくい不溶性の色素化合物を意味する。典型的には、組成物中に粒子として分散された状態で存在する色素化合物を意味する。ここで、溶剤とは、任意の溶剤が挙げられ、水、後述する有機溶剤の欄で例示する溶剤が挙げられる。顔料は、例えば、プロピレングリコールモノメチルエーテルアセテ-トおよび水のいずれに対しても、25℃における溶解度が0.1g/100gSolvent以下が好ましい。
本発明の着色組成物の第一の態様は、着色剤と重合性化合物とを含み、着色剤の質量Pと重合性化合物の質量Mとの比率P/Mが、0.05~0.35であり、着色組成物の全固形分中における重合性化合物の含有量が25~65質量%であり、着色組成物の、波長400nm以上580nm未満の範囲における吸光度の最小値Aと、波長580nm以上770nm以下の範囲における吸光度の最小値Bとの比率A/Bが0.3~3であり、波長400nm以上750nm以下の範囲における吸光度の最小値Cと、波長850nm以上1300nm以下の範囲における吸光度の最大値Dとの比率C/Dが5以上である。
上述した吸光度の比率A/Bは、0.4~2.5が好ましく、0.5~2がより好ましい。また、上述した吸光度の比率C/Dは、10以上が好ましく、50以上がより好ましい。着色組成物の吸光度の比率A/B、C/Dを、それぞれ上記範囲とすることにより、可視光由来のノイズが少ない状態で近赤外線を透過可能な膜を形成しやすい。
上記吸光度の達成手段は、特に定めるものではないが、各着色剤の種類及び含有量を調整することにより、上記吸光度とすることが好ましい実施形態として挙げられる。また、その他の達成手段として、例えば、特定の波長を反射する材料を組み合わせることなどが挙げられる。
Aλ=-log(Tλ) ・・・(1)
Aλは、波長λにおける吸光度であり、Tλは、波長λにおける透過率である。
膜の膜厚は、膜を有する基板を、触針式表面形状測定器(ULVAC社製 DEKTAK150)を用いて測定することができる。
吸光度は、従来公知の分光光度計を用いて測定できる。吸光度の測定条件は特に限定はない。例えば、波長400nm以上580nm未満の範囲における吸光度の最小値Aが、0.1~3.0になるように調整した条件で測定することが好ましい。このような条件で吸光度を測定することで、測定誤差をより小さくできる。波長400nm以上580nm未満の範囲における吸光度の最小値Aが、0.1~3.0になるように調整する方法としては、特に限定はない。例えば、液状の状態で吸光度を測定する場合は、試料セルの光路長を調整する方法が挙げられる。また、膜の状態で吸光度を測定する場合は、膜厚を調整する方法などが挙げられる。
この態様において、着色剤は、更に赤色着色剤と紫色着色剤とを含み、赤色着色剤の着色剤全量に対する質量比である赤色着色剤/全着色剤が0.1~0.5(好ましくは0.1~0.4)であり、黄色着色剤の着色剤全量に対する質量比である黄色着色剤/全着色剤が0.1~0.4であり、青色着色剤の着色剤全量に対する質量比である青色着色剤/全着色剤が0.2~0.6であり、紫色着色剤の着色剤全量に対する質量比である紫色着色剤/全着色剤が0.01~0.3であることが好ましい。
着色剤全量に対する黄色着色剤と青色着色剤の比率、好ましくは、着色剤全量に対する黄色着色剤と青色着色剤と赤色着色剤と紫色着色剤との比率を、それぞれ上記範囲とすることにより、可視光由来のノイズが少ない状態で近赤外線を透過可能な膜を形成しやすい。
そして、本発明の着色組成物は、着色剤の質量Pと重合性化合物の質量Mとの比率P/Mが、0.05~0.35であり、着色組成物の全固形分中における重合性化合物の含有量が25~65質量%であることにより、皺の抑制された膜を形成できる。このような効果が得られる理由は、次によるものであると推測される。
すなわち、可視光由来のノイズが少ない状態で近赤外線を透過可能な膜を形成可能な着色組成物は、i線などの透過性が低いため、膜表面に比べて膜内部の硬化性が低い傾向にある。このため、膜表面が膜内部よりも先に硬化し易いため、従来は、重合性化合物の硬化に伴う収縮によって、膜表面に皺が発生しやすかった。着色剤の質量Pと重合性化合物の質量Mとの比率P/Mを0.05~0.35とし、着色組成物の全固形分中における重合性化合物の含有量を25~65質量%としたことにより、膜状に適用した着色組成物の膜表面と膜内部との硬化性をほぼ均一にできたため、皺の抑制された膜を形成できたと推測される。特に、膜厚が1.0μm以上、さらには、6.0μmの膜を形成する際に有益である。
以下、本発明の着色組成物の各成分について、説明する。
本発明の着色組成物は、着色剤を含有する。
着色剤は、顔料であってもよく、染料であってもよい。好ましくは、熱や光に対する耐性が高いという理由から顔料である。また、着色剤は、顔料の含有量が、着色剤の全量に対して95質量%以上であることが好ましく、97質量%以上であることがより好ましく、99質量%以上であることが更に好ましい。
C.I.Pigment Yellow 1,2,3,4,5,6,10,11,12,13,14,15,16,17,18,20,24,31,32,34,35,35:1,36,36:1,37,37:1,40,42,43,53,55,60,61,62,63,65,73,74,77,81,83,86,93,94,95,97,98,100,101,104,106,108,109,110,113,114,115,116,117,118,119,120,123,125,126,127,128,129,137,138,139,147,148,150,151,152,153,154,155,156,161,162,164,166,167,168,169,170,171,172,173,174,175,176,177,179,180,181,182,185,187,188,193,194,199,213,214等(以上、黄色顔料)、
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等(以上、赤色顔料)、
C.I.Pigment Green 7,10,36,37,58等(以上、緑色顔料)、
C.I.Pigment Violet 1,19,23,27,32,37,42等(以上、紫色顔料)、
C.I.Pigment Blue 1,2,15,15:1,15:2,15:3,15:4,15:6,16,22,60,64,66,79,80等(以上、青色顔料)、
C.I.Pigment Black 1等(以上、黒色顔料)。
これら有機顔料は、単独若しくは種々組合せて用いることができる。
無機顔料としては、金属酸化物、金属錯塩等で示される金属化合物を挙げることができ、具体的には、カーボンブラック(C.I.Pigment Black 7等)、チタンブラック等の黒色顔料、鉄、コバルト、アルミニウム、カドミウム、鉛、銅、チタン、マグネシウム、クロム、亜鉛、アンチモン等の金属酸化物、および上記金属の複合酸化物を挙げることができる。
化学構造としては、ピラゾールアゾ系、アニリノアゾ系、トリフェニルメタン系、アントラキノン系、アンスラピリドン系、ベンジリデン系、オキソノール系、ピラゾロトリアゾールアゾ系、ピリドンアゾ系、シアニン系、フェノチアジン系、ピロロピラゾールアゾメチン系、キサンテン系、フタロシアニン系、ベンゾピラン系、インジゴ系、ピロメテン系等の染料が使用できる。また、これらの染料の多量体を用いてもよい。
また、染料としては、酸性染料及び/又はその誘導体が好適に使用できる場合がある。
その他、直接染料、塩基性染料、媒染染料、酸性媒染染料、アゾイック染料、分散染料、油溶染料、食品染料、及び/又は、これらの誘導体等も有用に使用することができる。
acid alizarin violet N、
acid black 1,2,24,48、
acid blue 1,7,9,15,18,23,25,27,29,40~45,62,70,74,80,83,86,87,90,92,103,112,113,120,129,138,147,158,171,182,192,243,324:1、
acid chrome violet K、
acid Fuchsin;acid green 1,3,5,9,16,25,27,50、
acid orange 6,7,8,10,12,50,51,52,56,63,74,95、
acid red 1,4,8,14,17,18,26,27,29,31,34,35,37,42,44,50,51,52,57,66,73,80,87,88,91,92,94,97,103,111,114,129,133,134,138,143,145,150,151,158,176,183,198,211,215,216,217,249,252,257,260,266,274、
acid violet 6B,7,9,17,19、
acid yellow 1,3,7,9,11,17,23,25,29,34,36,42,54,72,73,76,79,98,99,111,112,114,116,184,243、
Food Yellow 3。
上述した酸性染料の誘導体も好ましく用いられる。また、上記以外の、アゾ系、キサンテン系、フタロシアニン系の酸性染料も好ましく、C.I.Solvent Blue 44、38;C.I.Solvent orange 45;Rhodamine B、Rhodamine 110等の酸性染料及びこれらの染料の誘導体も好ましく用いられる。
なかでも、染料としては、トリアリールメタン系、アントラキノン系、アゾメチン系、ベンジリデン系、オキソノール系、シアニン系、フェノチアジン系、ピロロピラゾールアゾメチン系、キサンテン系、フタロシアニン系、ベンゾピラン系、インジゴ系、ピラゾールアゾ系、アニリノアゾ系、ピラゾロトリアゾールアゾ系、ピリドンアゾ系、アンスラピリドン系ピロメテン系から選ばれる着色剤であることが好ましい。
