WO2021182268A1 - 樹脂組成物、膜、光学フィルタ、固体撮像素子、及び、画像表示装置 - Google Patents
樹脂組成物、膜、光学フィルタ、固体撮像素子、及び、画像表示装置 Download PDFInfo
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- WO2021182268A1 WO2021182268A1 PCT/JP2021/008332 JP2021008332W WO2021182268A1 WO 2021182268 A1 WO2021182268 A1 WO 2021182268A1 JP 2021008332 W JP2021008332 W JP 2021008332W WO 2021182268 A1 WO2021182268 A1 WO 2021182268A1
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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
-
- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
- G02F1/1333—Constructional arrangements; Manufacturing methods
- G02F1/1335—Structural association of cells with optical devices, e.g. polarisers or reflectors
- G02F1/133509—Filters, e.g. light shielding masks
- G02F1/133514—Colour filters
-
- 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
- H01L27/14601—Structural or functional details thereof
- H01L27/1462—Coatings
- H01L27/14621—Colour filter arrangements
Definitions
- the present invention relates to a resin composition, a film, an optical filter, a solid-state image sensor, and an image display device.
- a film containing a pigment such as a color filter is used for the solid-state image sensor.
- a film containing a color material such as a color filter is manufactured by using a resin composition containing the color material, a resin, and a solvent.
- Patent Document 1 describes a coloring composition for a color filter containing a colorant, a dispersant, a binder resin, an epoxy compound, and a solvent, wherein the dispersants are tetracarboxylic acid anhydride (b1) and tricarboxylic acid.
- a polyester moiety X1' having a carboxy group formed by reacting an acid anhydride group in one or more acid anhydrides (b) selected from the anhydride (b2) with a hydroxyl group in a hydroxyl group-containing compound (a), and
- the ethylenically unsaturated monomer (c) is radically polymerized and has a vinyl polymer moiety X2'having a thermally crosslinkable functional group, and the thermally crosslinkable functional group is a hydroxyl group, an oxetane group, or t-.
- An invention relating to a coloring composition for a color filter containing at least one dispersant (X) selected from the group consisting of a butyl group, a blocked isocyanate group, and a (meth) acryloyl group is described.
- an object of the present invention is to provide a novel resin composition, a film, an optical filter, a solid-state image sensor, and an image display device capable of expanding the process window of a process after manufacturing a film.
- ⁇ 1> Contains a coloring material, a resin, and a solvent.
- the resin contains a graft polymer having a main chain containing a molecular chain having a structure derived from a compound having an ethylenically unsaturated bond-containing group and a graft chain.
- the graft chain comprises a repeating unit p1 having an oxetane group.
- Resin composition containing a coloring material, a resin, and a solvent.
- the resin contains a graft polymer having a main chain containing a molecular chain having a structure derived from a compound having an ethylenically unsaturated bond-containing group and a graft chain.
- the graft chain comprises a repeating unit p1 having an oxetane group.
- ⁇ 6> The resin composition according to any one of ⁇ 1> to ⁇ 5>, wherein the main chain of the graft polymer contains a repeating unit represented by the formula (1);
- R 1 to R 3 independently represent a hydrogen atom, an alkyl group or an aryl group;
- L 1 and L 2 each independently represent a divalent linking group;
- X 1 represents a single bond, -O-, -COO-, -OCO-, -NHCOO-, -OCONH- or -NHCONH-;
- P 1 represents a graft chain containing the repeating unit p1.
- ⁇ 7> The resin composition according to any one of ⁇ 1> to ⁇ 6>, wherein the main chain of the graft polymer contains a repeating unit having a crosslinkable group.
- ⁇ 8> The resin composition according to any one of ⁇ 1> to ⁇ 7>, wherein the main chain of the graft polymer contains a repeating unit having an acid group.
- ⁇ 9> The resin composition according to any one of ⁇ 1> to ⁇ 8>, wherein the color material contains a near-infrared absorbing color material.
- ⁇ 10> The resin composition according to any one of ⁇ 1> to ⁇ 8>, wherein the color material contains a black color material.
- the color material includes at least one selected from Color Index Pigment Red 179, Color Index Pigment Red 264, Color Index Pigment Red 291 and Color Index Pigment Blue 16 and Color Index Pigment Yellow 215.
- Amin / B which is the ratio of the minimum absorbance Amin of the resin composition in the wavelength range of 400 to 640 nm and the absorbance B of the resin composition in the wavelength range of 1500 nm, is 5 or more.
- ⁇ 13> The resin composition according to any one of ⁇ 1> to ⁇ 12>, which further contains a polymerizable monomer.
- ⁇ 14> The resin composition according to any one of ⁇ 1> to ⁇ 13>, which further contains a photopolymerization initiator.
- ⁇ 15> The resin composition according to any one of ⁇ 1> to ⁇ 14>, which is used for a solid-state image sensor.
- ⁇ 16> A film obtained from the resin composition according to any one of ⁇ 1> to ⁇ 15>.
- ⁇ 17> An optical filter containing the film according to ⁇ 16>.
- ⁇ 18> A solid-state image sensor including the film according to ⁇ 16>.
- ⁇ 19> An image display device including the film according to ⁇ 16>.
- a novel resin composition capable of expanding the process window of a process after manufacturing a film are provided.
- the present invention is not limited to the specified embodiments.
- "-" is used to mean that the numerical values described before and after it are included as the lower limit value and the upper limit value.
- the notation not describing substitution and non-substitution also includes a group having a substituent (atomic group) as well as a group having no substituent (atomic group).
- the "alkyl group” includes not only an alkyl group having no substituent (unsubstituted alkyl group) but also an alkyl group having a substituent (substituted alkyl group).
- exposure includes not only exposure using light but also drawing using particle beams such as an electron beam and an ion beam, unless otherwise specified.
- the light used for exposure include the emission line spectrum of a mercury lamp, far ultraviolet rays typified by an excimer laser, extreme ultraviolet rays (EUV light), X-rays, active rays such as electron beams, or radiation.
- EUV light extreme ultraviolet rays
- active rays such as electron beams, or radiation.
- the (meth) allyl group represents both allyl and methallyl, or either, and "(meth) acrylate” represents both acrylate and methacrylate, or either, and "(meth)”.
- “Acrylic” represents both acrylic and / or methacryl, and “(meth) acryloyl” represents both / or both acryloyl and methacryloyl.
- the weight average molecular weight and the number average molecular weight are polystyrene-equivalent values measured by a GPC (gel permeation chromatography) method.
- the near infrared ray means light having a wavelength of 700 to 2500 nm.
- the total solid content means the total mass of all the components of the composition excluding the solvent.
- process does not only refer to an independent process, but even if it cannot be clearly distinguished from other processes, if the desired action of the process is achieved, the term is used. included. In the present specification, the combination of preferred embodiments is a more preferred embodiment.
- the resin composition of the present invention contains a coloring material, a resin, and a solvent.
- the resin contains a graft polymer having a main chain containing a molecular chain having a structure derived from a compound having an ethylenically unsaturated bond-containing group and a graft chain.
- the graft chain is characterized by containing a repeating unit p1 having an oxetane group.
- the resin composition of the present invention forms a film having excellent heat resistance, which is less likely to be decomposed even at a high temperature and is less likely to cause film shrinkage even after heat treatment at a high temperature. can. Therefore, even if a film is formed using the resin composition of the present invention and then the obtained film is heat-treated at a high temperature (for example, 300 ° C. or higher), the film shrinkage is suppressed and the film is formed on the film. Even when another film such as an inorganic film is formed, it is possible to suppress the occurrence of cracks in the other film.
- a high temperature for example, 300 ° C. or higher
- the process window of the process after manufacturing the film can be expanded.
- the detailed reason for obtaining such an effect is unknown, but it is presumed to be due to the following.
- the main chain of the specific resin contains a molecular chain having a structure derived from a compound having an ethylenically unsaturated bond-containing group, it is presumed that the bond energy of the main chain is large and the depolymerization temperature of the resin is improved.
- the graft chain contains a repeating unit p1 having an oxetane group, it is presumed that a strong crosslinked structure is formed by the oxetane group contained in the graft chain at the time of film formation.
- the resin composition of the present invention containing the above-mentioned specific resin can form a film having excellent heat resistance, which is less likely to be decomposed even at a high temperature and is less likely to cause film shrinkage even after heat treatment at a high temperature.
- the above-mentioned specific resin has an oxetane group at the site of the graft chain, the dispersibility of the coloring material in the resin composition can be improved, and the storage stability of the resin composition can be improved. You can also.
- the film was heat-treated at 300 ° C. for 5 hours in a nitrogen atmosphere.
- the thickness of the film is preferably 70% or more, more preferably 80% or more, and further preferably 90% or more of the thickness of the film before the heat treatment.
- the thickness of the film after being heat-treated at 350 ° C. for 5 hours in a nitrogen atmosphere is preferably 70% or more, preferably 80% or more of the thickness of the film before the heat treatment. Is more preferable, and 90% or more is further preferable.
- the above physical characteristics can be achieved by a method such as adjusting the type and content of the specific resin to be used.
- the rate of change ⁇ A of the absorbance of the film after the heat treatment represented by the following formula (A1) is preferably 50% or less, more preferably 45% or less, and more preferably 40% or less. It is more preferably 35% or less, and particularly preferably 35% or less.
- ⁇ A (%)
- A1 is the maximum value of the absorbance in the wavelength range of 400 to 1100 nm of the film before heat treatment.
- A2 is the absorbance of the film after the heat treatment, and is the absorbance at a wavelength indicating the maximum value of the absorbance of the film before the heat treatment in the wavelength range of 400 to 1100 nm.
- the above physical characteristics can be achieved by a method such as adjusting the type and content of the specific resin to be used.
- the wavelength ⁇ 1 indicating the maximum value of the absorbance of the film in the wavelength range of 400 to 1100 nm.
- the absolute value of the difference from the wavelength ⁇ 2, which indicates the maximum value of the absorbance of the film after heat-treating the film at 300 ° C. for 5 hours in a nitrogen atmosphere, is preferably 50 nm or less, preferably 45 nm or less. It is more preferable to have a wavelength of 40 nm or less.
- the above physical characteristics can be achieved by a method such as adjusting the type and content of the specific resin to be used.
- the film when the resin composition of the present invention was heated at 200 ° C. for 30 minutes to form a film having a thickness of 0.60 ⁇ m, the film was heat-treated at 300 ° C. for 5 hours in a nitrogen atmosphere.
- the maximum value of the rate of change ⁇ A ⁇ of the absorbance in the wavelength range of 400 to 1100 nm after the heat treatment is preferably 30% or less, more preferably 27% or less, and further preferably 25% or less. preferable.
- the rate of change in absorbance is a value calculated from the following formula (2).
- ⁇ A ⁇
- a ⁇ is the rate of change in absorbance at the wavelength ⁇ of the film after heat treatment.
- A1 ⁇ is the absorbance at the wavelength ⁇ of the film before heat treatment.
- A2 ⁇ is the absorbance at the wavelength ⁇ of the film after the heat treatment.
- the above physical characteristics can be achieved by a method such as adjusting the type and content of the specific resin to be used.
- the resin composition of the present invention is preferably used as a resin composition for an optical filter.
- the optical filter include a color filter, a near-infrared ray transmitting filter, a near-infrared ray cut filter, and the like, and a color filter is preferable.
- the resin composition of the present invention can be preferably used as a resin composition for a solid-state image sensor, and more preferably as a resin composition for forming pixels of an optical filter used in a solid-state image sensor.
- the color filter examples include a filter having colored pixels that transmit light of a specific wavelength, and at least one colored pixel selected from red pixels, blue pixels, green pixels, yellow pixels, cyan pixels, and magenta pixels. It is preferable that the filter has.
- the color filter can be formed by using a resin composition containing a chromatic color material.
- the near-infrared cut filter examples include a filter having a maximum absorption wavelength in the wavelength range of 700 to 1800 nm.
- the maximum absorption wavelength of the near-infrared cut filter is preferably in the wavelength range of 700 to 1300 nm, and more preferably in the wavelength range of 700 to 1100 nm.
- the transmittance of the near-infrared cut filter in the entire wavelength range of 400 to 650 nm is preferably 70% or more, more preferably 80% or more, and further preferably 90% or more. Further, the transmittance at at least one point in the wavelength range of 700 to 1800 nm is preferably 20% or less.
- the absorbance Amax / absorbance A550 which is the ratio of the absorbance Amax at the maximum absorption wavelength of the near-infrared cut filter to the absorbance A550 at a wavelength of 550 nm, is preferably 20 to 500, more preferably 50 to 500. , 70 to 450, more preferably 100 to 400.
- the near-infrared cut filter can be formed by using a resin composition containing a near-infrared absorbing color material.
- a near-infrared ray transmitting filter is a filter that transmits at least a part of near infrared rays.
- the near-infrared transmitting filter is preferably a filter that blocks at least a part of visible light and transmits at least a part of near-infrared light.
- the maximum value of the transmittance in the wavelength range of 400 to 640 nm is 20% or less (preferably 15% or less, more preferably 10% or less), and the transmittance in the wavelength range of 1100 to 1300 nm.
- a filter satisfying the spectral characteristics having a minimum value of 70% or more (preferably 75% or more, more preferably 80% or more) is preferably mentioned.
- the near-infrared transmission filter is preferably a filter that satisfies any of the following spectral characteristics (1) to (5).
- the maximum value of the transmittance in the wavelength range of 400 to 640 nm is 20% or less (preferably 15% or less, more preferably 10% or less), and the minimum value of the transmittance in the wavelength range of 800 to 1500 nm is.
- the maximum value of the transmittance in the wavelength range of 400 to 750 nm is 20% or less (preferably 15% or less, more preferably 10% or less), and the minimum value of the transmittance in the wavelength range of 900 to 1500 nm is.
- the maximum value of the transmittance in the wavelength range of 400 to 830 nm is 20% or less (preferably 15% or less, more preferably 10% or less), and the minimum value of the transmittance in the wavelength range of 1000 to 1500 nm is.
- the maximum value of the transmittance in the wavelength range of 400 to 950 nm is 20% or less (preferably 15% or less, more preferably 10% or less), and the minimum value of the transmittance in the wavelength range of 1100-1500 nm is.
- the maximum value of the transmittance in the wavelength range of 400 to 1050 nm is 20% or less (preferably 15% or less, more preferably 10% or less), and the minimum value of the transmittance in the wavelength range of 1200 to 1500 nm is.
- a filter that is 70% or more (preferably 75% or more, more preferably 80% or more).
- a preferred embodiment of the spectral characteristics of the resin composition of the present invention is that when a film having a thickness of 5 ⁇ m is formed using the resin composition, the wavelength of light transmittance in the thickness direction of the film is 360 to 700 nm.
- An embodiment in which the maximum value in the range satisfies the spectral characteristic of 50% or more can be mentioned.
- a resin composition satisfying such spectral characteristics can be preferably used as a resin composition for forming pixels of a color filter. Specifically, it can be preferably used as a resin composition for forming colored pixels selected from red pixels, blue pixels, green pixels, yellow pixels, cyan pixels and magenta colors.
- the resin composition having the above spectral characteristics preferably contains a chromatic coloring material.
- a resin composition containing a red color material and a yellow color material can be preferably used as a resin composition for forming red pixels.
- the resin composition containing the blue color material and the purple color material can be preferably used as the resin composition for forming blue pixels.
- the resin composition containing the green color material can be preferably used as the resin composition for forming green or cyan color pixels.
- Another preferred embodiment of the spectral characteristics of the resin composition of the present invention is that Amin / B, which is the ratio of the minimum absorbance Amin in the wavelength range of 400 to 640 nm to the absorbance B in the wavelength 1500 nm, is 5 or more.
- An embodiment satisfying a certain spectral characteristic can be mentioned.
- a resin composition satisfying such spectral characteristics can be preferably used as a resin composition for forming a near-infrared transmissive filter.
- the value of Amin / B which is the above-mentioned absorbance ratio, is preferably 7.5 or more, more preferably 15 or more, and even more preferably 30 or more.
- the absorbance A ⁇ at the wavelength ⁇ is defined by the following equation ( ⁇ 1).
- a ⁇ -log (T ⁇ / 100) ... ( ⁇ 1)
- a ⁇ is the absorbance at the wavelength ⁇
- T ⁇ is the transmittance (%) at the wavelength ⁇ .
- the absorbance value may be a value measured in a solution state or a value of a film formed by using the composition.
- the composition is applied onto a glass substrate by a method such as spin coating, and the film is dried at 100 ° C. for 120 seconds using a hot plate or the like for measurement. Is preferable.
- the resin composition of the present invention preferably satisfies any of the following spectral characteristics (Ir1) to (Ir5).
- (Ir1) The value of A1 / B1, which is the ratio of the minimum value A1 of the absorbance in the wavelength range of 400 to 640 nm and the maximum value B1 of the absorbance in the wavelength range of 800 to 1500 nm, is 4.5 or more. It is preferably 5 or more, more preferably 15 or more, and even more preferably 30 or more. According to this aspect, it is possible to form a film capable of blocking light having a wavelength in the range of 400 to 640 nm and transmitting light having a wavelength exceeding 750 nm.
- the value of A2 / B2 which is the ratio of the minimum absorbance A2 in the wavelength range of 400 to 750 nm and the maximum absorbance B2 in the wavelength range of 900 to 1500 nm, is 4.5 or more. It is preferably 5 or more, more preferably 15 or more, and even more preferably 30 or more. According to this aspect, it is possible to form a film capable of blocking light having a wavelength in the range of 400 to 750 nm and transmitting light having a wavelength exceeding 850 nm.
- A3 / B3 which is the ratio of the minimum absorbance A3 in the wavelength range of 400 to 830 nm and the maximum absorbance B3 in the wavelength range of 1000 to 1500 nm, is 4.5 or more. It is preferably 5 or more, more preferably 15 or more, and even more preferably 30 or more. According to this aspect, it is possible to form a film capable of blocking light having a wavelength in the range of 400 to 830 nm and transmitting light having a wavelength exceeding 950 nm.
- the value of A4 / B4 which is the ratio of the minimum absorbance A4 in the wavelength range of 400 to 950 nm and the maximum absorbance B4 in the wavelength range of 1100 to 1500 nm, is 4.5 or more. It is preferably 5 or more, more preferably 15 or more, and even more preferably 30 or more. According to this aspect, it is possible to form a film capable of blocking light having a wavelength in the range of 400 to 950 nm and transmitting light having a wavelength exceeding 1050 nm.
- the resin composition of the present invention is a resin composition for pattern formation by a photolithography method. According to this aspect, finely sized pixels can be easily formed. Therefore, it can be particularly preferably used as a resin composition for forming pixels of an optical filter used in a solid-state image sensor.
- a resin composition containing a component having an ethylenically unsaturated bond-containing group for example, a resin having an ethylenically unsaturated bond-containing group or a monomer having an ethylenically unsaturated bond-containing group
- a photopolymerization initiator can be preferably used as a resin composition for pattern formation in a photolithography method.
- the resin composition for pattern formation in the photolithography method preferably further contains an alkali-soluble resin.
- the resin composition of the present invention can also be used as a resin composition for forming a black matrix or a resin composition for forming a light-shielding film.
- the resin composition of the present invention contains a coloring material.
- the coloring material include a white coloring material, a black coloring material, a chromatic coloring material, and a near-infrared absorbing coloring material.
- the white color material includes not only pure white color material but also a light gray color material close to white (for example, grayish white, light gray, etc.).
- the coloring material preferably contains at least one selected from the group consisting of a chromatic color material, a black color material, and a near-infrared absorbing color material, and is selected from the group consisting of a chromatic color material and a near-infrared absorbing color material. It is more preferable to contain at least one chromatic color material, further preferably to contain a chromatic color material, and at least one chromatic color selected from the group consisting of a red color material, a yellow color material, a blue color material and a purple color material. It is more preferable to include a material.
- the coloring material preferably contains a chromatic color material and a near-infrared absorbing color material, and preferably includes two or more kinds of chromatic color materials and a near-infrared absorbing color material.
- black may be formed by a combination of two or more kinds of chromatic color materials.
- the coloring material preferably contains a black coloring material and a near-infrared absorbing coloring material.
- the resin composition of the present invention can be preferably used as a resin composition for forming a near-infrared transmission filter.
- Japanese Patent Application Laid-Open No. 2013-077009, Japanese Patent Application Laid-Open No. 2014-130338, International Publication No. 2015/166779 and the like can be referred to.
- the coloring material examples include dyes and pigments, and pigments are preferable from the viewpoint of heat resistance.
- the pigment may be either an inorganic pigment or an organic pigment, but is preferably an organic pigment from the viewpoints of many color variations, ease of dispersion, safety and the like. Further, the pigment preferably contains at least one selected from a chromatic pigment and a near-infrared absorbing pigment, and more preferably contains a chromatic pigment.
- the pigment may contain at least one selected from phthalocyanine pigments, dioxazine pigments, quinacridone pigments, anthraquinone pigments, perylene pigments, azo pigments, diketopyrrolopyrrole pigments, pyrolopyrrolop pigments, isoindolin pigments and quinophthalone pigments. It is more preferable that it contains at least one selected from a phthalocyanine pigment, a diketopyrrolopyrrole pigment and a pyrrolopyrrole pigment, and even more preferably it contains a phthalocyanine pigment or a diketopyrrolopyrrole pigment.
- the phthalocyanine pigment has a phthalocyanine pigment having no central metal and copper or zinc as the central metal because it is easy to form a film whose spectral characteristics do not easily fluctuate even after heating to a high temperature (for example, 300 ° C. or higher). Phthalocyanine pigments are preferred.
- the coloring material contained in the resin composition easily forms a film whose spectral characteristics do not easily fluctuate even after being heated to a high temperature (for example, 300 ° C. or higher), and thus absorbs red pigments, yellow pigments, blue pigments and near infrared rays. It is preferable to contain at least one selected from pigments, more preferably to contain at least one selected from red pigments and blue pigments, and even more preferably to include blue pigments.
- the coloring material contained in the resin composition preferably contains a pigment A that satisfies the following condition 1.
- a coloring material having such characteristics it is possible to form a film whose spectral characteristics are less likely to fluctuate even after heating to a high temperature (for example, 300 ° C. or higher).
- the ratio of the pigment A in the total amount of the pigment contained in the resin composition is preferably 20 to 100% by mass, more preferably 30 to 100% by mass, still more preferably 40 to 100% by mass. ..
- A11 is the maximum value of the absorbance in the wavelength range of 400 to 1100 nm of the film before heat treatment.
- A12 is the absorbance of the film after the heat treatment, which is the absorbance at the wavelength indicating the maximum value of the absorbance of the film before the heat treatment in the wavelength range of 400 to 1100 nm;
- Resin 1 is a resin having the following structure, and the numerical values added to the main chain are molar ratios, the weight average molecular weight is 11000, and the acid value is 32 mgKOH / g.
- Examples of the pigment A satisfying the above condition 1 include Color Index (CI) Pigment Red 254, C.I. I. Pigment Red 264, C.I. I. Pigment Red 272, C.I. I. Pigment Red 122, C.I. I. Pigment Red 177, C.I. I. Pigment Blue 15: 3, C.I. I. Pigment Blue 15: 4, C.I. I. Pigment Blue 15: 6, C.I. I. Pigment Blue 16 and the like.
- CI Color Index
- the resin composition of the present invention is C.I. I. Pigment Red 179, C.I. I. Pigment Red 264, C.I. I. Pigment Blue 16 and C.I. I. It is also preferable to include at least one selected from Pigment Yellow 215.
- the average primary particle size of the pigment is preferably 1 to 200 nm.
- the lower limit is preferably 5 nm or more, more preferably 10 nm or more.
- the upper limit is preferably 180 nm or less, more preferably 150 nm or less, and even more preferably 100 nm or less.
- the primary particle size of the pigment can be determined from a photograph obtained by observing the primary particles of the pigment with a transmission electron microscope. Specifically, the projected area of the primary particles of the pigment is obtained, and the corresponding circle-equivalent diameter is calculated as the primary particle diameter of the pigment.
- the average primary particle size in the present invention is an arithmetic mean value of the primary particle size for the primary particles of 400 pigments.
- the primary particles of the pigment refer to independent particles without agglomeration.
- the chromatic color material examples include a color material having a maximum absorption wavelength in the wavelength range of 400 to 700 nm. For example, a yellow color material, an orange color material, a red color material, a green color material, a purple color material, a blue color material, and the like can be mentioned. From the viewpoint of heat resistance, the chromatic color material is preferably a pigment (chromatic pigment), more preferably a red pigment, a yellow pigment, and a blue pigment, and further preferably a red pigment and a blue pigment. Specific examples of the chromatic pigment include those shown below.
- C.I. I. Pigment Red 254, C.I. I. Pigment Red 264, C.I. I. Pigment Red 272, C.I. I. Pigment Red 291 and C.I. I. Pigment Red 122, C.I. I. Pigment Red 177 is preferred.
- C.I. I. Pigment Blue 15: 3 is preferred.
- C.I. I. Pigment Blue 15: 4 is preferred.
- C.I. I. Pigment Blue 15: 6 is preferred.
- a halogenated zinc phthalocyanine having an average of 10 to 14 halogen atoms in one molecule, an average of 8 to 12 bromine atoms, and an average of 2 to 5 chlorine atoms. Pigments can also be used. Specific examples include the compounds described in WO 2015/118720. Further, as a green color material, the compound described in Chinese Patent Application No. 1069009027, the phthalocyanine compound having a phosphate ester described in International Publication No. 2012/10395 as a ligand, and Japanese Patent Application Laid-Open No. 2019-008014. , The phthalocyanine compound described in JP-A-2018-180023, the compound described in JP-A-2019-038958, and the like can also be used.
- an aluminum phthalocyanine compound having a phosphorus atom can also be used. Specific examples include the compounds described in paragraphs 0022 to 0030 of JP2012-247591A and paragraph numbers 0047 of JP2011-157478A.
- X 1 to X 16 independently represent a hydrogen atom or a halogen atom, and Z 1 represents an alkylene group having 1 to 3 carbon atoms.
- Specific examples of the compound represented by the formula (QP1) include the compounds described in paragraph No. 0016 of Japanese Patent No. 6443711.
- Y 1 ⁇ Y 3 represents a halogen atom independently.
- n and m represent integers of 0 to 6, and p represents an integer of 0 to 5.
- N + m is 1 or more.
- Specific examples of the compound represented by the formula (QP2) include the compounds described in paragraphs 0047 to 0048 of Japanese Patent No. 6432077.
- a red color material As a red color material, a diketopyrrolopyrrole compound in which at least one bromine atom is substituted in the structure described in JP-A-2017-2013384, and a diketopyrrolopyrrole compound described in paragraphs 0016 to 0022 of Patent No. 6248838. , Diketopyrrolopyrrole compound described in WO2012 / 102399, diketopyrrolopyrrole compound described in WO2012 / 117965, naphtholazo compound described in JP2012-229344, patent No. 6516119.
- the compound described in No. 6525101, the compound described in Japanese Patent No. 6525101, and the like can also be used.
