WO2021106423A1 - 組成物、膜、マイクロレンズ、固体撮像素子および表示装置 - Google Patents
組成物、膜、マイクロレンズ、固体撮像素子および表示装置 Download PDFInfo
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- WO2021106423A1 WO2021106423A1 PCT/JP2020/039207 JP2020039207W WO2021106423A1 WO 2021106423 A1 WO2021106423 A1 WO 2021106423A1 JP 2020039207 W JP2020039207 W JP 2020039207W WO 2021106423 A1 WO2021106423 A1 WO 2021106423A1
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- FYNROBRQIVCIQF-UHFFFAOYSA-N pyrrolo[3,2-b]pyrrole-5,6-dione Chemical compound C1=CN=C2C(=O)C(=O)N=C21 FYNROBRQIVCIQF-UHFFFAOYSA-N 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- IZMJMCDDWKSTTK-UHFFFAOYSA-N quinoline yellow Chemical compound C1=CC=CC2=NC(C3C(C4=CC=CC=C4C3=O)=O)=CC=C21 IZMJMCDDWKSTTK-UHFFFAOYSA-N 0.000 description 1
- 239000007870 radical polymerization initiator Substances 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000011342 resin composition Substances 0.000 description 1
- 150000003873 salicylate salts Chemical class 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 238000010008 shearing Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- 229920005573 silicon-containing polymer Polymers 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000012719 thermal polymerization Methods 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 125000000101 thioether group Chemical group 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- JOUDBUYBGJYFFP-FOCLMDBBSA-N thioindigo Chemical compound S\1C2=CC=CC=C2C(=O)C/1=C1/C(=O)C2=CC=CC=C2S1 JOUDBUYBGJYFFP-FOCLMDBBSA-N 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- WXAZIUYTQHYBFW-UHFFFAOYSA-N tris(4-methylphenyl)phosphane Chemical compound C1=CC(C)=CC=C1P(C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 WXAZIUYTQHYBFW-UHFFFAOYSA-N 0.000 description 1
- 238000001132 ultrasonic dispersion Methods 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/0041—Optical brightening agents, organic pigments
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L101/00—Compositions of unspecified macromolecular compounds
- C08L101/02—Compositions of unspecified macromolecular compounds characterised by the presence of specified groups, e.g. terminal or pendant functional groups
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
- C09B23/0008—Methine or polymethine dyes, e.g. cyanine dyes substituted on the polymethine chain
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
- C09B23/14—Styryl dyes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B57/00—Other synthetic dyes of known constitution
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
- G02B1/041—Lenses
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B3/00—Simple or compound lenses
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
- G02B5/22—Absorbing filters
-
- G—PHYSICS
- G09—EDUCATION; CRYPTOGRAPHY; DISPLAY; ADVERTISING; SEALS
- G09F—DISPLAYING; ADVERTISING; SIGNS; LABELS OR NAME-PLATES; SEALS
- G09F9/00—Indicating arrangements for variable information in which the information is built-up on a support by selection or combination of individual elements
- G09F9/30—Indicating arrangements for variable information in which the information is built-up on a support by selection or combination of individual elements in which the desired character or characters are formed by combining individual elements
-
- 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
Definitions
- the present invention relates to a composition for forming a member having a high refractive index such as a microlens.
- the present invention also relates to a film, a microlens, a solid-state image sensor, and a display device.
- Patent Document 1 describes an invention relating to a resin composition for forming a microlens, which contains a copolymer having a predetermined structural unit and a solvent.
- anomalous dispersion of the refractive index tends to occur in the vicinity of the maximum absorption wavelength of the substance.
- the refractive index of a substance tends to decrease as the wavelength of light becomes longer.
- Such a phenomenon is called normal dispersion of the refractive index.
- anomalous dispersion of the refractive index a phenomenon in which the refractive index rapidly increases or decreases as the wavelength becomes longer due to a large deviation from the normal dispersion.
- microlenses In microlenses, it has been thought that the light collection rate of visible light decreases when the refractive index is abnormally dispersed. Therefore, conventionally, microlenses have high transparency to visible light and near infrared light. It was used. In addition, attempts to include a near-infrared absorbing dye in a microlens have not been studied so far.
- an object of the present invention is to provide a novel composition, a film, a microlens, a solid-state image sensor, and a display device.
- composition according to ⁇ 1> wherein when a film having a thickness of 0.35 ⁇ m is formed using the above composition, the average transmittance of light having a wavelength of 800 to 870 nm of the film is 80% or less. .. ⁇ 3>
- the organic compound A is a compound having at least one structure selected from a fluorene structure, a triazine structure and a carbazole structure.
- ⁇ 4> The composition according to any one of ⁇ 1> to ⁇ 3>, which contains two or more of the above organic compounds A.
- ⁇ 5> In the total amount of the organic compound A contained in the above composition, the content of the organic compound having a refractive index of 1.63 or more with respect to light having a wavelength of 633 nm is 5 to 100% by mass, ⁇ 1> to ⁇ 4. > The composition according to any one of. ⁇ 6> The composition according to any one of ⁇ 1> to ⁇ 5>, wherein the content of the organic compound A in the total solid content of the composition is 50% by mass or more. ⁇ 7> The composition according to any one of ⁇ 1> to ⁇ 6>, wherein the content of the near-infrared absorbing dye in the total solid content of the composition is 1 to 20% by mass.
- the near-infrared absorbing dye is at least one selected from a pyrrolopyrrole compound, a phthalocyanine compound, a naphthalocyanine compound, and a polymethine compound. .. ⁇ 10> The composition according to any one of ⁇ 1> to ⁇ 9>, which is for a microlens.
- ⁇ 11> A film obtained by using the composition according to any one of ⁇ 1> to ⁇ 10>.
- ⁇ 12> A microlens having the film according to ⁇ 11>.
- ⁇ 13> A solid-state image sensor having the microlens according to ⁇ 12>.
- ⁇ 14> The display device having the microlens according to ⁇ 12>.
- a novel composition capable of forming a film such as a microlens having a near-infrared shielding property and a high collecting performance of visible light.
- a film, a microlens, a solid-state image sensor, and a display device using the composition can be provided.
- the notation not describing substitution and non-substitution includes a group having no substituent (atomic group) as well as a group having a 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).
- the term "exposure” as used herein includes not only exposure using light but also drawing using particle beams such as an electron beam and an ion beam.
- 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
- the numerical range represented by using "-" in the present specification means a range including the numerical values before and after "-" as the lower limit value and the upper limit value.
- the total solid content means the total mass of all the components of the composition excluding the solvent.
- “(meth) acrylate” represents both acrylate and methacrylate, or either
- “(meth) acrylic” represents both acrylic and methacrylic, or either.
- Allyl represents both allyl and methacrylic, or either, and“ (meth) acryloyl ”represents both acryloyl and methacrylic, or either.
- process is included in this term not only as an independent process but also as long as the desired action of the process is achieved even if it cannot be clearly distinguished from other processes. ..
- weight average molecular weight (Mw) and the number average molecular weight (Mn) are defined as polystyrene-equivalent values measured by gel permeation chromatography (GPC).
- composition Organic compound A having a refractive index of 1.58 or more with respect to light having a wavelength of 633 nm, Near-infrared absorbing pigment and A composition containing a solvent and The organic compound A is at least one selected from a polymerizable compound and a resin, and is When a film having a thickness of 0.35 ⁇ m is formed using the above composition, the above-mentioned film has a refractive index of 1.58 or more with respect to light having a wavelength of 633 nm, and the above-mentioned film transmits light having a wavelength of 400 to 600 nm.
- the minimum value of the rate is 85% or more.
- the composition of the present invention can provide a novel composition that has near-infrared shielding property and can form a film such as a microlens having high visible light condensing performance. That is, since the composition of the present invention contains a near-infrared absorbing dye, a film having near-infrared shielding property can be formed.
- the composition of the present invention further contains the organic compound A having a refractive index of 1.58 or more with respect to light having a wavelength of 633 nm, and when a film having a thickness of 0.35 ⁇ m is formed, the wavelength of the film is described above.
- the refractive index with respect to light of 633 nm is 1.58 or more and the minimum value of the light transmission of the above-mentioned film having a wavelength of 400 to 600 nm is 85% or more, it has near-infrared shielding property. While doing so, it is possible to form a film such as a microlens having a high ability to collect visible light.
- the composition of the present invention can be preferably used as a composition for a microlens. More preferably, it can be used for a microlens of a solid-state image sensor. More preferably, it can be used for a microlens of a solid-state image sensor provided with a color filter, which is arranged on an optical path on the light incident side to the color filter.
- the refractive index of the film with respect to light having a wavelength of 633 nm is 1.58 or more, preferably 1.60 or more. It is more preferably .62 or more.
- the average refractive index of the above-mentioned film with respect to light having a wavelength of 400 to 600 nm is preferably 1.60 or more, more preferably 1.62 or more, and further preferably 1.64 or more.
- the upper limit is not particularly limited, but may be 1.75 or less.
- Such a characteristic of refractive index can be achieved by adjusting the type and content of the organic compound A and the near-infrared absorbing dye. For example, it can be achieved by increasing the content of the organic compound A in the total solid content in the composition, using the organic compound A having a higher refractive index, or the like.
- the minimum value of the light transmittance of the film having a wavelength of 400 to 600 nm is 85% or more, and 90% or more. It is preferably 95% or more, and more preferably 95% or more.
- the average transmittance of light having a wavelength of 400 to 600 nm of the above-mentioned film is preferably 90% or more, more preferably 93% or more, and further preferably 96% or more.
- the content of a material having absorption in the visible region such as a chromatic colorant or a black colorant in the total solid content in the composition is reduced, and the visible transparency is achieved. This can be achieved by methods such as using a high near-infrared absorbing dye.
- the average transmittance of light having a wavelength of 800 to 870 nm of the above-mentioned film is preferably 80% or less, preferably 75% or less. Is more preferable, and 70% or less is further preferable. Further, the minimum value of the light transmittance of the above-mentioned film having a wavelength of 800 to 870 nm is preferably 70% or less, more preferably 65% or less, and further preferably 60% or less.
- the maximum value of the light transmittance of the above-mentioned film having a wavelength of 800 to 870 nm is preferably 85% or less, more preferably 82% or less, and further preferably 80% or less.
- Such a transmittance characteristic can be achieved by adjusting the type and content of the near-infrared absorbing dye. For example, it can be achieved by increasing the content of the near-infrared absorbing dye or using a near-infrared absorbing dye having a high absorption coefficient at the maximum absorption wavelength.
- the composition of the present invention does not substantially contain a chromatic colorant and a black colorant.
- the total content of the chromatic colorant and the black colorant is 0.1% by mass in the total solid content of the composition. It means that it is less than or equal to, preferably 0.05% by mass or less, further preferably 0.01% by mass or less, and particularly preferably not contained.
- the viscosity of the composition of the present invention at 25 ° C. is preferably 3 to 20 mPa ⁇ s from the viewpoint of coatability.
- the lower limit is preferably 4 mPa ⁇ s or more, and more preferably 5 mPa ⁇ s or more.
- the upper limit is preferably 15 mPa ⁇ s or less, and more preferably 13 mPa ⁇ s or less.
- the solid content concentration of the composition of the present invention is preferably 10 to 30% by mass from the viewpoint of coatability.
- the lower limit is preferably 13% by mass or more, more preferably 15% by mass or more.
- the upper limit is preferably 27% by mass or less, more preferably 25% by mass or less.
- the composition of the present invention contains an organic compound A having a refractive index of 1.58 or more with respect to light having a wavelength of 633 nm.
- the refractive index of the organic compound A with respect to light having a wavelength of 633 nm is preferably 1.63 or more.
- the upper limit of the refractive index is not particularly limited, but can be 1.80 or less.
- the content of the organic compound having a refractive index of 1.63 or more with respect to light having a wavelength of 633 nm in the total amount of the organic compound A contained in the composition is preferably 5 to 100% by mass, preferably 20 to 100% by mass. % Is more preferable, and 40 to 100% by mass is further preferable.
- the value of the refractive index of the organic compound A is such that the organic compound A is coated on a support such as a silicon wafer so that the film thickness after coating is 0.3 ⁇ m, and heated at 100 ° C. for 2 minutes and 200 ° C. for 5 minutes, and then an ellipsometer. It is a value measured using.
- Organic compound A is at least one selected from polymerizable compounds and resins.
- the polymerizable compound used as the organic compound A includes a compound having an ethylenically unsaturated bond-containing group, a compound having a cyclic ether group, a compound having a hydroxy group, a compound having a carboxy group, and a compound having an -NH 2 group.
- Examples of the ethylenically unsaturated bond-containing group include a vinyl group, a (meth) allyl group, and a (meth) acryloyl group.
- Examples of the cyclic ether group include an epoxy group and an oxetanyl group.
- the polymerizable compound used as the organic compound A may contain two or more kinds of polymerizable compounds.
- the polymerizable compound used as the organic compound A preferably contains at least one of a compound having an ethylenically unsaturated bond-containing group and a compound having a cyclic ether group.
- the organic compound A is preferably a monomer.
- the molecular weight of the organic compound A is preferably 200 to 1000.
- the upper limit is preferably 900 or less, more preferably 800 or less.
- the lower limit is preferably 250 or more, and more preferably 300 or more.
- the weight average molecular weight of the organic compound A is preferably 2000 to 100,000.
- the upper limit is preferably 90,000 or less, and more preferably 80,000 or less.
- the lower limit is preferably 3000 or more, and more preferably 4000 or more.
- the resin may have a polymerizable group such as an ethylenically unsaturated bond-containing group, a cyclic ether group, a hydroxy group, a carboxy group, or -NH 2 group.
- the composition of the present invention preferably contains two or more kinds of organic compounds A. Among them, it is preferable that one or more of the resin type organic compound A and the polymerizable compound type organic compound A are contained. According to such an aspect, it is possible to form a film having a small film shrinkage after film formation and a high strength.
- the composition of the present invention is a polymerizable compound type organic compound with respect to 100 parts by mass of the resin type organic compound A.
- the compound A is preferably contained in an amount of 10 to 800 parts by mass, more preferably 50 to 700 parts by mass. According to this aspect, the above-mentioned effect can be obtained more remarkably.
- the organic compound A is preferably a compound having at least one structure selected from a fluorene structure, a triazine structure and a carbazole structure. By using a compound having such a structure, a film having a high refractive index can be formed.