さらに、顔料と染料を組み合わせて使用してもよい。
ビスベンゾフラノン系顔料としては、特表2012-528448号公報、特表2010-534726号公報、特表2012-515234号公報などに記載のものが挙げられ、例えば、BASF社製の「IRGAPHOR BK」として入手可能である。
アゾメチン系顔料としては、特開平1-170601号公報、特開平2-34664号公報などに記載のものが挙げられ、例えば、大日精化社製の「クロモファインブラックA1103」として入手できる。
アゾ染料は、特に限定されないが、下記式(A-1)で表される化合物等を好適に挙げることができる。
赤色顔料は、例えば、C.I.Pigment Red 254が好ましい。黄色顔料は、例えばC.I.Pigment Yellow 139が好ましい。青色顔料は、例えばC.I.Pigment Blue 15:6が好ましい。紫色顔料は、例えばC.I.Pigment Violet 23が好ましい。
上述した各態様によれば、着色組成物の波長400nm以上580nm未満の範囲における吸光度の最小値Aと、波長580nm以上770nm以下の範囲における最小値Bとの比率A/Bが0.3~3であり、波長400nm以上750nm以下の範囲における吸光度の最小値Cと、波長850nm以上1300nm以下の範囲における吸光度の最大値Dとの比率C/Dが5以上である着色組成物を得ることができる。
本発明の着色組成物において、着色剤の含有量は、着色組成物の全固形分の1~60質量%であることが好ましく、3~50質量%であることがより好ましく、3~20質量%であることが更に好ましい。
本発明の着色組成物において、着色剤として顔料を用いる場合、顔料を、樹脂、有機溶剤、顔料誘導体等と共に分散させた顔料分散液の形態で用いることが好ましい。以下に顔料分散液の組成、顔料分散液の調製方法について詳述する。
顔料の平均粒子径は、20~300nmが好ましく、25~250nmがより好ましく、30~200nmが更に好ましい。ここでいう「平均粒子径」とは、顔料の一次粒子(単微結晶)が集合した二次粒子についての平均粒子径を意味する。顔料の平均粒子径は、走査型電子顕微鏡(SEM)あるいは透過型電子顕微鏡(TEM)で観察し、粒子が凝集していない部分で粒子サイズを100個計測し、平均値を算出することによって求めることができる。
また、顔料の二次粒子の粒子径分布(以下、単に「粒子径分布」という。)は、(平均粒子径±100)nmに入る二次粒子が全体の70質量%以上、好ましくは80質量%以上であることが好ましい。なお、粒子径分布は、散乱強度分布を用いて測定される。
本発明においては、微細でかつ整粒化された顔料を用いることが好ましい。顔料の微細化は、顔料と有機溶剤と水溶性無機塩類と共に高粘度な液状組成物を調製し、湿式粉砕装置等を使用して、応力を付加して摩砕する工程を経ることで達成される。
微細化工程における水溶性有機溶剤の使用量は、顔料100質量部に対して50~300質量部が好ましく、100~200質量部がより好ましい。
また、水溶性は低いか、或いは、水溶性を有しない他の溶剤を、廃水中に流失しない範囲で用いてもよい。他の溶剤としては、例えば、ベンゼン、トルエン、キシレン、エチルベンゼン、クロロベンゼン、ニトロベンゼン、アニリン、ピリジン、キノリン、テトラヒドロフラン、ジオキサン、酢酸エチル、酢酸イソプロピル、酢酸ブチル、ヘキサン、ヘプタン、オクタン、ノナン、デカン、ウンデカン、ドデカン、シクロヘキサン、メチルシクロヘキサン、ハロゲン化炭化水素、アセトン、メチルエチルケトン、メチルイソブチルケトン、シクロヘキサノン、ジメチルホルムアミド、ジメチルスルホキシド、N-メチルピロリドン等が挙げられる。
顔料の微細化工程に使用する有機溶剤は、1種のみでもよく、必要に応じて2種類以上を混合して使用してもよい。
微細化工程における水溶性無機塩類の使用量は、顔料1質量部に対し1~50質量部が好ましく、1~10質量部がより好ましい。また、水分が1%以下の水溶性無機塩類を用いることが好ましい。
顔料分散液の調製に用いうる樹脂(分散樹脂)としては、高分子分散剤〔例えば、アミン基を有する樹脂(ポリアミドアミンとその塩など)、オリゴイミン系樹脂、ポリカルボン酸とその塩、高分子量不飽和酸エステル、変性ポリウレタン、変性ポリエステル、変性ポリ(メタ)アクリレート、(メタ)アクリル系共重合体、ナフタレンスルホン酸ホルマリン縮合物〕、ポリオキシエチレンアルキルリン酸エステル、ポリオキシエチレンアルキルアミン、アルカノールアミン等の界面活性剤等を挙げることができる。
顔料表面へのアンカー部位を有する末端変性型高分子としては、例えば、特開平3-112992号公報、特表2003-533455号公報等に記載の末端にリン酸基を有する高分子、特開2002-273191号公報等に記載の末端にスルホン酸基を有する高分子、特開平9-77994号公報等に記載の有機色素の部分骨格や複素環を有する高分子などが挙げられる。また、特開2007-277514号公報に記載の高分子末端に2個以上の顔料表面へのアンカー部位(酸基、塩基性基、有機色素の部分骨格やヘテロ環等)を導入した高分子も分散安定性に優れ好ましい。
顔料表面へのアンカー部位を有するグラフト型高分子としては、例えば、特開昭54ー37082号公報、特表平8-507960号公報、特開2009-258668公報等に記載のポリ(低級アルキレンイミン)とポリエステルの反応生成物、特開平9-169821号公報等に記載のポリアリルアミンとポリエステルの反応生成物、特開平10-339949号、特開2004-37986号公報等に記載のマクロモノマーと、窒素原子モノマーとの共重合体、特開2003-238837号公報、特開2008-9426号公報、特開2008-81732号公報等に記載の有機色素の部分骨格や複素環を有するグラフト型高分子、特開2010-106268号公報等に記載のマクロモノマーと酸基含有モノマーの共重合体などが挙げられる。
顔料表面へのアンカー部位を有するグラフト型高分子をラジカル重合で製造する際に用いるマクロモノマーとしては、公知のマクロモノマーを用いることができる。例えば、東亜合成(株)製のマクロモノマーAA-6(末端基がメタクリロイル基であるポリメタクリル酸メチル)、AS-6(末端基がメタクリロイル基であるポリスチレン)、AN-6S(末端基がメタクリロイル基であるスチレンとアクリロニトリルの共重合体)、AB-6(末端基がメタクリロイル基であるポリアクリル酸ブチル)、ダイセル化学工業(株)製のプラクセルFM5(メタクリル酸2-ヒドロキシエチルのε-カプロラクトン5モル当量付加品)、FA10L(アクリル酸2-ヒドロキシエチルのε-カプロラクトン10モル当量付加品)、及び特開平2-272009号公報に記載のポリエステル系マクロモノマー等が挙げられる。これらの中でも、特に柔軟性且つ親溶剤性に優れるポリエステル系マクロモノマーが、顔料の分散性、分散安定性、及び顔料分散物を用いた着色組成物が示す現像性の観点から特に好ましく、更に、特開平2-272009号公報に記載のポリエステル系マクロモノマーで表されるポリエステル系マクロモノマーが最も好ましい。
顔料表面へのアンカー部位を有するブロック型高分子としては、特開2003-49110号公報、特開2009-52010号公報等に記載のブロック型高分子が好ましい。
W1、W2、W3、及び、W4はそれぞれ独立に酸素原子またはNHを表し、酸素原子が好ましい。
R3は、分岐若しくは直鎖のアルキレン基(炭素数は1~10が好ましく、2又は3であることがより好ましい)を表し、分散安定性の観点から、-CH2-CH(CH3)-で表される基、又は、-CH(CH3)-CH2-で表される基が好ましい。
Y1、Y2、Y3、及び、Y4はそれぞれ独立に2価の連結基であり、特に構造上制約されない。
上記グラフト共重合体については、特開2012-255128号公報の段落番号0025~0069の記載を参酌でき、本明細書には上記内容が組み込まれることとする。
上記グラフト共重合体の具体例としては、例えば、以下が挙げられる。また、特開2012-255128号公報の段落番号0072~0094に記載の樹脂を用いることができる。
オリゴイミン系樹脂は、例えば、下記式(I-1)で表される繰り返し単位と、式(I-2)で表される繰り返し単位、および/または、式(I-2a)で表される繰り返し単位とを含む樹脂などが挙げられる。
R8及びR9はR1と同義である。
Lは単結合、アルキレン基(炭素数1~6が好ましい)、アルケニレン基(炭素数2~6が好ましい)、アリーレン基(炭素数6~24が好ましい)、ヘテロアリーレン基(炭素数1~6が好ましい)、イミノ基(炭素数0~6が好ましい)、エーテル基、チオエーテル基、カルボニル基、またはこれらの組合せに係る連結基である。なかでも、単結合もしくは-CR5R6-NR7-(イミノ基がXもしくはYの方になる)であることが好ましい。ここで、R5R6は各々独立に、水素原子、ハロゲン原子、アルキル基(炭素数1~6が好ましい)を表す。R7は水素原子または炭素数1~6のアルキル基である。
LaはCR8CR9とNとともに環構造を形成する構造部位であり、CR8CR9の炭素原子と合わせて炭素数3~7の非芳香族複素環を形成する構造部位であることが好ましい。さらに好ましくは、CR8CR9の炭素原子及びN(窒素原子)を合わせて5~7員の非芳香族複素環を形成する構造部位であり、より好ましくは5員の非芳香族複素環を形成する構造部位であり、ピロリジンを形成する構造部位であることが特に好ましい。この構造部位はさらにアルキル基等の置換基を有していてもよい。
XはpKa14以下の官能基を有する基を表す。
Yは原子数40~10,000の側鎖を表す。
上記樹脂(オリゴイミン系樹脂)は、さらに式(I-3)、式(I-4)、および、式(I-5)で表される繰り返し単位から選ばれる1種以上を共重合成分として含有していてもよい。上記樹脂が、このような繰り返し単位を含むことで、顔料の分散性能を更に向上させることができる。