- red color material a compound having a structure in which an aromatic ring group in which a group in which an oxygen atom, a sulfur atom or a nitrogen atom is bonded is bonded to a diketopyrrolopyrrole skeleton is used for the aromatic ring.
- a compound having a structure in which an aromatic ring group in which a group in which an oxygen atom, a sulfur atom or a nitrogen atom is bonded is bonded to a diketopyrrolopyrrole skeleton is used for the aromatic ring.
- Such a compound is preferably a compound represented by the formula (DPP1), and more preferably a compound represented by the formula (DPP2).
- R 11 and R 13 independently represent a substituent
- R 12 and R 14 independently represent a hydrogen atom, an alkyl group, an aryl group or a heteroaryl group
- n 11 and n 13 are independent of each other.
- X 12 and X 14 independently represent an oxygen atom, a sulfur atom or a nitrogen atom
- m12 represents 1 and X.
- m12 represents 2 when X 14 is a nitrogen atom.
- the substituents represented by R 11 and R 13 include an alkyl group, an aryl group, a halogen atom, an acyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, a heteroaryloxycarbonyl group, an amide group, a cyano group, a nitro group and a trifluoro group.
- Preferred specific examples include a methyl group, a sulfoxide group, and a sulfo group.
- the chromatic dyes include pyrazole azo compounds, anilino azo compounds, triarylmethane compounds, anthraquinone compounds, anthrapylidene compounds, benzylidene compounds, oxonor compounds, pyrazorotriazole azo compounds, pyridone azo compounds, cyanine compounds, phenothiazine compounds, and pyropyrazole azomethine compounds. , Xanthene compound, phthalocyanine compound, benzopyran compound, indigo compound, pyromethene compound and the like.
- the chromatic dyes include a thiazole compound described in JP2012-158649A, an azo compound described in JP2011-184493, an azo compound described in JP2011-145540, and a Korean published patent.
- the triarylmethane dye polymer described in Japanese Patent Application Laid-Open No. 10-2020-0028160 and the xanthene compound described in JP-A-2020-117638 can also be preferably used.
- the chromatic coloring material the phthalocyanine compound described in International Publication No. 2020/174991 can be used.
- Two or more kinds of chromatic color materials may be used in combination. Further, when two or more kinds of chromatic color materials are used in combination, black may be formed by a combination of two or more kinds of chromatic color materials. Examples of such a combination include the following aspects (1) to (7).
- the resin composition of the present invention forms a near-infrared ray transmitting filter. It can be preferably used as a resin composition for use.
- An embodiment containing a red color material, a blue color material, and a yellow color material are examples of such a combination.
- An embodiment containing a red color material, a blue color material, a yellow color material, and a purple color material (3) An embodiment containing a red color material, a blue color material, a yellow color material, and a purple color material. (4) An embodiment containing a red color material, a blue color material, a yellow color material, a purple color material, and a green color material. (5) An embodiment containing a red color material, a blue color material, a yellow color material, and a green color material. (6) An embodiment containing a red color material, a blue color material, and a green color material. (7) An embodiment containing a yellow color material and a purple color material.
- White coloring materials include titanium oxide, strontium titanate, barium titanate, zinc oxide, magnesium oxide, zirconium oxide, aluminum oxide, barium sulfate, silica, talc, mica, aluminum hydroxide, calcium silicate, aluminum silicate, Examples thereof include hollow resin particles and inorganic pigments (white pigments) such as zinc sulfide.
- the white pigment is preferably particles having a titanium atom, and more preferably titanium oxide.
- the white pigment is preferably particles having a refractive index of 2.10 or more with respect to light having a wavelength of 589 nm. The above-mentioned refractive index is preferably 2.10 to 3.00, and more preferably 2.50 to 2.75.
- titanium oxide described in "Titanium Oxide Physical Properties and Applied Technology, by Manabu Kiyono, pp. 13-45, published on June 25, 1991, published by Gihodo Publishing" can also be used.
- the white pigment is not limited to a single inorganic substance, but particles compounded with other materials may be used. For example, particles having pores or other materials inside, particles in which a large number of inorganic particles are attached to core particles, core particles composed of core particles composed of polymer particles, and shell composite particles composed of a shell layer composed of inorganic nanoparticles are used. Is preferable.
- the core and shell composite particles composed of the core particles composed of the polymer particles and the shell layer composed of the inorganic nanoparticles for example, the description in paragraphs 0012 to 0042 of JP2015-047520 can be referred to. This content is incorporated herein by reference.
- Hollow inorganic particles can also be used as the white pigment.
- Hollow inorganic particles are inorganic particles having a structure having cavities inside, and are inorganic particles having cavities surrounded by an outer shell.
- Examples of the hollow inorganic particles include the hollow inorganic particles described in JP-A-2011-075786, International Publication No. 2013/061621, JP-A-2015-164881, and the like, and the contents thereof are incorporated in the present specification. Is done.
- Black color material The black color material is not particularly limited, and known materials can be used.
- examples of the inorganic black coloring material include inorganic pigments (black pigments) such as carbon black, titanium black, and graphite, with carbon black and titanium black being preferable, and titanium black being more preferable.
- Titanium black is black particles containing a titanium atom, and low-order titanium oxide or titanium oxynitride is preferable.
- the surface of titanium black can be modified as needed for the purpose of improving dispersibility and suppressing cohesion. For example, it is possible to coat the surface of titanium black with silicon oxide, titanium oxide, germanium oxide, aluminum oxide, magnesium oxide, or zirconium oxide.
- Titanium black preferably has a small primary particle size and an average primary particle size of each particle. Specifically, the average primary particle size is preferably 10 to 45 nm. Titanium black can also be used as a dispersion. For example, a dispersion containing titanium black particles and silica particles and having a content ratio of Si atoms and Ti atoms in the dispersion adjusted to be in the range of 0.20 to 0.50 can be mentioned.
- titanium black products include titanium black 10S, 12S, 13R, 13M, 13M-C, 13RN, 13MT (trade name: manufactured by Mitsubishi Materials Corporation), Tilak D (trade name: manufactured by Mitsubishi Materials Corporation). Product name: Ako Kasei Co., Ltd.) and the like.
- examples of the organic black color material include bisbenzofuranone compounds, azomethine compounds, perylene compounds, and azo compounds.
- examples of the bisbenzofuranone compound include the compounds described in Japanese Patent Publication No. 2010-534726, Japanese Patent Publication No. 2012-515233, Japanese Patent Publication No. 2012-515234, and the like. It is available.
- examples of the perylene compound include the compounds described in paragraphs 0016 to 0020 of JP-A-2017-226821, C.I. I. Pigment Black 31, 32 and the like can be mentioned.
- examples of the azomethine compound include the compounds described in JP-A-01-170601 and JP-A-02-0346664, and are available as, for example, "Chromofine Black A1103" manufactured by Dainichiseika.
- the coloring material used in the resin composition of the present invention may be only the above-mentioned black coloring material, or may further contain a chromatic coloring material. According to this aspect, it is easy to obtain a resin composition capable of forming a film having excellent light-shielding property in the visible region.
- chromatic color material 100: 10 to 300, preferably 100: 20 to 200. Is more preferable.
- Preferred combinations of the black color material and the chromatic color material include, for example, the following.
- A-1) An embodiment containing an organic black color material and a blue color material.
- A-2) An embodiment containing an organic black color material, a blue color material, and a yellow color material.
- A-3) An embodiment containing an organic black color material, a blue color material, a yellow color material, and a red color material.
- A-4) An embodiment containing an organic black color material, a blue color material, a yellow color material, and a purple color material.
- the near-infrared absorbing color material is preferably a pigment, more preferably an organic pigment. Further, the near-infrared absorbing color material preferably has a maximum absorption wavelength in a range of more than 700 nm and 1400 nm or less. The maximum absorption wavelength of the near-infrared absorbing color material is preferably 1200 nm or less, more preferably 1000 nm or less, and further preferably 950 nm or less.
- the near-infrared absorbing color material preferably has A 550 / A max, which is the ratio of the absorbance A 550 at a wavelength of 550 nm and the absorbance A max at the maximum absorption wavelength, to be 0.1 or less, preferably 0.05 or less. More preferably, it is more preferably 0.03 or less, and particularly preferably 0.02 or less.
- the lower limit is not particularly limited, but can be, for example, 0.0001 or more, or 0.0005 or more.
- the maximum absorption wavelength of the near-infrared absorbing color material and the value of the absorbance at each wavelength are values obtained from the absorption spectrum of the film formed by using the resin composition containing the near-infrared absorbing color material.
- the near-infrared absorbing coloring material is not particularly limited, but is pyrolopyrrole compound, cyanine compound, squarylium compound, phthalocyanine compound, naphthalocyanine compound, quaterylene compound, merocyanine compound, croconium compound, oxonor compound, iminium compound, dithiol compound, and tria.
- Examples thereof include a reelmethane compound, a pyromethene compound, an azomethine compound, an anthraquinone compound, a dibenzofuranone compound, and a dithiolene metal complex.
- Examples of the pyrrolopyrrole compound include the compounds described in paragraphs 0016 to 0058 of JP2009-263614, the compounds described in paragraphs 0037 to 0052 of JP2011-066731, and International Publication No. 2015/166783. Examples thereof include the compounds described in paragraphs 0010 to 0033.
- Examples of the squarylium compound include the compounds described in paragraphs 0044 to 0049 of JP2011-208101A, the compounds described in paragraphs 0060 to 0061 of Patent No. 6065169, and paragraph numbers 0040 of International Publication No. 2016/181987. , The compound described in JP-A-2015-176046, the compound described in paragraph number 0072 of International Publication No.
- JP2012-077153 the oxytitanium phthalocyanine described in JP2006-343631, and paragraphs 0013 to 0029 of JP2013-195480.
- Examples of the naphthalocyanine compound include the compounds described in paragraph No. 0093 of JP2012-077153.
- dithiolene metal complex include the compounds described in Japanese Patent No. 5733804.
- Examples of the near-infrared absorbing color material include a squarylium compound described in JP-A-2017-197437, a squarylium compound described in JP-A-2017-025311, a squarylium compound described in International Publication No. 2016/154782, and a patent.
- Squalylium compound described in Japanese Patent No. 5884953 Squalylium compound described in Japanese Patent No. 6036689
- Squalylium compound described in Japanese Patent No. 5810604 Squalylium compound described in paragraph Nos. 0090 to 0107 of International Publication No. 2017/213047.
- Amid-linked squarylium compound a compound having a pyrrolbis-type squarylium skeleton or a croconium skeleton described in JP-A-2017-141215, a dihydrocarbazolebis-type squarylium compound described in JP-A-2017-082029, JP-A-2017
- the content of the coloring material in the total solid content of the resin composition is preferably 20 to 90% by mass.
- the lower limit is preferably 30% by mass or more, more preferably 40% by mass or more, and further preferably 50% by mass or more.
- the upper limit is preferably 80% by mass or less, and more preferably 70% by mass or less.
- the content of the pigment in the total solid content of the resin composition is preferably 20 to 90% by mass.
- the lower limit is preferably 30% by mass or more, more preferably 40% by mass or more, and further preferably 50% by mass or more.
- the upper limit is preferably 80% by mass or less, and more preferably 70% by mass or less.
- the content of the dye in the coloring material is preferably 50% by mass or less, more preferably 40% by mass or less, and further preferably 30% by mass or less.
- the resin composition of the present invention does not substantially contain a dye because it is easy to more effectively suppress the change in film thickness when the obtained film is heated to a high temperature.
- the content of the dye in the total solid content of the resin composition of the present invention is preferably 0.1% by mass or less, preferably 0.05% by mass. The following is more preferable, and it is particularly preferable that the content is not contained.
- the resin composition of the present invention contains a resin.
- the resin contained in the resin composition has a main chain containing a molecular chain having a structure derived from a compound having an ethylenically unsaturated bond-containing group and a graft chain, and the graft chain has a repeating unit p1 having an oxetane group.
- the graft polymer is also referred to as a specific resin. Since this specific resin contains the above-mentioned graft chain, it is also excellent in dispersibility of the coloring material and can be preferably used as a dispersant.
- the specific resin may be used as a binder.
- a main chain means a molecular chain having the most branch points.
- the graft chain means a molecular chain branched from the main chain.
- the specific resin preferably contains at least one selected from an ethylenically unsaturated bond-containing group and an epoxy group. According to this aspect, a film having more excellent heat resistance can be formed.
- the ethylenically unsaturated bond-containing group include (meth) acryloyl group, (meth) acryloyloxy group, (meth) acrylamide group, vinylphenyl group, allyl group and the like, and (meth) acryloyl from the viewpoint of reactivity.
- An oxy group is preferred.
- the specific resin contains an ethylenically unsaturated bond-containing group or an epoxy group, these groups may be contained in the graft chain, or may be contained in the repeating unit constituting the main chain of the graft polymer. May be good.
- the epoxy group value of the specific resin is preferably 0.01 to 5 mmol / g from the viewpoint of storage stability and curability.
- the lower limit of the epoxy base value is preferably 0.02 mmol / g or more, more preferably 0.03 mmol / g or more, further preferably 0.05 mmol / g or more, and 0.10 mmol / g or more. The above is particularly preferable.
- the upper limit of the epoxy base value is preferably 3 mmol / g or less, more preferably 2 mmol / g or less, further preferably 1.5 mmol / g or less, and preferably 1 mmol / g or less. Especially preferable.
- the main chain of the specific resin preferably has a repeating unit represented by the formula (a1-1) as a repeating unit having the graft chain.
- a 1a represents a molecular chain having a structure derived from a compound having an ethylenically unsaturated bond-containing group
- L 1a represents a single bond or a divalent linking group
- P 1a repeats the above. Represents a graft chain containing the unit p1.
- the molecular chain of the structure derived from the compound having an ethylenically unsaturated bond-containing group represented by A 1a (meth) acrylic acid esters, crotonic acid esters, vinyl esters, maleic acid Compounds having ethylenically unsaturated bond-containing groups such as diesters, fumaric acid diesters, itaconic acid diesters, (meth) acrylamides, styrenes, vinyl ethers, vinyl ketones, olefins, maleimides, and (meth) acrylonitrile. Examples thereof include molecular chains having a structure formed by the polymerization of ethylene.
- a 1a examples include structures represented by the following formulas (A-1) to (A-5), and a structure represented by the formula (A-1) is preferable.
- * is a bond with L 1a of the formula (a1-1)
- Ra 1 to Ra 3 independently represent a hydrogen atom, an alkyl group or an aryl group, respectively.
- the number of carbon atoms of the alkyl group is preferably 1 to 10, more preferably 1 to 5, and even more preferably 1 to 3.
- the alkyl group may be linear, branched or cyclic, but is preferably linear or branched, more preferably linear.
- the aryl group preferably has 6 to 20 carbon atoms, more preferably 6 to 12 carbon atoms, and even more preferably 6 to 10 carbon atoms.
- Ra 1 is preferably a hydrogen atom or an alkyl group.
- Ra 2 and Ra 3 are preferably hydrogen atoms.
- the divalent linking group represented by L 1a includes an alkylene group (preferably an alkylene group having 1 to 12 carbon atoms), an arylene group (preferably an arylene group having 6 to 20 carbon atoms), and an arylene group.
- the alkylene group and the arylene group may have a substituent. Examples of the substituent include a hydroxy group and a halogen atom.
- the divalent linking group represented by L 1a is preferably a group represented by the formula (L-1).
- L 3a and L 4a each independently represent a divalent linking group
- X 1 is a single bond, -O-, -COO-, -OCO-, -NHCOO-,-. It represents OCONH- or -NHCONH-, where * 1 is a bond with P 1a and * 2 is a bond with A 1a.
- the divalent linking group represented by L 3a and L 4a of the formula (L-1) includes an alkylene group (preferably an alkylene group having 1 to 12 carbon atoms) and an arylene group (preferably an arylene group having 6 to 20 carbon atoms). ), - NH -, - SO -, - SO 2 -, - CO -, - O -, - COO -, - OCO -, - S -, - NHCO -, - CONH-, and combination of two or more of these There is a group of carbon.
- the alkylene group and the arylene group may have a substituent.
- L 3a and L 4a may be independently alkylene groups or arylene groups, respectively. It is preferably an alkylene group, more preferably an alkylene group.
- X 1 is preferably -O-, -COO-, -OCO-, -NHCOO-, -OCONH- or -NHCONH-, and more preferably -NHCOO- or -OCONH-.
- the graft chain represented by P 1a contains the repeating unit p1.
- the repeating unit p1 is preferably a repeating unit derived from a compound having an ethylenically unsaturated bond-containing group. Specific examples of the repeating unit p1 include repeating units represented by the formulas (p1-1) to (p1-4), and the repeating unit represented by the formula (p1-1) is preferable.
- Rp 1 to Rp 3 independently represent a hydrogen atom, an alkyl group or an aryl group;
- Lp 1 represents a divalent linking group;
- Rp 4 to Rp 8 independently represent hydrogen. Represents an atom or an alkyl group.
- the number of carbon atoms of the alkyl group represented by Rp 1 to Rp 3 is preferably 1 to 10, more preferably 1 to 5, and even more preferably 1 to 3.
- the alkyl group may be linear, branched or cyclic, but is preferably linear or branched, more preferably linear.
- the aryl group represented by Rp 1 to Rp 3 preferably has 6 to 20 carbon atoms, more preferably 6 to 12 carbon atoms, and even more preferably 6 to 10 carbon atoms.
- Rp 1 is preferably a hydrogen atom or an alkyl group.
- Rp 2 and Rp 3 are preferably hydrogen atoms.
- the number of carbon atoms of the alkyl group represented by Rp 4 to Rp 8 is preferably 1 to 10, and more preferably 1 to 5.
- the alkyl group may be linear, branched or cyclic, but is preferably linear or branched, more preferably linear.
- Rp 4 , Rp 5 , Rp 7 and Rp 8 are hydrogen atoms and Rp 6 is an alkyl group.
- Examples of the divalent linking group represented by Lp 1 include an alkylene group (preferably an alkylene group having 1 to 12 carbon atoms), an arylene group (preferably an arylene group having 6 to 20 carbon atoms), -NH-, and -SO-. -SO 2 -, - CO -, - O -, - COO -, - OCO -, - S -, - NHCO -, - CONH-, and include a group formed by combining two or more of these, an alkylene group It is preferable to have.
- the alkylene group and the arylene group may have a substituent. Examples of the substituent include a hydroxy group and a halogen atom.
- the graft chain represented by P 1a also preferably contains a repeating unit p2 having a group in which the carboxy group is protected by a pyrolytic group (hereinafter, also referred to as a protected carboxy group).
- a pyrolytic group is desorbed from the protected carboxy group to generate a carboxy group, and the generated carboxy group promotes the cross-linking reaction of the oxetane group contained in the graft chain. can.
- a carboxy group is generated in the vicinity of the oxetane group in the graft chain, the cross-linking reaction of the oxetane group can be promoted more effectively.
- the group in which the carboxy group is protected by a pyrolytic group is a group in which the pyrolytic group is eliminated by heat to generate a carboxy group.
- the group in which the carboxy group is protected by a pyrolytic group is preferably a group in which a carboxy group is produced by heating to a temperature of 120 to 290 ° C, more preferably 200 to 260 ° C.
- the protected carboxy group includes a group having a structure in which the carboxy group is protected by a tertiary alkyl group, a group having a structure in which the carboxy group is protected by an acetal group or a ketal group, and a structure in which the carboxy group is protected by a carbonate ester group. From the viewpoint of dispersion stability of the coloring material and ease of formation of a carboxy group by heating, it is preferable that the carboxy group is a group having a structure protected by a tertiary alkyl group. Specific examples of the protected carboxy group include groups represented by the formulas (b1-1) to (b1-3), from the viewpoint of dispersion stability of the coloring material and ease of formation of the carboxy group by heating.
- Rb 1 to Rb 3 independently represent an alkyl group or an aryl group, respectively, and Rb 1 and Rb 2 may be bonded to form a ring.
- Rb 4 represents an alkyl group or an aryl group
- Rb 5 and Rb 6 independently represent a hydrogen atom, an alkyl group or an aryl group, and at least one of Rb 5 and Rb 6. Is an alkyl group or an aryl group, and Rb 4 and Rb 5 may be bonded to form a ring.
- Rb 7 represents an alkyl group or an aryl group. * In equations (b1-1) to (b1-3) represent bonds.
- the number of carbon atoms of the alkyl group represented by Rb 1 to Rb 3 is preferably 1 to 10, more preferably 1 to 5, and even more preferably 1 to 3.
- the alkyl group may be linear, branched or cyclic, but is preferably linear or branched.
- the aryl group represented by Rb 1 to Rb 3 preferably has 6 to 20 carbon atoms, more preferably 6 to 12 carbon atoms, and even more preferably 6 to 10 carbon atoms.
- Rb 1 to Rb 3 are preferably independent alkyl groups, more preferably linear alkyl groups, more preferably linear alkyl groups having 1 to 5 carbon atoms, and directly.
- Rb 1 and Rb 2 may be combined to form a ring.
- the ring formed is preferably a 5-membered ring or a 6-membered ring.
- the number of carbon atoms of the alkyl group represented by Rb 4 to Rb 6 is preferably 1 to 20, more preferably 1 to 10, and even more preferably 1 to 10.
- the alkyl group may be linear, branched or cyclic, but is preferably linear or branched.
- the aryl group represented by Rb 4 to Rb 6 preferably has 6 to 20 carbon atoms, more preferably 6 to 12 carbon atoms, and even more preferably 6 to 10 carbon atoms.
- Rb 4 and Rb 5 may be combined to form a ring.
- the ring formed is preferably a 5-membered ring or a 6-membered ring.
- the number of carbon atoms of the alkyl group represented by Rb 7 is preferably 1 to 20, more preferably 1 to 10, and even more preferably 1 to 10.
- the alkyl group may be linear, branched or cyclic, but is preferably linear or branched.
- the aryl group represented by Rb 7 preferably has 6 to 20 carbon atoms, more preferably 6 to 12 carbon atoms, and even more preferably 6 to 10 carbon atoms.
- Rb 1 to Rb 3 of the formula (b1-1) are preferably independent alkyl groups, more preferably linear alkyl groups, and even more preferably methyl groups.
- the protected carboxy group include the groups shown below, and a group represented by the formula (bb-1), that is, a t-butyl ester group is preferable.
- the t-butyl ester group has an optimum decomposition temperature, and it is easy to generate a carboxy group by heat treatment during film formation. As a result, the cross-linking reaction of the oxetane group can be promoted more effectively, and the film has more heat resistance. Can be formed. Further, since the volume of the desorbed product of the t-butyl ester group is small, it is possible to suppress the generation of voids in the film.
- * represents a bond.
- repeating unit p2 examples include repeating units represented by the formulas (p2-1) to (p2-4).
- Rp 11 to Rp 13 independently represent a hydrogen atom, an alkyl group or an aryl group
- Lp 11 to Lp 14 independently represent a single bond or a divalent linking group
- B 1 Represents a group represented by the above formula (b1-1), a group represented by the above formula (b1-2), or a group represented by the above formula (b1-3).
- the number of carbon atoms of the alkyl group represented by Rp 11 to Rp 13 is preferably 1 to 10, more preferably 1 to 5, and even more preferably 1 to 3.
- the alkyl group may be linear, branched or cyclic, but is preferably linear or branched, more preferably linear.
- the aryl group represented by Rp 11 to Rp 13 preferably has 6 to 20 carbon atoms, more preferably 6 to 12 carbon atoms, and even more preferably 6 to 10 carbon atoms.
- Rp 11 is preferably a hydrogen atom or an alkyl group.
- Rp 12 and Rp 13 are preferably hydrogen atoms.
- the divalent linking group represented by Lp 11 to Lp 14 includes an alkylene group (preferably an alkylene group having 1 to 12 carbon atoms), an arylene group (preferably an arylene group having 6 to 20 carbon atoms), -NH-, and-.
- the alkylene group and the arylene group may have a substituent. Examples of the substituent include a hydroxy group and a halogen atom.
- B 1 represents a group represented by the above formula (b1-1), a group represented by the above formula (b1-2) or a group represented by the above formula (b1-3), and is represented by the above formula (b1-1). It is preferably a group represented by.
- the repeating unit p2 is preferably a repeating unit represented by the formula (p2-10).
- Rp 11 to Rp 13 independently represent a hydrogen atom, an alkyl group or an aryl group
- Rp 14 to Rp 16 represent an alkyl group or an aryl group
- Rp 14 and Rp 15 may be bonded to form a ring.
- the graft chain represented by P 1a may contain a repeating unit other than the repeating unit p1 and the repeating unit p2.
- the other repeating unit include a repeating unit having an ethylenically unsaturated bond-containing group, a repeating unit having an epoxy group, a repeating unit having a primary or secondary alkyl group, a repeating unit having an aryl group, and the like.
- the ethylenically unsaturated bond-containing group include a (meth) acryloyl group, a (meth) acryloyloxy group, a (meth) acrylamide group, a vinylphenyl group, an allyl group and the like.
- the other repeating unit contained in the graft chain represented by P 1a may be a repeating unit derived from a compound capable of copolymerizing with the repeating unit p1.
- the compound that can be copolymerized with the repeating unit p1 include (meth) acrylic acid ester monomer, crotonic acid ester monomer, vinyl ester monomer, maleic acid diester monomer, fumaric acid diester monomer, itaconic acid diester monomer, and (meth) acrylamide monomer.
- a heterocyclic group substituted with a vinyl group for example, vinylpyridine, N-vinylpyrrolidone, vinylcarbazole, etc.
- N-vinylformamide, N-vinylacetamide, N-vinylimidazole, vinylcaprolactone and the like can also be used.
- a monomer containing a pigment partial structure can also be used.
- Examples of the (meth) acrylic acid ester monomer include methyl (meth) acrylic acid, ethyl (meth) acrylic acid, n-propyl (meth) acrylic acid, isopropyl (meth) acrylic acid, n-butyl (meth) acrylic acid, and ( Isobutyl acrylate, t-butyl (meth) acrylate, amyl (meth) acrylate, n-hexyl (meth) acrylate, cyclohexyl (meth) acrylate, t-butylcyclohexyl (meth) acrylate, (meth) ) 2-Ethylhexyl acrylate, t-octyl acrylate, dodecyl (meth) acrylate, octadecyl (meth) acrylate, acetoxyethyl (meth) acrylate, phenyl (meth) acrylate, (meth)
- crotonic acid ester monomer examples include butyl crotonic acid and hexyl crotonic acid.
- vinyl ester monomer examples include vinyl acetate, vinyl chloroacetate, vinyl propionate, vinyl butyrate, vinyl methoxyacetate and vinyl benzoate.
- maleic acid diester monomer examples include dimethyl maleate, diethyl maleate, and dibutyl maleate.
- fumaric acid diesters examples include dimethyl fumarate, diethyl fumarate, and dibutyl fumarate.
- Examples of the itaconic acid diester monomer include dimethyl itaconic acid, diethyl itaconic acid, and dibutyl itaconic acid.