- the above-mentioned compound may be a monomer type compound or a resin type compound.
- Examples of the compound having a fluorene structure include a compound having a partial structure represented by the following formula (Fr). (Fr)
- R f1 and R f2 each represent a substituent
- m and n independently represent an integer of 0 to 5.
- m R f1s may be the same or different, and two R f1s out of m R f1s are bonded to each other to form a ring. May be good.
- n R f2s may be the same or different from each other, and two R f2s out of n R f2s are bonded to each other to form a ring. May be good.
- Examples of the substituent represented by R f1 and R f2 include a substituent T described later.
- Examples of the compound having a triazine structure include a compound having a partial structure represented by the following formula (Ta). The wavy line in the formula represents the bond. (Ta)
- the compound having a triazine structure is also preferably a compound having a group represented by the following formula (Ta-1). (Ta-1)
- C 1 to C 3 independently represent -NR N- , -O-, or -S-, respectively.
- RN represents a hydrogen atom, an alkyl group (preferably 1 to 7 carbon atoms), or an aryl group.
- C 1 to C 3 are preferably -NH-, -N (CH 3 )-, -O-, or -S-, and more preferably -NH-.
- Ar 1 and Ar 2 independently represent an aryl group or a heterocyclic group, respectively. As the aryl group, a phenyl group is preferable. Heterocyclic groups may or may not exhibit aromaticity, but are preferably aromatic.
- the number of heteroatoms constituting the heterocycle is preferably 1 to 3.
- the hetero atom constituting the hetero ring is preferably a nitrogen atom, an oxygen atom or a sulfur atom.
- the aryl group and the heterocyclic group may have a substituent. Examples of the substituent include a substituent T described later and a polymerizable group.
- the polymerizable group includes an ethylenically unsaturated bond-containing group such as a vinyl group, a (meth) allyl group, and a (meth) acryloyl group, a cyclic ether group such as an epoxy group and an oxetanyl group, a hydroxy group, a carboxy group, and -NH 2. The group and the like can be mentioned.
- Ar 3 represents an arylene group or a divalent heterocyclic group.
- arylene group a phenylene group is preferable.
- L A represents a single bond or a divalent linking group.
- the divalent linking group includes -NH-, -O-, -CO-, -CO-O-, an alkylene group (preferably 1 to 3 carbon atoms), or a combination thereof (for example, -O-alkylene).
- a group consisting of a group (etc.) is preferable.
- a preferable example of the compound having a triazine structure is a compound represented by the following formula (I).
- m represents an integer of 2 or more.
- n represents an integer of 0 or more.
- A represents a group represented by the formula (Ta-1).
- X represents a linking group having an m + n valence.
- B represents a polymer chain or substituent. It should be noted that the plurality of A's existing may be the same or different from each other. When there are a plurality of B's, the plurality of B's may be the same or different.
- the m + n-valent linking group represented by X is not particularly limited, and examples thereof include a group composed of the following structural units or a combination of two or more of the following structural units (which may form a ring structure). it can.
- the polymer chain represented by B is a chain having a plurality of predetermined repeating units.
- the structure of the polymer chain is not particularly limited and can be selected according to the purpose and the like.
- the polymer chain is a polymer selected from the group consisting of a polymer or copolymer of a vinyl monomer, an ester polymer, an ether polymer, a urethane polymer, an amide polymer, an epoxy polymer, and a silicone polymer.
- a polymer chain composed of a polymer chain is preferable, and a polymer chain composed of a polymer or copolymer of a (meth) acrylic compound is more preferable.
- the polymer chain may have a substituent.
- the weight average molecular weight of the polymer chain represented by B is preferably 200 to 10000, more preferably 300 to 5000. Further, as the substituent represented by B, a substituent T described later can be mentioned.
- the compound having a triazine structure it is also preferable that the compound is represented by the following formula (Ta-10). (Ta-10)
- C 1 to C 3 independently represent -NR N- , -O-, or -S-, respectively.
- RN represents a hydrogen atom, an alkyl group (preferably 1 to 7 carbon atoms), or an aryl group.
- C 1 to C 3 are preferably -NH-, -N (CH 3 )-, -O-, or -S-, and more preferably -NH-.
- Rt 1 to Rt 15 each independently represent a hydrogen atom or a substituent, and at least one of Rt 1 to Rt 15 represents a polymerizable group. Examples of the substituent include a substituent T described later and a polymerizable group.
- the polymerizable group includes an ethylenically unsaturated bond-containing group such as a vinyl group, a (meth) allyl group, and a (meth) acryloyl group, a cyclic ether group such as an epoxy group and an oxetanyl group, a hydroxy group, a carboxy group, and -NH. Two and the like can be mentioned. At least one of Rt 1 to Rt 5 and at least one of Rt 6 to Rt 10 preferably represent a polymerizable group, respectively, and any one of Rt 1 to Rt 5 and any one of Rt 6 to Rt 10 It is more preferable that each represents a polymerizable group.
- Examples of the compound having a carbazole structure include a compound having a partial structure represented by the following formula (Cz). (Cz)
- R c1 and R c2 each represent a substituent
- m2 and n2 independently represent an integer of 0 to 5.
- m2 R c1s may be the same or different, and two R c1s out of m2 R c1s are bonded to each other to form a ring. May be good.
- n2 is 2 or more, n2 pieces of R c2 may be the same or different, respectively, to form a n2 ring two R c2 are bonded to each other among the R c2 May be good.
- Examples of the substituent represented by R c1 and R c1 include the substituent T described later.
- organic compound A as a polymerizable compound examples include a compound having the following structure, Ogsol PG-100 (manufactured by Osaka Gas Chemical Co., Ltd., an epoxy compound having a fluorene structure), and Ogsol EG-200 (Osaka Gas). (Epoxy compound having a fluorene structure, manufactured by Chemical Co., Ltd.) and the like.
- organic compound A as a resin examples include a compound having the following structure, a resin described in Synthesis Example 1 of JP2013-139588A, and a resin described in Example 1 of JP2017-031311A. And so on.
- the content of the organic compound A in the total solid content of the composition is preferably 50% by mass or more, more preferably 55% by mass or more, still more preferably 60% by mass or more.
- the upper limit is preferably 98% by mass or less, more preferably 95% by mass or less.
- the content of the organic compound A in the total amount of the resin and the polymerizable compound contained in the composition is preferably 50 to 100% by mass, preferably 60 to 100%.
- the mass% is more preferable, and 70 to 100% by mass is further preferable.
- the composition of the present invention contains a near-infrared absorbing dye.
- the near-infrared absorbing dye used in the present invention is preferably a compound having a maximum absorption wavelength in the wavelength range of 750 to 1000 nm, and more preferably a compound having a maximum absorption wavelength in the wavelength range of 770 to 950 nm. It is more preferable that the compound has a maximum absorption wavelength in the wavelength range of 800 to 900 nm.
- the ratio A 1 / A 2 between the absorbance A 1 at the wavelength 500nm near-infrared absorbing dye and absorbance A 2 at the maximum absorption wavelength is more be preferably 0.08 or less, 0.04 or less preferable.
- the near-infrared absorbing dye may be a pigment or a dye.
- a pigment When a pigment is used, a film having excellent heat resistance and light resistance can be formed.
- a dye When a dye is used, a film having a small haze can be formed.
- Near-infrared absorbing dyes include pyrolopyrrole compounds, phthalocyanine compounds, naphthalocyanine compounds, polymethine compounds, iminium compounds, quaterylene compounds, dithiol compounds, triarylmethane compounds, pyromethene compounds, azomethine compounds, anthraquinone compounds, dibenzofuranone compounds and dithiolene metals. Examples thereof include at least one selected from a pyrolopyrrole compound, a phthalocyanine compound, a naphthalocyanine compound and a polymethine compound, and more preferably a pyrolopyrrole compound.
- the polymethine compound include a cyanine compound, a squarylium compound, and a croconium compound.
- the pyrrolopyrrole compound is preferably a compound represented by the formula (PP).
- R 1a and R 1b each independently represent an alkyl group, an aryl group or a heteroaryl group
- R 2 and R 3 each independently represent a hydrogen atom or a substituent
- R 2 and R 3 are. They may be bonded to each other to form a ring
- R 4 independently represents a hydrogen atom, an alkyl group, an aryl group, a heteroaryl group, -BR 4A R 4B , or a metal atom, where R 4 is R. It may be covalently or coordinated with at least one selected from 1a, R 1b and R 3 , where R 4A and R 4B each independently represent a substituent.
- R 1a and R 1b are each independently preferably an aryl group or a heteroaryl group, and more preferably an aryl group. Further, the alkyl group, aryl group and heteroaryl group represented by R 1a and R 1b may have a substituent or may be unsubstituted. Examples of the substituent include the substituents described in paragraphs 0020 to 0022 of JP-A-2009-263614 and the following substituents T. When the alkyl group, aryl group and heteroaryl group represented by R 1a and R 1b have two or more substituents, the substituents may be bonded to each other to form a ring.
- Alkyl group preferably an alkyl group having 1 to 30 carbon atoms
- an alkenyl group preferably an alkenyl group having 2 to 30 carbon atoms
- an alkynyl group preferably an alkynyl group having 2 to 30 carbon atoms
- an aryl group preferably an alkyl group having 2 to 30 carbon atoms.
- an amino group preferably an amino group having 0 to 30 carbon atoms
- an alkoxy group preferably an alkoxy group having 1 to 30 carbon atoms
- an aryloxy group preferably 6 to 30 carbon atoms.
- aryloxy group preferably acyl group having 1 to 30 carbon atoms
- alkoxycarbonyl group preferably alkoxycarbonyl group having 2 to 30 carbon atoms
- aryloxycarbonyl group preferably an acyl group having 2 to 30 carbon atoms.
- an acyloxy group preferably an acyloxy group having 2 to 30 carbon atoms
- an acylamino group preferably an acylamino group having 2 to 30 carbon atoms
- alkoxycarbonylamino group preferably).
- a carbamoyl group having 1 to 30 carbon atoms an alkylthio group (preferably an alkylthio group having 1 to 30 carbon atoms), an arylthio group (preferably an arylthio group having 6 to 30 carbon atoms), a heteroarylthio group (preferably a heteroarylthio group).
- alkylsulfonyl group preferably 1 to 30 carbon atoms
- arylsulfonyl group preferably 6 to 30 carbon atoms
- heteroarylsulfonyl group preferably 1 to 30 carbon atoms
- alkylsulfinyl group Preferably 1 to 30 carbon atoms
- arylsulfinyl group preferably 6 to 30 carbon atoms
- heteroarylsulfinyl group preferably 1 to 30 carbon atoms
- ureido group preferably 1 to 30 carbon atoms
- hydroxyl group , a carboxyl group, a sulfo group, a phosphoric acid group, a carboxylic acid amide group (preferably a group represented by -NHCOR A1, R A1 represents a hydrocarbon group or a heterocyclic group.
- substituent is preferably a halogen atom, more preferably a fluorine atom.
- a sulfonic acid amide group preferably by -NHSO 2 R A2 a is .
- R A2 is a group that is, a hydrocarbon group or a heterocyclic group.
- hydrocarbon The group and the heterocyclic group may further have a substituent.
- the substituent is preferably a halogen atom, more preferably a fluorine atom.
- Imidate group (preferably, -SO 2 NHSO 2 R A3, -CONHSO 2 R A4, .R A3 ⁇ R A6 is a group represented by -CONHCOR A5 or -SO 2 NHCOR A6 are each independently Represents a hydrocarbon group or a heterocyclic group.
- the hydrocarbon group and the heterocyclic group may further have a substituent), a mercapto group, a halogen atom, a cyano group, an alkylsulfino group, an arylsulfino group. , Hydradino group, imino group, heteroaryl group (preferably 1 to 30 carbon atoms).
- These groups may have additional substituents if they are further substitutable groups. Examples of the substituent include the group described in the above-mentioned Substituent T.
- R 1a and R 1b include an aryl group having an alkoxy group as a substituent, an aryl group having a hydroxyl group as a substituent, an aryl group having an acyloxy group as a substituent, and the like.
- R 2 and R 3 each independently represent a hydrogen atom or substituent.
- the substituent include the above-mentioned Substituent T.
- At least one of R 2 and R 3 is preferably an electron attracting group.
- a substituent having a positive Hammett substituent constant ⁇ value acts as an electron-attracting group.
- the substituent constants obtained by Hammett's law include ⁇ p value and ⁇ m value. These values can be found in many common books.
- a substituent having a Hammett substituent constant ⁇ value of 0.20 or more can be exemplified as an electron-attracting group.
- the ⁇ value is preferably 0.25 or more, more preferably 0.30 or more, and even more preferably 0.35 or more.
- the upper limit is not particularly limited, but is preferably 0.80 or less.
- Me represents a methyl group and Ph represents a phenyl group.
- ⁇ value for example, paragraphs 0017 to 0018 of JP2011-066731A can be referred to, and the contents thereof are incorporated in the present specification.
- R 2 preferably represents an electron-attracting group (preferably a cyano group) and R 3 preferably represents a heteroaryl group.
- the heteroaryl group is preferably a 5-membered ring or a 6-membered ring.
- the heteroaryl group is preferably a monocyclic ring or a condensed ring, preferably a monocyclic ring or a condensed ring having a condensed number of 2 to 8, and more preferably a monocyclic ring or a condensed ring having a condensed number of 2 to 4.
- the number of heteroatoms constituting the heteroaryl group is preferably 1 to 3, more preferably 1 to 2.
- hetero atom examples include a nitrogen atom, an oxygen atom, and a sulfur atom.
- the heteroaryl group preferably has one or more nitrogen atoms.
- Two R 2 together in the formula (PP) may be the same or may be different.
- two R 3 together in the formula (PP) may be the same or may be different.
- R 4 is preferably a hydrogen atom, an alkyl group, an aryl group, a heteroaryl group or a group represented by -BR 4A R 4B, preferably a hydrogen atom, an alkyl group, an aryl group or -BR. more preferably a group represented by 4A R 4B, and more preferably a group represented by -BR 4A R 4B.
- R 4A and R 4B a substituent represented by R 4A and R 4B , a halogen atom, an alkyl group, an alkoxy group, an aryl group or a heteroaryl group is preferable, an alkyl group, an aryl group or a heteroaryl group is more preferable, and an aryl group is preferable. Especially preferable.