Yaはアニオン基を有する原子数40~10,000の側鎖を表す。式(I-3)で表される繰り返し単位は、主鎖部に一級又は二級アミノ基を有する樹脂に、アミンと反応して塩を形成する基を有するオリゴマー又はポリマーを添加して反応させることで形成することが可能である。
ここで、顔料の量は、着色剤全量に含まれる顔料の総量を意味する。
顔料分散液は、更に、顔料誘導体を含有することが好ましい。
顔料誘導体とは、顔料の一部分を、酸性基、塩基性基、フタルイミドメチル基などで置換した構造を有する化合物である。顔料誘導体としては、分散性及び分散安定性の観点から、酸性基又は塩基性基を有する顔料誘導体を含有することが好ましい。
顔料誘導体を構成するための顔料としては、ジケトピロロピロール顔料、アゾ顔料、フタロシアニン顔料、アントラキノン顔料、キナクリドン顔料、ジオキサジン顔料、ペリノン顔料、ペリレン顔料、チオインジゴ顔料、イソインドリン顔料、イソインドリノン顔料、キノフタロン顔料、スレン顔料、金属錯体顔料等が挙げられる。
顔料誘導体が有する酸性基としては、スルホン酸基、カルボン酸基及びその4級アンモニウム塩が好ましく、カルボン酸基及びスルホン酸基がさらに好ましく、スルホン酸基が特に好ましい。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、特に三級アミノ基が好ましい。
顔料誘導体としては、キノリン顔料誘導体、ベンズイミダゾロン顔料誘導体及びイソインドリン顔料誘導体が好ましく、キノリン顔料誘導体及びベンズイミダゾロン顔料誘導体が特に好ましい。
顔料分散液における顔料誘導体の含有量は、顔料の全質量に対し、1~50質量%が好ましく、3~30質量%がさらに好ましい。顔料誘導体は、1種のみを用いてもよいし、2種以上を併用してもよい。
顔料分散液は有機溶剤を含有することが好ましい。
有機溶剤は、顔料分散液中に含まれる各成分の溶解性や、顔料分散液を着色組成物に応用した場合の塗布性などにより選択される。有機溶剤としては、エステル類、エーテル類、ケトン類、芳香族炭化水素類が用いられる。中でも、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、ジエチレングリコールモノエチルエーテルアセテート、ジエチレングリコールモノブチルエーテルアセテート、プロピレングリコールメチルエーテル、プロピレングリコールモノメチルエーテルアセテートが好ましい。また、後述する着色組成物に含むことができる有機溶剤を用いることも好ましい。
顔料分散液における有機溶剤の含有量としては、50~95質量%が好ましく、70~90質量%がより好ましい。
本発明の着色組成物は、重合性化合物を含有する。
重合性化合物は、重合性基を有する化合物であって、ラジカルにより重合可能な公知の重合性化合物を用いることができる。重合性基としては、エチレン性不飽和結合を有する基が好ましい。エチレン性不飽和結合を有する基としては、ビニル基、アリル基、メタリル基、アクリロイル基、メタクリロイル基、アリルオキシカルボニル基、メタリルオキシカルボニル基などが挙げられる。
重合性化合物は、例えば、モノマー、プレポリマー(すなわち2量体、3量体及びオリゴマー)、又はそれらの混合物並びにそれらの多量体などの化学的形態のいずれであってもよい。
重合性化合物は、感度の観点から、重合性基を1個以上有する化合物が好ましく、重合性基を2個以上有する化合物がより好ましい。中でも、重合性基を4個以上有する4官能以上の多官能重合性化合物が好ましく、5官能以上の多官能重合性化合物がさらに好ましい。
重合性化合物の分子量は100~2000が好ましく、1000~2000がより好ましい。また、重合性化合物の分子量の値を、重合性化合物中に含まれる重合性基の数で割った値は、100~300が好ましく、200~300がより好ましい。この態様によれば、重合性化合物の架橋密度が適度であるので、皺の発生をより効果的に抑制できる。
なお、重合性化合物の分子量の値は、重合性化合物がモノマーの場合は、分子構造から求めた理論値であり、重合性化合物がオリゴマー又はポリマーの場合は、重量平均分子量を意味する。
本発明は、アルキレンオキシ基を繰り返し単位として2以上含むアルキレンオキシ鎖を有する重合性化合物を含有するものを用いることが好ましい。アルキレンオキシ鎖を有する重合性化合物は、柔軟性を有しているため、重合性化合物の硬化に伴う膜の収縮を抑制でき、膜表面の皺の発生を効果的に抑制できる。
アルキレンオキシ鎖は、アルキレンオキシ基の繰り返し単位数が2~30であることが好ましく、2~20がより好ましく、5~15が更に好ましい。
アルキレンオキシ基の炭素数は、2以上が好ましく、2~10がより好ましく、2~4が更に好ましく、2が特に好ましい。アルキレンオキシ基は、直鎖、分岐のいずれであってもよいが、直鎖が好ましい。アルキレンオキシ基は、無置換であることが好ましい。
すなわち、アルキレンオキシ鎖は、「-((CH2)a-O)b-」で表されることが好ましい。式中、aは2以上が好ましく、2~20がより好ましい。bは、2以上が好ましく、2~10がより好ましい。
アルキレンオキシ鎖を有する重合性化合物は、エチレンオキシ基を繰り返し単位として2以上含むエチレンオキシ鎖を有する重合性化合物であることが好ましい。エチレンオキシ鎖を有する重合性化合物は、柔軟性が特に優れているので、膜表面の皺の発生をより効果的に抑制できる。
環状構造としては、芳香族環構造、脂環構造、ヘテロ環構造などが挙げられる。好ましくはヘテロ環構造である。ヘテロ環構造のヘテロ環は、5員環または6員環が好ましい。ヘテロ環は、単環、または、縮合環が好ましく、単環がより好ましい。ヘテロ環を構成するヘテロ原子としては、窒素原子、酸素原子、硫黄原子などが挙げられ、窒素原子が好ましい。ヘテロ原子の数は、1~3が好ましく、2~3がより好ましく、3が特に好ましい。
アルキレンオキシ鎖を有する重合性化合物は、下記一般式(1)で表される部分構造を有することが好ましい。式中の*は連結手である。
重合性基としては、ビニル基、アリル基、メタリル基、アクリロイル基、メタクリロイル基、アリルオキシカルボニル基、メタリルオキシカルボニル基から選ばれる1種以上が好ましい。
一般式(1a)において、X1~X3が複数存在する場合、複数存在するX1~X3は、それぞれ同一であってもよく、異なっていてもよい。
L1~L3が表す連結基としては、例えば、2価の連結基の場合、-((CH2)a-O)b-、-(CH2)c-、-CO-、および、-NH-から選ばれる1種または2種以上を組み合わせてなる基が挙げられる。
aは、2以上の整数を表し、2~10が好ましく、2~4がより好ましく、2が更に好ましい。
bは、2以上の整数を表し、2~30が好ましく、2~20がより好ましく、5~15が更に好ましい。
cは、1以上の整数を表し、1~30が好ましく、1~20がより好ましく、1~10が更に好ましい。
L1~L3が表す連結基が、3価以上の連結基の場合、上述した2価の連結基の例として挙げた基のうち、1個以上の水素原子を取り除いた基が挙げられる。
一般式(Z-4)中、アクリロイル基およびメタクリロイル基の合計は3個または4個であり、mは各々独立に0~10の整数を表し、mの少なくとも一つは2~10の整数を表し、各mの合計は2~40の整数である。
一般式(Z-5)中、アクリロイル基およびメタクリロイル基の合計は5個または6個であり、nは各々独立に0~10の整数を表し、nの少なくとも一つは2~10の整数を表し、各nの合計は2~60の整数である。
一般式(Z-5)中、nは、0~6の整数が好ましく、0~4の整数がより好ましい。
また、各nの合計は、3~60の整数が好ましく、3~24の整数がより好ましく、6~12の整数が特に好ましい。
また、一般式(Z-4)または一般式(Z-5)中の-((CH2)yCH2O)-または-((CH2)yCH(CH3)O)-は、酸素原子側の末端がXに結合する形態が好ましい。
具体的には、下記式(a)~(f)で表される化合物(以下、「例示化合物(a)~(f)」ともいう。)が挙げられ、中でも、例示化合物(a)、(b)、(e)、(f)が好ましい。
本発明の着色組成物は、アルキレンオキシ鎖を有する重合性化合物以外の重合性化合物(以下、「他の重合性化合物」という)を含有してもよい。他の重合性化合物としては、特に限定はなく、従来公知の重合性化合物を用いることができる。
例えば、不飽和カルボン酸(例えば、アクリル酸、メタクリル酸、イタコン酸、クロトン酸、イソクロトン酸、マレイン酸など)やそのエステル類、アミド類、並びにこれらの多量体が挙げられる。好ましくは、不飽和カルボン酸と脂肪族多価アルコール化合物とのエステル、及び不飽和カルボン酸と脂肪族多価アミン化合物とのアミド類、並びにこれらの多量体が挙げられる。
また、ヒドロキシル基やアミノ基、メルカプト基等の求核性置換基を有する不飽和カルボン酸エステル或いはアミド類と、単官能若しくは多官能イソシアネート類或いはエポキシ類との付加反応物や、単官能若しくは多官能のカルボン酸との脱水縮合反応物等も用いることができる。
また、イソシアネート基やエポキシ基等の親電子性置換基を有する不飽和カルボン酸エステル或いはアミド類と、単官能若しくは多官能のアルコール類、アミン類、チオール類との付加反応物、更に、ハロゲン基やトシルオキシ基等の脱離性置換基を有する不飽和カルボン酸エステル或いはアミド類と、単官能若しくは多官能のアルコール類、アミン類、チオール類との置換反応物も用いることができきる。
また、上記の不飽和カルボン酸の代わりに、不飽和ホスホン酸、スチレン等のビニルベンゼン誘導体、ビニルエーテル、アリルエーテル等に置き換えた化合物群を使用することも可能である。