- Examples of the (meth) acrylamide monomer include (meth) acrylamide, N-methyl (meth) acrylamide, N-ethyl (meth) acrylamide, N-propyl (meth) acrylamide, N-isopropyl (meth) acrylamide, and Nn-butyl.
- Styrene monomers include styrene, methylstyrene, dimethylstyrene, trimethylstyrene, ethylstyrene, isopropylstyrene, butylstyrene, hydroxystyrene, methoxystyrene, n-butoxystyrene, t-butoxystyrene, acetoxystyrene, chlorostyrene, dichlorostyrene, Examples thereof include bromostyrene, chloromethylstyrene, methyl vinylbenzoate, ⁇ -methylstyrene and inden.
- vinyl ether monomer examples include methyl vinyl ether, ethyl vinyl ether, 2-chloroethyl vinyl ether, hydroxyethyl vinyl ether, propyl vinyl ether, butyl vinyl ether, hexyl vinyl ether, octyl vinyl ether, methoxyethyl vinyl ether and phenyl vinyl ether.
- Examples of the vinyl ketone monomer include methyl vinyl ketone, ethyl vinyl ketone, propyl vinyl ketone, and phenyl vinyl ketone.
- olefin monomer examples include ethylene, propylene, isobutylene, butadiene, and isoprene.
- maleimide monomer examples include maleimide, N-phenylmaleimide, N-methylmaleimide, N-butylmaleimide, N-cyclohexylmaleimide and the like.
- the content of the repeating unit p1 in the graft chain is preferably 30 mol% or more, more preferably 50 mol% or more, and more preferably 70 mol, based on the total molar amount of the repeating units contained in the graft chain. It is more preferably% or more.
- the upper limit is not particularly limited and may be 100 mol% or less.
- the content of the repeating unit p1 in the specific resin is preferably 20 mol% or more, more preferably 30 mol% or more, based on the total molar amount of the repeating units contained in the specific resin. It is more preferably 40 mol% or more, further preferably 50 mol% or more, further preferably 60 mol% or more, and particularly preferably 70 mol% or more.
- the upper limit is not particularly limited, and may be 100 mol% or less, 90 mol% or less, or 95 mol% or less.
- the content of the repeating unit p2 in the graft chain is preferably 5 to 70 mol% with respect to the total molar amount of the repeating unit contained in the graft chain.
- the lower limit is preferably 10 mol% or more, more preferably 20 mol% or more.
- the upper limit is preferably 50 mol% or less, more preferably 40 mol% or less.
- the ratio of the repeating unit p1 to the repeating unit p2 is preferably 0.1 to 5 mol, preferably 0.2 to 3 mol, with respect to 1 mol of the repeating unit p1. More preferably, it is more preferably 0.3 to 1 mol.
- the total content of the repeating unit p1 and the repeating unit p2 in the graft chain is preferably 50 mol% or more, preferably 70 mol% or more, based on the total molar amount of the repeating units contained in the graft chain.
- the above is more preferable, and 85 mol% or more is further preferable.
- the total content of the repeating unit p1 and the repeating unit p2 in the specific resin is preferably 30 mol% or more, preferably 40 mol% or more, based on the total molar amount of the repeating units contained in the specific resin. It is more preferably 50 mol% or more, further preferably 60 mol% or more, further preferably 70 mol% or more, and 85 mol% or more. Is particularly preferable.
- the upper limit is not particularly limited, and may be 100 mol% or less, 90 mol% or less, or 95 mol% or less.
- the weight average molecular weight of the graft chain represented by P 1a is preferably 500 to 10000.
- the main chain of the specific resin preferably contains a repeating unit represented by the formula (a-1-1).
- Ra 11 to Ra 13 independently represent a hydrogen atom, an alkyl group or an aryl group
- La 11 represents a divalent linking group
- P 1a represents a graft chain containing the repeating unit p1.
- the graft chain represented by P 1a of the formula (a-1-1) has the same meaning as P 1a of the above-mentioned formula (a1-1), and the preferable range is also the same.
- the number of carbon atoms of the alkyl group represented by Ra 11 to Ra 13 is preferably 1 to 10, more preferably 1 to 5, and even more preferably 1 to 3.
- the alkyl group may be linear, branched or cyclic, but is preferably linear or branched, more preferably linear.
- the aryl group represented by Ra 11 to Ra 13 preferably has 6 to 20 carbon atoms, more preferably 6 to 12 carbon atoms, and even more preferably 6 to 10 carbon atoms.
- Ra 11 is preferably a hydrogen atom or an alkyl group.
- Ra 12 and Ra 13 are preferably hydrogen atoms.
- Examples of the divalent linking group represented by La 11 include an alkylene group (preferably an alkylene group having 1 to 12 carbon atoms), an arylene group (preferably an arylene group having 6 to 20 carbon atoms), -NH-, and -SO-. -SO 2 -, - CO -, - O -, - COO -, - OCO -, - S -, - NHCO -, - CONH-, and include a group formed by combining two or more of these.
- the alkylene group and the arylene group may have a substituent. Examples of the substituent include a hydroxy group and a halogen atom.
- the divalent linking group represented by La 11 is preferably a group represented by the above formula (L-1).
- the main chain of the specific resin contains a repeating unit represented by the formula (1).
- R 1 to R 3 independently represent a hydrogen atom, an alkyl group or an aryl group
- L 1 and L 2 each independently represent a divalent linking group
- X 1 represents a single bond, -O-, -COO-, -OCO-, -NHCOO-, -OCONH- or -NHCONH-
- P 1 represents a graft chain containing the repeating unit p1.
- the graft chain represented by P 1 of the formula (1) has the same meaning as P 1 a of the above formula (a1-1), and the preferable range is also the same.
- R 1 to R 3 of the formula (1) have the same meaning as Ra 11 to Ra 13 of the above formula (a-1-1), and the preferable range is also the same.
- Examples of the divalent linking group represented by L 1 and L 2 in the formula (1) include an alkylene group (preferably an alkylene group having 1 to 12 carbon atoms), an arylene group (preferably an arylene group having 6 to 20 carbon atoms), and an arylene group.
- an alkylene group preferably an alkylene group having 1 to 12 carbon atoms
- an arylene group preferably an arylene group having 6 to 20 carbon atoms
- the alkylene group and the arylene group may have a substituent.
- L 1 and L 2 may be independently alkylene or arylene groups, respectively. It is preferably an alkylene group, more preferably an alkylene group.
- X 1 is preferably -O-, -COO-, -OCO-, -NHCOO-, -OCONH- or -NHCONH-, and more preferably -NHCOO- or -OCONH-.
- a repeating unit having the graft chain in the specific resin (preferably a repeating unit represented by the formula (a1-1), more preferably a repeating unit represented by the formula (a-1-1), still more preferably a formula.
- the content of the repeating unit (shown in (1)) is preferably 5 mol% or more, more preferably 10 mol% or more, based on the total molar amount of the repeating unit contained in the main chain of the specific resin. It is more preferably 15 mol% or more, and even more preferably 20 mol% or more.
- the upper limit is not particularly limited, and can be 100 mol% or less, 90 mol% or less, 80 mol% or less, 70 mol% or less, 60 mol% or less. It can be less than or equal to 50 mol% or less.
- a repeating unit having the graft chain in the specific resin preferably a repeating unit represented by the formula (a1-1), more preferably a repeating unit represented by the formula (a-1-1), still more preferable.
- the content of the repeating unit represented by the formula (1) is preferably 30% by mass or more, more preferably 40% by mass or more, and 50% by mass or more with respect to the mass of the specific resin. Is even more preferable.
- the upper limit can be 100% by mass or less, 95% by mass or less, 90% by weight or less, or 85% by weight or less.
- the main chain of the specific resin may contain a repeating unit (also referred to as another repeating unit) other than the repeating unit having the graft chain.
- Other repeating units include a repeating unit having an acid group, a repeating unit having a basic group, a repeating unit having a crosslinkable group, and a repeating unit in which a carboxy group is protected by a pyrolytic group (protected carboxy group). Units and the like can be mentioned.
- the dispersibility of the coloring material can be further improved.
- the acid group include a phenolic hydroxy group, a carboxy group, a sulfo group, a phosphoric acid group and the like.
- the structure of the repeating unit having an acid group include a polyester repeating unit, a polyether repeating unit, and a repeating unit derived from a compound having an ethylenically unsaturated bond-containing group. From the viewpoint of heat resistance of the obtained film, the repeating unit is ethylenically.
- the acid value of the specific resin is preferably 20 to 200 mgKOH / g.
- the lower limit of the acid value is preferably 30 mgKOH / g or more, and more preferably 50 mgKOH / g or more.
- the upper limit of the acid value is preferably 150 mgKOH / g or less.
- the content of the repeating unit having an acid group in the specific resin is preferably 30 to 90 mol%, preferably 50 to 85 mol%, based on the total molar amount of the repeating unit contained in the main chain of the specific resin. Is more preferable, and 60 to 80 mol% is further preferable.
- the monomer used for forming the repeating unit having an acid group is not particularly limited, and a compound copolymerizable with a compound having an ethylenically unsaturated bond-containing group constituting the molecular chain of the main chain is used.
- a compound having an acid group and an ethylenically unsaturated bond-containing group also referred to as an acid group-containing monomer
- Specific examples of the acid group-containing monomer include (meth) acrylic acid, p-vinylbenzoic acid, maleic acid, maleic acid monoalkyl ester, fumaric acid, itaconic acid, crotonic acid, cinnamic acid, acrylic acid dimer, and oxalic acid mono.
- the basic group is preferably an amino group, preferably a cyclic amino group, a secondary amino group or a tertiary amino group, and more preferably a tertiary amino group.
- the secondary amino group include a monoalkylamino group and a monoarylamino group, and a monoalkylamino group is preferable.
- the tertiary amino group include a dialkylamino group, a diarylamino group, an alkylarylamino group and the like, and a dialkylamino group is preferable.
- Examples of the structure of the repeating unit having a basic group include a polyester repeating unit, a polyether repeating unit, a repeating unit derived from a compound having an ethylenically unsaturated bond-containing group, and ethylene from the viewpoint of heat resistance of the obtained film. It is preferably a repeating unit derived from a compound having a sex unsaturated bond-containing group, and more preferably a polyvinyl repeating unit, a poly (meth) acrylic repeating unit and a (poly) styrene repeating unit.
- the amine value of the specific resin is preferably 20 to 200 mgKOH / g.
- the lower limit of the amine value is preferably 30 mgKOH / g or more, and more preferably 50 mgKOH / g or more.
- the upper limit of the amine value is preferably 150 mgKOH / g or less.
- the content of the repeating unit having a basic group in the specific resin is preferably 30 to 90 mol%, preferably 50 to 85 mol%, based on the total molar amount of the repeating unit contained in the main chain of the specific resin. It is more preferably%, and even more preferably 60 to 80 mol%.
- the monomer used for forming the repeating unit having a basic group is not particularly limited, and a compound copolymerizable with a compound having an ethylenically unsaturated bond-containing group constituting the molecular chain of the main chain is used.
- the crosslinkable group include an ethylenically unsaturated bond-containing group and a cyclic ether group.
- the ethylenically unsaturated bond-containing group include (meth) acryloyl group, (meth) acryloyloxy group, (meth) acrylamide group, vinylphenyl group, allyl group and the like, and (meth) acryloyl from the viewpoint of reactivity.
- An oxy group is preferred.
- Cyclic ether groups include epoxy groups and oxetane groups.
- Examples of the structure of the repeating unit having a crosslinkable group include a polyester repeating unit, a polyether repeating unit, a repeating unit derived from a compound having an ethylenically unsaturated bond-containing group, and ethylene from the viewpoint of heat resistance of the obtained film. It is preferably a repeating unit derived from a compound having a sex unsaturated bond-containing group, and more preferably a polyvinyl repeating unit, a poly (meth) acrylic repeating unit and a (poly) styrene repeating unit.
- the content of the repeating unit having a crosslinkable group in the specific resin is preferably 10 to 60 mol%, preferably 15 to 50 mol%, based on the total molar amount of the repeating unit contained in the main chain of the specific resin. More preferably, it is more preferably 20-40 mol%.
- the monomer used for forming the repeating unit having a crosslinkable group is not particularly limited, and a compound copolymerizable with a compound having an ethylenically unsaturated bond-containing group constituting the molecular chain of the main chain is used.
- the repeating unit in which the main chain of the specific resin has a protective carboxy group can further promote the cross-linking reaction of the oxetane group at the time of film formation, and it is easy to form a film having more excellent heat resistance.
- the protected carboxy group include groups having the above-mentioned structure, and the same applies to the preferred range.
- Examples of the structure of the repeating unit having a protective carboxy group include a polyester repeating unit, a polyether repeating unit, a repeating unit derived from a compound having an ethylenically unsaturated bond-containing group, and ethylene from the viewpoint of heat resistance of the obtained film.
- It is preferably a repeating unit derived from a compound having a sex unsaturated bond-containing group, and more preferably a polyvinyl repeating unit, a poly (meth) acrylic repeating unit and a (poly) styrene repeating unit.
- the content of the repeating unit having a protective carboxy group in the specific resin is preferably 10 to 60 mol%, preferably 15 to 50 mol%, based on the total molar amount of the repeating unit contained in the main chain of the specific resin. More preferably, it is more preferably 20-40 mol%.
- the repeating unit (other repeating unit) other than the repeating unit having the above-mentioned graft chain contained in the main chain of the specific resin may be a repeating unit derived from a compound capable of copolymerizing with the repeating unit p1.
- Examples of the compound that can be copolymerized with the repeating unit p1 include the compounds described as examples of the compounds that can be copolymerized with the repeating unit p1 described above.
- the weight average molecular weight (Mw) of the specific resin is preferably 5,000 to 100,000, more preferably 10,000 to 100,000, and even more preferably 10,000 to 50,000.
- the maximum value of the molar extinction coefficient of the specific resin at a wavelength of 400 to 1100 nm is preferably 0 to 1000 L ⁇ mol -1 ⁇ cm -1 , and more preferably 0 to 100 L ⁇ mol -1 ⁇ cm -1. ..
- the oxetane ratio of the specific resin is preferably 20 to 95 mol% because it is easy to form a film having better heat resistance (crack suppression and film shrinkage suppression).
- the lower limit of the oxetane ratio is preferably 30 mol% or more, more preferably 40 mol% or more, further preferably 50 mol% or more, and particularly preferably 60 mol% or more.
- the upper limit of the oxetane ratio is preferably 90 mol% or less, more preferably 85 mol% or less, and further preferably 80 mol% or less.
- the oxetane ratio of the specific resin means the mole fraction of the repeating unit having an oxetane group contained in all the repeating units of the specific resin. The higher the oxetane ratio of the specific resin, the better the heat resistance of the obtained film.
- the oxetane base value of the specific resin is preferably 0.01 to 5 mmol / g.
- the lower limit of the oxetane base value is preferably 0.02 mmol / g or more, more preferably 0.03 mmol / g or more, further preferably 0.05 mmol / g or more, and 0.10 mmol / g or more. The above is particularly preferable.
- the upper limit of the oxetane base value is preferably 3 mmol / g or less, more preferably 2 mmol / g or less, further preferably 1.5 mmol / g or less, and more preferably 1 mmol / g or less. Especially preferable.
- the oxetane base value of the specific resin is the number of oxetane groups contained in 1 g of the specific resin.
- the 5% mass reduction temperature of the specific resin by TG / DTA (thermogravimetric measurement / differential thermal measurement) in a nitrogen atmosphere is preferably 280 ° C. or higher, more preferably 300 ° C. or higher, and 320 ° C. or higher. Is more preferable.
- the upper limit of the 5% mass reduction temperature is not particularly limited, and may be, for example, 1,000 ° C. or lower.
- the 5% mass reduction temperature is determined by a known TG / DTA measuring method as a temperature at which the mass reduction rate becomes 5% when the mixture is allowed to stand at a specific temperature for 5 hours in a nitrogen atmosphere.
- the specific resin preferably has a mass reduction rate of 10% or less, more preferably 5% or less, and 2% or less when left to stand at 300 ° C. for 5 hours in a nitrogen atmosphere. More preferred.
- the lower limit of the mass reduction rate is not particularly limited, and may be 0% or more.
- the mass reduction rate is a value calculated as the rate of mass reduction in the specific resin before and after being allowed to stand at 300 ° C. for 5 hours in a nitrogen atmosphere.
- Specific examples of the specific resin include the resins (A-1) to (A-48) mentioned in the section of Examples described later, but the present invention is not limited thereto.
- the resin composition of the present invention may contain a resin other than the above-mentioned specific resin as the resin.
- other resins include resins having alkali developability, resins as dispersants, and the like.
- the resins described in paragraphs 0041 to 0060 of JP-A-2017-206689, the resins described in paragraphs 0022 to 0071 of JP-A-2018-010856, and JP-A-2017-057265. The resin described in JP-A-2017-032685, the resin described in JP-A-2017-075248, the resin described in JP-A-066240, the resin described in JP-A-2017-173787.
- a resin containing a structural unit having a ring structure in the chain and a structural unit having a biphenyl group in the side chain can also be used.
- the weight average molecular weight (Mw) of the alkali-developable resin is preferably 3000 to 2000000.
- the upper limit is more preferably 1,000,000 or less, and even more preferably 500,000 or less.
- the lower limit is more preferably 4000 or more, further preferably 5000 or more.
- alkali-developable resin examples include (meth) acrylic resin, polyimine resin, polyether resin, polyolefin resin, cyclic olefin resin, polyester resin, styrene resin, and polyimide resin, and (meth) acrylic resin and polyimine resin. Is preferable, and (meth) acrylic resin is more preferable.
- the resin having alkali developability it is preferable to use a resin having an acid group.
- the developability of the resin composition can be further improved.
- the acid group include a phenolic hydroxy group, a carboxy group, a sulfo group, a phosphoric acid group, a phosphonic acid group, an active imide group, a sulfonamide group and the like, and a carboxy group is preferable.
- a resin in which an acid group is introduced by reacting an acid anhydride with a hydroxy group generated by epoxy ring opening may be used. Examples of such a resin include the resin described in Japanese Patent No. 6349629.
- the resin having an acid group can be used as, for example, an alkali-soluble resin.
- the alkali-developable resin preferably contains a repeating unit having an acid group in the side chain, and more preferably contains 1 to 70 mol% of the repeating unit having an acid group in the side chain in all the repeating units of the resin.
- the upper limit of the content of the repeating unit having an acid group in the side chain is preferably 50 mol% or less, more preferably 40 mol% or less.
- the lower limit of the content of the repeating unit having an acid group in the side chain is preferably 2 mol% or more, and more preferably 5 mol% or more.
- the acid value of the alkali-developable resin is preferably 200 mgKOH / g or less, more preferably 150 mgKOH / g or less, further preferably 120 mgKOH / g or less, and particularly preferably 100 mgKOH / g or less.
- the acid value of the resin having an acid group is preferably 5 mgKOH / g or more, more preferably 10 mgKOH / g or more, and even more preferably 20 mgKOH / g or more.
- the resin having alkali developability further has an ethylenically unsaturated bond-containing group.
- the ethylenically unsaturated bond-containing group include a vinyl group, an allyl group, a (meth) acryloyl group, and the like, preferably an allyl group and a (meth) acryloyl group, and more preferably a (meth) acryloyl group.
- the resin having an ethylenically unsaturated bond-containing group preferably contains a repeating unit having an ethylenically unsaturated bond-containing group in the side chain, and the repeating unit having an ethylenically unsaturated bond-containing group in the side chain is the whole resin. More preferably, it contains 5-80 mol% in the repeating unit.
- the upper limit of the content of the repeating unit having an ethylenically unsaturated bond-containing group in the side chain is preferably 60 mol% or less, more preferably 40 mol% or less.
- the lower limit of the content of the repeating unit having an ethylenically unsaturated bond-containing group in the side chain is preferably 10 mol% or more, more preferably 15 mol% or more.
- the alkali-developable resin includes a compound represented by the following formula (ED1) and / or a compound represented by the following formula (ED2) (hereinafter, these compounds may be referred to as "ether dimer”). It is also preferable to include repeating units derived from the monomer component.
- R 1 and R 2 each independently represent a hydrocarbon group having 1 to 25 carbon atoms which may have a hydrogen atom or a substituent.
- R represents a hydrogen atom or an organic group having 1 to 30 carbon atoms.
- paragraph number 0317 of JP2013-209760A can be referred to, and this content is incorporated in the present specification.
- the alkali-developable resin preferably contains a repeating unit derived from the compound represented by the following formula (X).
- R 1 represents a hydrogen atom or a methyl group
- R 2 represents an alkylene group having 2 to 10 carbon atoms
- R 3 represents a hydrogen atom or a benzene ring having 1 to 20 carbon atoms.
- n represents an integer from 1 to 15.
- Examples of the resin having alkali developability include a resin having the following structure.
- Me represents a methyl group.
- the resin composition of the present invention may also contain a resin as a dispersant.
- the dispersant include an acidic dispersant (acidic resin) and a basic dispersant (basic resin).
- the acidic dispersant (acidic resin) represents a resin in which the amount of acid groups is larger than the amount of basic groups.
- the acidic dispersant (acidic resin) is preferably a resin in which the amount of acid groups accounts for 70 mol% or more when the total amount of the amount of acid groups and the amount of basic groups is 100 mol%, and is substantially an acid. A resin consisting only of groups is more preferable.
- the acid group of the acidic dispersant (acidic resin) is preferably a carboxy group.
- the acid value of the acidic dispersant (acidic resin) is preferably 40 to 105 mgKOH / g, more preferably 50 to 105 mgKOH / g, and even more preferably 60 to 105 mgKOH / g.
- the basic dispersant (basic resin) represents a resin in which the amount of basic groups is larger than the amount of acid groups.
- the basic dispersant (basic resin) is preferably a resin in which the amount of basic groups exceeds 50 mol% when the total amount of the amount of acid groups and the amount of basic groups is 100 mol%.
- the basic group contained in the basic dispersant is preferably an amino group.
- the resin used as the dispersant preferably contains a repeating unit having an acid group.
- the resin used as the dispersant is also preferably a graft polymer.
- the graft polymer include the resins described in paragraphs 0025 to 0094 of JP2012-255128, the contents of which are incorporated in the present specification.
- the resin used as the dispersant is a polyimine-based dispersant (polyimine resin) containing a nitrogen atom in at least one of the main chain and the side chain.
- the polyimine-based dispersant has a main chain having a partial structure having a functional group of pKa14 or less, a side chain having 40 to 10,000 atoms, and a basic nitrogen atom in at least one of the main chain and the side chain.
- the resin to have is preferable.
- the basic nitrogen atom is not particularly limited as long as it is a nitrogen atom exhibiting basicity.
- Examples of the polyimine-based dispersant include the resins described in paragraphs 0102 to 0166 of JP2012-255128A, the contents of which are incorporated in the present specification.
- the resin used as the dispersant is also preferably a resin having a structure in which a plurality of polymer chains are bonded to the core portion.
- a resin include a dendrimer (including a radial polymer).
- Specific examples of the dendrimer include polymer compounds C-1 to C-31 described in paragraphs 0196 to 0209 of JP2013-043962.
- the dispersant is also available as a commercially available product, and specific examples thereof include DISPERBYK series manufactured by BYK Chemie (for example, DISPERBYK-111, 161 etc.) and Solspace series manufactured by Lubrizol (for example, Solspire 36000 etc.). And so on. Further, the pigment dispersants described in paragraphs 0041 to 0130 of JP-A-2014-130338 can also be used, and the contents thereof are incorporated in the present specification. Dispersants include JP-A-2018-150498, JP-A-2017-100116, JP-A-2017-100115, JP-A-2016-108520, JP-A-2016-108519, and JP-A-2015. The compound described in Japanese Patent Application Laid-Open No. 232105 may be used.
- the resin described as the dispersant can also be used for purposes other than the dispersant.
- it can also be used as a binder.
- the content of the resin in the total solid content of the resin composition is preferably 5 to 60% by mass.
- the lower limit is preferably 10% by mass or more, more preferably 15% by mass or more.
- the upper limit is preferably 50% by mass or less, more preferably 40% by mass or less.
- the content of the above-mentioned specific resin in the total solid content of the resin composition is preferably 5 to 60% by mass.
- the lower limit is preferably 10% by mass or more, more preferably 15% by mass or more.
- the upper limit is preferably 50% by mass or less, more preferably 40% by mass or less.
- the content of the above-mentioned specific resin is preferably 10 to 80 parts by mass with respect to 100 parts by mass of the pigment.
- the lower limit is preferably 20 parts by mass or more, and more preferably 30 parts by mass or more.
- the upper limit is preferably 70 parts by mass or less, more preferably 50 parts by mass or less.
- the resin composition of the present invention preferably contains the specific resin in an amount of 20% by mass or more, more preferably 30% by mass or more, and more preferably 40% by mass, in the components obtained by removing the coloring material from the total solid content of the resin composition. It is more preferable to contain% or more.
- the upper limit can be 100% by mass, 90% by mass or less, or 85% by mass or less.
- the total content of the coloring material and the above-mentioned specific resin in the total solid content of the resin composition is preferably 25 to 100% by mass.
- the lower limit is more preferably 30% by mass or more, further preferably 40% by mass or more.
- the upper limit is more preferably 90% by mass or less, further preferably 80% by mass or less.
- the content of the above-mentioned other resin is preferably 230 parts by mass or less, more preferably 200 parts by mass or less, and 150 parts by mass with respect to 100 parts by mass of the above-mentioned specific resin.
- the lower limit may be 0 parts by mass, 5 parts by mass or more, or 10 parts by mass or more.
- the resin composition does not substantially contain the other resins described above. According to this aspect, it is easy to form a film having more excellent heat resistance.
- the case where the other resin is substantially not contained means that the content of the other resin in the total solid content of the resin composition is 0.1% by mass or less, and is 0.05% by mass or less. It is preferable, and it is more preferable that it is not contained.
- the resin composition of the present invention contains a solvent.
- the solvent is basically not particularly limited as long as it satisfies the solubility of each component and the coatability of the resin composition.
- the solvent is preferably an organic solvent.
- the organic solvent include ester solvents, ketone solvents, alcohol solvents, amide solvents, ether solvents, hydrocarbon solvents and the like.
- paragraph No. 0223 of WO 2015/166779 can be referred to, the contents of which are incorporated herein by reference.
- an ester solvent substituted with a cyclic alkyl group and a ketone solvent substituted with a cyclic alkyl group can also be preferably used.
- organic solvent examples include polyethylene glycol monomethyl ether, dichloromethane, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, ethyl cellosolve acetate, ethyl lactate, diethylene glycol dimethyl ether, butyl acetate, methyl 3-methoxypropionate, 2 -Heptanone, 2-pentanone, 3-pentanone, 4-heptanone, cyclohexanone, 2-methylcyclohexanone, 3-methylcyclohexanone, 4-methylcyclohexanone, cycloheptanone, cyclooctanone, 3-methoxybutanol, cyclohexyl acetate, cyclopenta Non-ethyl carbitol acetate, butyl carbitol acetate, propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, 3-methoxy-N, N-dimethyl
- aromatic hydrocarbons benzene, toluene, xylene, ethylbenzene, etc.