- These groups may further have substituents.
- Two R 4 together in the formula (PP) may be the same or may be different.
- R 4A and R 4B may be coupled to each other to form a ring.
- Examples of the compound represented by the formula (PP) include the compounds described in Examples described later.
- 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 paragraph numbers 0010 to 0033 of the issue.
- 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. 2016/190162, the compound described in paragraph number 0196-0228 of JP-A-2016-074649. , The compound described in paragraph No. 0124 of JP-A-2017-067963, the compound described in International Publication No.
- Examples of the croconium compound include the compounds described in JP-A-2017-082029.
- Examples of the iminium compound include the compounds described in JP-A-2008-528706, the compounds described in JP-A-2012-012399, the compounds described in JP-A-2007-092060, and International Publication No. 2018/043564.
- the compounds described in paragraph numbers 0048 to 0063 of the above are mentioned.
- Examples of the phthalocyanine compound include the compound described in paragraph No. 0093 of 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.
- Examples of the dithiolene metal complex include the compounds described in Japanese Patent No.
- Examples of the near-infrared absorbing dye 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 Patent No. Squalylium compounds described in 5884953, squalylium compounds described in Japanese Patent No. 6036689, squalylium compounds described in Japanese Patent No. 5810604, squalylium compounds described in paragraph numbers 0090 to 0107 of International Publication No.
- An amide-linked squalylium compound a compound having a pyrrolbis-type squalylium 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 near-infrared absorbing dye in the total solid content of the composition is preferably 1 to 20% by mass.
- the lower limit is preferably 2% by mass or more, and more preferably 3% by mass or more.
- the upper limit is preferably 17% by mass or less, more preferably 15% by mass or less.
- the total content of the above-mentioned organic compound A and the near-infrared absorbing dye in the total solid content of the composition is preferably 70% by mass or more, more preferably 75% by mass or more, and 80% by mass. It is more preferably% or more.
- the upper limit can be 100% by mass or less, and can be 98% by mass or less.
- the composition preferably contains 1 to 30 parts by mass of the near-infrared absorbing dye with respect to 100 parts by mass of the above-mentioned organic compound A.
- the lower limit is preferably 2 parts by mass or more, and more preferably 3 parts by mass or more.
- the upper limit is preferably 25 parts by mass or less, more preferably 20 parts by mass or less. According to this aspect, it is possible to achieve both high near-infrared absorption performance and high refractive index.
- composition of the present invention only one type of near-infrared absorbing dye may be used, or two or more types may be used. When two or more types are used, it is preferable that the total amount thereof is within the above range.
- the 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 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, cyclohexanone, cyclohexyl acetate, cyclopentanone, ethyl carbitol acetate, butyl carbitol acetate, propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, 3-methoxy-N, N-dimethylpropanamide, 3-butoxy-N , N-Dimethylpropanamide and the like.
- aromatic hydrocarbons (benzene, toluene, xylene, ethylbenzene, etc.) as organic solvents may need to be reduced for environmental reasons (for example, 50 mass ppm (parts) with respect to the total amount of organic solvent. Per million) or less, 10 mass ppm or less, or 1 mass ppm or less).
- a solvent having a low metal content it is preferable to use a solvent having a low metal content, and the metal content of the solvent is preferably, for example, 10 mass ppb (parts per parts) or less. If necessary, a solvent at the mass ppt (parts per trillion) level may be used, and such a high-purity 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 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 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 composition is preferably 70 to 90% by mass.
- the lower limit is preferably 73% by mass or more, and more preferably 75% by mass or more.
- the upper limit is preferably 87% by mass or less, and more preferably 85% by mass or less.
- the composition of the present invention can contain a polymerizable compound other than the above-mentioned organic compound A (hereinafter, also referred to as another polymerizable compound).
- the other polymerizable compound include a compound having an ethylenically unsaturated bond-containing group, a compound having a cyclic ether group, and the like, 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 oxetanyl group.
- the compound having an ethylenically unsaturated bond-containing group may be in any chemical form such as a monomer, a prepolymer, or an oligomer, but a monomer is preferable.
- the molecular weight of the compound having an ethylenically unsaturated bond-containing group 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 is preferably a compound containing 3 or more ethylenically unsaturated bond-containing groups, and preferably a compound containing 3 to 15 ethylenically unsaturated bond-containing groups. More preferably, it is a compound containing 3 to 6 ethylenically unsaturated bond-containing groups.
- 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, paragraph 0227 of JP2013-209760A, and paragraphs of JP2008-292970. Nos. 0254 to 0257, paragraphs 0034 to 0038 of JP2013-253224, 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.
- Examples of the compound 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).
- KAYARAD D-320 manufactured by Nippon Kayaku Co., Ltd.
- dipentaerythritol penta (meth) acrylate commercially available KAYARAD D-310; manufactured by Nihon Kayaku Co., Ltd.
- dipentaerythritol hexa (meth) acrylate commercially available
- KAYARAD DPHA manufactured by Nippon Kayaku Co., Ltd.
- NK ester A-DPH-12E manufactured by Shin-Nakamura Chemical Industry Co., Ltd.
- these (meth) acryloyl groups are ethylene glycol and / or propylene glycol residues.
- Examples thereof include compounds having a structure bound to each other (for example, SR454 and SR499 commercially available from Sartmer).
- Examples of the compound having an ethylenically unsaturated bond-containing group include trimethylolpropane tri (meth) acrylate, trimethylolpropane propyleneoxy-modified tri (meth) acrylate, trimethylolpropane ethyleneoxy-modified tri (meth) acrylate, and isocyanuric acid.
- Trifunctional (meth) acrylate compounds such as ethyleneoxy-modified tri (meth) acrylate and pentaerythritol tri (meth) acrylate can also be used.
- 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 acid group include a carboxyl group, a sulfo group, a phosphoric acid group and the like, and a carboxyl group is preferable.
- examples of commercially available products include Aronix M-510, M-520, and Aronix TO-2349 (manufactured by Toagosei Co., Ltd.).
- the compound having an ethylenically unsaturated bond-containing group is preferably 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.
- the compound having a cyclic ether group is preferably a compound having an epoxy group (hereinafter, also referred to as an epoxy compound).
- the epoxy compound include compounds having one or more epoxy groups in one molecule, and compounds having two or more epoxy groups are preferable.
- the epoxy compound is preferably a compound having 1 to 100 epoxy groups in one molecule.
- the upper limit of the epoxy group may be, for example, 10 or less, or 5 or less.
- the lower limit of the epoxy group is preferably two or more.
- Examples of the epoxy compound include the compounds described in paragraphs 0034 to 0036 of JP2013-011869, the compounds described in paragraphs 0147 to 0156 of JP2014-043556, and JP2014-089408.
- the compounds described in paragraph Nos. 0085 to 0092 of the above, and the compounds described in JP-A-2017-179172 can also be used.
- the epoxy compound may be a low molecular weight compound (for example, a molecular weight of less than 2000, further, a molecular weight of less than 1000), or a high molecular weight compound (macromolecule) (for example, a molecular weight of 1000 or more, and in the case of a polymer, a weight average molecular weight of 1000 or more). It may be any of.
- the weight average molecular weight of the epoxy compound is preferably 200 to 100,000, more preferably 500 to 50,000.
- the upper limit of the weight average molecular weight is preferably 10,000 or less, more preferably 5000 or less, and even more preferably 3000 or less.
- EHPE3150 manufactured by Daicel Co., Ltd.
- EPICLON N-695 manufactured by DIC Corporation
- Marproof G-0150M Marproof G-0150M, G-0105SA, G-0130SP, G. -0250SP, G-1005S, G-1005SA, G-1010S, G-2050M, G-01100, G-01758 (all manufactured by Nichiyu Co., Ltd., epoxy group-containing polymer) and the like can be mentioned.
- the content of the other polymerizable compound in the total solid content of the composition is preferably 30% by mass or less, more preferably 25% by mass or less, still more preferably 20% by mass or less. It is also preferable that the composition of the present invention does not substantially contain other polymerizable compounds. According to this aspect, a film having a higher refractive index can be formed.
- the composition of the present invention does not substantially contain other polymerizable compounds, it means that the content of the other polymerizable compounds is 0.1% by mass or less in the total solid content of the composition. However, it is preferably 0.05% by mass or less, more preferably 0.01% by mass or less, and particularly preferably not contained.
- the composition of the present invention can contain a resin other than the above-mentioned organic compound A (hereinafter, also referred to as another resin).
- the resin is blended, for example, for the purpose of dispersing particles such as pigments in the composition and for the purpose of a binder.
- the resin mainly used for dispersing particles and the like in the composition is also referred to as a dispersant.
- a dispersant such an application of the resin is an example, and the resin can be used for purposes other than such an application.
- the weight average molecular weight (Mw) of the other resin is preferably 2000 to 2000000.
- the upper limit is preferably 1,000,000 or less, and more preferably 500,000 or less.
- the lower limit is preferably 3000 or more, more preferably 4000 or more, and even more preferably 5000 or more.
- Examples of other resins include (meth) acrylic resin, (meth) acrylamide resin, epoxy resin, en-thiol resin, polycarbonate resin, polyether resin, polyarylate resin, polysulfone resin, polyethersulfone resin, polyphenylene resin, and the like.
- Examples thereof include polyarylene ether phosphine oxide resin, polyimide resin, polyamideimide resin, polyolefin resin, cyclic olefin resin, polyester resin, styrene resin, and siloxane resin.
- resins may have an acid group.
- the acid group include a carboxyl group, a phosphoric acid group, a sulfo group, and a phenolic hydroxy group. These acid groups may be only one kind or two or more kinds.
- the resin having an acid group can also be used as an alkali-soluble resin or a dispersant.
- the acid value of the acid group of the other resin is preferably 30 to 500 mgKOH / g.
- the lower limit is more preferably 50 mgKOH / g or more, and even more preferably 70 mgKOH / g or more.
- the upper limit is more preferably 400 mgKOH / g or less, further preferably 200 mgKOH / g or less, particularly preferably 150 mgKOH / g or less, and most preferably 120 mgKOH / g or less.
- the other resin is a repeating unit derived from 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 that the resin contains the resin.
- 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 the content thereof is incorporated in the present specification.
- resins may have an ethylenically unsaturated bond-containing group.
- the ethylenically unsaturated bond-containing group include a vinyl group, a (meth) allyl group, and a (meth) acryloyl group.
- Commercially available products of resins having an ethylenically unsaturated bond-containing group include Dianal NR series (manufactured by Mitsubishi Rayon Co., Ltd.), Photomer 6173 (carboxyl group-containing polyurethane acrylate oligomer, Diamond Shamlock Co., Ltd.), and Viscort R.
- KS Resist 106 (all manufactured by Osaka Organic Chemical Industry Co., Ltd.), Cyclomer P series (for example, ACA230AA), Praxel CF200 series (all manufactured by Daicel Co., Ltd.), Ebeclyl3800 (manufactured by Daicel UCB Co., Ltd.) ), Acrycure RD-F8 (manufactured by Nippon Catalyst Co., Ltd.), DP-1305 (manufactured by Fujifilm Fine Chemicals Co., Ltd.) and the like.
- Cyclomer P series for example, ACA230AA
- Praxel CF200 series all manufactured by Daicel Co., Ltd.
- Ebeclyl3800 manufactured by Daicel UCB Co., Ltd.
- Acrycure RD-F8 manufactured by Nippon Catalyst Co., Ltd.
- DP-1305 manufactured by Fujifilm Fine Chemicals Co., Ltd.
- the other resin is 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 carboxyl 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 is also preferably a graft copolymer. Since the graft copolymer has an affinity with a solvent due to the graft chain, it is excellent in the dispersibility of the pigment and the dispersion stability after aging.
- the description in paragraphs 0025 to 0094 of JP2012-255128A can be referred to, and the content thereof is incorporated in the present specification.
- Specific examples of the graft copolymer include the following resins. Further, examples of the graft copolymer include the resins described in paragraphs 0072 to 0094 of JP-A-2012-255128, the contents of which are incorporated in the present specification.
- an oligoimine resin containing a nitrogen atom in at least one of the main chain and the side chain is also preferable to use as the dispersant.
- the oligoimine-based resin has a structural unit having a partial structure X having a functional group of pKa14 or less, a side chain containing a side chain Y having 40 to 10,000 atoms, and at least a main chain and a side chain.
- a resin having a basic nitrogen atom on one side is preferable.
- the description in paragraphs 0102 to 0166 of JP2012-255128A can be referred to, and this content is incorporated in the present specification.
- As the oligoimine-based resin a resin having the following structure or the resin described in paragraphs 0168 to 0174 of JP2012-255128A can be used.
- Dispersants are also available as commercial products, and specific examples thereof include the Disperbyk series manufactured by Big Chemie (for example, Disperbyk-111, 2001, etc.) and the Solsparse series manufactured by Nippon Lubrizol Co., Ltd. For example, Solsparse 20000, 76500, etc.), Ajinomoto Fine Techno Co., Ltd.'s Ajispar series and the like can be mentioned. Further, the product described in paragraph number 0129 of JP2012-137564A and the product described in paragraph number 0235 of JP2017-194662 can also be used as a dispersant.
- the content of the other resin in the total solid content of the composition is preferably 30% by mass or less, more preferably 25% by mass or less, still more preferably 20% by mass or less. It is also preferable that the composition of the present invention does not substantially contain other resins. According to this aspect, a film having a higher refractive index can be formed.
- the case where the composition of the present invention does not substantially contain another resin means that the content of the other resin is 0.1% by mass or less in the total solid content of the composition, and 0. It is preferably 05% by mass or less, more preferably 0.01% by mass or less, and particularly preferably not contained.
- the composition of the present invention can contain a pigment derivative.
- the composition preferably contains a pigment derivative.
- the pigment derivative include compounds having a structure in which an acid group or a basic group is bonded to the pigment skeleton.
- the pigment skeletons constituting the pigment derivatives include quinoline pigment skeleton, benzoimidazolone pigment skeleton, benzoisoindole pigment skeleton, benzothiazole pigment skeleton, inimium pigment skeleton, squarylium pigment skeleton, croconium pigment skeleton, oxonol pigment skeleton, and pyrolopyrrole pigment.
- Examples of the acid group include a sulfo group, a carboxyl group, a phosphoric acid group and salts thereof.