これらの具体的な化合物としては、特開2009-288705号公報の段落番号〔0095〕~〔0108〕に記載されている化合物を本発明においても用いることができる。
多官能カルボン酸にグリシジル(メタ)アクリレート等の環状エーテル基とエチレン性不飽和基を有する化合物を反応させ得られる多官能(メタ)アクリレートなども挙げることができる。
また、特開2010-160418号、特開2010-129825号各公報、及び特許4364216号明細書等に記載される、カルド樹脂(例えば、フルオレン環を有し、エチレン性不飽和基を2官能以上有する化合物)も使用することもできる。
なお、一般式(MO-1)~(MO-5)において、Tがアルキレンオキシ基の場合には、炭素原子側の末端がRに結合する。
一般式(MO-1)~(MO-5)において、複数存在するRの少なくとも1つは、-OC(=O)CH=CH2、又は、-OC(=O)C(CH3)=CH2で表される基を表す。
一般式(MO-1)~(MO-5)で表される重合性化合物の具体例としては、特開2007-269779号公報の段落番号0248~段落番号0251に記載されている化合物を本発明においても好適に用いることができる。
カプロラクトン構造を有する重合性化合物としては、その分子内にカプロラクトン構造を有する限り特に限定されるものではないが、例えば、トリメチロールエタンやジトリメチロールエタン、トリメチロールプロパン、ジトリメチロールプロパン、ペンタエリスリトール、ジペンタエリスリトール、トリペンタエリスリトール、グリセリン、ジグリセロール、トリメチロールメラミン等の多価アルコールと、(メタ)アクリル酸およびε-カプロラクトンとをエステル化することにより得られる、ε-カプロラクトン変性多官能(メタ)アクリレートを挙げることができる。なかでも下記一般式(Z-1)で表されるカプロラクトン構造を有する重合性化合物が好ましい。
本発明の着色組成物において、着色組成物に含まれる着色剤の質量Pと、着色組成物に含まれる重合性化合物の質量Mとの比率P/Mは、0.05~0.35が好ましく、0.1~0.35がより好ましい。この態様によれば、膜状に適用した着色組成物の、膜表面と膜内部における硬化性をほぼ均一にでき、皺の発生をより効果的に抑制できる。更には、可視光由来のノイズがより少ない状態で近赤外線を透過可能な膜を形成することができる。更には、パターン形成時における残渣の発生を抑制できる。
本発明の着色組成物は、重合性化合物の反応を促進させることなどを目的として、分子内に2個以上のメルカプト基を有する多官能チオール化合物を含んでいてもよい。多官能チオール化合物は、2級のアルカンチオール類であることが好ましく、特に下記一般式(I)で表される構造を有する化合物であることが好ましい。
多官能チオール化合物は、1種類のみを含んでいてもよいし、2種類以上含んでいてもよい。2種類以上含む場合は、その合計量が上記範囲となることが好ましい。
また、多官能チオール化合物は安定性、臭気、解像性、現像性、密着性等の改良を目的として添加してもよい。
本発明の着色組成物は樹脂を含有する。なお、本発明において、「樹脂」には、「重合性化合物」を含まないこととする。
樹脂は、ヒドロキシル基を有していることが好ましい。ヒドロキシル基を有することにより、基材に対する密着性を向上できる。
本発明の着色組成物において、樹脂の含有量は、着色組組成物の全固形分の10~80質量%が好ましく、20~70質量%がより好ましく、30~60質量%が更に好ましい。
本発明の着色組成物は、着色組成物に含まれる重合性化合物の質量Mと、着色組成物に含まれる樹脂の質量重合性化合物の質量Bとの比率M/Bは、0.4~3.0が好ましく、0.4~0.9がより好ましく、0.4~0.8が更に好ましい。この態様によれば、膜状に適用した着色組成物の、膜表面と膜内部における硬化性をほぼ均一にでき、皺の発生をより効果的に抑制できる。
樹脂は、上述した分散樹脂や、以下に示す、アルカリ可溶性樹脂などが挙げられる。
以下、アルカリ可溶性樹脂について説明する。
本発明の着色組成物は、樹脂としてアルカリ可溶性樹脂を含有することができる。アルカリ可溶性樹脂を含有することにより、現像性及びパターン形成性が向上する。
アルカリ可溶性樹脂の分子量としては、特に定めるものではないが、重量平均分子量(Mw)が5,000~100,000であることが好ましい。また、数平均分子量(Mn)は、1,000~20,000であることが好ましい。
アルカリ可溶性樹脂としては、線状有機高分子重合体であってもよく、分子(好ましくは、アクリル系共重合体、スチレン系共重合体を主鎖とする分子)中に少なくとも1つのアルカリ可溶性を促進する基を有するアルカリ可溶性樹脂の中から適宜選択することができる。
アルカリ可溶性樹脂としては、耐熱性の観点からは、ポリヒドロキシスチレン系樹脂、ポリシロキサン系樹脂、アクリル系樹脂、アクリルアミド系樹脂、アクリル/アクリルアミド共重合体樹脂が好ましく、現像性制御の観点からは、アクリル系樹脂、アクリルアミド系樹脂、アクリル/アクリルアミド共重合体樹脂が好ましい。
アルカリ可溶性を促進する基(以下、酸基ともいう)としては、例えば、カルボキシル基、リン酸基、スルホン酸基、フェノール性ヒドロキシル基などが挙げられるが、有機溶剤に可溶で弱アルカリ水溶液により現像可能なものが好ましく、(メタ)アクリル酸が特に好ましいものとして挙げられる。これら酸基は、1種のみであってもよいし、2種以上であってもよい。
ノボラック樹脂としては、例えば、フェノール類とアルデヒド類とを酸触媒の存在下に縮合させて得られるものが挙げられる。上記フェノール類としては、例えば、フェノール、クレゾール、エチルフェノール、ブチルフェノール、キシレノール、フェニルフェノール、カテコール、レゾルシノール、ピロガロール、ナフトール、又はビスフェノールA等が挙げられる。アルデヒド類としては、例えば、ホルムアルデヒド、パラホルムアルデヒド、アセトアルデヒド、プロピオンアルデヒド、又はベンズアルデヒド等が挙げられる。フェノール類及びアルデヒド類は、単独若しくは2種以上を組み合わせて用いることができる。
ノボラック樹脂の具体例としては、例えば、メタクレゾール、パラクレゾール又はこれらの混合物とホルマリンとの縮合生成物が挙げられる。
ノボラック樹脂は分別等の手段を用いて分子量分布を調節してもよい。又、ビスフェノールCやビスフェノールA等のフェノール系ヒドロキシル基を有する低分子量成分をノボラック樹脂に混合してもよい。
重合性基を含有するアルカリ可溶性樹脂としては、予めイソシアネート基とヒドロキシル基を反応させ、未反応のイソシアネート基を1つ残し、かつ(メタ)アクリロイル基等の重合性基を含む化合物と、カルボキシル基を含むアクリル樹脂とを反応させて得られるウレタン変性したアルカリ可溶性樹脂;カルボキシル基を含むアクリル樹脂と、分子内にエポキシ基及び重合性二重結合を有する化合物との反応によって得られるアルカリ可溶性樹脂;酸ペンダント型エポキシアクリレート樹脂;ヒドロキシル基を含むアクリル樹脂と重合性二重結合を有する2塩基酸無水物を反応させて得られるアルカリ可溶性樹脂;ヒドロキシル基を含むアクリル樹脂と、イソシアネート及び重合性基を有する化合物を反応させて得られるアルカリ可溶性樹脂;特開2002-229207号公報及び特開2003-335814号公報に記載されるα位又はβ位にハロゲン原子或いはスルホネート基などの脱離基を有するエステル基を側鎖に有する樹脂を、塩基性処理して得られるアルカリ可溶性樹脂;などが好ましい。
重合性基を含有するアルカリ可溶性樹脂としては、ダイヤナ-ルNRシリーズ(三菱レイヨン株式会社製)、Photomer6173(COOH含有 polyurethane acrylic oligomer.Diamond Shamrock Co.Ltd.,製)、ビスコートR-264、KSレジスト106(いずれも大阪有機化学工業株式会社製)、サイクロマーPシリーズ、プラクセル CF200シリーズ(いずれもダイセル化学工業株式会社製)、Ebecryl3800(ダイセルユーシービー株式会社製)などが挙げられる。
上記炭化水素基としては、特に制限はないが、例えば、メチル、エチル、n-プロピル、イソプロピル、n-ブチル、イソブチル、t-ブチル、t-アミル、ステアリル、ラウリル、2-エチルヘキシル等の直鎖状又は分岐状のアルキル基;フェニル等のアリール基;シクロヘキシル、t-ブチルシクロヘキシル、ジシクロペンタジエニル、トリシクロデカニル、イソボルニル、アダマンチル、2-メチル-2-アダマンチル等の脂環式基;1-メトキシエチル、1-エトキシエチル等のアルコキシで置換されたアルキル基;ベンジル等のアリール基で置換されたアルキル基;等が挙げられる。これらの中でも特に、メチル、エチル、シクロヘキシル、ベンジル等のような酸や熱で脱離しにくい1級又は2級炭素の炭化水素基が耐熱性の点で好ましい。
樹脂(a)は、エーテルダイマーと共に、その他の単量体を共重合させた共重合体であってもよい。
また、樹脂(a)が酸基を有する場合には、酸価は30~500mgKOH/gが好ましく、50~400mgKOH/gがより好ましい。
樹脂(a)の合成に適用される重合方法としては、特に制限はなく、従来公知の各種重合方法を採用することができるが、特に、溶液重合法によることが好ましい。詳細には、例えば、特開2004-300204号公報に記載される樹脂(a)の合成方法に準じて、樹脂(a)を合成することができる。
以下、樹脂(a)の例示化合物を示すが、本発明はこれらに限定されるものではない。下記に示す例示化合物の組成比はモル%である。
上記式(X)で示されるエチレン性不飽和単量体に由来する構造単位を含む樹脂の具体例としては、特開2012-247591号公報、特開2013-24934号公報に記載されている樹脂等が挙げられる。
アルカリ可溶性樹脂の含有量は、着色組成物の全固形分に対して、10~80質量%が好ましく、20~70質量%がより好ましく、30~60質量%が更に好ましい。