- organic solvents may need to be reduced for environmental reasons (for example, 50 mass ppm (parts) with respect to the total amount of organic solvent. Per million) or less, 10 mass ppm or less, or 1 mass ppm or less).
- an organic solvent having a low metal content it is preferable to use an organic solvent having a low metal content, and the metal content of the organic solvent is preferably, for example, 10 mass ppb (parts per parts) or less. If necessary, an organic solvent at the mass ppt (parts per trillion) level may be used, and such an organic solvent is provided by, for example, Toyo Synthetic Co., Ltd. (The Chemical Daily, November 13, 2015).
- Examples of the method for removing impurities such as metals from the organic solvent include distillation (molecular distillation, thin film distillation, etc.) and filtration using a filter.
- the filter pore diameter of the filter used for filtration is preferably 10 ⁇ m or less, more preferably 5 ⁇ m or less, and even more preferably 3 ⁇ m or less.
- the filter material is preferably polytetrafluoroethylene, polyethylene or nylon.
- the organic solvent may contain isomers (compounds having the same number of atoms but different structures). Further, only one kind of isomer may be contained, or a plurality of kinds may be contained.
- the content of peroxide in the organic solvent is preferably 0.8 mmol / L or less, and more preferably substantially free of peroxide.
- the content of the solvent in the resin composition is preferably 10 to 95% by mass, more preferably 20 to 90% by mass, and even more preferably 30 to 90% by mass.
- the resin composition of the present invention preferably contains a pigment derivative.
- the pigment derivative include compounds having a structure in which a part of the chromophore is replaced with an acid group, a basic group or a phthalimide methyl group.
- the colorants constituting the pigment derivative include quinoline skeleton, benzoimidazolone skeleton, diketopyrrolopyrrole skeleton, azo skeleton, phthalocyanine skeleton, anthracinone skeleton, quinacridone skeleton, dioxazine skeleton, perinone skeleton, perylene skeleton, thioindigo skeleton, and iso.
- the azo skeleton and the benzoimidazolone skeleton are more preferable.
- the acid group contained in the pigment derivative a sulfo group and a carboxy group are preferable, and a sulfo group is more preferable.
- the basic group contained in the pigment derivative an amino group is preferable, and a tertiary amino group is more preferable.
- a pigment derivative having excellent visible light transparency (hereinafter, also referred to as a transparent pigment derivative) can be used.
- the maximum value of the molar extinction coefficient in the wavelength region of 400 ⁇ 700 nm of the transparent pigment derivative (.epsilon.max) is that it is preferable, 1000L ⁇ mol -1 ⁇ cm -1 or less is not more than 3000L ⁇ mol -1 ⁇ cm -1 Is more preferable, and 100 L ⁇ mol -1 ⁇ cm -1 or less is further preferable.
- the lower limit of ⁇ max is, for example, 1 L ⁇ mol -1 ⁇ cm -1 or more, and may be 10 L ⁇ mol -1 ⁇ cm -1 or more.
- pigment derivative examples include Japanese Patent Application Laid-Open No. 56-118462, Japanese Patent Application Laid-Open No. 63-264674, Japanese Patent Application Laid-Open No. 01-2170777, Japanese Patent Application Laid-Open No. 03-009961, and Japanese Patent Application Laid-Open No. 03-026767.
- JP-A-2015-172732 examples thereof include the compounds described in JP-A-2014-199308, JP-A-2014-0855562, JP-A-2014-035351, JP-A-2008-081565, and JP-A-2019-109512.
- the content of the pigment derivative is preferably 1 to 30 parts by mass, more preferably 3 to 20 parts by mass with respect to 100 parts by mass of the pigment. Only one type of pigment derivative may be used, or two or more types may be used in combination.
- the resin composition of the present invention preferably contains a polymerizable monomer.
- a polymerizable monomer for example, a known compound that can be crosslinked by radicals, acids or heat can be used. Examples thereof include a compound having an ethylenically unsaturated bond-containing group and a compound having a cyclic ether group, and a compound having an ethylenically unsaturated bond-containing group is preferable.
- the ethylenically unsaturated bond-containing group include a vinyl group, a (meth) allyl group, and a (meth) acryloyl group.
- the cyclic ether group include an epoxy group and an oxetane group.
- a compound having an ethylenically unsaturated bond-containing group can be preferably used as a radically polymerizable monomer.
- the compound having a cyclic ether group can be preferably used as a cationically polymerizable monomer.
- the polymerizable monomer is preferably a polyfunctional polymerizable monomer. That is, the polymerizable monomer is preferably a monomer having two or more polymerizable groups such as an ethylenically unsaturated bond-containing group and a cyclic ether group.
- the molecular weight of the polymerizable monomer is preferably 100 to 3000.
- the upper limit is more preferably 2000 or less, and even more preferably 1500 or less.
- the lower limit is more preferably 150 or more, and even more preferably 250 or more.
- the compound having an ethylenically unsaturated bond-containing group used as the polymerizable monomer is preferably a polyfunctional compound. That is, it is preferably a compound containing two or more ethylenically unsaturated bond-containing groups, more preferably a compound containing three or more ethylenically unsaturated bond-containing groups, and three ethylenically unsaturated bond-containing groups. A compound containing up to 15 is more preferable, and a compound containing 3 to 6 ethylenically unsaturated bond-containing groups is even more preferable.
- the compound having an ethylenically unsaturated bond-containing group is preferably a (meth) acrylate compound having 3 to 15 functionalities, and more preferably a (meth) acrylate compound having 3 to 6 functionalities.
- Specific examples of the compound having an ethylenically unsaturated bond-containing group include paragraphs 0905 to 0108 of JP2009-288705A, paragraphs 0227 of JP2013-029760A, and paragraphs of JP2008-292970A. Nos. 0254 to 0257, paragraphs 0034 to 0038 of JP2013-253224A, paragraph numbers 0477 of JP2012-208494A, JP-A-2017-048367, JP-A-6057891 and Patent No. 6031807. , JP2017-194662, and the contents thereof are incorporated in the present specification.
- Compounds having an ethylenically unsaturated bond-containing group include dipentaerythritol triacrylate (commercially available KAYARAD D-330; manufactured by Nippon Kayaku Co., Ltd.) and dipentaerythritol tetraacrylate (commercially available KAYARAD D-).
- Compounds having a structure to which they are bound together are preferable.
- Compounds having an ethylenically unsaturated bond-containing group include diglycerin EO (ethylene oxide) modified (meth) acrylate (commercially available M-460; manufactured by Toa Synthetic), pentaerythritol tetraacrylate (Shin-Nakamura Chemical Industry Co., Ltd.).
- NK ester A-TMMT (manufactured by Nippon Kayaku Co., Ltd.), 1,6-hexanediol diacrylate (manufactured by Nippon Kayaku Co., Ltd., KAYARAD HDDA), RP-1040 (manufactured by Nippon Kayaku Co., Ltd.), Aronix TO-2349 (manufactured by Nippon Kayaku Co., Ltd.)
- NK Oligo UA-7200 Shin-Nakamura Chemical Co., Ltd.
- 8UH-1006 8UH-1012
- Light Acrylate POB-A0 (Kyoeisha Chemical Co., Ltd.)
- Etc. can also be used.
- trimethylolpropane tri (meth) acrylate trimethylolpropane propyleneoxy-modified tri (meth) acrylate, trimethylolpropane ethyleneoxy-modified tri (meth) acrylate, and ethylene isocyanurate.
- a trifunctional (meth) acrylate compound such as an oxy-modified tri (meth) acrylate or pentaerythritol tri (meth) acrylate.
- trifunctional (meth) acrylate compounds include Aronix M-309, M-310, M-321, M-350, M-360, M-313, M-315, M-306, and M-305. , M-303, M-452, M-450 (manufactured by Toa Synthetic Co., Ltd.), NK ester A9300, A-GLY-9E, A-GLY-20E, A-TMM-3, A-TMM-3L, A -TMM-3LM-N, A-TMPT, TMPT (manufactured by Shin Nakamura Chemical Industry Co., Ltd.), KAYARAD GPO-303, TMPTA, THE-330, TPA-330, PET-30 (manufactured by Nippon Kayaku Co., Ltd.) And so on.
- a compound having an acid group can also be used as the compound having an ethylenically unsaturated bond-containing group.
- the generation of development residue can be suppressed.
- the acid group include a carboxy group, a sulfo group, a phosphoric acid group and the like, and a carboxy group is preferable.
- Examples of commercially available products of the polymerizable monomer having an acid group include Aronix M-305, M-510, M-520, and Aronix TO-2349 (manufactured by Toagosei Co., Ltd.).
- the preferable acid value of the polymerizable monomer having an acid group is 0.1 to 40 mgKOH / g, and more preferably 5 to 30 mgKOH / g.
- the acid value of the polymerizable compound is 0.1 mgKOH / g or more, the solubility in a developing solution is good, and when it is 40 mgKOH / g or less, it is advantageous in production and handling.
- the compound having an ethylenically unsaturated bond-containing group is a compound having a caprolactone structure.
- Compounds having a caprolactone structure are commercially available from Nippon Kayaku Co., Ltd. as the KAYARAD DPCA series, and examples thereof include DPCA-20, DPCA-30, DPCA-60, and DPCA-120.
- a compound having an alkyleneoxy group can also be used as the compound having an ethylenically unsaturated bond-containing group.
- the compound having an alkyleneoxy group is preferably a compound having an ethyleneoxy group and / or a propyleneoxy group, more preferably a compound having an ethyleneoxy group, and a 3 to 6 functional (meth) acrylate having 4 to 20 ethyleneoxy groups.
- Compounds are more preferred.
- Commercially available products of compounds having an alkyleneoxy group include SR-494, which is a tetrafunctional (meth) acrylate having four ethyleneoxy groups manufactured by Sartmer, and a trifunctional (meth) acrylate having three isobutyleneoxy groups.
- a certain KAYARAD TPA-330 and the like can be mentioned.
- a compound having a fluorene skeleton can also be used as the compound having an ethylenically unsaturated bond-containing group.
- examples of commercially available compounds having a fluorene skeleton include Ogsol EA-0200 and EA-0300 (manufactured by Osaka Gas Chemical Co., Ltd., a (meth) acrylate monomer having a fluorene skeleton).
- the compound having an ethylenically unsaturated bond-containing group it is also preferable to use a compound that does not substantially contain an environmentally regulated substance such as toluene.
- an environmentally regulated substance such as toluene.
- commercially available products of such compounds include KAYARAD DPHA LT and KAYARAD DPEA-12 LT (manufactured by Nippon Kayaku Co., Ltd.).
- Examples of the compound having an ethylenically unsaturated bond-containing group are described in Japanese Patent Application Laid-Open No. 48-041708, Japanese Patent Application Laid-Open No. 51-0371993, Japanese Patent Application Laid-Open No. 02-032293, and Japanese Patent Application Laid-Open No. 02-016765.
- Such urethane acrylates and urethane compounds having an ethylene oxide-based skeleton described in Japanese Patent Publication No. 58-049860, Japanese Patent Publication No. 56-017654, Japanese Patent Publication No. 62-039417, and Japanese Patent Publication No. 62-039418. Is also suitable.
- a polymerizable compound having an amino structure or a sulfide structure in the molecule described in JP-A-63-277653, JP-A-63-260909, and JP-A-01-105238.
- the polymerizable compounds are UA-7200 (manufactured by Shin Nakamura Chemical Industry Co., Ltd.), DPHA-40H (manufactured by Nippon Kayaku Co., Ltd.), UA-306H, UA-306T, UA-306I, AH-600, Commercially available products such as T-600, AI-600, and LINK-202UA (manufactured by Kyoeisha Chemical Co., Ltd.) can also be used.
- Examples of the compound having a cyclic ether group, which is also used as a polymerizable monomer, include a compound having an epoxy group (hereinafter, also referred to as an epoxy compound) and a compound having an oxetane group (hereinafter, also referred to as an oxetane compound).
- the epoxy compound is preferably a polyfunctional epoxy compound. That is, the epoxy compound is preferably a compound having two or more epoxy groups. The upper limit of the number of epoxy groups is preferably 20 or less, and more preferably 10 or less.
- the oxetane compound is preferably a polyfunctional oxetane compound. That is, the oxetane compound is preferably a compound having two or more oxetane groups. The upper limit of the number of oxetane groups is preferably 20 or less, and more preferably 10 or less.
- epoxy compounds include JER828, JER1007, JER157S70 (manufactured by Mitsubishi Chemical Corporation), JER157S65 (manufactured by Mitsubishi Chemical Holdings, Inc.), and the like, which are described in paragraph 0189 of JP2011-221494. Can be mentioned.
- Other commercially available products include ADEKA RESIN EP-4000S, EP-4003S, EP-4010S, EP-4011S (above, manufactured by ADEKA Corporation), NC-2000, NC-3000, NC-7300, XD-1000, EPPN.
- OXT-201 Commercially available products of oxetane compounds include OXT-201, OXT-211, OXT-212, OXT-213, OXT-121, OXT-221, OX-SQ TX-100, etc. (all manufactured by Toagosei Co., Ltd.) Can be used.
- the content of the polymerizable monomer in the total solid content of the resin composition is preferably 0.1 to 40% by mass.
- the lower limit is preferably 0.5% by mass or more, and more preferably 1% by mass or more.
- the upper limit is preferably 30% by mass or less, more preferably 20% by mass or less.
- the content of the compound having an ethylenically unsaturated bond-containing group as the polymerizable monomer is 1 with respect to 100 parts by mass of the above-mentioned specific resin. It is preferably about 50 parts by mass.
- the lower limit is preferably 3 parts by mass or more, and more preferably 5 parts by mass or more.
- the upper limit is preferably 40 parts by mass or less, and more preferably 30 parts by mass or less.
- the content of the compound having a cyclic ether group as a polymerizable monomer may be 1 to 50 parts by mass with respect to 100 parts by mass of the above-mentioned specific resin.
- the lower limit is preferably 3 parts by mass or more, and more preferably 5 parts by mass or more.
- the upper limit is preferably 40 parts by mass or less, and more preferably 30 parts by mass or less.
- the resin composition contains a cyclic ether with respect to 100 parts by mass of the compound having an ethylenically unsaturated bond-containing group. It is preferable to contain 10 to 500 parts by mass of the compound having a group.
- the lower limit is preferably 20 parts by mass or more, and more preferably 30 parts by mass or more.
- the upper limit is preferably 400 parts by mass or less, and more preferably 300 parts by mass or less.
- the resin composition of the present invention preferably contains a photopolymerization initiator.
- the photopolymerization initiator is not particularly limited and may be appropriately selected from known photopolymerization initiators. For example, a compound having photosensitivity to light rays in the ultraviolet region to the visible region is preferable.
- the photopolymerization initiator is preferably a photoradical polymerization initiator.
- the photopolymerization initiator examples include halogenated hydrocarbon derivatives (for example, compounds having a triazine skeleton, compounds having an oxadiazole skeleton, compounds having an imidazole skeleton, etc.), acylphosphine compounds, hexaarylbiimidazole, oxime compounds, and organic compounds.
- halogenated hydrocarbon derivatives for example, compounds having a triazine skeleton, compounds having an oxadiazole skeleton, compounds having an imidazole skeleton, etc.
- acylphosphine compounds examples include peroxides, thio compounds, ketone compounds, aromatic onium salts, ⁇ -hydroxyketone compounds, and ⁇ -aminoketone compounds.
- the photopolymerization initiator is a trihalomethyltriazine compound, a biimidazole compound, a benzyl dimethyl ketal compound, an ⁇ -hydroxyketone compound, an ⁇ -aminoketone compound, an acylphosphine compound, a phosphine oxide compound, a metallocene compound, or an oxime compound.
- Triarylimidazole dimer onium compound, benzothiazole compound, benzophenone compound, acetophenone compound, cyclopentadiene-benzene-iron complex, halomethyloxaziazole compound and 3-aryl substituted coumarin compound, preferably biimidazole compound,
- a compound selected from an oxime compound, an ⁇ -hydroxyketone compound, an ⁇ -aminoketone compound, and an acylphosphine compound is more preferable, and an oxime compound is further preferable.
- the photopolymerization initiator include compounds described in paragraphs 0065 to 0111 of JP-A-2014-130173, compounds described in Japanese Patent No.
- biimidazole compound examples include 2,2-bis (2-chlorophenyl) -4,4', 5,5'-tetraphenylbiimidazole and 2,2'-bis (o-chlorophenyl) -4,4', 5 , 5-Tetrakis (3,4,5-trimethoxyphenyl) -1,2'-biimidazole, 2,2'-bis (2,3-dichlorophenyl) -4,4', 5,5'-tetraphenyl Examples thereof include biimidazole and 2,2'-bis (o-chlorophenyl) -4,4,5,5'-tetraphenyl-1,2'-biimidazole.
- ⁇ -hydroxyketone compounds include Omnirad 184, Omnirad 1173, Omnirad 2959, Omnirad 127 (all manufactured by IGM Resins BV), Irgacure 184, Irgacure 1173, Irgacare 1173, Irgacure29. (Manufactured by the company) and the like.
- Commercially available ⁇ -aminoketone compounds include Omnirad 907, Omnirad 369, Omnirad 369E, Omnirad 379EG (above, IGM Resins BV), Irgacare 907, Irgacare 369, Irgacure 369, Irgacure 369, Irgar (Made) and so on.
- acylphosphine compounds examples include Omnirad 819, Omnirad TPO (above, manufactured by IGM Resins BV), Irgacure 819, and Irgacure TPO (above, manufactured by BASF).
- Examples of the oxime compound include the compounds described in JP-A-2001-233842, the compounds described in JP-A-2000-080068, and the compounds described in JP-A-2006-342166.
- oxime compound examples include 3-benzoyloxyiminobutane-2-one, 3-acetoxyiminobutane-2-one, 3-propionyloxyiminobutane-2-one, 2-acetoxyiminopentane-3-one, 2-Acetoxyimino-1-phenylpropan-1-one, 2-benzoyloxyimino-1-phenylpropane-1-one, 3- (4-toluenesulfonyloxy) iminobutane-2-one, and 2-ethoxycarbonyloxy Examples thereof include imino-1-phenylpropane-1-one.
- An oxime compound having a fluorene ring can also be used as the photopolymerization initiator.
- Specific examples of the oxime compound having a fluorene ring include the compounds described in JP-A-2014-137466.
- an oxime compound having a skeleton in which at least one benzene ring of the carbazole ring is a naphthalene ring can also be used.
- Specific examples of such an oxime compound include the compounds described in International Publication No. 2013/083505.
- An oxime compound having a fluorine atom can also be used as the photopolymerization initiator.
- Specific examples of the oxime compound having a fluorine atom are described in the compounds described in JP-A-2010-262028, compounds 24, 36-40 described in JP-A-2014-500852, and JP-A-2013-164471. Compound (C-3) and the like.
- an oxime compound in which a substituent having a hydroxy group is bonded to the carbazole skeleton can also be used.
- Examples of such a photopolymerization initiator include the compounds described in International Publication No. 2019/088055.
- An oxime compound having a nitro group can be used as the photopolymerization initiator.
- the oxime compound having a nitro group is also preferably a dimer.
- Specific examples of the oxime compound having a nitro group include the compounds described in paragraphs 0031 to 0047 of JP2013-114249A and paragraphs 0008-0012 and 0070-0079 of JP2014-137466. Examples thereof include the compound described in paragraphs 0007 to 0025 of Japanese Patent No. 4223071, ADEKA ARKULS NCI-831 (manufactured by ADEKA Corporation).
- An oxime compound having a benzofuran skeleton can also be used as the photopolymerization initiator.
- Specific examples include OE-01 to OE-75 described in International Publication No. 2015/036910.
- an oxime compound in which a substituent having a hydroxy group is bonded to the carbazole skeleton can also be used.
- Examples of such a photopolymerization initiator include the compounds described in International Publication No. 2019/088055.
- the oxime compound is preferably a compound having a maximum absorption wavelength in the wavelength range of 350 to 500 nm, and more preferably a compound having a maximum absorption wavelength in the wavelength range of 360 to 480 nm.
- the molar extinction coefficient of the oxime compound at a wavelength of 365 nm or a wavelength of 405 nm is preferably high, more preferably 1000 to 300,000, further preferably 2000 to 300,000, and more preferably 5000 to 200,000. It is particularly preferable to have.
- the molar extinction coefficient of a compound can be measured using a known method. For example, it is preferable to measure at a concentration of 0.01 g / L using ethyl acetate with a spectrophotometer (Cary-5 spectrophotometer manufactured by Varian).
- a bifunctional or trifunctional or higher functional photoradical polymerization initiator may be used as the photopolymerization initiator.
- a photoradical polymerization initiator two or more radicals are generated from one molecule of the photoradical polymerization initiator, so that good sensitivity can be obtained.
- the crystallinity is lowered, the solubility in a solvent or the like is improved, the precipitation is less likely to occur with time, and the stability of the resin composition with time can be improved.
- Specific examples of the bifunctional or trifunctional or higher functional photo-radical polymerization initiators include JP-A-2010-527339, JP-A-2011-524436, International Publication No.
- the content of the photopolymerization initiator in the total solid content of the resin composition is preferably 0.1 to 30% by mass.
- the lower limit is preferably 0.5% by mass or more, and more preferably 1% by mass or more.
- the upper limit is preferably 20% by mass or less, more preferably 15% by mass or less. Only one type of photopolymerization initiator may be used, or two or more types may be used.
- the resin composition of the present invention can contain a silane coupling agent.
- the silane coupling agent means a silane compound having a hydrolyzable group and other functional groups.
- the hydrolyzable group refers to a substituent that is directly linked to a silicon atom and can form a siloxane bond by at least one of a hydrolysis reaction and a condensation reaction.
- Examples of the hydrolyzable group include a halogen atom, an alkoxy group, an acyloxy group and the like, and an alkoxy group is preferable. That is, the silane coupling agent is preferably a compound having an alkoxysilyl group.
- Examples of the functional group other than the hydrolyzable group include a vinyl group, a (meth) allyl group, a (meth) acryloyl group, a mercapto group, an epoxy group, an amino group, a ureido group, a sulfide group, an isocyanate group and a phenyl group. And the like, an amino group, a (meth) acryloyl group and an epoxy group are preferable.
- Specific examples of the silane coupling agent include the compounds described in paragraphs 0018 to 0036 of JP2009-288703A and the compounds described in paragraphs 0056 to 0066 of JP2009-242604A. The contents of are incorporated herein by reference.
- the content of the silane coupling agent in the total solid content of the resin composition is preferably 0.1 to 5% by mass.
- the upper limit is preferably 3% by mass or less, and more preferably 2% by mass or less.
- the lower limit is preferably 0.5% by mass or more, and more preferably 1% by mass or more.
- the silane coupling agent may be only one kind or two or more kinds.
- the resin composition of the present invention may further contain a curing accelerator for the purpose of accelerating the reaction of the resin or the polymerizable compound and lowering the curing temperature.
- the curing accelerator is a methylol-based compound (for example, a compound exemplified as a cross-linking agent in paragraph No. 0246 of JP-A-2015-034963), amines, a phosphonium salt, an amidin salt, and an amide compound (for example, JP-A-2015).
- cyanate compound for example, Japanese Patent Application Laid-Open No. 2012-150180.
- alkoxysilane compound for example, alkoxysilane compound having an epoxy group described in JP-A-2011-253504
- onium salt compound eg, JP-A-2015-034963
- a compound exemplified as an acid generator in 0216, a compound described in JP-A-2009-180949) and the like can also be used.
- the content of the curing accelerator is preferably 0.3 to 8.9% by mass, preferably 0.8 to 6.4% by mass, based on the total solid content of the resin composition. More preferably by mass.
- the resin composition of the present invention can contain a polymerization inhibitor.
- the polymerization inhibitor include hydroquinone, p-methoxyphenol, di-tert-butyl-p-cresol, pyrogallol, tert-butylcatechol, benzoquinone, 4,4'-thiobis (3-methyl-6-tert-butylphenol), and the like. Examples thereof include 2,2'-methylenebis (4-methyl-6-t-butylphenol) and N-nitrosophenylhydroxyamine salts (ammonium salt, primary cerium salt, etc.). Of these, p-methoxyphenol is preferable.
- the content of the polymerization inhibitor in the total solid content of the resin composition is preferably 0.0001 to 5% by mass.
- the resin composition of the present invention can contain a surfactant.
- a surfactant various surfactants such as a fluorine-based surfactant, a nonionic surfactant, a cationic surfactant, an anionic surfactant, and a silicone-based surfactant can be used.
- the surfactant the surfactant described in paragraph Nos. 0238 to 0245 of International Publication No. 2015/166779 is mentioned, and the content thereof is incorporated in the present specification.
- the surfactant is preferably a fluorine-based surfactant.
- a fluorine-based surfactant in the resin composition, the liquid characteristics (particularly, fluidity) can be further improved, and the liquid saving property can be further improved. It is also possible to form a film having a small thickness unevenness. It is also preferable that the surfactant is a silicone-based surfactant.
- the fluorine content in the fluorine-based surfactant is preferably 3 to 40% by mass, more preferably 5 to 30% by mass, and particularly preferably 7 to 25% by mass.
- a fluorine-based surfactant having a fluorine content within this range is effective in terms of uniformity of coating film thickness and liquid saving property, and has good solubility in a resin composition.
- fluorine-based surfactant examples include the surfactants described in paragraphs 0060 to 0064 of Japanese Patent Application Laid-Open No. 2014-041318 (paragraphs 0060 to 0064 of the corresponding international publication No. 2014/017669), and Japanese Patent Application Laid-Open No. 2011-.
- the surfactants described in paragraphs 0117 to 0132 of JP 132503 are mentioned and their contents are incorporated herein by reference.
- Commercially available products of fluorine-based surfactants include, for example, Megafuck F-171, F-172, F-173, F-176, F-177, F-141, F-142, F-143, F-144.
- the fluorine-based surfactant it is also preferable to use a polymer of a fluorine atom-containing vinyl ether compound having a fluorinated alkyl group or a fluorinated alkylene ether group and a hydrophilic vinyl ether compound.
- a fluorine-based surfactant the description in JP-A-2016-216602 can be referred to, and the content thereof is incorporated in the present specification.
- a block polymer can also be used as the fluorine-based surfactant.
- the fluorine-based surfactant has a repeating unit derived from a (meth) acrylate compound having a fluorine atom and 2 or more (preferably 5 or more) alkyleneoxy groups (preferably ethyleneoxy groups and propyleneoxy groups) (meth).
- a fluorine-containing polymer compound containing a repeating unit derived from an acrylate compound can also be preferably used.
- the following compounds are also exemplified as the fluorine-based surfactant used in the present invention.
- the weight average molecular weight of the above compounds is preferably 3000 to 50000, for example 14000.
- % indicating the ratio of the repeating unit is mol%.
- a fluorine-based surfactant a fluorine-containing polymer having an ethylenically unsaturated bond-containing group in the side chain can also be used.