- the atoms or groups that make up the salt include alkali metal ions (Li + , Na + , K +, etc.), alkaline earth metal ions (Ca 2+ , Mg 2+, etc.), ammonium ions, imidazolium ions, pyridinium ions, etc.
- Examples include phosphonium ions.
- Examples of the basic group include an amino group, a pyridinyl group and a salt thereof, a salt of an ammonium group, and a phthalimide methyl group.
- Examples of the atom or atomic group constituting the salt include hydroxide ion, halogen ion, carboxylic acid ion, sulfonic acid ion, and phenoxide ion.
- pigment derivative examples include the compounds described in Examples described later, JP-A-56-118462, JP-A-63-246674, JP-A-01-217777, and JP-A-03-009961.
- Japanese Patent Application Laid-Open No. 03-026767 Japanese Patent Application Laid-Open No. 03-153780
- Japanese Patent Application Laid-Open No. 03-045662 Japanese Patent Application Laid-Open No. 04-285669
- Japanese Patent Application Laid-Open No. 06-145546 Japanese Patent Application Laid-Open No. 06-212088, Kaihei 06-240158
- Japanese Patent Application Laid-Open No. 10-030063 Japanese Patent Application Laid-Open No.
- the content of the pigment derivative is preferably 1 to 30 parts by mass, more preferably 3 to 20 parts by mass with respect to 100 parts by mass of the pigment. Only one type of pigment derivative may be used, or two or more types may be used in combination. When two or more types are used in combination, the total amount thereof is preferably in the above range.
- the composition of the present invention may contain a photopolymerization initiator.
- the photopolymerization initiator is not particularly limited and may be appropriately selected from known photopolymerization initiators. For example, a compound having photosensitivity to light rays in the ultraviolet region to the visible region is preferable.
- the photopolymerization initiator is preferably a photoradical polymerization initiator.
- photopolymerization initiator examples include halogenated hydrocarbon derivatives (for example, compounds having a triazine skeleton, compounds having an oxadiazole skeleton, etc.), acylphosphine compounds, hexaarylbiimidazoles, oxime compounds, organic peroxides, and thio compounds. , Ketone compounds, aromatic onium salts, ⁇ -hydroxyketone compounds, ⁇ -aminoketone compounds and the like.
- the photopolymerization initiator is a trihalomethyltriazine compound, a benzyl dimethyl ketal compound, an ⁇ -hydroxyketone compound, an ⁇ -aminoketone compound, an acylphosphine compound, a phosphine oxide compound, a metallocene compound, an oxime compound, or a triarylimidazole.
- It is preferably a dimer, an onium compound, a benzothiazole compound, a benzophenone compound, an acetophenone compound, a cyclopentadiene-benzene-iron complex, a halomethyloxaziazole compound and a 3-aryl substituted coumarin compound, and an oxime compound and an ⁇ -hydroxyketone compound.
- ⁇ -Aminoketone compound, and an acylphosphine compound are more preferable, and an oxime compound is further preferable.
- the photopolymerization initiator the compounds described in paragraphs 0065 to 0111 of JP-A-2014-130173 and JP-A-6301489, MATERIAL STAGE 37-60p, vol.
- ⁇ -hydroxyketone compounds Commercially available products of the ⁇ -hydroxyketone compound include Omnirad 184, Omnirad 1173, Omnirad 2959, Omnirad 127 (manufactured by IGM Resins BV), Irgacare 184, Irgacare 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-propionyloxyiminovtan-2-one, 2-acetoxyimiminopentane-3-one, 2-acetoxyimino-1-phenylpropane-1-one, 2-benzoyloxyimino-1-phenylpropane-1-one, 3- (4-toluenesulfonyloxy) iminobutane-2-one, and 2-ethoxycarbonyloxy Examples thereof include imino-1-phenylpropane-1-one.
- an oxime compound having a fluorene ring can also be used.
- Specific examples of the oxime compound having a fluorene ring include the compounds described in JP-A-2014-137466.
- an oxime compound having a skeleton in which at least one benzene ring of the carbazole ring is a naphthalene ring can also be used.
- Specific examples of such an oxime compound include the compounds described in International Publication No. 2013/083505.
- an oxime compound having a fluorine atom can also be used as the photopolymerization initiator.
- Specific examples of the oxime compound having a fluorine atom are described in the compounds described in JP-A-2010-262028, compounds 24, 36-40 described in JP-A-2014-500852, and JP-A-2013-164471. Compound (C-3) and the like.
- an oxime compound having a nitro group can be used as the photopolymerization initiator.
- the oxime compound having a nitro group is also preferably a dimer.
- Specific examples of the oxime compound having a nitro group include the compounds described in paragraphs 0031 to 0047 of JP2013-114249A and paragraphs 0008-0012 and 0070-0079 of JP2014-137466. Examples thereof include the compound described in paragraphs 0007 to 0025 of Japanese Patent No. 4223071, ADEKA ARKULS NCI-831 (manufactured by ADEKA Corporation).
- an oxime compound having a benzofuran skeleton can also be used.
- 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 an ethyl acetate solvent 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.
- 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 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 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. When two or more types are used, it is preferable that the total amount thereof is within the above range.
- the composition of the present invention can contain a white or colorless pigment (hereinafter, also referred to as a white pigment).
- a white pigment at least one element selected from Ti, Zr, Sn, Sb, Cu, Fe, Mn, Pb, Cd, As, Cr, Hg, Zn, Al, Mg, Si, P and S can be used.
- oxide particles containing, and preferably oxide particles containing at least one element selected from Ti, Zr, Sn, Al, and Si As the oxide, titanium oxide and zirconium oxide are preferable, and titanium oxide is more preferable.
- titanium oxide examples include rutile-type titanium oxide, anatase-type titanium oxide, and amorphous titanium oxide, and rutile-type titanium oxide is preferable. It is also preferable that the above oxide is surface-treated with a surface treatment agent.
- the surface treatment agent include inorganic compounds and organic compounds. Inorganic compounds and organic compounds may be used in combination. Specific examples of the surface treatment agent include polyol, aluminum oxide, aluminum hydroxide, amorphous silica, hydrous silica, alkanolamine, stearic acid, organosiloxane, zirconium oxide, hydrogen dimethicone, silane coupling agent, and titanate coupling agent. And so on.
- an isotropic shape for example, a spherical shape, a polyhedral shape, etc.
- an anisotropic shape for example, a needle shape, a rod shape, a plate shape, etc.
- an amorphous shape and the like can be mentioned.
- the weight average particle size of the primary particles of the white pigment is preferably 150 nm or less, more preferably 100 nm or less, and further preferably 80 nm or less. There is no particular lower limit, but it is preferably 1 nm or more.
- the mixed liquid or the dispersion liquid containing the white pigment is diluted 80 times with propylene glycol monomethyl ether acetate, and the obtained diluted liquid is dynamically diluted. It is obtained by measuring using the light scattering method. The measured value in this case is the weight average particle diameter obtained by using the Microtrack (trade name) UPA-EX150 manufactured by Nikkiso Co., Ltd.
- the specific surface area of the white pigment is preferably 10 to 400 m 2 / g, more preferably 20 to 200 m 2 / g, and even more preferably 30 to 150 m 2 / g.
- the refractive index of the white pigment is preferably 1.6 to 3.0.
- the lower limit is preferably 1.7 or more, and more preferably 1.8 or more.
- the upper limit is preferably 2.9 or less, and more preferably 2.8 or less.
- the method for measuring the refractive index of white pigments conforms to the Japanese Industrial Standards (JIS K 0062: 1992).
- a commercially available product may be used as the white pigment.
- TTO series TTO-51 (A), TTO-51 (C), TTO-55 (C), etc.
- TTO-S V series (TTO-S-1, TTO-S-).
- TTO-V-3, etc. above, product name, manufactured by Ishihara Sangyo Co., Ltd.
- MT series MT-01, MT-05, etc.
- TAYCA Corporation product name
- the composition of the present invention can contain a curing accelerator.
- the curing accelerator include thiol compounds, methylol compounds, amine compounds (aliphatic amines, aromatic amines, heterocyclic amines, etc.), phosphonium salt compounds, amidin salt compounds, amide compounds, base generators, isocyanate compounds, and alkoxysilanes. Examples thereof include compounds, onium salt compounds, and phosphorus compounds.
- Specific examples of the curing accelerator include the compounds described in paragraphs 0094 to 0097 of WO2018 / 056189, the compounds described in paragraphs 0246 to 0253 of JP2015-034963, and JP2013-014165.
- the content of the curing accelerator in the total solid content of the composition is preferably 0.3 to 8.9% by mass, more preferably 0.8 to 6.4% by mass.
- only one type of curing accelerator may be used, or two or more types may be used. When two or more types are used, it is preferable that the total amount thereof is within the above range.
- the composition of the present invention can contain a silane coupling agent.
- a silane coupling agent a silane compound having at least two kinds of functional groups having different reactivity in one molecule is preferable.
- the silane coupling agent includes at least one group selected from a vinyl group, an epoxy group, a styrene group, a methacryl group, an amino group, an isocyanurate group, a ureido group, a mercapto group, a sulfide group, and an isocyanate group, and an alkoxy group.
- silane coupling agent examples include N-2- (aminoethyl) -3-aminopropylmethyldimethoxysilane (manufactured by Shin-Etsu Chemical Industry Co., Ltd., KBM-602), N-2- (aminoethyl) -3.
- the content of the silane coupling agent in the total solid content of the composition is preferably 0.001 to 20% by mass, more preferably 0.01 to 10% by mass, and particularly preferably 0.1% to 5% by mass. ..
- the composition of the present invention may contain only one type of silane coupling agent, or may contain two or more types of silane coupling agent. When two or more types are contained, it is preferable that the total amount thereof is within the above range.
- the composition of the present invention can contain a polymerization inhibitor.
- the polymerization inhibitor include hydroquinone, p-methoxyphenol, di-t-butyl-p-cresol, pyrogallol, t-butylcatechol, benzoquinone, quaternary-thiobis (3-methyl-6-t-butylphenol), and the like. Examples thereof include 2,2'-methylenebis (4-methyl-6-t-butylphenol), N-nitrosophenylhydroxyamine salt (ammonium salt, first cerium salt, etc.).
- the content of the polymerization inhibitor in the total solid content of the composition is preferably 0.0001 to 5% by mass.
- the composition of the present invention may contain only one type of polymerization inhibitor, or may contain two or more types of polymerization inhibitors. When two or more types are contained, it is preferable that the total amount thereof is within the above range.
- the composition of the present invention can contain an ultraviolet absorber.
- the ultraviolet absorber include conjugated diene compounds, aminodiene compounds, salicylate compounds, benzophenone compounds, benzotriazole compounds, acrylonitrile compounds, hydroxyphenyltriazine compounds, indol compounds, and triazine compounds. Examples of such compounds include paragraph numbers 0038 to 0052 of JP2009-217221A, paragraph numbers 0052 to 0072 of JP2012-208374A, and paragraph numbers 0317 to 0334 of JP2013-068814. Examples include the compounds described in paragraphs 0061 to 0080 of JP 2016-162946, the contents of which are incorporated herein.
- benzotriazole compound examples include the MYUA series made by Miyoshi Oil & Fat Co., Ltd. (The Chemical Daily, February 1, 2016). Further, as the ultraviolet absorber, the compounds described in paragraphs 0049 to 0059 of Japanese Patent No. 6268967 can also be used.
- the content of the ultraviolet absorber in the total solid content of the composition is preferably 0.1 to 10% by mass, more preferably 0.1 to 5% by mass, and particularly preferably 0.1 to 3% by mass.
- the composition of the present invention may contain only one kind of ultraviolet absorber, or may contain two or more kinds of ultraviolet absorbers. When two or more types are contained, it is preferable that the total amount thereof is within the above range.
- the composition of the present invention can contain an antioxidant.
- the antioxidant include phenol compounds, phosphite ester compounds, thioether compounds and the like.
- the phenol compound any phenol compound known as a phenolic antioxidant can be used.
- Preferred phenolic compounds include hindered phenolic compounds.
- a compound having a substituent at a site (ortho position) adjacent to the phenolic hydroxy group is preferable.
- a substituted or unsubstituted alkyl group having 1 to 22 carbon atoms is preferable.
- the antioxidant a compound having a phenol group and a phosphite ester group in the same molecule is also preferable.
- a phosphorus-based antioxidant can also be preferably used.
- a phosphorus-based antioxidant tris [2-[[2,4,8,10-tetrakis (1,1-dimethylethyl) dibenzo [d, f] [1,3,2] dioxaphosfepine-6 -Il] Oxy] Ethyl] amine, Tris [2-[(4,6,9,11-tetra-tert-butyldibenzo [d, f] [1,3,2] dioxaphosfepin-2-yl] ) Oxy] ethyl] amine, ethylbis phosphite (2,4-di-tert-butyl-6-methylphenyl) and the like.
- antioxidants include, for example, Adekastab AO-20, Adekastab AO-30, Adekastab AO-40, Adekastab AO-50, Adekastab AO-50F, Adekastab AO-60, Adekastab AO-60G, Adekastab AO-80. , ADEKA STAB AO-330 (above, manufactured by ADEKA Corporation) and the like.
- the antioxidant the compounds described in paragraphs 0023 to 0048 of Japanese Patent No. 6268967, the compounds described in International Publication No. 2017/006600, and the compounds described in International Publication No. 2017/164024 are used. It can also be used.
- the content of the antioxidant in the total solid content of the composition is preferably 0.01 to 20% by mass, more preferably 0.3 to 15% by mass.
- the composition of the present invention may contain only one type of antioxidant, or may contain two or more types of antioxidants. When two or more types are contained, it is preferable that the total amount thereof is within the above range.
- the composition of the present invention can contain a surfactant.
- a surfactant various surfactants such as a fluorine-based surfactant, a nonionic surfactant, a cationic surfactant, an anionic surfactant, and a silicon-based surfactant can be used.
- the surfactant the surfactant described in paragraph Nos. 0238 to 0245 of International Publication No. 2015/166779 is mentioned, and the content thereof is incorporated in the present specification.
- the surfactant is preferably a fluorine-based surfactant.
- the liquid characteristics particularly, fluidity
- the liquid saving property can be further improved. It is also possible to form a film having a small thickness unevenness.