本発明の着色組成物は、光重合開始剤を含有することが好ましい。
光重合開始剤としては、重合性化合物の重合を開始する能力を有する限り、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の光線に対して感光性を有するものが好ましい。また、光励起された増感剤と何らかの作用を生じ、活性ラジカルを生成する光重合開始剤であってもよく、重合性化合物の種類に応じてカチオン重合を開始させるような光重合開始剤であってもよい。
ヒドロキシアセトフェノン系開始剤としては、IRGACURE-184、DAROCUR-1173、IRGACURE-500、IRGACURE-2959、IRGACURE-127(商品名:いずれもBASF社製)を用いることができる。アミノアセトフェノン系開始剤としては、市販品であるIRGACURE-907、IRGACURE-369、及び、IRGACURE-379(商品名:いずれもBASF社製)を用いることができる。アミノアセトフェノン系開始剤として、365nmまたは405nm等の長波光源に吸収波長がマッチングされた特開2009-191179号公報に記載の化合物も用いることができる。また、アシルホスフィン系開始剤としては市販品であるIRGACURE-819やDAROCUR-TPO(商品名:いずれもBASF社製)を用いることができる。
着色組成物が、光重合開始剤としてオキシム化合物を含有することにより、着色組成物の塗布から露光までの時間(PCD:Post Coating Delay)に対するパターンの特性依存性(「PCD依存性」とも言う)が良好なものとなる。
オキシム化合物の具体例としては、特開2001-233842号公報記載の化合物、特開2000-80068号公報記載の化合物、特開2006-342166号公報記載の化合物を用いることができる。
市販品ではIRGACURE OXE-01(BASF社製)、IRGACURE OXE-02(BASF社製)、TRONLY TR-PBG-304、TRONLY TR-PBG-309、TRONLY TR-PBG-305(常州強力電子新材料有限公司(CHANGZHOU TRONLY NEW ELECTRONIC MATERIALS CO.,LTD)製)、アデカアークルズNCI-831、アデカアークルズNCI-930(ADEKA社製)も好適に用いられる。
好ましくは、例えば、特開2013-29760号公報の段落0274~0275を参酌することができ、この内容は本願明細書に組み込まれる。
具体的には、オキシム化合物としては、下記一般式(OX-1)で表される化合物が好ましい。なお、オキシムのN-O結合が(E)体のオキシム化合物であっても、(Z)体のオキシム化合物であっても、(E)体と(Z)体との混合物であってもよい。
一般式(OX-1)中、Rで表される一価の置換基としては、一価の非金属原子団であることが好ましい。一価の非金属原子団としては、アルキル基、アリール基、アシル基、アルコキシカルボニル基、アリールオキシカルボニル基、複素環基、アルキルチオカルボニル基、アリールチオカルボニル基等が挙げられる。これらの基は、1以上の置換基を有していてもよい。置換基としてはハロゲン原子、アリールオキシ基、アルコキシカルボニル基またはアリールオキシカルボニル基、アシルオキシ基、アシル基、アルキル基、アリール基等が挙げられる。
一般式(OX-1)中、Bで表される一価の置換基としては、アリール基、複素環基、アリールカルボニル基、又は、複素環カルボニル基が好ましい。これらの基は1以上の置換基を有していてもよい。置換基としては、前述した置換基が例示できる。
一般式(OX-1)中、Aで表される二価の有機基としては、炭素数1~12のアルキレン基、シクロアルキレン基、アルキニレン基が好ましい。これらの基は1以上の置換基を有していてもよい。置換基としては、前述した置換基が例示できる。
オキシム化合物は、365nm又は405nmにおけるモル吸光係数は、感度の観点から、1,000~300,000であることが好ましく、2,000~300,000であることがより好ましく、5,000~200,000であることが特に好ましい。
化合物のモル吸光係数は、公知の方法を用いることができる。具体的には、例えば、紫外可視分光光度計(Varian社製Carry-5 spectrophotometer)にて、酢酸エチルを用い、0.01g/Lの濃度で測定することが好ましい。
光重合開始剤は、1種のみを用いてもよく、2種以上を組み合わせて使用してもよい。2種以上を組み合わせて用いる場合は、合計の含有量が上記範囲であることが好ましい。
本発明の着色組成物は、紫外線吸収剤を含有することができる。
紫外線吸収剤は、波長365nmにおける1g当りの吸光係数が100超であってかつ波長400nm以上における1g当りの吸光係数が10以下である化合物が好ましい。波長365nmにおける1g当りの吸光係数が100超であれば、少量であっても優れた紫外線吸収効果が得られる。また、波長400nm以上における1g当りの吸光係数が10以下であれば、可視領域のデバイス分光への影響を低減できる。なお、吸光係数は、紫外可視分光光度計(Varian社製、Carry-5 spectrophotometer)にて、酢酸エチルを用いて0.01g/Lの濃度で測定される値である。
R3及びR4は、電子吸引基を表す。電子吸引基は、ハメットの置換基定数σp値(以下、単に「σp値」という。)が、0.20以上1.0以下の電子吸引性基が好ましく、σp値が0.30以上0.8以下の電子吸引性基がより好ましい。
ハメット則は、ベンゼン誘導体の反応又は平衡に及ぼす置換基の影響を定量的に論ずるために、1935年にL. P. Hammettにより提唱された経験則であるが、これは今日広く妥当性が認められている。ハメット則により求められた置換基定数には、σp値とσm値とがあり、これらの値は多くの一般的な成書に記載があるが、例えば、J.A. Dean編「Lange’s Handbook of Chemistry」第12版、1979年(Mc Graw-Hill)や「化学の領域増刊」、122号、96~103頁、1979年(南江堂)、Chemical Reviews, 91巻、165頁~195頁、1991年に詳しく記載されている。本発明では、これらの成書に記載の文献既知の値がある置換基にのみ限定されるという意味ではなく、その値が文献未知であってもハメット則に基づいて測定した場合にその範囲内に含まれる限り包含されることは勿論である。
R3としては、シアノ基、-COOR5、-CONHR5、-COR5、-SO2R5より選択される基が好ましい。R4としては、シアノ基、-COOR6、-CONHR6、-COR6、-SO2R6より選択される基が好ましい。R5及びR6は、各々独立に、炭素原子数1~20のアルキル基、又は炭素原子数6~20のアリール基を表す。
R3及びR4は、互いに結合して環を形成してもよい。
R1、R2、R3、及びR4の少なくとも1つは、連結基を介して、ビニル基と結合したモノマーより導かれるポリマーの形になっていてもよい。また、他のモノマーとの共重合体であってもよい。
紫外線吸収剤は1種のみを用いてもよく、2種以上を組み合わせて使用してもよい。2種以上を組み合わせて用いる場合は、合計の含有量が上記範囲であることが好ましい。
本発明の着色組成物が、光重合開始剤と紫外線吸収剤とを含む場合、光重合開始剤の質量(D)と紫外線吸収剤の質量(B)との比率(D/B)は、0.25~1.25が好ましく、0.3~1.1がより好ましく、0.4~1.0の範囲が特に好ましい。前述した比率が上記範囲であれば、感度が良好で、さらには、微細なパターン形状(特に矩形)を精細に形成できる。
本発明の着色組成物は、有機溶剤を含有することができる。有機溶剤は、各成分の溶解性や着色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が、特に紫外線吸収剤、アルカリ可溶性樹脂等の溶解性、着色組成物の塗布性、安全性を考慮して選ばれることが好ましい。
エステル類として、例えば、酢酸エチル、酢酸-n-ブチル、酢酸イソブチル、酢酸シクロヘキシル、ギ酸アミル、酢酸イソアミル、酢酸イソブチル、プロピオン酸ブチル、酪酸イソプロピル、酪酸エチル、酪酸ブチル、乳酸メチル、乳酸エチル、オキシ酢酸アルキル(例えば、オキシ酢酸メチル、オキシ酢酸エチル、オキシ酢酸ブチル(例えば、メトキシ酢酸メチル、メトキシ酢酸エチル、メトキシ酢酸ブチル、エトキシ酢酸メチル、エトキシ酢酸エチル等))、3-オキシプロピオン酸アルキルエステル類(例えば、3-オキシプロピオン酸メチル、3-オキシプロピオン酸エチル等(例えば、3-メトキシプロピオン酸メチル、3-メトキシプロピオン酸エチル、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等))、2-オキシプロピオン酸アルキルエステル類(例:2-オキシプロピオン酸メチル、2-オキシプロピオン酸エチル、2-オキシプロピオン酸プロピル等(例えば、2-メトキシプロピオン酸メチル、2-メトキシプロピオン酸エチル、2-メトキシプロピオン酸プロピル、2-エトキシプロピオン酸メチル、2-エトキシプロピオン酸エチル))、2-オキシ-2-メチルプロピオン酸メチル及び2-オキシ-2-メチルプロピオン酸エチル(例えば、2-メトキシ-2-メチルプロピオン酸メチル、2-エトキシ-2-メチルプロピオン酸エチル等)、ピルビン酸メチル、ピルビン酸エチル、ピルビン酸プロピル、アセト酢酸メチル、アセト酢酸エチル、2-オキソブタン酸メチル、2-オキソブタン酸エチル等、