- the compounds described in paragraphs 0050 to 0090 and paragraph numbers 0289 to 0295 of JP2010-164965 for example, Megafuck RS-101, RS-102, RS-718K manufactured by DIC Corporation. , RS-72-K and the like.
- the fluorine-based surfactant the compounds described in paragraphs 0015 to 0158 of JP2015-117327A can also be used.
- a fluorine-containing imide salt compound represented by the formula (fi-1) is also preferable to use as a surfactant.
- m represents 1 or 2
- n represents an integer of 1 to 4
- a represents 1 or 2
- X a + represents a-valent metal ion, primary ammonium ion, and first.
- secondary ammonium ion represents a tertiary ammonium ion, a quaternary ammonium ion or NH 4 +.
- Nonionic surfactants include glycerol, trimethylolpropane, trimethylolethane and their ethoxylates and propoxylates (eg, glycerol propoxylates, glycerol ethoxylates, etc.), polyoxyethylene lauryl ethers, polyoxyethylene stearyl ethers, etc.
- cationic surfactant examples include tetraalkylammonium salt, alkylamine salt, benzalkonium salt, alkylpyridium salt, imidazolium salt and the like. Specific examples include dihydroxyethylstearylamine, 2-heptadecenyl-hydroxyethylimidazoline, lauryldimethylbenzylammonium chloride, cetylpyridinium chloride, stearamide methylpyridinium chloride and the like.
- anionic surfactants include dodecylbenzene sulfonic acid, sodium dodecylbenzene sulfonate, sodium lauryl sulfate, sodium alkyldiphenyl ether disulfonate, sodium alkylnaphthalene sulfonate, sodium dialkyl sulfosuccinate, sodium stearate, potassium oleate, and sodium dioctyl.
- Sulfosuccinate sodium polyoxyethylene alkyl ether sulfate, sodium polyoxyethylene alkylate sulfate, sodium polyoxyethylene alkylphenyl ether sulfate, sodium dialkyl sulfosuccinate, sodium stearate, sodium oleate, t-octylphenoxyethoxypolyethoxyethyl Examples thereof include sodium sulfate.
- Silicone-based surfactants include DC3PA, SH7PA, DC11PA, SH21PA, SH28PA, SH29PA, SH30PA, SH8400, SH 8400 FLUID, FZ-2122, 67 Additive, 74 Additive, M Aditive, SF 84 (Manufactured by Co., Ltd.), TSF-4300, TSF-4445, TSF-4460, TSF-4452 (all manufactured by Momentive Performance Materials), KP-341, KF-6000, KF-6001, KF-6002, KF-6003 (above, manufactured by Shin-Etsu Chemical Co., Ltd.), BYK-307, BYK-322, BYK-323, BYK-330, BYK-333, BYK-3760, BYK-UV3510 (above, manufactured by Big Chemie), etc. Can be mentioned.
- a compound having the following structure can also be used as the silicone-based surfactant.
- the content of the surfactant in the total solid content of the resin composition is preferably 0.001% by mass to 5.0% by mass, more preferably 0.005 to 3.0% by mass.
- the surfactant may be only one kind or two or more kinds. In the case of two or more types, the total amount is preferably in the above range.
- the resin composition of the present invention can contain an ultraviolet absorber.
- an ultraviolet absorber a conjugated diene compound, an aminodiene compound, a salicylate compound, a benzophenone compound, a benzotriazole compound, an acrylonitrile compound, a hydroxyphenyltriazine compound, an indol compound, a triazine compound and the like can be used.
- paragraph numbers 0052 to 0072 of JP2012-208374A paragraph numbers 0317 to 0334 of JP2013-068814, and paragraph numbers 0061 to 0080 of JP2016-162946.
- UV absorbers examples include UV-503 (manufactured by Daito Kagaku Co., Ltd.), Tinuvin series manufactured by BASF, Uvinul series, and Sumisorb series manufactured by Sumika Chemtex Co., Ltd. ..
- benzotriazole compound examples include the MYUA series made by Miyoshi Oil & Fat Co., Ltd. (The Chemical Daily, February 1, 2016).
- the ultraviolet absorber is a compound described in paragraphs 0049 to 0059 of Japanese Patent No. 6268967, a compound described in paragraph numbers 0059 to 0076 of International Publication No. 2016/181987, and International Publication No. 2020/137819.
- the thioaryl group-substituted benzotriazole type ultraviolet absorber described in the above can also be used.
- the content of the ultraviolet absorber in the total solid content of the resin composition is preferably 0.01 to 10% by mass, more preferably 0.01 to 5% by mass. Only one kind of ultraviolet absorber may be used, or two or more kinds may be used. When two or more types are used, the total amount is preferably in the above range.
- the resin composition of the present invention can contain an antioxidant.
- the antioxidant include a phenol compound, a phosphite ester compound, a thioether compound and the like.
- the phenol compound any phenol compound known as a phenolic antioxidant can be used.
- Preferred phenolic compounds include hindered phenolic compounds.
- a compound having a substituent at a site (ortho position) adjacent to the phenolic hydroxy group is preferable.
- a substituted or unsubstituted alkyl group having 1 to 22 carbon atoms is preferable.
- the antioxidant a compound having a phenol group and a phosphite ester group in the same molecule is also preferable. Further, as the antioxidant, a phosphorus-based antioxidant can also be preferably used. Further, as the antioxidant, the compound described in Korean Patent Publication No. 10-2019-0059371 can also be used.
- the content of the antioxidant in the total solid content of the resin composition is preferably 0.01 to 20% by mass, more preferably 0.3 to 15% by mass. Only one type of antioxidant may be used, or two or more types may be used. When two or more types are used, the total amount is preferably in the above range.
- the resin composition of the present invention if necessary, sensitizers, fillers, thermosetting accelerators, plasticizers and other auxiliaries (eg, conductive particles, fillers, defoamers, flame retardants, leveling). Agents, peeling accelerators, fragrances, surface tension modifiers, chain transfer agents, etc.) may be included. By appropriately containing these components, properties such as film physical characteristics can be adjusted. These components are described in, for example, paragraph No. 0183 and subsequent paragraphs of JP2012-003225A (paragraph number 0237 of the corresponding US Patent Application Publication No. 2013/0034812), paragraphs of JP-A-2008-250074. The descriptions of Nos. 0101 to 0104, 0107 to 0109, etc.
- the resin composition may contain a latent antioxidant, if necessary.
- the latent antioxidant is a compound in which the site that functions as an antioxidant is protected by a protecting group, and is heated at 100 to 250 ° C. or at 80 to 200 ° C. in the presence of an acid / base catalyst.
- Examples of the latent antioxidant include compounds described in International Publication No. 2014/021023, International Publication No. 2017/030005, and JP-A-2017-008219.
- Examples of commercially available products include ADEKA ARKULS GPA-5001 (manufactured by ADEKA Corporation) and the like. Further, as described in Japanese Patent Application Laid-Open No. 2018-155881, C.I. I. Pigment Yellow 129 may be added for the purpose of improving weather resistance.
- the resin composition of the present invention may contain a metal oxide in order to adjust the refractive index of the obtained film.
- the metal oxide include TiO 2 , ZrO 2 , Al 2 O 3 , SiO 2 and the like.
- the primary particle size of the metal oxide is preferably 1 to 100 nm, more preferably 3 to 70 nm, and even more preferably 5 to 50 nm.
- the metal oxide may have a core-shell structure. Further, in this case, the core portion may be hollow.
- the resin composition of the present invention may contain a light resistance improving agent.
- the light resistance improving agent include the compounds described in paragraphs 0036 to 0037 of JP-A-2017-198787, the compounds described in paragraphs 0029 to 0034 of JP-A-2017-146350, and JP-A-2017-129774.
- the resin composition of the present invention preferably contains a free metal that is not bonded or coordinated with a pigment or the like to be 100 ppm or less, more preferably 50 ppm or less, and further preferably 10 ppm or less. , It is particularly preferable that it is not substantially contained.
- stabilization of pigment dispersibility agglomeration suppression
- improvement of spectral characteristics due to improvement of dispersibility agglomeration suppression
- stabilization of curable components suppression of conductivity fluctuation due to elution of metal atoms / metal ions
- Effects such as improvement of characteristics can be expected.
- the types of free metals include Na, K, Ca, Sc, Ti, Mn, Cu, Zn, Fe, Cr, Co, Mg, Al, Sn, Zr, Ga, Ge, Ag, Au, Pt, and the like.
- examples thereof include Cs, Ni, Cd, Pb and Bi.
- the resin composition of the present invention preferably has a content of free halogen that is not bonded or coordinated with a pigment or the like of 100 ppm or less, more preferably 50 ppm or less, and more preferably 10 ppm or less. It is more preferable, and it is particularly preferable that it is not substantially contained.
- the halogen include F, Cl, Br, I and their anions.
- Examples of the method for reducing free metals and halogens in the resin composition include methods such as washing with ion-exchanged water, filtration, ultrafiltration, and purification with an ion-exchange resin.
- the resin composition of the present invention does not substantially contain a terephthalic acid ester.
- substantially free means that the content of the terephthalic acid ester is 1000 mass ppb or less in the total amount of the resin composition, and more preferably 100 mass ppb or less. Zero is particularly preferred.
- Perfluoroalkyl sulfonic acid and perfluoroalkyl carboxylic acid may need to be reduced due to environmental reasons.
- the content of perfluoroalkyl sulfonic acid and perfluoroalkyl carboxylic acid is 0.01 to 0.01 in the solid content of the resin composition. It is preferably 1000 mass ppb, more preferably 0.05 to 500 mass ppb, and even more preferably 0.1 to 300 mass ppb. Further, it is also preferable to substitute the compounds having different carbon atoms in a mode in which these compounds are substantially not contained.
- the storage container for the resin composition of the present invention is not particularly limited, and a known storage container can be used.
- a storage container a multi-layer bottle in which the inner wall of the container is composed of 6 types and 6 layers of resin and a bottle in which 6 types of resin are composed of 7 layers are used for the purpose of suppressing impurities from being mixed into raw materials and resin compositions. It is also preferable to use. Examples of such a container include the container described in Japanese Patent Application Laid-Open No. 2015-123351.
- the inner wall of the container is preferably made of glass or stainless steel for the purpose of preventing metal elution from the inner wall of the container, improving the storage stability of the resin composition, and suppressing deterioration of the components.
- the resin composition of the present invention can be prepared by mixing the above-mentioned components.
- all the components may be simultaneously dissolved and / or dispersed in an organic solvent to prepare the resin composition, or if necessary, two or more solutions or dispersions of each component may be appropriately prepared. However, these may be mixed at the time of use (at the time of application) to prepare a resin composition.
- the mechanical force used for dispersing the pigment includes compression, squeezing, impact, shearing, cavitation and the like.
- Specific examples of these processes include bead mills, sand mills, roll mills, ball mills, paint shakers, microfluidizers, high speed impellers, sand grinders, flow jet mixers, high pressure wet atomization, ultrasonic dispersion and the like.
- the process and disperser for dispersing pigments are "Dispersion Technology Complete Works, published by Information Organization, Inc., July 15, 2005" and "Dispersion technology centered on suspension (solid / liquid dispersion system) and industrial. Practical application The process and disperser described in Paragraph No.
- JP-A-2015-157893 "Comprehensive Data Collection, Published by Management Development Center Publishing Department, October 10, 1978" can be preferably used.
- the particles may be miniaturized in the salt milling step.
- the materials, equipment, processing conditions, etc. used in the salt milling step for example, the descriptions in JP-A-2015-194521 and JP-A-2012-046629 can be referred to.
- any filter that has been conventionally used for filtration or the like can be used without particular limitation.
- fluororesins such as polytetrafluoroethylene (PTFE) and polyvinylidene fluoride (PVDF)
- polyamide resins such as nylon (eg, nylon-6, nylon-6,6)
- polyolefin resins such as polyethylene and polypropylene (PP)
- filters using materials such as (including high-density, ultra-high molecular weight polyolefin resin).
- polypropylene (including high-density polypropylene) and nylon are preferable.
- the pore size of the filter is preferably 0.01 to 7.0 ⁇ m, more preferably 0.01 to 3.0 ⁇ m, and even more preferably 0.05 to 0.5 ⁇ m. If the pore size of the filter is within the above range, fine foreign matter can be removed more reliably.
- the nominal value of the filter manufacturer can be referred to.
- various filters provided by Nippon Pole Co., Ltd. DFA4201NXEY, DFA4201NAEY, DFA4201J006P, etc.
- Advantech Toyo Co., Ltd. Japan Entegris Co., Ltd. (formerly Nippon Microlith Co., Ltd.), KITZ Microfilter Co., Ltd., etc.
- KITZ Microfilter Co., Ltd. etc.
- fibrous filter medium examples include polypropylene fiber, nylon fiber, glass fiber and the like.
- examples of commercially available products include SBP type series (SBP008, etc.), TPR type series (TPR002, TPR005, etc.) and SHPX type series (SHPX003, etc.) manufactured by Roki Techno Co., Ltd.
- filters for example, a first filter and a second filter
- the filtration with each filter may be performed only once or twice or more.
- filters having different pore diameters may be combined within the above-mentioned range.
- the filtration with the first filter may be performed only on the dispersion liquid, and after mixing the other components, the filtration may be performed with the second filter.
- the filter can be appropriately selected according to the hydrophobicity of the resin composition.
- the film of the present invention is a film obtained from the resin composition of the present invention described above.
- the film of the present invention can be used for optical filters such as color filters, near-infrared transmission filters, and near-infrared cut filters.
- the film of the present invention can also be used as a black matrix, a light-shielding film, or the like.
- the film thickness of the film of the present invention can be appropriately adjusted according to the purpose.
- the film thickness is preferably 20 ⁇ m or less, more preferably 10 ⁇ m or less, and even more preferably 5 ⁇ m or less.
- the lower limit of the film thickness is preferably 0.1 ⁇ m or more, more preferably 0.2 ⁇ m or more, and further preferably 0.3 ⁇ m or more.
- the film of the present invention When the film of the present invention is used as a color filter, the film of the present invention preferably has a hue of green, red, blue, cyan, magenta or yellow. Further, the film of the present invention can be preferably used as a colored pixel of a color filter. Examples of the colored pixel include a red pixel, a green pixel, a blue pixel, a magenta color pixel, a cyan color pixel, and a yellow pixel.
- the maximum absorption wavelength of the film of the present invention preferably exists in the wavelength range of 700 to 1800 nm, more preferably in the wavelength range of 700 to 1300 nm. It is more preferably present in the wavelength range of 700 to 1100 nm.
- the transmittance of the film in the entire wavelength range of 400 to 650 nm is preferably 70% or more, more preferably 80% or more, and further preferably 90% or more. Further, the transmittance at at least one point in the wavelength range of 700 to 1800 nm of the film is preferably 20% or less.
- the absorbance Amax / absorbance A550 which is the ratio of the absorbance Amax at the maximum absorption wavelength to the absorbance A550 at a wavelength of 550 nm, is preferably 20 to 500, more preferably 50 to 500, and 70 to 450. It is more preferably present, and particularly preferably 100 to 400.
- the film of the present invention preferably has, for example, any of the following spectral characteristics (i1) to (i5).
- (I1) The maximum value of the transmittance in the wavelength range of 400 to 640 nm is 20% or less (preferably 15% or less, more preferably 10% or less), and the minimum value of the transmittance in the wavelength range of 800 to 1500 nm is.
- a film having such spectral characteristics can block light in the wavelength range of 400 to 640 nm and transmit light having a wavelength of more than 750 nm.
- the maximum value of the transmittance in the wavelength range of 400 to 750 nm is 20% or less (preferably 15% or less, more preferably 10% or less), and the minimum value of the transmittance in the wavelength range of 900 to 1500 nm is.
- a film having such spectral characteristics can block light in the wavelength range of 400 to 750 nm and transmit light having a wavelength exceeding 850 nm.
- the maximum value of the transmittance in the wavelength range of 400 to 830 nm is 20% or less (preferably 15% or less, more preferably 10% or less), and the minimum value of the transmittance in the wavelength range of 1000 to 1500 nm is.
- a film having such spectral characteristics can block light in the wavelength range of 400 to 830 nm and transmit light having a wavelength exceeding 950 nm.
- the maximum value of the transmittance in the wavelength range of 400 to 950 nm is 20% or less (preferably 15% or less, more preferably 10% or less), and the minimum value of the transmittance in the wavelength range of 1100-1500 nm is.
- a film having such spectral characteristics can block light in the wavelength range of 400 to 950 nm and transmit light having a wavelength exceeding 1050 nm.
- the maximum value of the transmittance in the wavelength range of 400 to 1050 nm is 20% or less (preferably 15% or less, more preferably 10% or less), and the minimum value of the transmittance in the wavelength range of 1200 to 1500 nm is.
- a film having such spectral characteristics can block light in the wavelength range of 400 to 1050 nm and transmit light having a wavelength exceeding 1150 nm.
- the thickness of the film of the present invention after heat treatment at 300 ° C. for 5 hours in a nitrogen atmosphere is preferably 70% or more, preferably 80% or more of the thickness of the film before heat treatment. More preferably, it is more preferably 90% or more.
- the thickness of the film after being heat-treated at 350 ° C. for 5 hours in a nitrogen atmosphere is preferably 70% or more, preferably 80% or more of the thickness of the film before the heat treatment. Is more preferable, and 90% or more is further preferable.
- the thickness of the film after being heat-treated at 400 ° C. for 5 hours in a nitrogen atmosphere is preferably 70% or more, preferably 80% or more of the thickness of the film before the heat treatment. Is more preferable, and 90% or more is further preferable.
- the film of the present invention can be produced through the steps of applying the above-mentioned resin composition of the present invention onto a support.
- the film manufacturing method of the present invention preferably further includes a step of forming a pattern (pixel).
- Examples of the pattern (pixel) forming method include a photolithography method and a dry etching method, and the photolithography method is preferable.
- Pattern formation by the photolithography method includes a step of forming a resin composition layer on a support using the resin composition of the present invention, a step of exposing the resin composition layer in a pattern, and a step of exposing the resin composition layer in a pattern. It is preferable to include a step of developing and removing the exposed portion to form a pattern (pixel). If necessary, a step of baking the resin composition layer (pre-baking step) and a step of baking the developed pattern (pixels) (post-baking step) may be provided.
- the resin composition layer of the present invention is used to form the resin composition layer on the support.
- the support is not particularly limited and may be appropriately selected depending on the intended use.
- a glass substrate, a silicon substrate, and the like can be mentioned, and a silicon substrate is preferable.
- a charge-coupled device (CCD), a complementary metal oxide semiconductor (CMOS), a transparent conductive film, or the like may be formed on the silicon substrate.
- CMOS complementary metal oxide semiconductor
- a black matrix that isolates each pixel may be formed on the silicon substrate.
- the silicon substrate may be provided with a base layer for improving the adhesion with the upper layer, preventing the diffusion of substances, or flattening the surface of the substrate.
- the surface contact angle of the base layer is preferably 20 to 70 ° when measured with diiodomethane. Further, it is preferably 30 to 80 ° when measured with water. When the surface contact angle of the base layer is within the above range, the coating property of the resin composition is good.
- the surface contact angle of the base layer can be adjusted by, for example, adding a surfactant.
- a known method can be used as a method for applying the resin composition.
- a dropping method drop casting
- a slit coating method for example, a spray method; a roll coating method; a rotary coating method (spin coating); a casting coating method; a slit and spin method; a pre-wet method (for example, JP-A-2009-145395).
- Methods described in the publication Inkjet (for example, on-demand method, piezo method, thermal method), ejection system printing such as nozzle jet, flexographic printing, screen printing, gravure printing, reverse offset printing, metal mask printing, etc.
- Various printing methods; transfer method using a mold or the like; nano-imprint method and the like can be mentioned.
- the method of application to inkjet is not particularly limited, and is, for example, the method shown in "Expandable and usable inkjet-infinite possibilities seen in patents-, published in February 2005, Sumi Betechno Research" (especially from page 115). (Page 133), and the methods described in JP-A-2003-262716, JP-A-2003-185831, JP-A-2003-261827, JP-A-2012-126830, JP-A-2006-169325, and the like. Can be mentioned. Further, as a method for applying the resin composition, the methods described in International Publication No. 2017/030174 and International Publication No. 2017/018419 can also be used, and these contents are incorporated in the present specification.
- the resin composition layer formed on the support may be dried (prebaked).
- the prebaking temperature is preferably 150 ° C. or lower, more preferably 120 ° C. or lower, and even more preferably 110 ° C. or lower.
- the lower limit can be, for example, 50 ° C. or higher, or 80 ° C. or higher.
- the prebaking time is preferably 10 to 300 seconds, more preferably 40 to 250 seconds, and even more preferably 80 to 220 seconds. Pre-baking can be performed on a hot plate, an oven, or the like.
- the resin composition layer is exposed in a pattern (exposure step).
- the resin composition layer can be exposed in a pattern by exposing the resin composition layer through a mask having a predetermined mask pattern using a stepper exposure machine, a scanner exposure machine, or the like. As a result, the exposed portion can be cured.
- Examples of radiation (light) that can be used for exposure include g-line and i-line. Further, light having a wavelength of 300 nm or less (preferably light having a wavelength of 180 to 300 nm) can also be used. Examples of the light having a wavelength of 300 nm or less include KrF line (wavelength 248 nm) and ArF line (wavelength 193 nm), and KrF line (wavelength 248 nm) is preferable. Further, a long wave light source having a diameter of 300 nm or more can also be used.
- the pulse exposure is an exposure method of a method of repeatedly irradiating and pausing light in a cycle of a short time (for example, a millisecond level or less).
- the pulse width is preferably 100 nanoseconds (ns) or less, more preferably 50 nanoseconds or less, and even more preferably 30 nanoseconds or less.
- the lower limit of the pulse width is not particularly limited, but may be 1 femtosecond (fs) or more, and may be 10 femtoseconds or more.
- the frequency is preferably 1 kHz or higher, more preferably 2 kHz or higher, and even more preferably 4 kHz or higher.
- the upper limit of the frequency is preferably 50 kHz or less, more preferably 20 kHz or less, and further preferably 10 kHz or less.
- Maximum instantaneous intensity is preferably at 50000000W / m 2 or more, more preferably 100000000W / m 2 or more, more preferably 200000000W / m 2 or more.
- the upper limit of the maximum instantaneous intensity is preferably at 1000000000W / m 2 or less, more preferably 800000000W / m 2 or less, further preferably 500000000W / m 2 or less.
- the pulse width is the time during which light is irradiated in the pulse period.
- the frequency is the number of pulse cycles per second.
- the maximum instantaneous illuminance is the average illuminance within the time during which the light is irradiated in the pulse period.
- the pulse cycle is a cycle in which light irradiation and pause in pulse exposure are one cycle.
- Irradiation dose for example, preferably 0.03 ⁇ 2.5J / cm 2, more preferably 0.05 ⁇ 1.0J / cm 2.
- the oxygen concentration at the time of exposure can be appropriately selected, and in addition to the operation in the atmosphere, for example, in a low oxygen atmosphere having an oxygen concentration of 19% by volume or less (for example, 15% by volume, 5% by volume, or substantially). It may be exposed in an oxygen-free environment) or in a high oxygen atmosphere (for example, 22% by volume, 30% by volume, or 50% by volume) in which the oxygen concentration exceeds 21% by volume.
- the exposure illuminance can be set as appropriate, and is usually selected from the range of 1000 W / m 2 to 100,000 W / m 2 (for example, 5000 W / m 2 , 15,000 W / m 2 , or 35,000 W / m 2). Can be done. Oxygen concentration and exposure illuminance may appropriately combined conditions, for example, illuminance 10000 W / m 2 at an oxygen concentration of 10 vol%, oxygen concentration of 35 vol% can be such illuminance 20000W / m 2.
- the unexposed portion of the resin composition layer is developed and removed to form a pattern (pixel).
- the unexposed portion of the resin composition layer can be developed and removed using a developing solution.
- the resin composition layer of the unexposed portion in the exposure step is eluted in the developing solution, and only the photocured portion remains.
- the temperature of the developing solution is preferably, for example, 20 to 30 ° C.
- the development time is preferably 20 to 180 seconds. Further, in order to improve the residue removability, the steps of shaking off the developing solution every 60 seconds and further supplying a new developing solution may be repeated several times.
- Examples of the developing solution include organic solvents and alkaline developing solutions, and alkaline developing solutions are preferably used.
- the alkaline developer an alkaline aqueous solution (alkaline developer) obtained by diluting an alkaline agent with pure water is preferable.
- the alkaline agent include ammonia, ethylamine, diethylamine, dimethylethanolamine, diglycolamine, diethanolamine, hydroxyamine, ethylenediamine, tetramethylammonium hydroxide, tetraethylammonium hydroxide, tetrapropylammonium hydroxide, and tetrabutylammonium hydroxide.
- Ethyltrimethylammonium hydroxide Ethyltrimethylammonium hydroxide, benzyltrimethylammonium hydroxide, dimethylbis (2-hydroxyethyl) ammonium hydroxide, choline, pyrrole, piperidine, 1,8-diazabicyclo [5.4.0] -7-undecene and other organic substances.
- alkaline compounds examples include alkaline compounds and inorganic alkaline compounds such as sodium hydroxide, potassium hydroxide, sodium carbonate, sodium hydrogencarbonate, sodium silicate and sodium metasilicate.
- the alkaline agent a compound having a large molecular weight is preferable in terms of environment and safety.
- the concentration of the alkaline agent in the alkaline aqueous solution is preferably 0.001 to 10% by mass, more preferably 0.01 to 1% by mass.
- the developer may further contain a surfactant.
- the surfactant include the above-mentioned surfactants, and nonionic surfactants are preferable.
- the developer may be once produced as a concentrated solution and diluted to a concentration required for use from the viewpoint of convenience of transfer and storage.
- the dilution ratio is not particularly limited, but can be set in the range of, for example, 1.5 to 100 times. It is also preferable to wash (rinse) with pure water after development.
- the rinsing is performed by supplying the rinsing liquid to the developed resin composition layer while rotating the support on which the developed resin composition layer is formed. It is also preferable to move the nozzle for discharging the rinse liquid from the central portion of the support to the peripheral edge of the support. At this time, when moving the nozzle from the central portion of the support to the peripheral portion, the nozzle may be moved while gradually reducing the moving speed. By rinsing in this way, in-plane variation of rinsing can be suppressed. Further, the same effect can be obtained by gradually reducing the rotation speed of the support while moving the nozzle from the central portion to the peripheral portion of the support.
- Additional exposure treatment and post-baking are post-development curing treatments to complete the curing.
- the heating temperature in the post-baking is, for example, preferably 100 to 240 ° C, more preferably 200 to 240 ° C. Further, the heating temperature in the post-baking can be 240 to 400 ° C, 250 to 350 ° C, or 300 to 350 ° C.
- the heating time in the post-baking is, for example, preferably 5 minutes to 5 hours, more preferably 1 to 4 hours, and even more preferably 2 to 4 hours.