- the fluorine content in the fluorine-based surfactant is preferably 3 to 40% by mass, more preferably 5 to 30% by mass, and particularly preferably 7 to 25% by mass.
- a fluorine-based surfactant having a fluorine content within this range is effective in terms of uniformity of coating film thickness and liquid saving property, and has good solubility in the composition.
- fluorine-based surfactant examples include the surfactants described in paragraphs 0060 to 0064 of Japanese Patent Application Laid-Open No. 2014-041318 (paragraphs 0060 to 0064 of the corresponding International Publication No. 2014/017669) and the like, 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.
- fluorine-based surfactants include, for example, Megafuck F171, F172, F173, F176, F177, F141, F142, F143, F144, R30, F437, F475, F479, F482, F554, F780, EXP, MFS.
- the fluorine-based surfactant has a molecular structure having a functional group containing a fluorine atom, and an acrylic compound in which a portion of the functional group containing a fluorine atom is cut off and the fluorine atom volatilizes when heat is applied.
- fluorine-based surfactants include the Megafuck DS series manufactured by DIC Corporation (The Chemical Daily (February 22, 2016), Nikkei Sangyo Shimbun (February 23, 2016)), for example, Megafuck. DS-21 can be mentioned.
- 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 include the fluorine-based surfactants described in JP-A-2016-216602, the contents of which are incorporated in the present specification.
- the fluorine-based surfactant a block polymer can also be used.
- the fluorine-based surfactant has a repeating unit derived from a (meth) acrylate compound having a fluorine atom and 2 or more (preferably 5 or more) alkyleneoxy groups (preferably ethyleneoxy groups and propyleneoxy groups) (meth).
- a fluorine-containing polymer compound containing a repeating unit derived from an acrylate compound can also be preferably used.
- the fluorine-containing surfactants described in paragraphs 0016 to 0037 of JP-A-2010-032698 and the following compounds are also exemplified as the fluorine-based surfactants used in the present invention.
- the weight average molecular weight of the above compounds is preferably 3000-50000, for example 14000.
- % indicating the ratio of the repeating unit is mol%.
- a fluorine-based surfactant a fluorine-containing polymer having an ethylenically unsaturated bond-containing group in the side chain can also be used.
- the compounds described in paragraphs 0050 to 0090 and paragraph numbers 0289 to 0295 of JP2010-164965, Megafuck RS-101, RS-102, RS-718K manufactured by DIC Corporation, RS-72-K and the like can be mentioned.
- the fluorine-based surfactant the compounds described in paragraphs 0015 to 0158 of JP2015-117327A can also be used.
- Nonionic surfactants include glycerol, trimethylolpropane, trimethylolethane, their ethoxylates and propoxylates (eg, glycerol propoxylate, glycerol ethoxylate, etc.), polyoxyethylene lauryl ethers, polyoxyethylene stearyl ethers, etc.
- Examples of the silicon-based surfactant include Torre Silicone DC3PA, Torre Silicone SH7PA, Torre Silicone DC11PA, Torre Silicone SH21PA, Torre Silicone SH28PA, Torre Silicone SH29PA, Torre Silicone SH30PA, Torre Silicone SH8400 (above, Toray Dow Corning Co., Ltd.). ), TSF-4440, TSF-4300, TSF-4445, TSF-4460, TSF-4452 (above, manufactured by Momentive Performance Materials), KP-341, KF-6001, KF-6002 (above, (Shinetsu Silicone Co., Ltd.), BYK307, BYK323, BYK330 (all manufactured by Big Chemie) and the like.
- the content of the surfactant in the total solid content of the composition is preferably 0.001 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, it is preferable that the total amount thereof is within the above range.
- additives such as fillers, adhesion promoters, antioxidants, anti-aggregation agents and the like can be added to the composition of the present invention, if necessary.
- additives include the additives described in paragraphs 0155 to 0156 of JP-A-2004-295116, the contents of which are incorporated in the present specification.
- the composition of the present invention may contain a latent antioxidant.
- the latent antioxidant is a compound whose 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.
- Specific examples of the latent antioxidant include the 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.
- the composition of the present invention may contain a sensitizer and a photostabilizer described in paragraph No. 0078 of JP-A-2004-295116, and a thermal polymerization inhibitor described in paragraph No. 1981 of the same publication. ..
- the storage container for the composition of the present invention is not particularly limited, and a known storage container can be used.
- a storage container for the purpose of suppressing impurities from being mixed into raw materials and compositions, 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. It is also preferable to use it. Examples of such a container include the container described in Japanese Patent Application Laid-Open No. 2015-123351.
- the composition of the present invention can be produced by mixing the above-mentioned components. In the production of the composition, all the components may be simultaneously dissolved and / or dispersed in a solvent to produce the composition, or if necessary, each component may be appropriately prepared as two or more solutions or dispersions. , These may be mixed at the time of use (at the time of application) to produce a composition.
- a process of dispersing particles such as pigments may be included.
- 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 pulverization of the pigment in the sand mill it is preferable to use beads having a small diameter and to process under the condition that the pulverization efficiency is increased by increasing the filling rate of the beads. Further, it is preferable to remove coarse particles, beads, impurities mixed due to wear of the beads, impurities mixed due to wear of the disperser, and the like by filtration, centrifugation, or the like after the pulverization treatment.
- the amount of impurities mixed from the beads and the disperser is preferably 2000 ppm or less with respect to the total composition.
- the process and disperser for dispersing pigments are "Dispersion Technology Taizen, published by Information Organization Co., Ltd., July 15, 2005” and "Dispersion technology and industrial application centered on suspension (solid / liquid dispersion system)".
- the process and disperser described in Paragraph No. 0022 of 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), polyamide resins such as nylon (eg, nylon-6, nylon-6,6), and polyolefin resins such as polyethylene and polypropylene (PP) (high density, ultrahigh molecular weight).
- PTFE polytetrafluoroethylene
- nylon eg, nylon-6, nylon-6,6)
- polyolefin resins such as polyethylene and polypropylene (PP) (high density, ultrahigh molecular weight).
- PP polypropylene
- the pore size of the filter is preferably 0.01 to 7.0 ⁇ m, more preferably 0.01 to 3.0 ⁇ m, and even more preferably 0.05 to 0.5 ⁇ m. If the pore size of the filter is within the above range, fine foreign matter can be removed more reliably.
- the nominal value of the filter manufacturer can be referred to.
- various filters provided by Nippon Pole Co., Ltd. (DFA4201NIEY, etc.), Advantech Toyo Co., Ltd., Japan Integris Co., Ltd. (formerly Nippon Microlith Co., Ltd.), KITZ Microfilter Co., Ltd., etc. can be used.
- fibrous filter medium examples include polypropylene fiber, nylon fiber, glass fiber and the like.
- examples of commercially available products include SBP type series (SBP008, etc.), TPR type series (TPR002, TPR005, etc.) and SHPX type series (SHPX003, etc.) manufactured by 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 film of the present invention is obtained by using the composition of the present invention described above.
- the film of the present invention can be preferably used for a microlens or the like.
- the microlens of the present invention has the film of the present invention described above.
- the refractive index of the microlens of the present invention with respect to light having a wavelength of 633 nm is preferably 1.58 or more, more preferably 1.60 or more, and even more preferably 1.62 or more.
- the average refractive index of the microlens of the present invention with respect to light having a wavelength of 400 to 600 nm is preferably 1.60 or more, more preferably 1.62 or more, and further preferably 1.64 or more. ..
- the upper limit is not particularly limited, but may be 1.75 or less.
- the minimum value of the transmittance of light having a wavelength of 400 to 600 nm is preferably 85% or more, more preferably 90% or more, still more preferably 95% or more.
- the average transmittance of light having a wavelength of 400 to 600 nm is preferably 90% or more, more preferably 93% or more, and further preferably 96% or more.
- the average transmittance of light having a wavelength of 800 to 870 nm is preferably 80% or less, more preferably 75% or less, and further preferably 70% or less.
- the minimum value of the transmittance of light having a wavelength of 800 to 870 nm is preferably 70% or less, more preferably 65% or less, and further preferably 60% or less. preferable.
- the maximum value of the transmittance of light having a wavelength of 800 to 870 nm is preferably 85% or less, more preferably 82% or less, and further preferably 80% or less. preferable.
- the lens shape of the microlens is not particularly limited, and various shapes derived by the optical system design can be taken. For example, a convex shape, a concave shape, and the like can be mentioned. Further, the radius of curvature of the lens is not particularly limited, and it is preferable to appropriately set it within a range in which a desired effect is obtained.
- the thickness of the microlens is preferably 0.1 to 1.0 ⁇ m.
- the upper limit is preferably 0.9 ⁇ m or less, and more preferably 0.8 ⁇ m or less.
- the lower limit is preferably 0.15 ⁇ m or more, and more preferably 0.2 ⁇ m or more.
- the thickness of the microlens means the thickness of the thickest portion of the microlens. For example, in the case of a double-sided convex lens, it is the distance from the apex of one convex surface to the apex of the other convex surface.
- the method for producing a microlens preferably includes a step of applying the composition of the present invention described above on a support to form a composition layer, and a step of processing the composition layer into a lens shape.
- a step of applying the composition of the present invention described above on a support to form a composition layer preferably includes a step of applying the composition of the present invention described above on a support to form a composition layer, and a step of processing the composition layer into a lens shape.
- each step will be described.
- the composition layer of the present invention is used to form the composition layer on the support.
- the support include a glass substrate, a polycarbonate substrate, a polyester substrate, an aromatic polyamide substrate, a polyamide-imide substrate, a polyimide substrate, and the like.
- An organic light emitting layer may be formed on these substrates.
- a color filter may be further formed on the organic light emitting layer.
- the substrate or the color filter may be provided with an undercoat layer for improving the adhesion with the upper layer, preventing the diffusion of substances, or flattening the surface.
- a known method can be used as a method for applying the 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, regarding the method of applying the composition, the description of International Publication No. 2017/030174 and International Publication No. 2017/018419 can be referred to, and these contents are incorporated in the present specification.
- the composition layer formed on the support may be dried (prebaked).
- the prebaking temperature is preferably 100 ° C. or lower, more preferably 90 ° C. or lower, further preferably 80 ° C. or lower, and particularly preferably 70 ° C. or lower.
- the lower limit can be, for example, 40 ° C. or higher.
- the prebaking time is preferably 10 to 3600 seconds. Pre-baking can be performed on a hot plate, an oven, or the like.
- a method for processing the composition layer into a lens shape As a method for processing the composition layer into a lens shape, a conventionally known processing method can be used. For example, it can be produced by using a transfer method, an imprint method, a heat dripping method, or the like. Of these, the transfer method is preferable because it is easy to control the lens shape.
- the composition layer formed on the support is cured to form a cured product layer, a resist layer is formed on the cured product layer, and the resist layer is patterned into a lens shape, and this pattern is formed.
- the cured product layer can be dry-etched using the formed resist layer as a mask, and the lens shape can be transferred to the cured product layer for production.
- a method for manufacturing a lens using a transfer method is described in JP-A-2006-073655, JP-A-2006-190903, JP-A-2008-281414, JP-A-2014-029524 and the like. Methods can also be used and these contents are incorporated herein by reference.
- a mold having a pattern is pressed onto a composition layer formed on a support to sandwich the composition layer between the mold and the support, and the composition layer is exposed in such a sandwiched state. It can be cured by peeling the mold from the support and then manufactured.
- the composition layer formed on the support is cured to form a cured product layer, and the cured product layer is heated to cause the surface of the cured product layer to be heat-dripping to form the cured product layer. It can be processed into a lens shape.
- the step of processing into a lens shape may include a step of exposing the composition layer.
- the exposure is used as a curing process for the composition layer.
- the exposure is preferably performed by irradiating the composition layer with radiation.
- radiation include g-line and i-line.
- light having a wavelength of 300 nm or less preferably light having a wavelength of 180 to 300 nm
- 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.
- a long wave light source having a diameter of 300 nm or more can also be used.
- pulse exposure is an exposure method of a method of repeatedly irradiating and pausing light in a cycle of a short time (for example, a millisecond level or less).
- 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 solid-state image sensor of the present invention has the microlens of the present invention described above.
- the configuration of the solid-state image sensor is not particularly limited as long as it includes the microlens of the present invention and functions as a solid-state image sensor, and examples thereof include the following configurations.
- a solid-state image sensor CCD (charge-coupled device) image sensor, CMOS (complementary metal oxide semiconductor) image sensor, etc.
- a transfer electrode made of polysilicon or the like.
- the color filter may have a structure in which each colored pixel is embedded in a space partitioned by a partition wall, for example, in a grid pattern.
- the partition wall preferably has a lower refractive index than each colored pixel. Examples of an imaging apparatus having such a structure are described in JP2012-227478A, Japanese Patent Application Laid-Open No. 2014-179757, International Publication No. 2018/043654, and US Patent Application Publication No. 2018/0040656. Equipment is mentioned.
- 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 display device of the present invention has the microlens of the present invention described above.
- Examples of the display device include a liquid crystal display device and an organic electroluminescence display device.
- Examples of each display device see, for example, “Electronic Display Device (Akio Sasaki, Kogyo Chosakai Co., Ltd., published in 1990)", “Display Device (Junaki Ibuki, Sangyo Tosho Co., Ltd.)” (Issued in 1989) ”and so on.
- 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 organic electroluminescence display device may have a light source composed of a white organic electroluminescence element.
- the white organic electroluminescence device preferably has a tandem structure.
- Japanese Patent Application Laid-Open No. 2003-045676 supervised by Akiyoshi Mikami, "Frontiers of Organic EL Technology Development-High Brightness, High Precision, Long Life, Know-how Collection-", Technical Information Association It is described on pages 326-328, 2008 and the like.
- the spectrum of white light emitted by the organic EL element preferably has strong maximum emission peaks in the blue region (430 nm-485 nm), the green region (530 nm-580 nm), and the yellow region (580 nm-620 nm). In addition to these emission peaks, those having a maximum emission peak in the red region (650 nm-700 nm) are more preferable.
- P-1 to P-4 Compounds with the following structure
- P-5 Near-infrared absorbing compound A-43 (croconium compound) described in International Publication No. 2018/043185.
- P-6 Cyanine compound e described in Japanese Patent Application Laid-Open No. 2015-172004
- P-1 to P-6 are compounds having a maximum absorption wavelength in the wavelength range of 800 to 900 nm.