エーテル類として、例えば、ジエチレングリコールジメチルエーテル、テトラヒドロフラン、エチレングリコールモノメチルエーテル、エチレングリコールモノエチルエーテル、メチルセロソルブアセテート、エチルセロソルブアセテート、ジエチレングリコールモノメチルエーテル、ジエチレングリコールモノエチルエーテル、ジエチレングリコールモノブチルエーテル、プロピレングリコールモノメチルエーテル、プロピレングリコールモノメチルエーテルアセテート、プロピレングリコールモノエチルエーテルアセテート、プロピレングリコールモノプロピルエーテルアセテート等、
ケトン類として、例えば、メチルエチルケトン、シクロペンタノン、シクロヘキサノン、2-ヘプタノン、3-ヘプタノン等、並びに、
芳香族炭化水素類として、例えば、トルエン、キシレン等が好適に挙げられる。
有機溶剤を2種以上組み合わせて用いる場合、特に好ましくは、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、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メチルエーテル、及びプロピレングリコールメチルエーテルアセテートから選択される2種以上で構成される混合溶液である。
本発明の着色組成物は、光重合開始剤のラジカル発生効率の向上、感光波長の長波長化の目的で、増感剤を含有していてもよい。
増感剤としては、300nm~450nmの波長領域に吸収波長を有する増感剤が挙げられる。増感剤は、光重合開始剤に対し、電子移動機構又はエネルギー移動機構で増感させるものが好ましい。
増感剤としては、例えば、フェナントレン、アントラセン、ピレン、ペリレン、トリフェニレン、9,10-ジアルコキシアントラセンのような多核芳香族類、フルオレッセイン、エオシン、エリスロシン、ローダミンB、ローズベンガルのようなキサンテン類、チオキサントン類、シアニン類、メロシアニン類、フタロシアニン類、チオニン、メチレンブルー、トルイジンブルーのようなチアジン類、アクリジン類、アントラキノン類、スクアリリウム類、クマリン類、フェノチアジン類、フェナジン類、スチリルベンゼン類、アゾ化合物、ジフェニルメタン、トリフェニルメタン、ジスチリルベンゼン類、カルバゾール類、ポルフィリン、スピロ化合物、キナクリドン、インジゴ、スチリル、ピリリウム化合物、ピロメテン化合物、ピラゾロトリアゾール化合物、ベンゾチアゾール化合物、バルビツール酸誘導体、チオバルビツール酸誘導体、アセトフェノン、ベンゾフェノン、ミヒラーズケトンなどの芳香族ケトン化合物、N-アリールオキサゾリジノンなどのヘテロ環化合物などが挙げられる。
また、例えば、特開2008-32803号公報の段落番号〔0101〕~〔0154〕に記載される化合物が挙げられる。
着色組成物中における増感剤の含有量は、深部への光吸収効率と開始分解効率の観点から、固形分換算で、0.1~20質量%であることが好ましく、0.5~15質量%がより好ましい。
増感剤は、1種単独で用いてもよいし、2種以上を併用してもよい。2種以上を併用する場合は、合計量が上記範囲であることが好ましい。
本発明の着色組成物には、用いる光重合開始剤によっては、連鎖移動剤を加えることが好ましい。連鎖移動剤としては、N,N-ジアルキルアミノ安息香酸アルキルエステルやチオール系化合物があげられ、チオール系化合物としては、2-メルカプトベンゾチアゾール、2-メルカプト-1-フェニルベンズイミダゾール、3-メルカプトプロピオン酸、などを単独又は2種以上混合して使用することができる。
本発明における着色組成物は、着色組成物の製造中又は保存中において、重合性化合物の不要な熱重合を阻止するために、重合禁止剤を含有させてもよい。
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-t-ブチル-p-クレゾール、ピロガロール、t-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-t-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。
重合禁止剤の添加量は、着色組成物の質量に対して、0.01~5質量%が好ましい。
本発明の着色組成物は、基板密着性を向上させる目的で、基板密着剤を含有させてもよい。
基板密着剤としては、シラン系カップリング剤、チタネート系カップリング剤、アルミニウム系カップリング剤を用いることが好ましい。シラン系カップリング剤としては、例えば、γ-メタクリロキシプロピルトリメトキシシラン、γ-メタクリロキシプロピルトリエトキシシラン、γ-アクリロキシプロピルトリメトキシシラン、γ-アクリロキシプロピルトリエトキシシラン、γ-メルカプトプロピルトリメトキシシラン、γ-アミノプロピルトリエトキシシラン、フェニルトリメトキシシラン、等が挙げられる。中でも、基板密着剤としては、γ-メタクリロキシプロピルトリメトキシシランが好ましい。
基板密着剤の含有量は、着色組成物を露光、現像した際に、未露光部に残渣が残らないようにする観点から、着色組成物の全固形分に対して、0.1~30質量%が好ましく、0.5~20質量%がより好ましく、1~10質量%が特に好ましい。
本発明の着色組成物は、塗布性をより向上させる観点から、各種の界面活性剤を含有してもよい。界面活性剤としては、フッ素系界面活性剤、ノニオン系界面活性剤、カチオン系界面活性剤、アニオン系界面活性剤、シリコーン系界面活性剤などの各種界面活性剤を使用できる。
界面活性剤の含有量は、着色組成物の全質量に対して、0.001~2.0質量%が好ましく、0.005~1.0質量%がより好ましい。
本発明における着色組成物は、必要に応じて、熱重合開始剤;熱重合成分、エポキシ化合物、ジオクチルフタレートなどの可塑剤;低分子量有機カルボン酸などの現像性向上剤;その他充填剤;酸化防止剤;凝集防止剤;などの各種添加物を含有することができる。
着色組成物は、上述した各成分を混合することで調製することができる。
なお、着色組成物の調製に際しては、着色組成物を構成する各成分を一括配合してもよいし、各成分を溶剤に溶解又は分散した後に逐次配合してもよい。また、配合する際の投入順序や作業条件は特に制約を受けない。例えば、全成分を同時に溶剤に溶解又は分散して着色組成物を調製してもよいし、必要に応じては、各成分を適宜2つ以上の溶液又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組成物として調製してもよい。
フィルタとしては、従来から濾過用途等に用いられているフィルタであれば特に限定されることなく用いることができる。
フィルタの材質の例としては、ポリテトラフルオロエチレン(PTFE)等のフッ素樹脂;ナイロン-6、ナイロン-6,6等のポリアミド系樹脂;ポリエチレン、ポリプロピレン(PP)等のポリオレフィン樹脂(高密度、超高分子量を含む);等が挙げられる。これら素材の中でもポリプロピレン(高密度ポリプロピレンを含む)が好ましい。
フィルタの孔径は特に限定はないが、例えば0.01~7.0μmが好ましく、0.01~2.5μmがより好ましく、0.01~2.0μmが更に好ましい。フィルタの孔径を上記範囲とすることにより、微細な粒子をより効果的に取り除くことができ、着色組成物の濁度をより低減することができる。ここで、フィルタの孔径は、フィルタメーカーの公称値を参照することができる。市販のフィルタとしては、例えば、日本ポール株式会社、アドバンテック東洋株式会社、日本インテグリス株式会社(旧日本マイクロリス株式会社)又は株式会社キッツマイクロフィルタ等が提供する各種フィルタの中から選択することができる。
例えば、まず第1のフィルタを用いて濾過を行い、次に、第1のフィルタとは孔径が異なる第2のフィルタを用いて濾過を行うことができる。
その際、第1のフィルタでのフィルタリング及び第2のフィルタでのフィルタリングは、それぞれ、1回のみでもよいし、2回以上行ってもよい。
第2のフィルタは、上述した第1のフィルタと同様の材料等で形成されたものを使用することができる。
本発明の着色組成物は、25℃における粘度が1~200mPa・sが好ましく、50~200mPa・sがより好ましく、100~150mPa・sが特に好ましい。
特に、着色組成物の25℃における粘度は、膜厚が、0.1~2μmの膜(カラーフィルタ)を形成する場合は、1~50mPa・sが好ましく、1~20mPa・sがより好ましく、1~15mPa・sがさらに好ましい。
また、膜厚が、2~20μmの膜(カラーフィルタ)を形成する場合は、着色組成物の25℃における粘度は、50~200mPa・sが好ましく、50~150mPa・sがより好ましく、100~150mPa・sが特に好ましい。
粘度は、例えば、東機産業製 粘度計 RE85L(ローター:1°34’×R24測定範囲0.6~1200mPa・s)を使用し、25℃に温度調整を施した状態で測定することができる。
本発明の着色組成物は、乾燥後の膜厚が12.0μmの膜を製膜した際に、膜の厚み方向における光の透過率であって、波長400~780nmの範囲における透過率の最大値が15%以下であり、波長850nmの透過率が80%以上であることが好ましい。波長400~780nmの範囲における透過率の最大値は、15%以下が好ましく、10%以下がより好ましく、5%以下が特に好ましい。波長850nmの透過率は、80%以上が好ましく、85%以上がより好ましく、90%以上が特に好ましい。また、波長850~1300nmの範囲における透過率の最小値は、80%以上が好ましく、85%以上がより好ましく、90%以上が特に好ましい。
次に、本発明の一態様である膜について説明する。
膜は、上述した本発明の着色組成物を硬化してなるものである。かかる膜はカラーフィルタに好ましく用いられる。
膜は、膜の厚み方向における光の透過率の、波長400~780nmの範囲における最大値が15%以下であり、波長850~1300nmの範囲における最小値が80%以上であることが好ましい。このような分光特性を有することにより、可視光由来のノイズが少ない状態で近赤外線を透過可能な膜とすることができる。