- Post-baking can be performed on the developed film in a continuous or batch manner using a heating means such as a hot plate, a convection oven (hot air circulation dryer), or a high-frequency heater so as to meet the above conditions. ..
- a heating means such as a hot plate, a convection oven (hot air circulation dryer), or a high-frequency heater so as to meet the above conditions. ..
- the light used for the exposure is preferably light having a wavelength of 400 nm or less. Further, the additional exposure process may be performed by the method described in Korean Patent Publication No. 10-2017-0122130.
- Pattern formation by the dry etching method includes a step of forming a resin composition layer on a support using the resin composition of the present invention and curing the entire resin composition layer to form a cured product layer.
- the optical filter of the present invention has the above-mentioned film of the present invention.
- the type of optical filter include a color filter, a near-infrared ray transmitting filter, a near-infrared ray cut filter, and the like, and a color filter is preferable.
- the color filter it is preferable to have the film of the present invention as the colored pixels of the color filter.
- the optical filter of the present invention can be used for a solid-state image sensor such as a CCD (charge-coupled device) or CMOS (complementary metal oxide semiconductor), an image display device, or the like.
- the film thickness of the film of the present invention can be appropriately adjusted according to the purpose.
- the film thickness is preferably 5 ⁇ m or less, more preferably 1 ⁇ m or less, and even more preferably 0.6 ⁇ m or less.
- the lower limit of the film thickness is preferably 0.1 ⁇ m or more, more preferably 0.2 ⁇ m or more, and further preferably 0.3 ⁇ m or more.
- the width of the pixels included in the optical filter is preferably 0.4 to 10.0 ⁇ m.
- the lower limit is preferably 0.4 ⁇ m or more, more preferably 0.5 ⁇ m or more, and further preferably 0.6 ⁇ m or more.
- the upper limit is preferably 5.0 ⁇ m or less, more preferably 2.0 ⁇ m or less, further preferably 1.0 ⁇ m or less, and even more preferably 0.8 ⁇ m or less.
- the Young's modulus of the pixel is preferably 0.5 to 20 GPa, more preferably 2.5 to 15 GPa.
- each pixel included in the optical filter has high flatness.
- the surface roughness Ra of the pixel is preferably 100 nm or less, more preferably 40 nm or less, and further preferably 15 nm or less.
- the lower limit is not specified, but it is preferably 0.1 nm or more, for example.
- the surface roughness of the pixels can be measured using, for example, an AFM (atomic force microscope) Measurement 3100 manufactured by Veeco.
- the contact angle of water on the pixel can be appropriately set to a preferable value, but is typically in the range of 50 to 110 °.
- the contact angle can be measured using, for example, a contact angle meter CV-DT ⁇ A type (manufactured by Kyowa Interface Science Co., Ltd.). Further, it is preferable that the volume resistance value of the pixel is high. Specifically, it is preferred that the volume resistivity value of the pixel is 10 9 ⁇ ⁇ cm or more, and more preferably 10 11 ⁇ ⁇ cm or more. The upper limit is not specified, but it is preferably 10 14 ⁇ ⁇ cm or less, for example.
- the volume resistance value of the pixel can be measured using an ultra-high resistance meter 5410 (manufactured by Advantest).
- a protective layer may be provided on the surface of the film of the present invention.
- various functions such as oxygen blocking, low reflection, hydrophobicization, and shielding of light of a specific wavelength (ultraviolet rays, near infrared rays, etc.) can be imparted.
- the thickness of the protective layer is preferably 0.01 to 10 ⁇ m, more preferably 0.1 to 5 ⁇ m.
- the method for forming the protective layer include a method of applying a resin composition for forming a protective layer dissolved in an organic solvent to form the protective layer, a chemical vapor deposition method, a method of attaching the molded resin with an adhesive, and the like.
- the components constituting the protective layer include (meth) acrylic resin, en-thiol resin, polycarbonate resin, polyether resin, polyarylate resin, polysulfone resin, polyethersulfone resin, polyphenylene resin, polyarylene ether phosphine oxide resin, and polyimide.
- Resin polyamideimide resin, polyolefin resin, cyclic olefin resin, polyester resin, styrene resin, polyol resin, polyvinylidene chloride resin, melamine resin, urethane resin, aramid resin, polyamide resin, alkyd resin, epoxy resin, modified silicone resin, fluorine Examples thereof include resins, polycarbonate resins, polyacrylonitrile resins, cellulose resins, Si, C, W, Al 2 O 3 , Mo, SiO 2 , and Si 2 N 4, and two or more of these components may be contained.
- the protective layer preferably contains a polyol resin, SiO 2 , and Si 2 N 4 .
- the protective layer preferably contains a (meth) acrylic resin and a fluororesin.
- the protective layer forming resin composition When the protective layer forming resin composition is applied to form the protective layer, known methods such as a spin coating method, a casting method, a screen printing method, and an inkjet method are used as the coating method of the protective layer forming resin composition. Can be used.
- a known organic solvent for example, propylene glycol 1-monomethyl ether 2-acetate, cyclopentanone, ethyl lactate, etc.
- the protective layer is formed by a chemical vapor deposition method
- the chemical vapor deposition method is a known chemical vapor deposition method (thermochemical vapor deposition method, plasma chemical vapor deposition method, photochemical vapor deposition method). Can be used.
- the protective layer may be an additive such as organic / inorganic fine particles, an absorber for light of a specific wavelength (for example, ultraviolet rays, near infrared rays, etc.), a refractive index adjuster, an antioxidant, an adhesive, a surfactant, etc., if necessary. May be contained.
- organic / inorganic fine particles include polymer fine particles (for example, silicone resin fine particles, polystyrene fine particles, melamine resin fine particles), titanium oxide, zinc oxide, zirconium oxide, indium oxide, aluminum oxide, titanium nitride, and titanium oxynitride. , Magnesium fluoride, hollow silica, silica, calcium carbonate, barium sulfate and the like.
- a known absorbent can be used as the light absorber of a specific wavelength.
- the content of these additives can be adjusted as appropriate, but is preferably 0.1 to 70% by mass, more preferably 1 to 60% by mass, based on the total mass of the protective layer.
- the protective layer the protective layer described in paragraphs 0073 to 0092 of JP-A-2017-151176 can also be used.
- the optical filter may have a structure in which each pixel is embedded in a space partitioned by a partition wall, for example, in a grid pattern.
- the resin composition of the present invention can also be suitably used for the pixel configuration described in International Publication No. 2019/1028887.
- the solid-state image sensor of the present invention has the above-mentioned film of the present invention.
- the configuration of the solid-state image sensor of the present invention is not particularly limited as long as it includes the film of the present invention and functions as a solid-state image sensor, and examples thereof include the following configurations.
- a solid-state image sensor CCD (charge coupling element) image sensor, CMOS (complementary metal oxide semiconductor) image sensor, etc.
- a transfer electrode made of polysilicon or the like.
- the configuration has a color filter on the device protective film.
- the color filter may have a structure in which each colored pixel is embedded in a space partitioned by a partition wall, for example, in a grid pattern.
- the partition wall preferably has a lower refractive index than each colored pixel. Examples of an imaging apparatus having such a structure are described in JP2012-227478A, Japanese Patent Application Laid-Open No. 2014-179757, International Publication No. 2018/043654, and US Patent Application Publication No.
- an ultraviolet absorbing layer may be provided in the structure of the solid-state image sensor to improve the light resistance.
- the image pickup device provided with the solid-state image pickup device of the present invention can be used not only for digital cameras and electronic devices having an image pickup function (mobile phones and the like), but also for in-vehicle cameras and surveillance cameras.
- the solid-state image sensor incorporating the color filter of the present invention may incorporate another color filter, a near-infrared cut filter, an organic photoelectric conversion film, or the like in addition to the color filter of the present invention.
- the image display device of the present invention has the above-mentioned film of the present invention.
- the image display device include a liquid crystal display device and an organic electroluminescence display device.
- the liquid crystal display device is described in, for example, “Next Generation Liquid Crystal Display Technology (edited by Tatsuo Uchida, Kogyo Chosakai Co., Ltd., published in 1994)”.
- the liquid crystal display device to which the present invention can be applied is not particularly limited, and for example, it can be applied to various types of liquid crystal display devices described in the above-mentioned "next-generation liquid crystal display technology".
- the acid value of the sample represents the mass of potassium hydroxide required to neutralize the acidic component per 1 g of solid content in the sample.
- the acid value was calculated by the following formula with the inflection point of the titration pH curve as the titration end point.
- A 56.11 ⁇ Vs ⁇ 0.5 ⁇ f / w
- f Titer of 0.1 mol / L potassium hydroxide aqueous solution
- the weight average molecular weight (Mw) of the resin A-1 was 30600 and the acid value was 70 mgKOH / g.
- the numerical value added to the main chain of the repeating unit represents the mol% of the repeating unit, and the description of "Polym” is a structure in which the repeating unit of the structure indicated by “Polym” is combined by the number of subscripts. It is shown that the polymer chain of the above is bonded to the sulfur atom (S).
- the table below shows the weight average molecular weight (Mw) of the macromonomers used in the synthesis of the resins A-1 to A-48, the weight average molecular weight (Mw) of the resins A-1 to A-48, the acid value, and the oxetane ratio, respectively. ..
- the oxetane ratio is the mole fraction of the repeating unit having an oxetane group contained in all the repeating units of the resin.
- a mixed solution containing the raw materials listed in the table below is mixed and dispersed for 3 hours using a bead mill (using zirconia beads having a diameter of 0.3 mm), and then a high-pressure disperser with a decompression mechanism NANO-3000-10 (Nippon BEE).
- a dispersion treatment was carried out at a flow rate of 500 g / min under a pressure of 2000 MPa using (manufactured by Co., Ltd.). This dispersion treatment was repeated 10 times to obtain each dispersion.
- Pigment Red 179 (red pigment, perylene pigment) PO71: C.I. I. Pigment Orange 71 (orange pigment, diketopyrrolopyrrole pigment)
- PB15 6: C.I. I. Pigment Blue 15: 6 (blue pigment, phthalocyanine pigment)
- PB16 C.I. I. Pigment Blue 16 (blue pigment, phthalocyanine pigment)
- PG7 C.I. I. Pigment Green 7 (green pigment, phthalocyanine pigment)
- PG36 C.I. I. Pigment Green 36 (green pigment, phthalocyanine pigment)
- PG58 C.I. I. Pigment Green 58 (green pigment, phthalocyanine pigment)
- PY185 C.I. I.
- Pigment Yellow 185 (yellow pigment, isoindoline pigment)
- PY215 C.I. I. Pigment Yellow 215 (yellow pigment, pteridine pigment)
- PV23 C.I. I. Pigment Violet 23 (purple pigment, dioxazine pigment)
- IR dye A compound having the following structure (near-infrared absorbing pigment, in the structural formula, Me represents a methyl group and Ph represents a phenyl group).
- IRGAPHORE Irgaphor Black S 0100 CF (manufactured by BASF, compound with the following structure, lactam pigment)
- PBk32 C.I. I. Pigment Black 32 (compound with the following structure, perylene pigment)
- CA-1 Resin having the following structure (weight average molecular weight is 10885, acid value is 74 mgKOH / g. In the description of "Polym”, the repeating units of the structure indicated by “Polym” are combined by the number of subscripts. It shows that the polymer chain of the structure is bonded to the sulfur atom (S).)
- Dispersions R1 to R15, B1 to B13, G1 to G13, I1 to I6, Bk1 to Bk20, CR1, CB1, CG1, CI1, CBk1 to 3 Dispersions described above
- Aa-1 Resin having the following structure (numerical value added to the main chain) Is a molar ratio.
- Aa-2 Resin having the following structure (the numerical value added to the main chain is the molar ratio.
- Ab-1 Resin having the following structure (the numerical value added to the main chain is the molar ratio.
- Ab-2 Resin having the following structure (weight average molecular weight 10000)
- D-1 Acrylate compound (KAYARAD DPHA, manufactured by Nippon Kayaku Co., Ltd.)
- D-2 Epoxy compound (TETRAD-X, manufactured by Mitsubishi Gas Chemical Company, Inc.)
- D-3 Oxetane compound (OXT-221, manufactured by Toagosei Co., Ltd.)
- D-4 Oxetane compound (OX-SQ TX-100, manufactured by Toagosei Co., Ltd.)
- E-1 Omnirad 379EG (manufactured by IGM Resins BV)
- E-2 Irgacure OXE01 (manufactured by BASF)
- E-3 Irgacure OXE03 (manufactured by BASF)
- ⁇ Vis was 0.5 mPa ⁇ s or less.
- B ⁇ Vis exceeded 0.5 mPa ⁇ s and was 1.0 mPa ⁇ s or less.
- C ⁇ Vis exceeded 1.0 mPa ⁇ s and was 2.0 mPa ⁇ s or less.
- D ⁇ Vis exceeded 2.0 mPa ⁇ s and was 2.5 mPa ⁇ s or less.
- the resin composition was spin-coated on a glass substrate, dried (prebaked) at 100 ° C. for 120 seconds using a hot plate, and then heated at 200 ° C. for 30 minutes using an oven. (Post-baked) to produce a film having a thickness of 0.60 ⁇ m.
- a Cary 5000 UV-Vis-NIR spectrophotometer manufactured by Agilent Technologies
- the light transmittance Tr1 of the obtained film having a wavelength of 450 nm was measured.
- the obtained membrane was heat-treated at 300 ° C. for 5 hours under a nitrogen atmosphere.
- Tr2 of light having a wavelength of 450 nm of the film after the heat treatment was measured.
- the absolute value ⁇ T of the difference between Tr1 and Tr2 was calculated, and the spectral change was evaluated according to the following evaluation criteria. It can be said that the smaller ⁇ T is, the less the spectral change is likely to occur, which is preferable.
- Both Tr1 and Tr2 were measured in a laboratory where the temperature and humidity were controlled to 22 ⁇ 5 ° C. and 60 ⁇ 20%, with the substrate temperature adjusted to 25 ° C.
- ⁇ T was 0.1% or less.
- B ⁇ T was more than 0.1% and 0.5% or less.
- C ⁇ T was more than 0.5% and 1% or less.
- D ⁇ T was more than 1% and 5% or less.
- E ⁇ T exceeded 5%.
- the resin composition was spin-coated on a glass substrate, dried (prebaked) at 100 ° C. for 120 seconds using a hot plate, and then heated at 200 ° C. for 30 minutes using an oven. (Post-baked) to produce a film having a thickness of 0.60 ⁇ m.
- the film thickness is measured by scraping a part of the film to expose the surface of the glass substrate and measuring the step between the glass substrate surface and the coating film (the film thickness of the coating film) using a stylus type profilometer (DectakXT, manufactured by BRUKER). bottom.
- the obtained membrane was heat-treated at 300 ° C. for 5 hours under a nitrogen atmosphere.
- the film shrinkage rate was obtained from the following formula, and the film shrinkage rate was evaluated according to the following evaluation criteria.