- Dispersions 1 to 12 Dispersions 1 to 12 described above
- Dye-1 compound having the following structure (part of i-C 8 H 17 and i-C 10 H 21 is an isomeric mixture of branched positional difference between the number of carbon atoms.)
- M-1 Compound with the following structure (refractive index for light with a wavelength of 633 nm is 1.63 or more)
- M-2 Compound with the following structure (refractive index for light with a wavelength of 633 nm is 1.63 or more)
- M-3 Compound with the following structure (refractive index for light with a wavelength of 633 nm is 1.58 or more and less than 1.63)
- M-4 Ogsol PG-100 (manufactured by Osaka Gas Chemical Co., Ltd., an epoxy compound having a fluorene structure.
- Refractive index with respect to light having a wavelength of 633 nm is 1.63 or more
- M-5 Ogsol EG-200 (manufactured by Osaka Gas Chemical Co., Ltd., an epoxy compound having a fluorene structure. Refractive index with respect to light having a wavelength of 633 nm is 1.58 or more and less than 1.63)
- M-6 EHPE3150 (Epoxy compound manufactured by Daicel Corporation. Refractive index with respect to light with a wavelength of 633 nm is less than 1.58)
- B-7 Resin having the following structure (the numerical value added to the main chain is the molar ratio.
- A-1 ADEKA STAB AO-80 (manufactured by ADEKA Corporation)
- A-2 2-Ethyl-4-methylimidazole
- A-3 Triphenylphosphine
- A-4 Compound with the following structure
- A-5 Tris (4-methylphenyl) phosphine
- the refractive index (refractive index 1) of the obtained film with respect to light having a wavelength of 633 nm was measured using ellipsometry VUV-VASE (manufactured by JA Woolam Japan). Further, with respect to the obtained film, the transmittance of light having a wavelength of 400 to 1100 nm was measured using a multi-channel spectroscope MCPD-9800 (manufactured by Otsuka Electronics Co., Ltd.), and the minimum value of the transmittance for light having a wavelength of 400 to 600 nm was determined. The average transmittance for light having a wavelength of 800 to 870 nm was measured. When measuring the refractive index, the back surface was polished so that there was no reflection from the back surface of the glass, and the back surface was processed into a frosted glass shape for measurement.
- Example 1 to 25 the minimum value of the transmittance of light having a wavelength of 400 to 600 nm was 85% or more. Further, in Examples 1 to 25, the average transmittance of light having a wavelength of 800 to 870 nm was 80% or less.
- a coloring composition for forming green pixels was applied onto an 8-inch (20.32 cm) silicon wafer by a spin coating method so that the film thickness after film formation was 0.5 ⁇ m. Then, using a hot plate, it was heated at 100 ° C. for 2 minutes. Next, using an i-line stepper exposure apparatus FPA-3000i5 + (manufactured by Canon Inc.) , exposure was performed at an exposure amount of 1000 mJ / cm 2 through a mask having a Bayer pattern of 0.8 ⁇ m square. Then, paddle development was carried out at 23 ° C. for 60 seconds using a 0.3% by mass aqueous solution of tetramethylammonium hydroxide (TMAH).
- TMAH tetramethylammonium hydroxide
- a lens material composition layer having a film thickness of 1.2 ⁇ m was formed by heating at 200 ° C. for 5 minutes. Then, a microlens was manufactured by processing the lens material composition layer so that the height from the lens top to the lens bottom was 400 nm by using a transfer method by etch back, which is a known technique.
- the microlenses produced using the compositions of Examples 1 to 25 had high light transmittance and refractive index in the visible region, and were also excellent in near-infrared shielding property. For this reason, the solid-state image sensor in which a microlens is manufactured using the composition of the example enhances the ability to collect visible light on each pixel of the color filter, and also causes near-infrared rays to be incident on each pixel of the color filter. I was able to suppress it. Therefore, a clear image can be detected, and the image recognition accuracy is excellent. Further, the same result can be obtained when the surfactant is removed from Example 1. Similar results can be obtained when the polymerization inhibitor is removed from Example 1.
- P-7 to P-10 are compounds having a maximum absorption wavelength in the wavelength range of 800 to 900 nm.
- P-7 Compound No. described in JP2012-224595A. 1
- P-8 Near-infrared absorbing compound A-44 (croconium compound) described in International Publication No. 2018/043185.
- P-9 Compound with the following structure
- P-10 Compound with the following structure
- the microlens produced by using the composition of Comparative Example 1 had a low refractive index of light in the visible region, so that the ability to collect visible light to each pixel of the color filter was inferior to that of the example. Therefore, the solid-state image sensor in which a microlens is manufactured using the composition of the comparative example is inferior in image recognition accuracy to that of the example.
- Coloring composition for forming green pixels The following components were mixed, stirred, and then filtered through a nylon filter (manufactured by Nippon Pole Co., Ltd.) having a pore size of 0.45 ⁇ m to prepare a coloring composition for forming green pixels.
- Coloring composition for forming red pixels The following components were mixed, stirred, and then filtered through a nylon filter (manufactured by Nippon Pole Co., Ltd.) having a pore size of 0.45 ⁇ m to prepare a coloring composition for forming red pixels.
- Coloring composition for forming blue pixels The following components were mixed, stirred, and then filtered through a nylon filter (manufactured by Nippon Pole Co., Ltd.) having a pore size of 0.45 ⁇ m to prepare a coloring composition for forming blue pixels.
- the raw materials used for preparing the coloring composition for forming green pixels, the coloring composition for forming red pixels, and the coloring composition for forming blue pixels are as follows.
- a high-pressure disperser with a decompression mechanism NANO-3000-10 manufactured by Nippon BEE Co., Ltd. was used to perform dispersion treatment at a flow rate of 500 g / min under a pressure of 2000 kg / cm3. This dispersion treatment was repeated 10 times to obtain a green pigment dispersion liquid.
- a mixed solution consisting of 4.3 parts by mass of Pigment Yellow 139, 6.8 parts by mass of a dispersant (Disperbyk-161, manufactured by BYK Chemie), and 79.3 parts by mass of PGMEA was mixed with a bead mill (zirconia beads 0. 3 mm diameter) was mixed and dispersed for 3 hours to prepare a pigment dispersion.
- a high-pressure disperser with a decompression mechanism NANO-3000-10 (manufactured by Nippon BEE Co., Ltd.) was used to perform dispersion treatment at a flow rate of 500 g / min under a pressure of 2000 kg / cm3. This dispersion treatment was repeated 10 times to obtain a red pigment dispersion liquid.
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Abstract
Description
<1> 波長633nmの光に対する屈折率が1.58以上の有機化合物Aと、
近赤外線吸収色素と、
溶剤と、を含む組成物であり、
上記有機化合物Aは、重合性化合物および樹脂から選ばれる少なくとも1種であり、
上記組成物を用いて厚さ0.35μmの膜を形成した際に、上記膜の波長633nmの光に対する屈折率が1.58以上であり、上記膜の波長400~600nmの光の透過率の最小値が85%以上である、組成物。
<2> 上記組成物を用いて厚さ0.35μmの膜を形成した際に、上記膜の波長800~870nmの光の平均透過率が80%以下である、<1>に記載の組成物。
<3> 上記有機化合物Aは、フルオレン構造、トリアジン構造およびカルバゾール構造から選ばれる少なくとも1種の構造を有する化合物である、<1>または<2>に記載の組成物。
<4> 上記有機化合物Aを2種以上含む、<1>~<3>のいずれか1つに記載の組成物。
<5> 上記組成物に含まれる有機化合物Aの全量中における、波長633nmの光に対する屈折率が1.63以上の有機化合物の含有量が5~100質量%である、<1>~<4>のいずれか1つに記載の組成物。
<6> 上記組成物の全固形分中における上記有機化合物Aの含有量が50質量%以上である、<1>~<5>のいずれか1つに記載の組成物。
<7> 上記組成物の全固形分中における上記近赤外線吸収色素の含有量が1~20質量%である、<1>~<6>のいずれか1つに記載の組成物。
<8> 上記近赤外線吸収色素は、波長750~1000nmの範囲に極大吸収波長を有する化合物である、<1>~<7>のいずれか1つに記載の組成物。
<9> 上記近赤外線吸収色素は、ピロロピロール化合物、フタロシアニン化合物、ナフタロシアニン化合物、およびポリメチン化合物から選ばれる少なくとも1種である、<1>~<8>のいずれか1つに記載の組成物。
<10> マイクロレンズ用である、<1>~<9>のいずれか1つに記載の組成物。