膜の分光特性は、紫外可視近赤外分光光度計(日立ハイテクノロジーズ社製 U-4100)の分光光度計(ref.ガラス基板)を用いて、波長300~1300nmの範囲において透過率を測定した値である。
膜厚は、特に限定はないが、0.1~20μmが好ましく、0.5~15μmがより好ましく、3~15μmが特に好ましい。上記分光特性を有する膜は、膜厚が大きくなるほど、膜表面に皺が発生し易い傾向にあるが、本発明によれば、膜厚が大きくても皺の発生を抑制できるので、膜厚が大きい場合において、本発明の効果が顕著に得られる。
次に、本発明の一態様であるパターン形成方法およびカラーフィルタについて、その製造方法を通じて詳述する。また、本発明の一態様である、パターン形成方法を用いたカラーフィルタの製造方法についても説明する。
パターン形成方法は、着色組成物を支持体上に適用して着色組成物層を形成する工程と、着色組成物層をパターン状に露光する工程と、未露光部を現像除去して着色パターンを形成する工程とを含む。このようなパターン形成方法は、カラーフィルタの着色層の製造に用いられる。すなわち、本明細書では、パターン形成方法を含むカラーフィルタの製造方法についても開示する。
以下、パターン形成方法における各工程については、固体撮像素子用カラーフィルタの製造方法を通じて詳細に説明するが、本発明はこの方法に限定されるものではない。以下、固体撮像素子用カラーフィルタを単に「カラーフィルタ」ということがある。
着色組成物層を形成する工程では、支持体上に、本発明の着色組成物を適用して着色組成物層を形成する。
また、これらの支持体上には、必要により、上部の層との密着改良、物質の拡散防止或いは基板表面の平坦化のために下塗り層を設けてもよい。
露光工程では、着色組成物層を、例えば、ステッパー等の露光装置を用い、所定のマスクパターンを有するマスクを介してパターン露光する。これにより、硬化膜が得られる。
露光に際して用いることができる放射線(光)としては、g線、i線等の紫外線が好ましく、i線がより好ましく用いられる。照射量(露光量)は30~1500mJ/cm2が好ましく、50~1000mJ/cm2がより好ましく、80~500mJ/cm2が特に好ましい。
露光工程に次いで、現像工程を行うことにより、露光後の未硬化部を現像液に溶出させ、光硬化した部分を残存させる。この現像工程により、着色パターンを形成することができる。
現像方式は、デイップ方式、シャワー方式、スプレー方式、パドル方式などいずれでもよく、これらにスウィング方式、スピン方式、超音波方式などを組み合わせてもよい。
現像液に触れる前に、被現像面を予め水等で湿しておくことで、現像むらを防ぐこともできる。
現像液は、アルカリ剤を含むことが好ましい。アルカリ剤としては、例えば、アンモニア水、エチルアミン、ジエチルアミン、ジメチルエタノールアミン、テトラメチルアンモニウムヒドロキシド、テトラエチルアンモニウムヒドロキシド、テトラブチルアンモニウムヒドロキシド、ベンジルトリメチルアンモニウムヒドロキシド、コリン、ピロール、ピペリジン、1,8-ジアザビシクロ-[5,4,0]-7-ウンデセンなどの有機アルカリ性化合物、水酸化ナトリウム、水酸化カリウム、炭酸水素ナトリウム、炭酸水素カリウム等の無機化合物等が挙げられる。
現像液は、上述したアルカリ剤を、0.001~10質量%、好ましくは0.01~1質量%となるように、純水で希釈したアルカリ性水溶液が好ましく使用される。なお、このようなアルカリ性水溶液からなる現像液を使用した場合には、一般に現像後、純水で洗浄(リンス)して余剰の現像液を洗浄除去し、乾燥を施すことが好ましい。
ポストベークは、現像後の膜を、上記条件になるようにホットプレートやコンベクションオーブン(熱風循環式乾燥機)、高周波加熱機等の加熱手段を用いて、連続式あるいはバッチ式で行うことができる。
光を用いる場合には、g線、h線、i線、KrFやArFなどのエキシマレーザ、電子線、X線等により行うことができるが、既存の高圧水銀灯で20~50℃程度の低温で行うことが好ましい。照射時間としては、10~180秒が好ましく、30~60秒がより好ましい。後露光と後加熱との併用の場合、後露光を先に実施することが好ましい。
なお、上述した特定の分光特性を示す膜を用いた着色画素だけでカラーフィルタを構成してもよいし、特定の分光特性を示す膜を用いた着色画素と、赤、緑、青、マゼンタ、黄、シアン、黒、無色等の着色画素とを有するカラーフィルタを構成してもよい。特定の分光特性を示す膜を用いた着色画素を他の色の画素と共にカラーフィルタを構成する場合は、特定の分光特性を示す膜を用いた着色画素を先に設けても、後から設けてもよい。
本発明の一態様である固体撮像素子は、固体撮像素子用カラーフィルタを備える。固体撮像素子の構成としては、固体撮像素子用カラーフィルタとして本発明の一態様であるカラーフィルタが備えられた構成であり、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。
さらに、デバイス保護膜上であって固体撮像素子用カラーフィルタの下(支持体に近い側)に集光手段(例えば、マイクロレンズ等。以下同じ)を有する構成や、カラーフィルタ上に集光手段を有する構成等であってもよい。
本発明の一態様である赤外線センサは、カラーフィルタを備える。赤外線センサの構成としては、本発明の一態様であるカラーフィルタが備えられた構成であり、赤外線センサ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。
更に、デバイス保護膜上であってカラーフィルタの下(基板に近い側)に集光手段(例えば、マイクロレンズ等。以下同じ)を有する構成や、カラーフィルタ上に集光手段を有する構成等であってもよい。
図1に示すように、赤外線センサ100は固体撮像素子110を有する。
固体撮像素子110上に設けられている撮像領域には、近赤外線吸収フィルタ111とカラ-フィルタ112が設けられている。
近赤外線吸収フィルタ111は、可視光領域の光(例えば、波長300~700nmの光)を透過し、赤外領域の光(例えば、波長800~1300nmの光、好ましくは波長900~1300nmの光、更に好ましくは波長1000~1300nmの光)を遮蔽するもので構成されている。
カラーフィルタ112は、可視光領域における特定波長の光を透過及び吸収する画素が形成されており、例えば、赤色(R)、緑色(G)、青色(B)の画素が形成されている。
近赤外線透過フィルタ113と固体撮像素子110との間には近赤外線吸収フィルタ111が形成されていない領域114が設けられている。領域114には、赤外線透過フィルタ113を透過した波長の光が透過可能な樹脂層(例えば、透明樹脂層など)が配置されている。
近赤外線透過フィルタ113は、可視光遮蔽性を有し、かつ、特定波長の赤外線を透過させるフィルタであって、上述した特定の分光特性を有するカラーフィルタで構成されている。近赤外線透過フィルタ113は、例えば、波長400~780nmの光を遮光し、波長850~1300nmの光を透過させることが好ましい。
カラ-フィルタ112および近赤外線透過フィルタ113の入射光hν側には、マイクロレンズ115が配置されている。マイクロレンズ115を覆うように平坦化層116が形成されている。
図1に示す実施形態では、領域114に樹脂層が配置されているが、領域114に赤外線透過フィルタ113を形成してもよい。すなわち、固体撮像素子110上に、赤外線透過フィルタ113を形成してもよい。
また、図1に示す実施形態では、カラ-フィルタ112の膜厚と、赤外線透過フィルタ113の膜厚が同一であるが、両者の膜厚は異なっていてもよい。
また、図1に示す実施形態では、カラ-フィルタ112が、近赤外線吸収フィルタ111よりも入射光hν側に設けられているが、近赤外線吸収フィルタ111と、カラ-フィルタ112との順序を入れ替えて、近赤外線吸収フィルタ111を、カラ-フィルタ112よりも入射光hν側に設けてもよい。
また、図1に示す実施形態では、近赤外線吸収フィルタ111とカラ-フィルタ112は隣接して積層しているが、両フィルタは必ずしも隣接している必要はなく、間に他の層が設けられていても良い。
この赤外線センサによれば、画像情報を同時に取り込むことができるため、動きを検知する対象を認識したモーションセンシングなどが可能である。更には、距離情報を取得できるため、3D情報を含んだ画像の撮影等も可能である。
図2は、撮像装置の機能ブロック図である。撮像装置は、レンズ光学系1と、固体撮像素子10と、信号処理部20と、信号切替部30と、制御部40と、信号蓄積部50と、発光制御部60と、赤外光を発光する発光素子の赤外LED70と、画像出力部80および81とを備える。なお、固体撮像素子10としては、上述した赤外線センサ100を用いることができる。また、固体撮像素子10とレンズ光学系1以外の構成は、そのすべてが、または、その一部が、同一の半導体基板に形成することもできる。撮像装置の各構成については、特開2011-233983号公報の段落0032~0036を参酌することができ、この内容は本願明細書に組み込まれる。
〔顔料分散液B-1の調製〕
下記組成の混合液を、0.3mm径のジルコニアビーズを使用して、ビーズミル(減圧機構付き高圧分散機NANO-3000-10(日本ビーイーイー(株)製))で、3時間、混合及び分散して、顔料分散液B-1を調製した。
・赤色顔料(C.I.Pigment Red 254)及び黄色顔料(C.I.Pigment Yellow 139)からなる混合顔料
14.8部
・分散剤:BYK社製 BYK-111 6.8部
・有機溶剤:プロピレングリコールメチルエーテルアセテート(PGMEA)
78.4部