- T0 and T1 below were measured in a laboratory where the temperature and humidity were controlled to 22 ⁇ 5 ° C. and 60 ⁇ 20%, with the substrate temperature adjusted to 25 ° C. It can be said that the smaller the film shrinkage rate, the more the film shrinkage is suppressed, which is a preferable result.
- Membrane shrinkage rate (%) (1- (T1 / T0)) x 100
- T1 Film thickness after heat treatment at 300 ° C for 5 hours in a nitrogen atmosphere-evaluation criteria-
- A The membrane contraction rate was 1% or less.
- B The membrane contraction rate was more than 1% and 5% or less.
- C The membrane contraction rate was more than 5% and 10% or less.
- D The membrane contraction rate was more than 10% and 30% or less.
- E The membrane contraction rate exceeded 30%.
- the resin composition was spin-coated on a glass substrate, dried (prebaked) at 100 ° C. for 120 seconds using a hot plate, and then heated at 200 ° C. for 30 minutes using an oven. (Post-baked) to produce a film having a thickness of 0.60 ⁇ m.
- SiO 2 was laminated at 200 nm on the surface of the obtained film by a sputtering method to form an inorganic film.
- the film on which the inorganic film was formed was heat-treated at 300 ° C. for 5 hours in a nitrogen atmosphere.
- the surface of the inorganic film after the heat treatment was observed with an optical microscope, the number of cracks per 1 cm 2 was counted, and the presence or absence of cracks was evaluated according to the following evaluation criteria.
- E The number of cracks per 1 cm 2 was 101 or more.
- the resin compositions of Examples 1 to 37 and 68 to 71 can be preferably used as the resin composition for forming colored pixels of a color filter.
- the resin compositions of Examples 38 to 43 can be preferably used as the resin composition for forming a near-infrared cut filter.
- the resin compositions of Examples 44 to 67 can be preferably used as the resin composition for forming a near-infrared ray transmitting filter.
- Example 67 even when any of the dispersions I1 to I6 is further added as the dispersion, the same effect as in Example 67 can be obtained.
- Example 100 Pattern formation by photolithography method
- the resin composition of Example 1 is applied on a silicon wafer by spin coating, dried (prebaked) at 100 ° C. for 120 seconds using a hot plate, and then heated (post-baked) at 200 ° C. for 30 minutes using an oven.
- a resin composition layer having a thickness of 0.60 ⁇ m was formed.
- an i-line stepper exposure apparatus FPA-3000i5 + (Canon, Inc.) is provided via a mask pattern in which square non-masked portions having a side of 1.1 ⁇ m are arranged in a region of 4 mm ⁇ 3 mm.
- the produced patterned silicon wafer was divided into two, and one was heat-treated at 300 ° C. for 5 hours in a nitrogen atmosphere (hereinafter, one is a substrate before heat treatment at 300 ° C. and the other is a substrate after heat treatment at 300 ° C.).
- one is a substrate before heat treatment at 300 ° C. and the other is a substrate after heat treatment at 300 ° C.
- the cross section of the resist pattern formed on the substrate before the heat treatment at 300 ° C. and the substrate after the heat treatment at 300 ° C. was evaluated by a scanning electron microscope (SEM), the resist pattern formed on the substrate after the heat treatment at 300 ° C. was evaluated.
- the height of the resist pattern was 75% of the height of the resist pattern formed on the substrate before heat treatment at 300 ° C.
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Abstract
Description
<1> 色材と、樹脂と、溶剤とを含み、
上記樹脂は、エチレン性不飽和結合含有基を有する化合物由来の構造の分子鎖を含む主鎖と、グラフト鎖と、を有するグラフトポリマーを含み、
上記グラフト鎖は、オキセタン基を有する繰り返し単位p1を含む、
樹脂組成物。
<2> 上記繰り返し単位p1は、式(p1-1)で表される繰り返し単位である、<1>に記載の樹脂組成物;
Lp1は、2価の連結基を表す;
Rp4~Rp8は、それぞれ独立して水素原子またはアルキル基を表す。
<3> 上記グラフト鎖は、カルボキシ基が熱分解性基で保護された基を有する繰り返し単位を含む、<1>または<2>に記載の樹脂組成物。
<4> 上記グラフト鎖は、t-ブチルエステル基を有する繰り返し単位を含む、<1>または<2>に記載の樹脂組成物。
<5> 上記グラフト鎖は、式(p2-10)で表される繰り返し単位を含む、<1>または<2>に記載の樹脂組成物;
Rp14~Rp16は、アルキル基またはアリール基を表し、Rp14とRp15は結合して環を形成してもよい。
<6> 上記グラフトポリマーの主鎖は式(1)で示される繰り返し単位を含む、<1>~<5>のいずれか1つに記載の樹脂組成物;
L1およびL2は、それぞれ独立して2価の連結基を表す;
X1は単結合、-O-、-COO-、-OCO-、-NHCOO-、-OCONH-または-NHCONH-を表す;
P1は上記繰り返し単位p1を含むグラフト鎖を表す。
<7> 上記グラフトポリマーの主鎖は、架橋性基を有する繰り返し単位を含む、<1>~<6>のいずれか1つに記載の樹脂組成物。
<8> 上記グラフトポリマーの主鎖は、酸基を有する繰り返し単位を含む、<1>~<7>のいずれか1つに記載の樹脂組成物。
<9> 上記色材は、近赤外線吸収色材を含む、<1>~<8>のいずれか1つに記載の樹脂組成物。
<10> 上記色材は、黒色色材を含む、<1>~<8>のいずれか1つに記載の樹脂組成物。
<11> 上記色材は、カラーインデックスピグメントレッド179、カラーインデックスピグメントレッド264、カラーインデックスピグメントレッド291、カラーインデックスピグメントブルー16、およびカラーインデックスピグメントイエロー215から選ばれる少なくとも1種を含む、<1>~<10>のいずれか1つに記載の樹脂組成物。
<12> 上記樹脂組成物の波長400~640nmの範囲における吸光度の最小値Aminと、上記樹脂組成物の波長1500nmにおける吸光度Bとの比であるAmin/Bが5以上である、<1>~<11>のいずれか1つに記載の樹脂組成物。
<13> 更に重合性モノマーを含む、<1>~<12>のいずれか1つに記載の樹脂組成物。
<14> 更に光重合開始剤を含む、<1>~<13>のいずれか1つに記載の樹脂組成物。
<15> 固体撮像素子用である、<1>~<14>のいずれか1つに記載の樹脂組成物。
<16> <1>~<15>のいずれか1つに記載の樹脂組成物から得られる膜。
<17> <16>に記載の膜を含む光学フィルタ。
<18> <16>に記載の膜を含む固体撮像素子。
<19> <16>に記載の膜を含む画像表示装置。
本明細書において、「~」とはその前後に記載される数値を下限値及び上限値として含む意味で使用される。
本明細書における基(原子団)の表記において、置換及び無置換を記していない表記は、置換基を有さない基(原子団)と共に置換基を有する基(原子団)をも包含する。例えば、「アルキル基」とは、置換基を有さないアルキル基(無置換アルキル基)のみならず、置換基を有するアルキル基(置換アルキル基)をも包含する。
本明細書において「露光」とは、特に断らない限り、光を用いた露光のみならず、電子線、イオンビーム等の粒子線を用いた描画も露光に含める。また、露光に用いられる光としては、水銀灯の輝線スペクトル、エキシマレーザに代表される遠紫外線、極紫外線(EUV光)、X線、電子線等の活性光線又は放射線が挙げられる。
本明細書において、(メタ)アリル基は、アリル及びメタリルの双方、又は、いずれかを表し、「(メタ)アクリレート」は、アクリレート及びメタクリレートの双方、又は、いずれかを表し、「(メタ)アクリル」は、アクリル及びメタクリルの双方、又は、いずれかを表し、「(メタ)アクリロイル」は、アクリロイル及びメタクリロイルの双方、又は、いずれかを表す。
本明細書において、重量平均分子量及び数平均分子量は、GPC(ゲルパーミエーションクロマトグラフィ)法により測定したポリスチレン換算値である。
本明細書において、近赤外線とは、波長700~2500nmの光をいう。
本明細書において、全固形分とは、組成物の全成分から溶剤を除いた成分の総質量をいう。
本明細書において「工程」との語は独立した工程だけを指すのではなく、他の工程と明確に区別できない場合であってもその工程の所期の作用が達成されれば、本用語に含まれる。
本明細書において、好ましい態様の組み合わせは、より好ましい態様である。
本発明の樹脂組成物は、色材と、樹脂と、溶剤とを含み、
上記樹脂は、エチレン性不飽和結合含有基を有する化合物由来の構造の分子鎖を含む主鎖と、グラフト鎖と、を有するグラフトポリマーを含み、
上記グラフト鎖は、オキセタン基を有する繰り返し単位p1を含むことを特徴とする。
また、上記膜を窒素雰囲気下にて350℃で5時間加熱処理した後の膜の厚さは、加熱処理前の膜の厚さの70%以上であることが好ましく、80%以上であることがより好ましく、90%以上であることが更に好ましい。
また、上記膜を窒素雰囲気下にて400℃で5時間加熱処理した後の膜の厚さは、加熱処理前の膜の厚さの70%以上であることが好ましく、80%以上であることがより好ましく、90%以上であることが更に好ましい。
上記物性は、用いる特定樹脂の種類や含有量を調整する等の方法により達成することができる。
ΔA(%)=|100-(A2/A1)×100| ・・・(A1)
ΔAは、加熱処理後の膜の吸光度の変化率であり、
A1は、加熱処理前の膜の波長400~1100nmの範囲における吸光度の最大値であり、
A2は、加熱処理後の膜の吸光度であって、加熱処理前の膜の波長400~1100nmの範囲における吸光度の最大値を示す波長での吸光度である。
上記物性は、用いる特定樹脂の種類や含有量を調整する等の方法により達成することができる。
上記物性は、用いる特定樹脂の種類や含有量を調整する等の方法により達成することができる。
ΔAλ=|100-(A2λ/A1λ)×100| ・・・(2)
ΔAλは、加熱処理後の膜の波長λにおける吸光度の変化率であり、
A1λは、加熱処理前の膜の波長λにおける吸光度であり、
A2λは、加熱処理後の膜の波長λにおける吸光度である。
上記物性は、用いる特定樹脂の種類や含有量を調整する等の方法により達成することができる。
(1):波長400~640nmの範囲における透過率の最大値が20%以下(好ましくは15%以下、より好ましくは10%以下)であり、波長800~1500nmの範囲における透過率の最小値が70%以上(好ましくは75%以上、より好ましくは80%以上)であるフィルタ。
(2):波長400~750nmの範囲における透過率の最大値が20%以下(好ましくは15%以下、より好ましくは10%以下)であり、波長900~1500nmの範囲における透過率の最小値が70%以上(好ましくは75%以上、より好ましくは80%以上)であるフィルタ。
(3):波長400~830nmの範囲における透過率の最大値が20%以下(好ましくは15%以下、より好ましくは10%以下)であり、波長1000~1500nmの範囲における透過率の最小値が70%以上(好ましくは75%以上、より好ましくは80%以上)であるフィルタ。
(4):波長400~950nmの範囲における透過率の最大値が20%以下(好ましくは15%以下、より好ましくは10%以下)であり、波長1100~1500nmの範囲における透過率の最小値が70%以上(好ましくは75%以上、より好ましくは80%以上)であるフィルタ。
(5):波長400~1050nmの範囲における透過率の最大値が20%以下(好ましくは15%以下、より好ましくは10%以下)であり、波長1200~1500nmの範囲における透過率の最小値が70%以上(好ましくは75%以上、より好ましくは80%以上)であるフィルタ。
Aλ=-log(Tλ/100) ・・・(λ1)
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。
本発明において、吸光度の値は、溶液の状態で測定した値であってもよく、組成物を用いて製膜した膜の値であってもよい。膜の状態で吸光度を測定する場合は、ガラス基板上にスピンコート等の方法によって組成物を塗布し、ホットプレート等を用いて100℃、120秒間乾燥して得られた膜を用いて測定することが好ましい。
(Ir1):波長400~640nmの範囲における吸光度の最小値A1と、波長800~1500nmの範囲における吸光度の最大値B1との比であるA1/B1の値は4.5以上であり、7.5以上であることが好ましく、15以上であることがより好ましく、30以上であることが更に好ましい。この態様によれば、波長400~640nmの範囲の光を遮光して、波長750nmを超える光を透過させることができる膜を形成することができる。
(Ir2):波長400~750nmの範囲における吸光度の最小値A2と、波長900~1500nmの範囲における吸光度の最大値B2との比であるA2/B2の値は4.5以上であり、7.5以上であることが好ましく、15以上であることがより好ましく、30以上であることが更に好ましい。この態様によれば、波長400~750nmの範囲の光を遮光して、波長850nmを超える光を透過させることができる膜を形成することができる。
(Ir3):波長400~830nmの範囲における吸光度の最小値A3と、波長1000~1500nmの範囲における吸光度の最大値B3との比であるA3/B3の値は4.5以上であり、7.5以上であることが好ましく、15以上であることがより好ましく、30以上であることが更に好ましい。この態様によれば、波長400~830nmの範囲の光を遮光して、波長950nmを超える光を透過させることができる膜を形成することができる。
(Ir4):波長400~950nmの範囲における吸光度の最小値A4と、波長1100~1500nmの範囲における吸光度の最大値B4との比であるA4/B4の値は4.5以上であり、7.5以上であることが好ましく、15以上であることがより好ましく、30以上であることが更に好ましい。この態様によれば、波長400~950nmの範囲の光を遮光して、波長1050nmを超える光を透過させることができる膜を形成することができる。
(Ir5):波長400~1050nmの範囲における吸光度の最小値A5と、波長1200~1500nmの範囲における吸光度の最大値B5との比であるA5/B5の値は4.5以上であり、7.5以上であることが好ましく、15以上であることがより好ましく、30以上であることが更に好ましい。この態様によれば、波長400~1050nmの範囲の光を遮光して、波長1150nmを超える光を透過させることができる膜を形成することができる。
本発明の樹脂組成物は、色材を含有する。色材としては白色色材、黒色色材、有彩色色材、近赤外線吸収色材が挙げられる。なお、本発明において、白色色材には純白色のみならず、白に近い明るい灰色(例えば灰白色、薄灰色など)の色材も含まれる。
顔料Aを6質量%と、樹脂1を10質量%と、プロピレングリコールモノメチルエーテルアセテートを84質量%含む組成物を用いて、200℃で30分加熱して厚さ0.60μmの膜を形成した際に、上記膜を窒素雰囲気下にて300℃で5時間加熱処理したとき、加熱処理後の膜の下記式(A10)で表される吸光度の変化率ΔA10が50%以下である;
ΔA10=|100-(A12/A11)×100| ・・・(A10)
ΔA10は、加熱処理後の膜の吸光度の変化率であり、
A11は、加熱処理前の膜の波長400~1100nmの範囲における吸光度の最大値であり、
A12は、加熱処理後の膜の吸光度であって、加熱処理前の膜の波長400~1100nmの範囲における吸光度の最大値を示す波長での吸光度である;
樹脂1は、下記構造の樹脂であって、主鎖に付記した数値はモル比であり、重量平均分子量は11000であり、酸価は32mgKOH/gである。
有彩色色材としては、波長400~700nmの範囲に極大吸収波長を有する色材が挙げられる。例えば、黄色色材、オレンジ色色材、赤色色材、緑色色材、紫色色材、青色色材などが挙げれる。耐熱性の観点から有彩色色材は、顔料(有彩色顔料)であることが好ましく、赤色顔料、黄色顔料、及び青色顔料がより好ましく、赤色顔料及び青色顔料が更に好ましい。有彩色顔料の具体例としては、例えば、以下に示すものが挙げられる。
C.I.ピグメントオレンジ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.ピグメントレッド1,2,3,4,5,6,7,9,10,14,17,22,23,31,38,41,48:1,48:2,48:3,48:4,49,49:1,49:2,52:1,52:2,53:1,57:1,60:1,63:1,66,67,81:1,81:2,81:3,83,88,90,105,112,119,122,123,144,146,149,150,155,166,168,169,170,171,172,175,176,177,178,179,184,185,187,188,190,200,202,206,207,208,209,210,216,220,224,226,242,246,254,255,264,269,270,272,279,291,294(キサンテン系、Organo Ultramarine、Bluish Red),295(モノアゾ系),296(ジアゾ系),297(アミノケトン系)等(以上、赤色顔料)、
C.I.ピグメントグリーン7,10,36,37,58,59,62,63,64(フタロシアニン系),65(フタロシアニン系),66(フタロシアニン系)等(以上、緑色顔料)、
C.I.ピグメントバイオレット1,19,23,27,32,37,42,60(トリアリールメタン系),61(キサンテン系)等(以上、紫色顔料)、
C.I.ピグメントブルー1,2,15,15:1,15:2,15:3,15:4,15:6,16,22,29,60,64,66,79,80,87(モノアゾ系),88(メチン系)等(以上、青色顔料)。
有彩色色材として、国際公開第2020/174991号に記載のフタロシアニン化合物を用いることができる。
(1)赤色色材と青色色材とを含有する態様。
(2)赤色色材と青色色材と黄色色材とを含有する態様。
(3)赤色色材と青色色材と黄色色材と紫色色材とを含有する態様。
(4)赤色色材と青色色材と黄色色材と紫色色材と緑色色材とを含有する態様。
(5)赤色色材と青色色材と黄色色材と緑色色材とを含有する態様。
(6)赤色色材と青色色材と緑色色材とを含有する態様。
(7)黄色色材と紫色色材とを含有する態様。
白色色材としては、酸化チタン、チタン酸ストロンチウム、チタン酸バリウム、酸化亜鉛、酸化マグネシウム、酸化ジルコニウム、酸化アルミニウム、硫酸バリウム、シリカ、タルク、マイカ、水酸化アルミニウム、ケイ酸カルシウム、ケイ酸アルミニウム、中空樹脂粒子、硫化亜鉛などの無機顔料(白色顔料)が挙げられる。白色顔料は、チタン原子を有する粒子が好ましく、酸化チタンがより好ましい。また、白色顔料は、波長589nmの光に対する屈折率が2.10以上の粒子であることが好ましい。前述の屈折率は、2.10~3.00であることが好ましく、2.50~2.75であることがより好ましい。
黒色色材としては特に限定されず、公知のものを用いることができる。例えば、無機黒色色材としては、カーボンブラック、チタンブラック、グラファイト等の無機顔料(黒色顔料)が挙げられ、カーボンブラック、チタンブラックが好ましく、チタンブラックがより好ましい。チタンブラックとは、チタン原子を含有する黒色粒子であり、低次酸化チタンや酸窒化チタンが好ましい。チタンブラックは、分散性向上、凝集性抑制などの目的で必要に応じ、表面を修飾することが可能である。例えば、酸化珪素、酸化チタン、酸化ゲルマニウム、酸化アルミニウム、酸化マグネシウム、又は、酸化ジルコニウムでチタンブラックの表面を被覆することが可能である。また、特開2007-302836号公報に表されるような撥水性物質での処理も可能である。黒色顔料として、カラーインデックス(C.I.)Pigment Black 1,7等が挙げられる。チタンブラックは、個々の粒子の一次粒子径及び平均一次粒子径のいずれもが小さいことが好ましい。具体的には、平均一次粒子径が10~45nmであることが好ましい。チタンブラックは、分散物として用いることもできる。例えば、チタンブラック粒子とシリカ粒子とを含み、分散物中のSi原子とTi原子との含有比が0.20~0.50の範囲に調整された分散物などが挙げられる。上記分散物については、特開2012-169556号公報の段落0020~0105の記載を参酌でき、この内容は本明細書に組み込まれる。チタンブラックの市販品の例としては、チタンブラック10S、12S、13R、13M、13M-C、13R-N、13M-T(商品名:三菱マテリアル(株)製)、ティラック(Tilack)D(商品名:赤穂化成(株)製)などが挙げられる。
(A-1)有機黒色色材と青色色材とを含有する態様。
(A-2)有機黒色色材と青色色材と黄色色材とを含有する態様。
(A-3)有機黒色色材と青色色材と黄色色材と赤色色材とを含有する態様。
(A-4)有機黒色色材と青色色材と黄色色材と紫色色材とを含有する態様。
上記(A-2)の態様において、有機黒色色材と青色色材と黄色色材の質量比は、有機黒色色材:青色色材:黄色色材=100:10~90:10~90であることが好ましく、100:15~85:15~80であることがより好ましく、100:20~80:20~70であることが更に好ましい。
上記(A-3)の態様において、有機黒色色材と青色色材と黄色色材と赤色色材との質量比は、有機黒色色材:青色色材:黄色色材:赤色色材=100:20~150:1~60:10~100であることが好ましく、100:30~130:5~50:20~90であることがより好ましく、100:40~120:10~40:30~80であることが更に好ましい。
上記(A-4)の態様において、有機黒色色材と青色色材と黄色色材と紫色色材との質量比は、有機黒色色材:青色色材:黄色色材:紫色色材=100:20~150:1~60:10~100であることが好ましく、100:30~130:5~50:20~90であることがより好ましく、100:40~120:10~40:30~80であることが更に好ましい。
近赤外線吸収色材は、顔料であることが好ましく、有機顔料であることがより好ましい。また、近赤外線吸収色材は、波長700nmを超え1400nm以下の範囲に極大吸収波長を有することが好ましい。また、近赤外線吸収色材の極大吸収波長は、1200nm以下であることが好ましく、1000nm以下であることがより好ましく、950nm以下であることが更に好ましい。また、近赤外線吸収色材は、波長550nmにおける吸光度A550と極大吸収波長における吸光度Amaxとの比であるA550/Amaxが0.1以下であることが好ましく、0.05以下であることがより好ましく、0.03以下であることが更に好ましく、0.02以下であることが特に好ましい。下限は、特に限定はないが、例えば、0.0001以上とすることができ、0.0005以上とすることもできる。上述の吸光度の比が上記範囲であれば、可視光透明性及び近赤外線遮蔽性に優れた近赤外線吸収色材とすることができる。なお、本発明において、近赤外線吸収色材の極大吸収波長及び各波長における吸光度の値は、近赤外線吸収色材を含む樹脂組成物を用いて形成した膜の吸収スペクトルから求めた値である。
また、樹脂組成物の全固形分中における顔料の含有量は20~90質量%であることが好ましい。下限は、30質量%以上であることが好ましく、40質量%以上であることがより好ましく、50質量%以上であることが更に好ましい。上限は、80質量%以下であることが好ましく、70質量%以下であることがより好ましい。
また、色材中における染料の含有量は50質量%以下であることが好ましく、40質量%以下であることがより好ましく、30質量%以下であることが更に好ましい。
また、本発明の樹脂組成物は、得られる膜を高温に加熱した際の膜厚変化をより効果的に抑制しやすいという理由から染料を実質的に含有しないことも好ましい。本発明の樹脂組成物が染料を実質的に含まない場合、本発明の樹脂組成物の全固形分中における染料の含有量が0.1質量%以下であることが好ましく、0.05質量%以下であることがより好ましく、含有しないことが特に好ましい。
(特定樹脂)
本発明の樹脂組成物は樹脂を含む。樹脂組成物に含まれる樹脂は、エチレン性不飽和結合含有基を有する化合物由来の構造の分子鎖を含む主鎖と、グラフト鎖と、を有し、上記グラフト鎖がオキセタン基を有する繰り返し単位p1を含むグラフトポリマーを含む。以下、上記グラフトポリマーを特定樹脂ともいう。この特定樹脂は、上記のグラフト鎖を含むので、色材の分散性にも優れており、分散剤として好ましく用いることができる。また、特定樹脂は、バインダーとして用いてもよい。なお、本明細書において、主鎖とは、分岐点が最も多い分子鎖のことを意味する。また、グラフト鎖とは、主鎖から枝分かれした分子鎖のことを意味する。
式(b1-2)中、Rb4は、アルキル基またはアリール基を表し、Rb5およびRb6はそれぞれ独立して、水素原子、アルキル基またはアリール基を表し、Rb5およびRb6の少なくとも一方は、アルキル基またはアリール基であり、Rb4とRb5は結合して環を形成してもよい。
式(b1-3)中、Rb7は、アルキル基またはアリール基を表す。
式(b1-1)~式(b1-3)の*は結合手を表す。
Rb1~Rb3が表すアリール基の炭素数は、6~20が好ましく、6~12がより好ましく、6~10が更に好ましい。
Rb1~Rb3は、それぞれ独立してアルキル基であることが好ましく、直鎖のアルキル基であることがより好ましく、直鎖の炭素数1~5のアルキル基であることがより好ましく、直鎖の炭素数1~3のアルキル基であることが更に好ましく、メチル基であることが特に好ましい。
式(b1-1)において、Rb1とRb2は結合して環を形成してもよい。形成される環は5員環または6員環であることが好ましい。
Rb4~Rb6が表すアリール基の炭素数は、6~20が好ましく、6~12がより好ましく、6~10が更に好ましい。
式(b1-2)において、Rb4とRb5は結合して環を形成してもよい。形成される環は5員環または6員環であることが好ましい。
Rb7が表すアリール基の炭素数は、6~20が好ましく、6~12がより好ましく、6~10が更に好ましい。
Rp14~Rp16は、アルキル基またはアリール基を表し、Rp14とRp15は結合して環を形成してもよい。
L1およびL2は、それぞれ独立して2価の連結基を表す;
X1は単結合、-O-、-COO-、-OCO-、-NHCOO-、-OCONH-または-NHCONH-を表す;
P1は上記繰り返し単位p1を含むグラフト鎖を表す。
式(1)のR1~R3は、上述した式(a-1-1)のRa11~Ra13と同義であり、好ましい範囲も同様である。
また、特定樹脂は、窒素雰囲気下で300℃、5時間静置したときの質量減少率が10%以下であることが好ましく、5%以下であることがより好ましく、2%以下であることがさらに好ましい。上記質量減少率の下限は特に限定されず、0%以上であればよい。
上記質量減少率は、窒素雰囲気下で300℃、5時間静置する前後の特定樹脂における質量の減少の割合として算出される値である。
本発明の樹脂組成物は、樹脂として上述した特定樹脂以外の他の樹脂を含んでもよい。他の樹脂としては、例えば、アルカリ現像性を有する樹脂、又は、分散剤としての樹脂等が挙げられる。また、他の樹脂として、特開2017-206689号公報の段落番号0041~0060に記載の樹脂、特開2018-010856号公報の段落番号0022~0071に記載の樹脂、特開2017-057265号公報に記載の樹脂、特開2017-032685号公報に記載の樹脂、特開2017-075248号公報に記載の樹脂、特開2017-066240号公報に記載の樹脂、特開2017-173787号公報に記載の樹脂、特開2020-122052号公報に記載の樹脂、特開2020-111656号公報に記載の樹脂、特開2020-139021号公報に記載の樹脂、特開2017-138503号公報に記載の主鎖に環構造を有する構成単位と側鎖にビフェニル基を有する構成単位とを含む樹脂を用いることもできる。
アルカリ現像性を有する樹脂の重量平均分子量(Mw)は、3000~2000000が好ましい。上限は、1000000以下がより好ましく、500000以下がさらに好ましい。下限は、4000以上がより好ましく、5000以上がさらに好ましい。
本発明の樹脂組成物は、分散剤としての樹脂を含むこともできる。分散剤は、酸性分散剤(酸性樹脂)、塩基性分散剤(塩基性樹脂)が挙げられる。ここで、酸性分散剤(酸性樹脂)とは、酸基の量が塩基性基の量よりも多い樹脂を表す。酸性分散剤(酸性樹脂)は、酸基の量と塩基性基の量の合計量を100モル%としたときに、酸基の量が70モル%以上を占める樹脂が好ましく、実質的に酸基のみからなる樹脂がより好ましい。酸性分散剤(酸性樹脂)が有する酸基は、カルボキシ基が好ましい。酸性分散剤(酸性樹脂)の酸価は、40~105mgKOH/gが好ましく、50~105mgKOH/gがより好ましく、60~105mgKOH/gがさらに好ましい。また、塩基性分散剤(塩基性樹脂)とは、塩基性基の量が酸基の量よりも多い樹脂を表す。塩基性分散剤(塩基性樹脂)は、酸基の量と塩基性基の量の合計量を100モル%としたときに、塩基性基の量が50モル%を超える樹脂が好ましい。塩基性分散剤が有する塩基性基は、アミノ基であることが好ましい。
また、樹脂組成物の全固形分中における色材と上述した特定樹脂の合計の含有量は、25~100質量%が好ましい。下限は、30質量%以上がより好ましく、40質量%以上がさらに好ましい。上限は、90質量%以下がより好ましく、80質量%以下がさらに好ましい。
本発明の樹脂組成物は、溶剤を含有する。溶剤としては、各成分の溶解性や樹脂組成物の塗布性を満足すれば基本的には特に制限はない。溶剤は有機溶剤であることが好ましい。有機溶剤としては、エステル系溶剤、ケトン系溶剤、アルコール系溶剤、アミド系溶剤、エーテル系溶剤、炭化水素系溶剤などが挙げられる。これらの詳細については、国際公開第2015/166779号の段落番号0223を参酌でき、この内容は本明細書に組み込まれる。また、環状アルキル基が置換したエステル系溶剤、環状アルキル基が置換したケトン系溶剤を好ましく用いることもできる。有機溶剤の具体例としては、ポリエチレングリコールモノメチルエーテル、ジクロロメタン、3-エトキシプロピオン酸メチル、3-エトキシプロピオン酸エチル、エチルセロソルブアセテート、乳酸エチル、ジエチレングリコールジメチルエーテル、酢酸ブチル、3-メトキシプロピオン酸メチル、2-ヘプタノン、2-ペンタノン、3-ペンタノン、4-ヘプタノン、シクロヘキサノン、2-メチルシクロヘキサノン、3-メチルシクロヘキサノン、4-メチルシクロヘキサノン、シクロヘプタノン、シクロオクタノン、3-メトキシブタノール、酢酸シクロヘキシル、シクロペンタノン、エチルカルビトールアセテート、ブチルカルビトールアセテート、プロピレングリコールモノメチルエーテル、プロピレングリコールモノメチルエーテルアセテート、3-メトキシ-N,N-ジメチルプロパンアミド、3-ブトキシ-N,N-ジメチルプロパンアミド、ガンマブチロラクトン、N-メチル-2-ピロリドン、プロピレングリコールジアセテート、スルホラン、アニソール、1,4-ジアセトキシブタン、ジエチレングリコールモノエチルエーテルアセタート、二酢酸ブタン-1,3-ジイル、ジプロピレングリコールメチルエーテルアセタート、ジアセトンアルコール(別名としてダイアセトンアルコール、4-ヒドロキシ-4-メチル-2-ペンタノン)、2-メトキシプロピルアセテート、2-メトキシ-1-プロパノール、イソプロピルアルコールなどが挙げられる。溶剤は2種以上を用いてもよい。ただし有機溶剤としての芳香族炭化水素類(ベンゼン、トルエン、キシレン、エチルベンゼン等)は、環境面等の理由により低減したほうがよい場合がある(例えば、有機溶剤全量に対して、50質量ppm(parts per million)以下とすることもでき、10質量ppm以下とすることもでき、1質量ppm以下とすることもできる)。