<11> <1>~<10>のいずれか1つに記載の組成物を用いて得られる膜。
<12> <11>に記載の膜を有するマイクロレンズ。
<13> <12>に記載のマイクロレンズを有する固体撮像素子。
<14> <12>に記載のマイクロレンズを有する表示装置。
本明細書における基(原子団)の表記において、置換および無置換を記していない表記は、置換基を有さない基(原子団)と共に置換基を有する基(原子団)をも包含するものである。例えば、「アルキル基」とは、置換基を有さないアルキル基(無置換アルキル基)のみならず、置換基を有するアルキル基(置換アルキル基)をも包含するものである。
本明細書において「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、一般的に、水銀灯の輝線スペクトル、エキシマレーザーに代表される遠紫外線、極紫外線(EUV光)、X線、電子線等の活性光線または放射線が挙げられる。
本明細書において「~」を用いて表される数値範囲は、「~」の前後に記載される数値を下限値および上限値として含む範囲を意味する。
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合計質量をいう。
本明細書において、「(メタ)アクリレート」は、アクリレートおよびメタクリレートの双方、または、いずれかを表し、「(メタ)アクリル」は、アクリルおよびメタクリルの双方、または、いずれかを表し、「(メタ)アリル」は、アリルおよびメタリルの双方、または、いずれかを表し、「(メタ)アクリロイル」は、アクリロイルおよびメタクリロイルの双方、または、いずれかを表す。
本明細書において「工程」との語は、独立した工程だけではなく、他の工程と明確に区別できない場合であってもその工程の所期の作用が達成されれば、本用語に含まれる。
本明細書において、重量平均分子量(Mw)および数平均分子量(Mn)は、ゲルパーミエーションクロマトグラフィ(GPC)により測定したポリスチレン換算値として定義される。
本発明の組成物は、
波長633nmの光に対する屈折率が1.58以上の有機化合物Aと、
近赤外線吸収色素と、
溶剤と、を含む組成物であり、
上記有機化合物Aは、重合性化合物および樹脂から選ばれる少なくとも1種であり、
上記組成物を用いて厚さ0.35μmの膜を形成した際に、前述の膜の波長633nmの光に対する屈折率が1.58以上であり、前述の膜の波長400~600nmの光の透過率の最小値が85%以上であることを特徴とする。
本発明の組成物は、波長633nmの光に対する屈折率が1.58以上の有機化合物Aを含む。有機化合物Aの波長633nmの光に対する屈折率は、1.63以上であることが好ましい。屈折率の上限は特にされないが1.80以下とすることができる。
また、組成物に含まれる有機化合物Aの全量中における、波長633nmの光に対する屈折率が1.63以上の有機化合物の含有量は、5~100質量%であることが好ましく、20~100質量%がより好ましく、40~100質量%が更に好ましい。
なお、有機化合物Aの屈折率の値は、シリコンウエハなどの支持体上に塗布後の膜厚が0.3μmとなるように塗布し、100℃2分、200℃5分加熱し、エリプソメーターを用いて測定した値である。
C1~C3はそれぞれ独立に、-NRN-、-O-、又は、-S-を表す。RNは、水素原子、アルキル基(好ましくは炭素数1~7)、又は、アリール基を表す。C1~C3はそれぞれ独立に、-NH-、-N(CH3)-、-O-、又は、-S-が好ましく、-NH-がより好ましい。
Ar1及びAr2は、それぞれ独立に、アリール基又はヘテロ環基を表す。アリール基としては、フェニル基が好ましい。ヘテロ環基は、芳香族性を示しても、示さなくてもよいが、芳香族性を示すのが好ましい。ヘテロ環を構成するヘテロ原子の数は1~3が好ましい。ヘテロ環を構成するヘテロ原子は、窒素原子、酸素原子または硫黄原子が好ましい。アリール基及びヘテロ環基は、置換基を有していてもよい。置換基としては、後述する置換基Tや、重合性基が挙げられる。重合性基としては、ビニル基、(メタ)アリル基、(メタ)アクリロイル基などのエチレン性不飽和結合含有基、エポキシ基、オキセタニル基などの環状エーテル基、ヒドロキシ基、カルボキシ基、-NH2基などが挙げられる。
Ar3は、アリーレン基又は二価のヘテロ環基を表す。アリーレン基としては、フェニレン基が好ましい。
LAは、単結合又は二価の連結基を表す。二価の連結基としては、-NH-、-O-、-CO-、-CO-O-、アルキレン基(好ましくは炭素数1~3)、又は、これらの組み合わせ(例えば、-O-アルキレン基-など)からなる基が好ましい。
(A)m-X-(B)n (I)
式(I)中、mは、2以上の整数を表す。nは、0以上の整数を表す。
Aは、式(Ta-1)で表される基を表す。
Xは、m+n価の連結基を表す。
Bは、ポリマー鎖又は置換基を表す。
なお、複数存在するAは、それぞれ同一でも異なっていてもよい。Bが複数存在する場合、複数存在するBは、それぞれ同一でも異なっていてもよい。
Rt1~Rt15はそれぞれ独立に、水素原子または置換基を表し、Rt1~Rt15の少なくとも一つは重合性基を表す。置換基としては、後述する置換基Tや、重合性基が挙げられる。重合性基としては、ビニル基、(メタ)アリル基、(メタ)アクリロイル基などのエチレン性不飽和結合含有基や、エポキシ基、オキセタニル基などの環状エーテル基、ヒドロキシ基、カルボキシ基、-NH2基などが挙げられる。
Rt1~Rt5の少なくとも一つと、Rt6~Rt10の少なくとも一つはそれぞれ重合性基を表すことが好ましく、Rt1~Rt5のいずれか一つと、Rt6~Rt10のいずれか一つがそれぞれ重合性基を表すことがより好ましい。
また、有機化合物Aが重合性化合物または樹脂の場合、組成物中に含まれる樹脂と重合性化合物との合計量中における有機化合物Aの含有量は、50~100質量%が好ましく、60~100質量%がより好ましく、70~100質量%が更に好ましい。
本発明の組成物は、近赤外線吸収色素を含有する。本発明で用いられる近赤外線吸収色素は、波長750~1000nmの範囲に極大吸収波長を有する化合物であることが好ましく、波長770~950nmの範囲に極大吸収波長を有する化合物であることがより好ましく、波長800~900nmの範囲に極大吸収波長を有する化合物であることが更に好ましい。また、近赤外線吸収色素の波長500nmにおける吸光度A1と極大吸収波長における吸光度A2との比率A1/A2は、0.08以下であることが好ましく、0.04以下であることがより好ましい。
アルキル基(好ましくは炭素数1~30のアルキル基)、アルケニル基(好ましくは炭素数2~30のアルケニル基)、アルキニル基(好ましくは炭素数2~30のアルキニル基)、アリール基(好ましくは炭素数6~30のアリール基)、アミノ基(好ましくは炭素数0~30のアミノ基)、アルコキシ基(好ましくは炭素数1~30のアルコキシ基)、アリールオキシ基(好ましくは炭素数6~30のアリールオキシ基)、ヘテロアリールオキシ基、アシル基(好ましくは炭素数1~30のアシル基)、アルコキシカルボニル基(好ましくは炭素数2~30のアルコキシカルボニル基)、アリールオキシカルボニル基(好ましくは炭素数7~30のアリールオキシカルボニル基)、アシルオキシ基(好ましくは炭素数2~30のアシルオキシ基)、アシルアミノ基(好ましくは炭素数2~30のアシルアミノ基)、アルコキシカルボニルアミノ基(好ましくは炭素数2~30のアルコキシカルボニルアミノ基)、アリールオキシカルボニルアミノ基(好ましくは炭素数7~30のアリールオキシカルボニルアミノ基)、スルファモイル基(好ましくは炭素数0~30のスルファモイル基)、カルバモイル基(好ましくは炭素数1~30のカルバモイル基)、アルキルチオ基(好ましくは炭素数1~30のアルキルチオ基)、アリールチオ基(好ましくは炭素数6~30のアリールチオ基)、ヘテロアリールチオ基(好ましくは炭素数1~30)、アルキルスルホニル基(好ましくは炭素数1~30)、アリールスルホニル基(好ましくは炭素数6~30)、ヘテロアリールスルホニル基(好ましくは炭素数1~30)、アルキルスルフィニル基(好ましくは炭素数1~30)、アリールスルフィニル基(好ましくは炭素数6~30)、ヘテロアリールスルフィニル基(好ましくは炭素数1~30)、ウレイド基(好ましくは炭素数1~30)、水酸基、カルボキシル基、スルホ基、リン酸基、カルボン酸アミド基(好ましくは-NHCORA1で表される基であり、RA1は、炭化水素基または複素環基を表す。炭化水素基および複素環基は、さらに置換基を有してもよい。置換基としては、ハロゲン原子であることが好ましく、フッ素原子であることがより好ましい。)、スルホン酸アミド基(好ましくは-NHSO2RA2で表される基である。RA2は、炭化水素基または複素環基を表す。炭化水素基および複素環基は、さらに置換基を有してもよい。置換基としては、ハロゲン原子であることが好ましく、フッ素原子であることがより好ましい。)、イミド酸基(好ましくは、-SO2NHSO2RA3、-CONHSO2RA4、-CONHCORA5または-SO2NHCORA6で表される基である。RA3~RA6は、それぞれ独立して炭化水素基または複素環基を表す。炭化水素基および複素環基は、さらに置換基を有してもよい。)、メルカプト基、ハロゲン原子、シアノ基、アルキルスルフィノ基、アリールスルフィノ基、ヒドラジノ基、イミノ基、ヘテロアリール基(好ましくは炭素数1~30)。
これらの基は、さらに置換可能な基である場合、さらに置換基を有してもよい。置換基としては、上述した置換基Tで説明した基が挙げられる。
本発明の組成物は、溶剤を含有する。溶剤は、各成分の溶解性や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も好ましく用いることもできる。有機溶剤の具体例としては、ポリエチレングリコールモノメチルエーテル、ジクロロメタン、3-エトキシプロピオン酸メチル、3-エトキシプロピオン酸エチル、エチルセロソルブアセテート、乳酸エチル、ジエチレングリコールジメチルエーテル、酢酸ブチル、3-メトキシプロピオン酸メチル、2-ヘプタノン、シクロヘキサノン、酢酸シクロヘキシル、シクロペンタノン、エチルカルビトールアセテート、ブチルカルビトールアセテート、プロピレングリコールモノメチルエーテル、プロピレングリコールモノメチルエーテルアセテート、3-メトキシ-N,N-ジメチルプロパンアミド、3-ブトキシ-N,N-ジメチルプロパンアミドなどが挙げられる。ただし有機溶剤としての芳香族炭化水素類(ベンゼン、トルエン、キシレン、エチルベンゼン等)は、環境面等の理由により低減したほうがよい場合がある(例えば、有機溶剤全量に対して、50質量ppm(parts per million)以下とすることもでき、10質量ppm以下とすることもでき、1質量ppm以下とすることもできる)。
本発明の組成物は、上述した有機化合物A以外の重合性化合物(以下、他の重合性化合物ともいう)を含有することができる。他の重合性化合物としては、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、オキセタニル基などが挙げられる。
また、本発明の組成物は他の重合性化合物を実質的に含有しないことも好ましい。この態様によれば、より屈折率の高い膜を形成することができる。なお、本発明の組成物が他の重合性化合物を実質的に含有しない場合とは、他の重合性化合物の含有量が組成物の全固形分中0.1質量%以下であることを意味し、0.05質量%以下であることが好ましく、0.01質量%以下であることが更に好ましく、含有しないことが特に好ましい。
本発明の組成物は上述した有機化合物A以外の樹脂(以下、他の樹脂ともいう)を含有することができる。樹脂は、例えば、顔料などの粒子を組成物中で分散させる用途や、バインダーの用途で配合される。なお、主に粒子等を組成物中で分散させるために用いられる樹脂を分散剤ともいう。ただし、樹脂のこのような用途は一例であって、このような用途以外を目的として樹脂を使用することもできる。
また、本発明の組成物は他の樹脂を実質的に含有しないことも好ましい。この態様によれば、より屈折率の高い膜を形成することができる。なお、本発明の組成物が他の樹脂を実質的に含有しない場合とは、他の樹脂の含有量が組成物の全固形分中0.1質量%以下であることを意味し、0.05質量%以下であることが好ましく、0.01質量%以下であることが更に好ましく、含有しないことが特に好ましい。
本発明の組成物は、顔料誘導体を含有することができる。顔料タイプの近赤外線吸収色素を用いた場合は、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、色素骨格に酸基または塩基性基が結合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色素骨格としては、キノリン色素骨格、ベンゾイミダゾロン色素骨格、ベンゾイソインドール色素骨格、ベンゾチアゾール色素骨格、イニミウム色素骨格、スクアリリウム色素骨格、クロコニウム色素骨格、オキソノール色素骨格、ピロロピロール色素骨格、ジケトピロロピロール色素骨格、アゾ色素骨格、アゾメチン色素骨格、フタロシアニン色素骨格、ナフタロシアニン色素骨格、アントラキノン色素骨格、キナクリドン色素骨格、ジオキサジン色素骨格、ペリノン色素骨格、ペリレン色素骨格、チオインジゴ色素骨格、イソインドリン色素骨格、イソインドリノン色素骨格、キノフタロン色素骨格、イミニウム色素骨格、ジチオール色素骨格、トリアリールメタン色素骨格、ピロメテン色素骨格等が挙げられる。酸基としては、スルホ基、カルボキシル基、リン酸基及びこれらの塩が挙げられる。塩を構成する原子または原子団としては、アルカリ金属イオン(Li+、Na+、K+など)、アルカリ土類金属イオン(Ca2+、Mg2+など)、アンモニウムイオン、イミダゾリウムイオン、ピリジニウムイオン、ホスホニウムイオンなどが挙げられる。塩基性基としては、アミノ基、ピリジニル基およびその塩、アンモニウム基の塩、並びにフタルイミドメチル基が挙げられる。塩を構成する原子または原子団としては、水酸化物イオン、ハロゲンイオン、カルボン酸イオン、スルホン酸イオン、フェノキシドイオンなどが挙げられる。
本発明の組成物は光重合開始剤を含有していてもよい。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。
本発明の組成物は白色または無色の顔料(以下、白色系顔料ともいう)を含有することができる。白色系顔料としては、Ti、Zr、Sn、Sb、Cu、Fe、Mn、Pb、Cd、As、Cr、Hg、Zn、Al、Mg、Si、PおよびSから選択される少なくとも一種の元素を含む酸化物の粒子が挙げられ、Ti、Zr、Sn、AlおよびSiから選択される少なくとも一種の元素を含む酸化物の粒子であることが好ましい。酸化物としては、酸化チタンおよび酸化ジルコニウムが好ましく、酸化チタンがより好ましい。また、酸化チタンとしては、ルチル型酸化チタン、アナターゼ型酸化チタン、アモルファス型酸化チタンが挙げられ、ルチル型酸化チタンが好ましい。また、上記の酸化物は、表面処理剤で表面処理されていることも好ましい。表面処理剤としては、無機化合物、有機化合物が挙げられる。無機化合物と有機化合物とを併用してもよい。表面処理剤の具体例としては、ポリオール、酸化アルミニウム、水酸化アルミニウム、非晶質シリカ、含水シリカ、アルカノールアミン、ステアリン酸、オルガノシロキサン、酸化ジルコニウム、ハイドロゲンジメチコン、シランカップリング剤、チタネートカップリング剤などが挙げられる。
本発明の組成物は、硬化促進剤を含有することができる。硬化促進剤としては、チオール化合物、メチロール化合物、アミン化合物(脂肪族アミン、芳香族アミン、複素環式アミンなど)、ホスホニウム塩化合物、アミジン塩化合物、アミド化合物、塩基発生剤、イソシアネート化合物、アルコキシシラン化合物、オニウム塩化合物、リン化合物などが挙げられる。硬化促進剤の具体例としては、国際公開第2018/056189号の段落番号0094~0097に記載の化合物、特開2015-034963号公報の段落番号0246~0253に記載の化合物、特開2013-041165号公報の段落番号0186~0251に記載の化合物、特開2014-055114号公報に記載のイオン性化合物、特開2012-150180号公報の段落番号0071~0080に記載の化合物、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、特許第5765059号公報の段落番号0085~0092に記載の化合物、特開2017-036379号公報に記載のカルボキシル基含有エポキシ硬化剤などが挙げられる。
本発明の組成物は、シランカップリング剤を含有することができる。シランカップリング剤としては、一分子中に少なくとも2種の反応性の異なる官能基を有するシラン化合物が好ましい。シランカップリング剤は、ビニル基、エポキシ基、スチレン基、メタクリル基、アミノ基、イソシアヌレート基、ウレイド基、メルカプト基、スルフィド基、および、イソシアネート基から選ばれる少なくとも1種の基と、アルコキシ基とを有するシラン化合物が好ましい。シランカップリング剤の具体例としては、N-2-(アミノエチル)-3-アミノプロピルメチルジメトキシシラン(信越化学工業(株)製、KBM-602)、N-2-(アミノエチル)-3-アミノプロピルトリメトキシシラン(信越化学工業(株)製、KBM-603)、3-アミノプロピルトリメトキシシラン(信越化学工業(株)製、KBM-903)、3-アミノプロピルトリエトキシシラン(信越化学工業(株)製、KBE-903)、3-メタクリロキシプロピルトリメトキシシラン(信越化学工業(株)製、KBM-503)、3-グリシドキシプロピルトリメトキシシラン(信越化学工業(株)製、KBM-403)等が挙げられる。シランカップリング剤の詳細については、特開2013-254047号公報の段落番号0155~0158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-t-ブチル-p-クレゾール、ピロガロール、t-ブチルカテコール、ベンゾキノン、4,4’-チオビス(3-メチル-6-t-ブチルフェノール)、2,2’-メチレンビス(4-メチル-6-t-ブチルフェノール)、N-ニトロソフェニルヒドロキシアミン塩(アンモニウム塩、第一セリウム塩等)等が挙げられる。