下記組成の混合液を、0.3mm径のジルコニアビーズを使用して、ビーズミル(減圧機構付き高圧分散機NANO-3000-10(日本ビーイーイー(株)製))で、3時間、混合、分散して、顔料分散液B-2を調製した。
・青色顔料(C.I.Pigment Blue 15:6)及び紫色顔料(C.I.Pigment Violet 23)からなる混合顔料
12.8部
・分散剤:BYK社製 BYK-111 2.0部
・アルカリ可溶性樹脂1 3.2部
・有機溶剤:シクロヘキサノン 31.0部
・有機溶剤:PGMEA 51.0部
〔着色組成物の調製〕
下記の成分を混合して、実施例1の着色組成物を調製した。
・顔料分散液B-1(各顔料の質量比は下記表1を参照) 11.2部
・顔料分散液B-2(各顔料の質量比は下記表1を参照) 9.1部
・下記アルカリ可溶性樹脂1の40質量%PGMEA溶液 54.2部
・下記重合性化合物1 13.6部
・下記光重合開始剤1 2.0部
・界面活性剤1:DIC株式会社製Megafac F-781Fの10質量%PGMEA溶液
0.42部
・下記紫外線吸収剤1 0.41部
・重合禁止剤:p-メトキシフェノール 0.01部
・有機溶剤1:PGMEA 9.2部
実施例1の着色組成物の調製において、顔料分散液、アルカリ可溶性樹脂、重合性化合物、光重合開始剤及び有機溶剤を下記表2に示すもの及び量(質量部)に変更して(顔料分散液における各顔料の質量比は表1を参照。また、表2中、数値が無いものは使用していないことを意味する。)、実施例2~8及び比較例1~4の着色組成物を調製した。
アルカリ可溶性樹脂1:下記構造(繰り返し単位における比はモル比である)
=470)
ポストベーク後の膜厚が12μmとなるように着色組成物をガラス基板に塗布し、このガラス基板に着色層を形成した。具体的には、着色組成物をガラス基板上にスピンコートし、100℃、120秒間ホットプレートで乾燥し、乾燥した後、さらに、200℃のホットプレートを用いて300秒間加熱処理(ポストベーク)を行った。
着色層を有するガラス基板について、紫外可視近赤外分光光度計U-4100(日立ハイテク製)(ref.ガラス基板)を用いて、波長400nm以上580nm未満の範囲における吸光度の最小値A、波長580nm以上770nm以下の範囲における吸光度の最小値B、波長400nm以上750nm以下の範囲における吸光度の最小値C、波長850nm以上1300nm以下の範囲における吸光度の最大値D、波長400~780nmの範囲における透過率の最小値、及び波長850nmにおける透過率を測定した。
着色組成物の25℃における粘度を、B型粘度計(TOKI産業製)を用いて測定した。
着色組成物を、シリコンウェハ上に乾燥後の膜厚が12μmになるようにスピンコーターを用いて塗布し、100℃のホットプレートを用いて120秒間加熱処理(プリベーク)して、塗布膜を形成した。
次いで、i線ステッパー露光装置FPA-3000i5+(Canon(株)製)を使用して、1.4μm角の正方形ピクセルパターンが形成されるフォトマスクを用いて、最適露光量にて露光を行った。最適露光量は、50~750mJ/cm2まで50mJ/cm2ずつ上昇させて、上記正方形ピクセルパターンを解像する露光量に基づいて決定した。
その後、露光された塗布膜が形成されているシリコンウェハをスピン・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、CD-2060(富士フイルムエレクトロニクスマテリアルズ(株)製)を用いて23℃で60秒間パドル現像を行い、シリコンウェハ上に着色パターンを形成した。
着色パターンが形成されたシリコンウェハを純水でリンス処理し、その後スプレー乾燥した。
さらに、200℃のホットプレートを用いて300秒間加熱処理(ポストベーク)を行い、それぞれ、実施例1~8および比較例1~4のカラーフィルタとしての、着色パターンを有するシリコンウェハを得た。
[ノイズ]
可視光領域(波長400~700nm)での平均透過率t1と、波長825~1300nmでの平均透過率t2の比(t1/t2)を求め、以下の評価基準でノイズを評価した。t1/t2の値が小さいほど、可視光由来のノイズの少ないカラーフィルタである。
3:t1/t2が0.085未満
2:t1/t2が0.085以上0.1未満
1:t1/t2が0.1以上
[皺]
カラーフィルタの表面をAFM(原子間力顕微鏡)にて測定し、表面粗さ(Ra)を計算により求めた。
3:表面粗さ(Ra)が10nm未満
2:表面粗さ(Ra)が10nm以上、20nm未満
1:表面粗さ(Ra)が20nm以上
[残渣]
ガラス基板上にカラーフィルタを塗布、現像した後、非露光部の透過率を分光光度計にて測定し、現像残渣により生じる、塗布膜作製前のガラス基板の透過率に対する分光の変動率を評価した。なお、測定した領域における最大の変動率を与える箇所、かつ可視光領域(波長400~700nm)のうち最大の変動率を与える波長で測定した値を変動率とした。
3:透過率の変動が1%未満
2:透過率の変動が1%以上5%未満
1:透過率の変動が5%以上
[密着]
カラーフィルタの作製に際する塗布膜の現像後の状態を光学式顕微鏡にて観察し、正方形ピクセルパターンが剥がれている数をカウントした。
3:パターンの剥がれが見られない
2:パターンの剥がれが10個未満
1:パターンの剥がれが10個以上
一方、比較例1、3、4は、膜表面の皺が多かった。また、比較例2は、ノイズが多かった。
Claims (15)
- 着色剤と重合性化合物と樹脂とを含む着色組成物であって、
前記着色剤の質量Pと、前記重合性化合物の質量Mとの比率P/Mが、0.05~0.35であり、
前記着色組成物の全固形分中における前記重合性化合物の含有量が25~65質量%であり、
前記着色組成物の、波長400nm以上580nm未満の範囲における吸光度の最小値Aと、波長580nm以上770nm以下の範囲における吸光度の最小値Bとの比率A/Bが0.3~3であり、波長400nm以上750nm以下の範囲における吸光度の最小値Cと、波長850nm以上1300nm以下の範囲における吸光度の最大値Dとの比率C/Dが5以上である、着色組成物。
- 前記重合性化合物の質量Mと、前記樹脂の質量Bとの比率M/Bが、0.4~3.0である、請求項1に記載の着色組成物。
- 着色剤と重合性化合物とを含む着色組成物であって、
前記着色剤の質量Pと、前記重合性化合物の質量Mとの比率P/Mが、0.05~0.35であり、
前記着色組成物の全固形分中における前記重合性化合物の含有量が25~65質量%であり、
前記着色剤は、黄色着色剤と青色着色剤とを少なくとも含み、
前記黄色着色剤の前記着色剤全量に対する質量比である黄色着色剤/全着色剤が0.1~0.5であり、
前記青色着色剤の前記着色剤全量に対する質量比である青色着色剤/全着色剤が0.1~0.6である、着色組成物。
- 前記着色剤は、更に赤色着色剤と紫色着色剤とを含み、
前記赤色着色剤の前記着色剤全量に対する質量比である赤色着色剤/全着色剤が0.1~0.5であり、
前記黄色着色剤の前記着色剤全量に対する質量比である黄色着色剤/全着色剤が0.1~0.4であり、
前記青色着色剤の前記着色剤全量に対する質量比である青色着色剤/全着色剤が0.2~0.6であり、
前記紫色着色剤の前記着色剤全量に対する質量比である紫色着色剤/全着色剤が0.01~0.3である、請求項3に記載の着色組成物。
- 前記着色剤は、青色顔料と赤色顔料と黄色顔料と紫色顔料とを含む、請求項1~4のいずれか1項に記載の着色組成物。
- 前記重合性化合物は、アルキレンオキシ基を繰り返し単位として2以上含むアルキレンオキシ鎖を有する重合性化合物を含有する、請求項1~5のいずれか1項に記載の着色組成物。
- 前記重合性化合物の分子量の値を、前記重合性化合物中に含まれる重合性基の数で割った値が100~300である、請求項1~6のいずれか1項に記載の着色組成物。
- 乾燥後の膜厚が12.0μmの膜を形成した際に、波長400~780nmの範囲における透過率の最大値が15%以下であり、波長850nmの透過率が80%以上である請求項1~7のいずれか1項に記載の着色組成物。
- 25℃における粘度が100~150mP・sである、請求項1~8のいずれか1項に記載の着色組成物。
- 請求項1~9のいずれか1項に記載の着色組成物を硬化してなる膜。
- 請求項10に記載の膜を有するカラーフィルタ。
- 請求項1~9のいずれか1項に記載の着色組成物を支持体上に適用して着色組成物層を形成する工程と、
前記着色組成物層をパターン状に露光する工程と、
未露光部を現像除去して着色パターンを形成する工程と、
を含むパターン形成方法。
- 請求項12に記載のパターン形成方法を含む、カラーフィルタの製造方法。
- 請求項11に記載のカラーフィルタまたは請求項13に記載のカラーフィルタの製造方法により得られたカラーフィルタ、を有する固体撮像素子。
- 請求項11に記載のカラーフィルタまたは請求項13に記載のカラーフィルタの製造方法により得られたカラーフィルタ、を有する赤外線センサ。
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TWI636324B (zh) | 2018-09-21 |
JPWO2015182278A1 (ja) | 2017-04-20 |
JP6227132B2 (ja) | 2017-11-08 |
TW201544901A (zh) | 2015-12-01 |
KR20160132913A (ko) | 2016-11-21 |
KR101779467B1 (ko) | 2017-09-18 |
US10401726B2 (en) | 2019-09-03 |
US20170023858A1 (en) | 2017-01-26 |
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