本発明の樹脂組成物は顔料誘導体を含有することが好ましい。顔料誘導体としては、発色団の一部分を、酸基、塩基性基又はフタルイミドメチル基で置換した構造を有する化合物が挙げられる。顔料誘導体を構成する発色団としては、キノリン骨格、ベンゾイミダゾロン骨格、ジケトピロロピロール骨格、アゾ骨格、フタロシアニン骨格、アンスラキノン骨格、キナクリドン骨格、ジオキサジン骨格、ペリノン骨格、ペリレン骨格、チオインジゴ骨格、イソインドリン骨格、イソインドリノン骨格、キノフタロン骨格、スレン骨格、金属錯体系骨格等が挙げられ、キノリン骨格、ベンゾイミダゾロン骨格、ジケトピロロピロール骨格、アゾ骨格、キノフタロン骨格、イソインドリン骨格及びフタロシアニン骨格が好ましく、アゾ骨格及びベンゾイミダゾロン骨格がより好ましい。顔料誘導体が有する酸基としては、スルホ基、カルボキシ基が好ましく、スルホ基がより好ましい。顔料誘導体が有する塩基性基としては、アミノ基が好ましく、三級アミノ基がより好ましい。
本発明の樹脂組成物は、重合性モノマーを含有することが好ましい。重合性モノマーは、例えば、ラジカル、酸または熱により架橋可能な公知の化合物を用いることができる。エチレン性不飽和結合含有基を有する化合物、環状エーテル基を有する化合物などが挙げられ、エチレン性不飽和結合含有基を有する化合物であることが好ましい。エチレン性不飽和結合含有基としては、ビニル基、(メタ)アリル基、(メタ)アクリロイル基などが挙げられる。環状エーテル基としては、エポキシ基、オキセタン基などが挙げられる。エチレン性不飽和結合含有基を有する化合物はラジカル重合性モノマーとして好ましく用いることができる。また、環状エーテル基を有する化合物はカチオン重合性モノマーとして好ましく用いることができる。重合性モノマーは、多官能の重合性モノマーであることが好ましい。すなわち、重合性モノマーは、エチレン性不飽和結合含有基や環状エーテル基などの重合性基を2個以上有するモノマーであることが好ましい。
重合性モノマーとして用いられるエチレン性不飽和結合含有基を有する化合物としては、多官能の化合物であることが好ましい。すなわち、エチレン性不飽和結合含有基を2個以上含む化合物であることが好ましく、エチレン性不飽和結合含有基を3個以上含む化合物であることがより好ましく、エチレン性不飽和結合含有基を3~15個含む化合物であることが更に好ましく、エチレン性不飽和結合含有基を3~6個含む化合物であることがより一層好ましい。また、エチレン性不飽和結合含有基を有する化合物は、3~15官能の(メタ)アクリレート化合物であることが好ましく、3~6官能の(メタ)アクリレート化合物であることがより好ましい。エチレン性不飽和結合含有基を有する化合物の具体例としては、特開2009-288705号公報の段落番号0095~0108、特開2013-029760号公報の段落0227、特開2008-292970号公報の段落番号0254~0257、特開2013-253224号公報の段落番号0034~0038、特開2012-208494号公報の段落番号0477、特開2017-048367号公報、特許第6057891号公報、特許第6031807号公報、特開2017-194662号公報に記載されている化合物が挙げられ、これらの内容は本明細書に組み込まれる。
重合性モノマーとしても用いられる環状エーテル基を有する化合物としては、エポキシ基を有する化合物(以下、エポキシ化合物ともいう)、オキセタン基を有する化合物(以下、オキセタン化合物ともいう)が挙げられる。エポキシ化合物は、多官能のエポキシ化合物であることが好ましい。すなわち、エポキシ化合物は、エポキシ基を2個以上有する化合物であることが好ましい。エポキシ基の数の上限は、20個以下が好ましく、10個以下がより好ましい。また、オキセタン化合物は、多官能のオキセタン化合物であることが好ましい。すなわち、オキセタン化合物は、オキセタン基を2個以上有する化合物であることが好ましい。オキセタン基の数の上限は、20個以下が好ましく、10個以下がより好ましい。
本発明の樹脂組成物は光重合開始剤を含むことが好ましい。光重合開始剤としては、特に制限はなく、公知の光重合開始剤の中から適宜選択することができる。例えば、紫外線領域から可視領域の光線に対して感光性を有する化合物が好ましい。光重合開始剤は光ラジカル重合開始剤であることが好ましい。
本発明の樹脂組成物は、シランカップリング剤を含有することができる。本発明において、シランカップリング剤は、加水分解性基とそれ以外の官能基とを有するシラン化合物を意味する。また、加水分解性基とは、ケイ素原子に直結し、加水分解反応及び縮合反応の少なくともいずれかによってシロキサン結合を生じ得る置換基をいう。加水分解性基としては、例えば、ハロゲン原子、アルコキシ基、アシルオキシ基などが挙げられ、アルコキシ基が好ましい。すなわち、シランカップリング剤は、アルコキシシリル基を有する化合物が好ましい。また、加水分解性基以外の官能基としては、例えば、ビニル基、(メタ)アリル基、(メタ)アクリロイル基、メルカプト基、エポキシ基、アミノ基、ウレイド基、スルフィド基、イソシアネート基、フェニル基などが挙げられ、アミノ基、(メタ)アクリロイル基及びエポキシ基が好ましい。シランカップリング剤の具体例としては、特開2009-288703号公報の段落番号0018~0036に記載の化合物、特開2009-242604号公報の段落番号0056~0066に記載の化合物が挙げられ、これらの内容は本明細書に組み込まれる。
本発明の樹脂組成物は、樹脂や重合性化合物の反応を促進させたり、硬化温度を下げる目的で、硬化促進剤をさらに含有することができる。硬化促進剤は、メチロール系化合物(例えば特開2015-034963号公報の段落番号0246において、架橋剤として例示されている化合物)、アミン類、ホスホニウム塩、アミジン塩、アミド化合物(以上、例えば特開2013-041165号公報の段落番号0186に記載の硬化剤)、塩基発生剤(例えば、特開2014-055114号公報に記載のイオン性化合物)、シアネート化合物(例えば、特開2012-150180号公報の段落番号0071に記載の化合物)、アルコキシシラン化合物(例えば、特開2011-253054号公報に記載のエポキシ基を有するアルコキシシラン化合物)、オニウム塩化合物(例えば、特開2015-034963号公報の段落番号0216に酸発生剤として例示されている化合物、特開2009-180949号公報に記載の化合物)などを用いることもできる。
本発明の樹脂組成物は、重合禁止剤を含有することができる。重合禁止剤としては、ハイドロキノン、p-メトキシフェノール、ジ-tert-ブチル-p-クレゾール、ピロガロール、tert-ブチルカテコール、ベンゾキノン、4,4’-チオビス(3-メチル-6-tert-ブチルフェノール)、2,2’-メチレンビス(4-メチル-6-t-ブチルフェノール)、N-ニトロソフェニルヒドロキシアミン塩(アンモニウム塩、第一セリウム塩等)が挙げられる。中でも、p-メトキシフェノールが好ましい。樹脂組成物の全固形分中における重合禁止剤の含有量は、0.0001~5質量%が好ましい。
本発明の樹脂組成物は、界面活性剤を含有することができる。界面活性剤としては、フッ素系界面活性剤、ノニオン性界面活性剤、カチオン性界面活性剤、アニオン性界面活性剤、シリコーン系界面活性剤などの各種界面活性剤を使用することができる。界面活性剤については、国際公開第2015/166779号の段落番号0238~0245に記載された界面活性剤が挙げられ、この内容は本明細書に組み込まれる。
本発明の樹脂組成物は、紫外線吸収剤を含有することができる。紫外線吸収剤は、共役ジエン化合物、アミノジエン化合物、サリシレート化合物、ベンゾフェノン化合物、ベンゾトリアゾール化合物、アクリロニトリル化合物、ヒドロキシフェニルトリアジン化合物、インドール化合物、トリアジン化合物などを用いることができる。これらの詳細については、特開2012-208374号公報の段落番号0052~0072、特開2013-068814号公報の段落番号0317~0334、特開2016-162946号公報の段落番号0061~0080の記載を参酌でき、これらの内容は本明細書に組み込まれる。紫外線吸収剤の市販品としては、例えば、UV-503(大東化学(株)製)、BASF社製のTinuvinシリーズ、Uvinul(ユビナール)シリーズ、住化ケムテックス(株)製のSumisorbシリーズなどが挙げられる。また、ベンゾトリアゾール化合物としては、ミヨシ油脂製のMYUAシリーズ(化学工業日報、2016年2月1日)が挙げられる。また、紫外線吸収剤は、特許第6268967号公報の段落番号0049~0059に記載された化合物、国際公開第2016/181987号の段落番号0059~0076に記載された化合物、国際公開第2020/137819号に記載されたチオアリール基置換ベンゾトリアゾール型紫外線吸収剤を用いることもできる。樹脂組成物の全固形分中における紫外線吸収剤の含有量は、0.01~10質量%が好ましく、0.01~5質量%がより好ましい。紫外線吸収剤は1種のみを用いてもよく、2種以上を用いてもよい。2種以上を用いる場合は、合計量が上記範囲となることが好ましい。
本発明の樹脂組成物は、酸化防止剤を含有することができる。酸化防止剤としては、フェノール化合物、亜リン酸エステル化合物、チオエーテル化合物などが挙げられる。フェノール化合物としては、フェノール系酸化防止剤として知られる任意のフェノール化合物を使用することができる。好ましいフェノール化合物としては、ヒンダードフェノール化合物が挙げられる。フェノール性ヒドロキシ基に隣接する部位(オルト位)に置換基を有する化合物が好ましい。前述の置換基としては炭素数1~22の置換又は無置換のアルキル基が好ましい。また、酸化防止剤は、同一分子内にフェノール基と亜リン酸エステル基を有する化合物も好ましい。また、酸化防止剤は、リン系酸化防止剤も好適に使用することができる。また、酸化防止剤は、韓国公開特許第10-2019-0059371号公報に記載の化合物を用いることもできる。樹脂組成物の全固形分中における酸化防止剤の含有量は、0.01~20質量%であることが好ましく、0.3~15質量%であることがより好ましい。酸化防止剤は1種のみを用いてもよく、2種以上を用いてもよい。2種以上を用いる場合は、合計量が上記範囲となることが好ましい。
本発明の樹脂組成物は、必要に応じて、増感剤、フィラー、熱硬化促進剤、可塑剤及びその他の助剤類(例えば、導電性粒子、充填剤、消泡剤、難燃剤、レベリング剤、剥離促進剤、香料、表面張力調整剤、連鎖移動剤など)を含有してもよい。これらの成分を適宜含有させることにより、膜物性などの性質を調整することができる。これらの成分は、例えば、特開2012-003225号公報の段落番号0183以降(対応する米国特許出願公開第2013/0034812号明細書の段落番号0237)の記載、特開2008-250074号公報の段落番号0101~0104、0107~0109等の記載を参酌でき、これらの内容は本明細書に組み込まれる。また、樹脂組成物は、必要に応じて、潜在酸化防止剤を含有してもよい。潜在酸化防止剤としては、酸化防止剤として機能する部位が保護基で保護された化合物であって、100~250℃で加熱するか、又は酸/塩基触媒存在下で80~200℃で加熱することにより保護基が脱離して酸化防止剤として機能する化合物が挙げられる。潜在酸化防止剤としては、国際公開第2014/021023号、国際公開第2017/030005号、特開2017-008219号公報に記載された化合物が挙げられる。市販品としては、アデカアークルズGPA-5001((株)ADEKA製)等が挙げられる。また、特開2018-155881号公報に記載されているように、C.I.ピグメントイエロー129を耐候性改良の目的で添加しても良い。
本発明の樹脂組成物の収容容器としては、特に限定はなく、公知の収容容器を用いることができる。また、収容容器として、原材料や樹脂組成物中への不純物混入を抑制することを目的に、容器内壁を6種6層の樹脂で構成する多層ボトルや6種の樹脂を7層構造にしたボトルを使用することも好ましい。このような容器としては例えば特開2015-123351号公報に記載の容器が挙げられる。また、容器内壁は、容器内壁からの金属溶出を防ぎ、樹脂組成物の保存安定性を高めたり、成分変質を抑制するなど目的で、ガラス製やステンレス製などにすることも好ましい。
本発明の樹脂組成物は、前述の成分を混合して調製できる。樹脂組成物の調製に際しては、全成分を同時に有機溶剤に溶解及び/又は分散して樹脂組成物を調製してもよいし、必要に応じて、各成分を適宜2つ以上の溶液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樹脂組成物を調製してもよい。
本発明の膜は、上述した本発明の樹脂組成物から得られる膜である。本発明の膜は、カラーフィルタ、近赤外線透過フィルタ、近赤外線カットフィルタなどの光学フィルタに用いることができる。また、本発明の膜は、ブラックマトリクスや遮光膜などに用いることもできる。
(i1):波長400~640nmの範囲における透過率の最大値が20%以下(好ましくは15%以下、より好ましくは10%以下)であり、波長800~1500nmの範囲における透過率の最小値が70%以上(好ましくは75%以上、より好ましくは80%以上)であるフィルタ。このような分光特性を有する膜は、波長400~640nmの範囲の光を遮光して、波長750nmを超える光を透過させることができる。
(i2):波長400~750nmの範囲における透過率の最大値が20%以下(好ましくは15%以下、より好ましくは10%以下)であり、波長900~1500nmの範囲における透過率の最小値が70%以上(好ましくは75%以上、より好ましくは80%以上)であるフィルタ。このような分光特性を有する膜は、波長400~750nmの範囲の光を遮光して、波長850nmを超える光を透過させることができる。
(i3):波長400~830nmの範囲における透過率の最大値が20%以下(好ましくは15%以下、より好ましくは10%以下)であり、波長1000~1500nmの範囲における透過率の最小値が70%以上(好ましくは75%以上、より好ましくは80%以上)であるフィルタ。このような分光特性を有する膜は、波長400~830nmの範囲の光を遮光して、波長950nmを超える光を透過させることができる。
(i4):波長400~950nmの範囲における透過率の最大値が20%以下(好ましくは15%以下、より好ましくは10%以下)であり、波長1100~1500nmの範囲における透過率の最小値が70%以上(好ましくは75%以上、より好ましくは80%以上)であるフィルタ。このような分光特性を有する膜は、波長400~950nmの範囲の光を遮光して、波長1050nmを超える光を透過させることができる。
(i5):波長400~1050nmの範囲における透過率の最大値が20%以下(好ましくは15%以下、より好ましくは10%以下)であり、波長1200~1500nmの範囲における透過率の最小値が70%以上(好ましくは75%以上、より好ましくは80%以上)であるフィルタ。このような分光特性を有する膜は、波長400~1050nmの範囲の光を遮光して、波長1150nmを超える光を透過させることができる。
また、上記膜を窒素雰囲気下にて350℃で5時間加熱処理した後の膜の厚さは、加熱処理前の膜の厚さの70%以上であることが好ましく、80%以上であることがより好ましく、90%以上であることが更に好ましい。
また、上記膜を窒素雰囲気下にて400℃で5時間加熱処理した後の膜の厚さは、加熱処理前の膜の厚さの70%以上であることが好ましく、80%以上であることがより好ましく、90%以上であることが更に好ましい。
本発明の膜は、上述した本発明の樹脂組成物を支持体上に塗布する工程を経て製造できる。本発明の膜の製造方法においては、更にパターン(画素)を形成する工程を含むことが好ましい。パターン(画素)の形成方法としては、フォトリソグラフィ法及びドライエッチング法が挙げられ、フォトリソグラフィ法が好ましい。
まず、フォトリソグラフィ法によりパターンを形成して膜を製造する場合について説明する。フォトリソグラフィ法によるパターン形成は、本発明の樹脂組成物を用いて支持体上に樹脂組成物層を形成する工程と、樹脂組成物層をパターン状に露光する工程と、樹脂組成物層の未露光部を現像除去してパターン(画素)を形成する工程と、を含むことが好ましい。必要に応じて、樹脂組成物層をベークする工程(プリベーク工程)、及び、現像されたパターン(画素)をベークする工程(ポストベーク工程)を設けてもよい。
ドライエッチング法でのパターン形成は、本発明の樹脂組成物を用いて支持体上に樹脂組成物層を形成し、この樹脂組成物層の全体を硬化させて硬化物層を形成する工程と、この硬化物層上にフォトレジスト層を形成する工程と、フォトレジスト層をパターン状に露光したのち、現像してレジストパターンを形成する工程と、このレジストパターンをマスクとして硬化物層に対してエッチングガスを用いてドライエッチングする工程と、を含むことが好ましい。フォトレジスト層の形成においては、更にプリベーク処理を施すことが好ましい。特に、フォトレジスト層の形成プロセスとしては、露光後の加熱処理、現像後の加熱処理(ポストベーク処理)を実施する形態が望ましい。ドライエッチング法でのパターン形成については、特開2013-064993号公報の段落番号0010~0067の記載を参酌でき、この内容は本明細書に組み込まれる。
本発明の光学フィルタは、上述した本発明の膜を有する。光学フィルタの種類としては、光学フィルタとしては、カラーフィルタ、近赤外線透過フィルタ、近赤外線カットフィルタなどが挙げられ、カラーフィルタであることが好ましい。カラーフィルタとしては、カラーフィルタの着色画素として本発明の膜を有することが好ましい。本発明の光学フィルタは、CCD(電荷結合素子)やCMOS(相補型金属酸化膜半導体)などの固体撮像素子や画像表示装置などに用いることができる。
本発明の固体撮像素子は、上述した本発明の膜を有する。本発明の固体撮像素子の構成としては、本発明の膜を備え、固体撮像素子として機能する構成であれば特に限定はないが、例えば、以下のような構成が挙げられる。
本発明の画像表示装置は、上述した本発明の膜を有する。画像表示装置としては、液晶表示装置や有機エレクトロルミネッセンス表示装置などが挙げられる。画像表示装置の定義や各画像表示装置の詳細については、例えば「電子ディスプレイデバイス(佐々木昭夫著、(株)工業調査会、1990年発行)」、「ディスプレイデバイス(伊吹順章著、産業図書(株)平成元年発行)」などに記載されている。また、液晶表示装置については、例えば「次世代液晶ディスプレイ技術(内田龍男編集、(株)工業調査会、1994年発行)」に記載されている。本発明が適用できる液晶表示装置に特に制限はなく、例えば、上記の「次世代液晶ディスプレイ技術」に記載されている色々な方式の液晶表示装置に適用できる。
試料の重量平均分子量は、ゲルパーミエーションクロマトグラフィ(GPC)により、以下の条件で測定した。
カラムの種類:TOSOH TSKgel Super HZM-Hと、TOSOH TSKgel Super HZ4000と、TOSOH TSKgel Super HZ2000とを連結したカラム
展開溶媒:テトラヒドロフラン
カラム温度:40℃
流量(サンプル注入量):1.0μL(サンプル濃度:0.1質量%)
装置名:東ソー製 HLC-8220GPC
検出器:RI(屈折率)検出器
検量線ベース樹脂:ポリスチレン樹脂
試料の酸価は、試料中の固形分1gあたりの酸性成分を中和するのに要する水酸化カリウムの質量を表したものである。試料の酸価は次のようにして測定した。すなわち、測定試料をテトラヒドロフラン/水=9/1(質量比)混合溶媒に溶解し、得られた溶液を、電位差滴定装置(商品名:AT-510、京都電子工業製)を用いて、25℃にて、0.1mol/L水酸化カリウム水溶液で中和滴定した。滴定pH曲線の変曲点を滴定終点として、次式により酸価を算出した。
A=56.11×Vs×0.5×f/w
A:酸価(mgKOH/g)
Vs:滴定に要した0.1mol/L水酸化カリウム水溶液の使用量(mL)
f:0.1mol/L水酸化カリウム水溶液の力価
w:試料の質量(g)(固形分換算)
(樹脂A-1の合成)
3つ口フラスコにプロピレングリコールモノメチルエーテルアセテート(PGMEA)を300g加え、窒素雰囲気下で60℃に加温した。これに(3-エチルオキセタン-3-イル)メチルアクリレート(大阪有機化学工業(株)製、OXE-10)の380gと、6-メルカプトヘキサノール(東京化成工業(株)製)の18.3gと、2,2’-アゾビスイソ酪酸ジメチル(富士フイルム和光純薬(株)製、V-601)の2.4gとPGMEAの300gの溶液を2時間かけて滴下した。そののち2,2’-アゾビスイソ酪酸ジメチルを2.4g加えてさらに4時間加熱してマクロモノマー前駆体を合成した。このマクロモノマー前駆体溶液を5℃に冷却したのち、ジブチルヒドロキシトルエン(BHT)の0.4gとネオスタンU-600(日東化成製)の0.16gを加えたのち、2-イソシアナトエチルメタクリレート(昭和電工(株)製、カレンズMOI)の22.1gを30分かけて滴下した。5℃で1時間さらに撹拌し、室温に戻してさらに6時間撹拌することで下記構造のマクロモノマーAA-1のPGMEA40%溶液を得た。得られたマクロモノマーAA-1の重量平均分子量(Mw)は2800であった。
樹脂A-1と同様の方法で、樹脂A-2~A-48を合成した。以下の式中、繰り返し単位の主鎖に付記した数値は繰り返し単位のモル%を表し、「Polym」の記載は、「Polym」で示す構造の繰り返し単位が添え字の数値の数で結合した構造のポリマー鎖が硫黄原子(S)に結合していることを示している。
下記表に記載の原料を混合した混合液を、ビーズミル(0.3mm径のジルコニアビーズを使用)を用いて3時間混合及び分散した後さらに減圧機構付き高圧分散機NANO-3000-10(日本ビーイーイー(株)製)を用いて、2000MPaの圧力下で流量500g/minとして分散処理を行った。この分散処理を10回繰り返して各分散液を得た。
〔色材〕
PR264 : C.I.ピグメントレッド264(赤色顔料、ジケトピロロピロール顔料)
PR254 : C.I.ピグメントレッド254(赤色顔料、ジケトピロロピロール顔料)
PR291 : C.I.ピグメントレッド291(赤色顔料、ジケトピロロピロール顔料)
PR122 : C.I.ピグメントレッド122(赤色顔料、キナクリドン顔料)
PR179 : C.I.ピグメントレッド179(赤色顔料、ペリレン顔料)
PO71 : C.I.ピグメントオレンジ71(オレンジ色顔料、ジケトピロロピロール顔料)
PB15:6 : C.I.ピグメントブルー15:6(青色顔料、フタロシアニン顔料)
PB16 : C.I.ピグメントブルー16(青色顔料、フタロシアニン顔料)
PG7 : C.I.ピグメントグリーン7(緑色顔料、フタロシアニン顔料)
PG36 : C.I.ピグメントグリーン36(緑色顔料、フタロシアニン顔料)
PG58 : C.I.ピグメントグリーン58(緑色顔料、フタロシアニン顔料)
PY185 : C.I.ピグメントイエロー185(黄色顔料、イソインドリン顔料)
PY215 : C.I.ピグメントイエロー215(黄色顔料、プテリジン顔料)
PV23 : C.I.ピグメントバイオレット23(紫色顔料、ジオキサジン顔料)
IR色素:下記構造の化合物(近赤外線吸収顔料、構造式中、Meはメチル基を表し、Phはフェニル基を表す)
A-1~A-42:上述した樹脂
CA-1:下記構造の樹脂(重量平均分子量は10885、酸価は74mgKOH/gである。「Polym」の記載は、「Polym」で示す構造の繰り返し単位が添え字の数値の数で結合した構造のポリマー鎖が硫黄原子(S)に結合していることを示している。)
S-1:プロピレングリコールモノメチルエーテルアセテート
S-2:プロピレングリコールモノメチルエーテル
S-3:シクロヘキサノン
各実施例及び比較例において、それぞれ、下記表に記載の原料を混合して実施例および比較例の樹脂組成物を調製した。下記表に記載の添加量の欄の数値の単位は質量部である。
分散液R1~R15、B1~B13、G1~G13、I1~I6、Bk1~Bk20、CR1、CB1、CG1、CI1、CBk1~3:上述した分散液
A-1、A-6、A-11、A-14、A-24、A-26、A-29、A-30:上述した樹脂
Aa-1:下記構造の樹脂(主鎖に付記した数値はモル比である。重量平均分子量11000)
D-1:アクリレート化合物(KAYARAD DPHA、日本化薬(株)製)
D-2:エポキシ化合物(TETRAD-X、三菱ガス化学(株)製)
D-3:オキセタン化合物(OXT-221、東亞合成(株)製)
D-4:オキセタン化合物(OX-SQ TX-100、東亞合成(株)製)
E-1:Omnirad 379EG(IGM Resins B.V.社製)
E-2:Irgacure OXE01(BASF社製)
E-3:Irgacure OXE03(BASF社製)
S-1:プロピレングリコールモノメチルエーテルアセテート
S-2:プロピレングリコールモノメチルエーテル
S-3:シクロヘキサノン
各実施例及び比較例において、それぞれ樹脂組成物の粘度(mPa・s)を、東機産業(株)製「RE-85L」にて測定した。上記測定後、樹脂組成物を45℃、遮光、3日間の条件にて静置し、再度粘度(mPa・s)を測定した。上記静置前後での粘度差(ΔVis)から下記評価基準に従って保存安定性を評価した。粘度差(ΔVis)の数値が小さいほど、組成物の保存安定性が良好であるといえる。上記粘度測定は、いずれも、温湿度を22±5℃、60±20%に管理した実験室で、樹脂組成物の温度を25℃に調整した状態で測定した。
A:ΔVisが0.5mPa・s以下であった。
B:ΔVisが0.5mPa・sを超え、1.0mPa・s以下であった。
C:ΔVisが1.0mPa・sを超え、2.0mPa・s以下であった。
D:ΔVisが2.0mPa・sを超え、2.5mPa・s以下であった。
E:ΔVisが2.5mPa・sを超えた。
各実施例及び比較例において、それぞれ樹脂組成物をガラス基板上にスピンコートで塗布し、ホットプレートを用いて100℃で120秒乾燥(プリベーク)した後に、オーブンを用いて200℃で30分加熱(ポストベーク)して厚さ0.60μmの膜を製造した。Cary 5000 UV-Vis-NIR 分光光度計(アジレントテクノロジー(株)製)を用いて、得られた膜の波長450nmの光の透過率Tr1を測定した。次いで、得られた膜を窒素雰囲気下にて300℃で5時間加熱処理した。加熱処理後の膜の波長450nmの光の透過率Tr2を測定した。Tr1とTr2の差の絶対値ΔTを算出し、下記評価基準に従って分光変化を評価した。ΔTが小さいほど、分光変化が起こりにくく好ましいといえる。上記Tr1及びTr2は、いずれも、温湿度を22±5℃、60±20%に管理した実験室で、基板温度を25℃に温度調整を施した状態で測定した。
A:ΔTが0.1%以下であった。
B:ΔTが0.1%を超え0.5%以下であった。
C:ΔTが0.5%を超え1%以下であった。
D:ΔTが1%を超え5%以下であった。
E:ΔTが5%を超えた。
各実施例及び比較例において、それぞれ樹脂組成物をガラス基板上にスピンコートで塗布し、ホットプレートを用いて100℃で120秒乾燥(プリベーク)した後に、オーブンを用いて200℃で30分加熱(ポストベーク)して厚さ0.60μmの膜を製造した。膜厚は、膜の一部を削ってガラス基板表面を露出し、ガラス基板表面と塗布膜の段差(塗布膜の膜厚)を触針式段差計(DektakXT、BRUKER社製)を用いて測定した。次いで、得られた膜を窒素雰囲気下にて300℃で5時間加熱処理した。加熱処理後の膜の膜厚を同様にして測定し、下記式より膜収縮率を求め、下記評価基準に従って膜収縮率を評価した。下記T0及びT1は、いずれも、温湿度を22±5℃、60±20%に管理した実験室で、基板温度を25℃に温度調整を施した状態で測定した。膜収縮率が小さいほど、膜収縮が抑制されており、好ましい結果であるといえる。
膜収縮率(%)=(1-(T1/T0))×100
T0:製造直後の膜の膜厚(=0.60μm)
T1:窒素雰囲気下にて300℃で5時間加熱処理した後の膜厚
-評価基準-
A:膜収縮率が1%以下であった。
B:膜収縮率が1%を超え5%以下であった。
C:膜収縮率が5%を超え10%以下であった。
D:膜収縮率が10%を超え30%以下であった。
E:膜収縮率が30%を超えた。
各実施例及び比較例において、それぞれ樹脂組成物をガラス基板上にスピンコートで塗布し、ホットプレートを用いて100℃で120秒乾燥(プリベーク)した後に、オーブンを用いて200℃で30分加熱(ポストベーク)して厚さ0.60μmの膜を製造した。
次いで、得られた膜の表面に、スパッタ法によりSiO2を200nm積層して無機膜を形成した。この無機膜が表面に形成された膜を、窒素雰囲気下にて300℃で5時間加熱処理した。加熱処理後の無機膜の表面を光学顕微鏡で観察し、クラックの1cm2当たりの個数をカウントして、下記評価基準に従ってクラックの有無を評価した。
-評価基準-
A:クラックの1cm2当たりの個数が0個であった。
B:クラックの1cm2当たりの個数が1~10個であった。
C:クラックの1cm2当たりの個数が11~50個であった。
D:クラックの1cm2当たりの個数が51個~100個であった。
E:クラックの1cm2当たりの個数が101個以上であった。
また、実施例1~37、68~71の樹脂組成物は、カラーフィルタの着色画素形成用の樹脂組成物として好ましく用いることができる。また、実施例38~43の樹脂組成物は、近赤外線カットフィルタ形成用の樹脂組成物として好ましく用いることができる。また、実施例44~67の樹脂組成物は、近赤外線透過フィルタ形成用の樹脂組成物として好ましく用いることができる。
シリコンウエハ上に、実施例1の樹脂組成物をスピンコートで塗布し、ホットプレートを用いて100℃で120秒乾燥(プリベーク)した後に、オーブンを用いて200℃で30分加熱(ポストベーク)して厚さ0.60μmの樹脂組成物層を形成した。
次いで、この樹脂組成物層に対して、一辺1.1μmの正方形状の非マスク部が4mm×3mmの領域に配列されたマスクパターンを介して、i線ステッパー露光装置FPA-3000i5+(Canon(株)製)を使用して波長365nmの光を500mJ/cm2の露光量で照射して露光した。
次いで、露光後の樹脂組成物層が形成されているシリコンウエハを、スピン・シャワー現像機(DW-30型、(株)ケミトロニクス製)の水平回転テーブル上に載置し、現像液(CD-2000、富士フイルムエレクトロニクスマテリアルズ(株)製)を用い、23℃で60秒間パドル現像した。次いで、シリコンウエハを回転数50rpmで回転させつつ、その回転中心の上方より純水を噴出ノズルからシャワー状に供給してリンス処理を行ない、その後スプレー乾燥してパターン(画素)を形成した。
Claims (19)
- 色材と、樹脂と、溶剤とを含み、
前記樹脂は、エチレン性不飽和結合含有基を有する化合物由来の構造の分子鎖を含む主鎖と、グラフト鎖と、を有するグラフトポリマーを含み、
前記グラフト鎖は、オキセタン基を有する繰り返し単位p1を含む、
樹脂組成物。 - 前記グラフト鎖は、カルボキシ基が熱分解性基で保護された基を有する繰り返し単位を含む、請求項1または2に記載の樹脂組成物。
- 前記グラフト鎖は、t-ブチルエステル基を有する繰り返し単位を含む、請求項1または2に記載の樹脂組成物。
- 前記グラフトポリマーの主鎖は、架橋性基を有する繰り返し単位を含む、請求項1~6のいずれか1項に記載の樹脂組成物。
- 前記グラフトポリマーの主鎖は、酸基を有する繰り返し単位を含む、請求項1~7のいずれか1項に記載の樹脂組成物。
- 前記色材は、近赤外線吸収色材を含む、請求項1~8のいずれか1項に記載の樹脂組成物。
- 前記色材は、黒色色材を含む、請求項1~8のいずれか1項に記載の樹脂組成物。
- 前記色材は、カラーインデックスピグメントレッド179、カラーインデックスピグメントレッド264、カラーインデックスピグメントレッド291、カラーインデックスピグメントブルー16、およびカラーインデックスピグメントイエロー215から選ばれる少なくとも1種を含む、請求項1~10のいずれか1項に記載の樹脂組成物。
- 前記樹脂組成物の波長400~640nmの範囲における吸光度の最小値Aminと、前記樹脂組成物の波長1500nmにおける吸光度Bとの比であるAmin/Bが5以上である、請求項1~11のいずれか1項に記載の樹脂組成物。
- 更に重合性モノマーを含む、請求項1~12のいずれか1項に記載の樹脂組成物。
- 更に光重合開始剤を含む、請求項1~13のいずれか1項に記載の樹脂組成物。
- 固体撮像素子用である、請求項1~14のいずれか1項に記載の樹脂組成物。
- 請求項1~15のいずれか1項に記載の樹脂組成物から得られる膜。
- 請求項16に記載の膜を含む光学フィルタ。
- 請求項16に記載の膜を含む固体撮像素子。
- 請求項16に記載の膜を含む画像表示装置。
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JP (1) | JP7385739B2 (ja) |
KR (1) | KR20220138395A (ja) |
CN (1) | CN115315482B (ja) |
TW (1) | TW202136340A (ja) |
WO (1) | WO2021182268A1 (ja) |
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2021
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- 2021-03-04 JP JP2022505991A patent/JP7385739B2/ja active Active
- 2021-03-04 KR KR1020227030652A patent/KR20220138395A/ko not_active Application Discontinuation
- 2021-03-04 CN CN202180019266.9A patent/CN115315482B/zh active Active
- 2021-03-09 TW TW110108225A patent/TW202136340A/zh unknown
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JP2002332344A (ja) * | 2001-05-08 | 2002-11-22 | Kansai Paint Co Ltd | 熱硬化性組成物及びそれを用いた被膜形成方法 |
JP2007246559A (ja) * | 2006-03-13 | 2007-09-27 | Jsr Corp | 側鎖不飽和重合体、感放射線性樹脂組成物および液晶表示素子用スペーサー |
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WO2016148095A1 (ja) * | 2015-03-18 | 2016-09-22 | 富士フイルム株式会社 | 下層膜形成用樹脂組成物、インプリント形成用キット、積層体、パターン形成方法およびデバイスの製造方法 |
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JP7385739B2 (ja) | 2023-11-22 |
US20230050872A1 (en) | 2023-02-16 |
CN115315482B (zh) | 2024-07-05 |
CN115315482A (zh) | 2022-11-08 |
KR20220138395A (ko) | 2022-10-12 |
TW202136340A (zh) | 2021-10-01 |
JPWO2021182268A1 (ja) | 2021-09-16 |
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