本発明の組成物は、紫外線吸収剤を含有することができる。紫外線吸収剤としては、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が挙げられる。このような化合物としては、特開2009-217221号公報の段落番号0038~0052、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に記載された化合物が挙げられ、これらの内容は本明細書に組み込まれる。また、ベンゾトリアゾール化合物としては、ミヨシ油脂製のMYUAシリーズ(化学工業日報、2016年2月1日)が挙げられる。また、紫外線吸収剤は、特許第6268967号公報の段落番号0049~0059に記載された化合物を用いることもできる。
本発明の組成物は、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。リン系酸化防止剤としてはトリス[2-[[2,4,8,10-テトラキス(1,1-ジメチルエチル)ジベンゾ[d,f][1,3,2]ジオキサホスフェピン-6-イル]オキシ]エチル]アミン、トリス[2-[(4,6,9,11-テトラ-tert-ブチルジベンゾ[d,f][1,3,2]ジオキサホスフェピン-2-イル)オキシ]エチル]アミン、亜リン酸エチルビス(2,4-ジ-tert-ブチル-6-メチルフェニル)などが挙げられる。酸化防止剤の市販品としては、例えば、アデカスタブ AO-20、アデカスタブ AO-30、アデカスタブ AO-40、アデカスタブ AO-50、アデカスタブ AO-50F、アデカスタブ AO-60、アデカスタブ AO-60G、アデカスタブ AO-80、アデカスタブ AO-330(以上、(株)ADEKA製)などが挙げられる。また、酸化防止剤は、特許第6268967号公報の段落番号0023~0048に記載された化合物、国際公開第2017/006600号に記載された化合物、国際公開第2017/164024号に記載された化合物を使用することもできる。
本発明の組成物は、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、ノニオン系界面活性剤、カチオン系界面活性剤、アニオン系界面活性剤、シリコ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。
本発明の組成物には、必要に応じて、各種添加剤、例えば、充填剤、密着促進剤、酸化防止剤、凝集防止剤等を配合することができる。これらの添加剤としては、特開2004-295116号公報の段落番号0155~0156に記載の添加剤を挙げることができ、この内容は本明細書に組み込まれる。
本発明の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。
本発明の組成物は、前述の成分を混合して製造できる。組成物の製造に際しては、全成分を同時に溶剤に溶解および/または分散して組成物を製造してもよいし、必要に応じて、各成分を適宜2つ以上の溶液または分散液としておいて、使用時(塗布時)にこれらを混合して組成物を製造してもよい。
本発明の膜は、上述した本発明の組成物を用いて得られたものである。本発明の膜は、マイクロレンズなどに好ましく用いることができる。
本発明のマイクロレンズは、上述した本発明の膜を有する。
次に、マイクロレンズの製造方法について説明する。マイクロレンズの製造方法は、支持体上に上述した本発明の組成物を塗布して組成物層を形成する工程と、組成物層をレンズ形状に加工する工程とを含むことが好ましい。以下、各工程について説明する。
組成物層を形成する工程では、本発明の組成物を用いて、支持体上に組成物層を形成する。支持体としては、ガラス基板、ポリカーボネート基板、ポリエステル基板、芳香族ポリアミド基板、ポリアミドイミド基板、ポリイミド基板等が挙げられる。これらの基板上には有機発光層が形成されていてもよい。また、有機発光層上には更にカラーフィルタが形成されていてもよい。また、基板やカラーフィルタには、上部の層との密着性改良、物質の拡散防止或いは表面の平坦化のために下塗り層が設けられていてもよい。
組成物層をレンズ形状に加工する方法としては、従来公知の加工方法を用いることができる。例えば、転写法、インプリント法、熱だれ法などを用いて製造できる。なかでも、レンズ形状の制御が行いやすいという理由から転写法が好ましい。
本発明の固体撮像素子は、上述した本発明のマイクロレンズを有する。固体撮像素子の構成としては、本発明のマイクロレンズを備え、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。
本発明の表示装置は、上述した本発明のマイクロレンズを有する。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。表示装置の定義や各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。
下記の表に記載の原料を混合し、更に直径0.3mmのジルコニアビーズ230質量部を加えて、ペイントシェーカーを用いて5時間分散処理を行い、ビーズをろ過で分離して分散液を製造した。
(近赤外線吸収色素)
P-1~P-4:下記構造の化合物
P-6:特開2015-172004号公報に記載のシアニン化合物e
P-1~P-6は、波長800~900nmの範囲に極大吸収波長を有する化合物である。
D-1:下記構造の樹脂。主鎖に付記した数値はモル比であり、側鎖に付記した数値は繰り返し単位の数である。Mw=20,000。
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(PGMEA)
下記の表に記載の原料を混合して、実施例および比較例の組成物を調製した。下記の表に記載の数値は質量部である。
分散液1~12:上述した分散液1~12
M-1:下記構造の化合物(波長633nmの光に対する屈折率が1.63以上)
M-2:下記構造の化合物(波長633nmの光に対する屈折率が1.63以上)
M-3:下記構造の化合物(波長633nmの光に対する屈折率が1.58以上1.63未満)
M-4:オグソールPG-100(大阪ガスケミカル(株)製、フルオレン構造を有するエポキシ化合物。波長633nmの光に対する屈折率が1.63以上)
M-5:オグソールEG-200(大阪ガスケミカル(株)製、フルオレン構造を有するエポキシ化合物。波長633nmの光に対する屈折率が1.58以上1.63未満)
M-6:EHPE3150((株)ダイセル製、エポキシ化合物。波長633nmの光に対する屈折率が1.58未満)
B-1:下記構造の樹脂(Mw=5000、波長633nmの光に対する屈折率が1.58以上1.63未満)
B-2:特開2013-139588号公報の段落番号0122~0126の合成例1に記載の方法で製造したフルオレン構造を有する樹脂(Mw=4300、波長633nmの光に対する屈折率が1.63以上)
B-3:特開2017-031311号公報の段落番号0085~0086の実施例1に記載の方法で製造したフルオレン構造を有する樹脂(Mw=28800、波長633nmの光に対する屈折率が1.63以上)
B-4:下記構造の樹脂(Mw=10000、波長633nmの光に対する屈折率が1.63以上)
B-5:下記構造の樹脂(Mw=8000、波長633nmの光に対する屈折率が1.63以上)
B-6:下記構造の樹脂(Mw=13000、波長633nmの光に対する屈折率が1.63以上)
B-7:下記構造の樹脂(主鎖に付記した数値はモル比である。Mw=10000、波長633nmの光に対する屈折率が1.58未満)
B-8:下記構造の樹脂(Mw=3100、波長633nmの光に対する屈折率が1.63以上)
B-9:下記構造の樹脂(鎖に付記した数値はモル比である。Mw=20000、波長633nmの光に対する屈折率が1.63以上)
B-10:下記構造の樹脂(主鎖に付記した数値はモル比である。Mw=40000、波長633nmの光に対する屈折率が1.58以上、1.63未満)
A-1:アデカスタブ AO-80((株)ADEKA製)
A-2:2-エチル-4-メチルイミダゾール
A-3:トリフェニルホスフィン
A-4:下記構造の化合物
In-1:p-メトキシフェノール
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(PGMEA)
S-2:プロピレングリコールモノメチルエーテル(PGME)
S-3:シクロヘキサノン
各組成物をポストベーク後の膜厚が0.35μmとなるようにスピンコーター(ミカサ(株)製)を用いて石英ガラス基板上に塗布して塗膜を形成した。次いで、ホットプレートを用いて、100℃、120秒間の加熱(プリベーク)を行った後、再度ホットプレートを用いて200℃、300秒間の加熱(ポストベーク)を行い、厚さ0.35μmの膜を得た。得られた膜について、エリプソメトリー VUV-VASE(ジェー・エー・ウーラム・ジャパン社製)を用いて波長633nmの光に対する屈折率(屈折率1)を測定した。また、得られた膜について、波長400~1100nmの光の透過率をマルチチャンネル分光器 MCPD-9800(大塚電子社製)を用いて測定し、波長400~600nmの光に対する透過率の最小値、波長800~870nmの光に対する平均透過率をそれぞれ測定した。屈折率測定の際は、ガラス裏面からの反射がないように裏面を研磨し、すりガラス状に加工し測定した。
8インチ(20.32cm)のシリコンウエハ上に、緑色画素形成用着色組成物を製膜後の膜厚が0.5μmになるようにスピンコート法で塗布した。次いで、ホットプレートを用い、100℃で2分間加熱した。次いで、i線ステッパー露光装置FPA-3000i5+(Canon(株)製)を用い、1000mJ/cm2の露光量にて、0.8μm四方のBayerパターンを有するマスクを介して露光した。次いで、水酸化テトラメチルアンモニウム(TMAH)0.3質量%水溶液を用い、23℃で60秒間パドル現像を行った。その後、スピンシャワーにてリンスを行い、さらに純水にて水洗した。次いで、ホットプレートを用い、200℃で5分間加熱することで、シリコンウエハ上に緑色画素(パターンサイズ0.8μm、厚さ0.5μm)を形成した。次いで、赤色画素形成用着色組成物、青色画素形成用着色組成物を順次パターニングし、緑色画素の抜け部に、赤色画素(パターンサイズ0.8μm、厚さ0.5μm)、青色画素(パターンサイズ0.8μm、厚さ0.5μm)をそれぞれ形成してカラーフィルタを形成した。
次に、カラーフィルタ上に、実施例1~25および比較例1の組成物をスピンコート法で塗布し、次いで、ホットプレートを用いて100℃で2分間加熱し、次いで、ホットプレートを用いて200℃で5分間加熱して膜厚1.2μmのレンズ材組成物層を形成した。
その後、公知の技術であるエッチバックによる転写方法を用いて、レンズトップからレンズボトムまでの高さが400nmになるようにレンズ材組成物層を加工することにより、マイクロレンズを製造した。
P-7~P-10は、波長800~900nmの範囲に極大吸収波長を有する化合物である。
P-7:特開2012-224593号公報に記載の化合物No.1
P-8:国際公開第2018/043185号に記載の近赤外線吸収化合物A-44(クロコニウム化合物)
P-9:下記構造の化合物
下記成分を混合し、撹拌した後、孔径0.45μmのナイロン製フィルタ(日本ポール(株)製)でろ過して、緑色画素形成用着色組成物を調製した。
緑色顔料分散液 ・・・88.74質量部
樹脂1 ・・・0.40質量部
重合性化合物1 ・・・1.62質量部
光重合開始剤(Irgacure OXE01、BASF製) ・・・1.09質量部
重合禁止剤(p-メトキシフェノール)・・・0.0008質量部
界面活性剤1 ・・・4.17質量部
紫外線吸収剤(UV-503、大東化学(株)製) ・・・0.3質量部
PGMEA ・・・3.68質量部
下記成分を混合し、撹拌した後、孔径0.45μmのナイロン製フィルタ(日本ポール(株)製)でろ過して、赤色画素形成用着色組成物を調製した。
赤色顔料分散液 ・・51.7質量部
樹脂1 ・・・0.6質量部
重合性化合物4 ・・・0.6質量部
光重合開始剤(Irgacure OXE01、BASF製) ・・・0.4質量部
界面活性剤1 ・・・4.2質量部
紫外線吸収剤(UV-503、大東化学(株)製) ・・・0.3質量部
PGMEA ・・・42.6質量部
下記成分を混合し、撹拌した後、孔径0.45μmのナイロン製フィルタ(日本ポール(株)製)でろ過して、青色画素形成用着色組成物を調製した。
青色顔料分散液 ・・・44.9質量部
樹脂1 ・・・2.1質量部
重合性化合物1 ・・・1.5質量部
重合性化合物4 ・・・0.7質量部
光重合開始剤(Irgacure OXE01、BASF製) ・・・0.8質量部
界面活性剤1 ・・・4.2質量部
紫外線吸収剤(UV-503、大東化学(株)製) ・・・0.3質量部
PGMEA ・・・45.8質量部
C.I.Pigment Green 36の8.15質量部と、C.I.Pigment Yellow 150の3.33質量部と、以下に示す分散剤1の0.97質量部と、以下に示す分散剤2の2.50質量部と、PGMEAの66.01質量部と、PGMEの1.09質量部と、シクロヘキサノンの5.09質量部からなる混合液を、ビーズミル(ジルコニアビーズ0.3mm径)により3時間混合および分散して、顔料分散液を調製した。その後さらに、減圧機構付き高圧分散機NANO-3000-10(日本ビーイーイー(株)製)を用いて、2000kg/cm3の圧力下で流量500g/minとして分散処理を行なった。この分散処理を10回繰り返し、緑色顔料分散液を得た。
C.I.Pigment Red 254の9.6質量部と、C.I.Pigment Yellow 139の4.3質量部と、分散剤(Disperbyk-161、BYKChemie社製)の6.8質量部と、PGMEAの79.3質量部とからなる混合液を、ビーズミル(ジルコニアビーズ0.3mm径)により3時間混合および分散して、顔料分散液を調製した。その後さらに、減圧機構付き高圧分散機NANO-3000-10(日本ビーイーイー(株)製)を用いて、2000kg/cm3の圧力下で流量500g/minとして分散処理を行なった。この分散処理を10回繰り返し、赤色顔料分散液を得た。
C.I.Pigment Blue 15:6の9.7質量部と、C.I.Pigment Violet 23の2.4質量部と、分散剤(Disperbyk-161、BYKChemie社製)の5.5質量部と、PGMEAの82.4質量部とからなる混合液を、ビーズミル(ジルコニアビーズ0.3mm径)により3時間混合および分散して、顔料分散液を調製した。その後さらに、減圧機構付き高圧分散機NANO-3000-10(日本ビーイーイー(株)製)を用いて、2000kg/cm3の圧力下で流量500g/minとして分散処理を行なった。この分散処理を10回繰り返し、青色顔料分散液を得た。
Claims (14)
- 波長633nmの光に対する屈折率が1.58以上の有機化合物Aと、
近赤外線吸収色素と、
溶剤と、を含む組成物であり、
前記有機化合物Aは、重合性化合物および樹脂から選ばれる少なくとも1種であり、
前記組成物を用いて厚さ0.35μmの膜を形成した際に、前記膜の波長633nmの光に対する屈折率が1.58以上であり、前記膜の波長400~600nmの光の透過率の最小値が85%以上である、組成物。 - 前記組成物を用いて厚さ0.35μmの膜を形成した際に、前記膜の波長800~870nmの光の平均透過率が80%以下である、請求項1に記載の組成物。
- 前記有機化合物Aは、フルオレン構造、トリアジン構造およびカルバゾール構造から選ばれる少なくとも1種の構造を有する化合物である、請求項1または2に記載の組成物。
- 前記有機化合物Aを2種以上含む、請求項1~3のいずれか1項に記載の組成物。
- 前記組成物に含まれる有機化合物Aの全量中における、波長633nmの光に対する屈折率が1.63以上の有機化合物の含有量が5~100質量%である、請求項1~4のいずれか1項に記載の組成物。
- 前記組成物の全固形分中における前記有機化合物Aの含有量が50質量%以上である、請求項1~5のいずれか1項に記載の組成物。
- 前記組成物の全固形分中における前記近赤外線吸収色素の含有量が1~20質量%である、請求項1~6のいずれか1項に記載の組成物。
- 前記近赤外線吸収色素は、波長750~1000nmの範囲に極大吸収波長を有する化合物である、請求項1~7のいずれか1項に記載の組成物。
- 前記近赤外線吸収色素は、ピロロピロール化合物、フタロシアニン化合物、ナフタロシアニン化合物、およびポリメチン化合物から選ばれる少なくとも1種である、請求項1~8のいずれか1項に記載の組成物。
- マイクロレンズ用である、請求項1~9のいずれか1項に記載の組成物。
- 請求項1~10のいずれか1項に記載の組成物を用いて得られる膜。
- 請求項11に記載の膜を有するマイクロレンズ。
- 請求項12に記載のマイクロレンズを有する固体撮像素子。
- 請求項12に記載のマイクロレンズを有する表示装置。
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JP2004200360A (ja) * | 2002-12-18 | 2004-07-15 | Toppan Printing Co Ltd | 固体撮像素子及びその製造方法 |
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WO2019058888A1 (ja) * | 2017-09-21 | 2019-03-28 | 富士フイルム株式会社 | 組成物、膜、レンズ、固体撮像素子、化合物 |
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