WO2022168741A1 - 着色組成物、膜、光学フィルタ、固体撮像素子、画像表示装置および化合物 - Google Patents
着色組成物、膜、光学フィルタ、固体撮像素子、画像表示装置および化合物 Download PDFInfo
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- WO2022168741A1 WO2022168741A1 PCT/JP2022/003236 JP2022003236W WO2022168741A1 WO 2022168741 A1 WO2022168741 A1 WO 2022168741A1 JP 2022003236 W JP2022003236 W JP 2022003236W WO 2022168741 A1 WO2022168741 A1 WO 2022168741A1
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
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- 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
- C08K5/16—Nitrogen-containing compounds
- C08K5/29—Compounds containing one or more carbon-to-nitrogen double bonds
-
- 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
-
- 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
- C09B55/00—Azomethine 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
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/006—Preparation of organic pigments
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- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
-
- 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
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
Definitions
- the present invention relates to a coloring composition containing a coloring agent.
- the present invention also relates to a film, an optical filter, a solid-state imaging device, and an image display device using the colored composition.
- the present invention also relates to azomethine metal complex compounds.
- a color filter usually comprises three primary color pixels of red, green and blue and serves to separate the transmitted light into the three primary colors.
- Patent Document 1 discloses a pigment composition for color filters containing a phthalocyanine-based pigment and an azomethine copper complex-based pigment, wherein the mass ratio of the phthalocyanine-based pigment to the azomethine copper complex-based pigment is 99.9/ A color filter pigment composition is described which is from 0.1 to 96.5/3.5.
- C.I. Pigment Yellow 129 is used as an azomethine copper complex-based pigment.
- C. I. Pigment Yellow 129 is a compound having the structure shown below. According to the study of the present inventor, the film obtained using the composition containing the azomethine copper complex-based pigment described in the examples of Patent Document 1 cannot be said to have sufficient light resistance, and there is room for improvement. It turns out there is.
- a coloring composition containing a coloring agent and a resin A coloring composition in which the coloring agent contains a compound Y in which a compound represented by formula (1) is coordinated to a metal atom;
- R 1 represents a hydrogen atom, an alkyl group or an aryl group
- X 2 to X 9 each independently represents a nitrogen atom, CH or CR x
- R x represents a substituent
- Adjacent two of X 6 to X 9 in formula (1) are CR x , and R x of two adjacent CR x are bonded to form a ring, ⁇ 1 >
- the coloring composition described in . ⁇ 3> The colored composition according to ⁇ 1> or ⁇ 2>, wherein at least one of X 2 to X 9 in formula (1) is CR x , and R x is a heteroatom-containing group.
- At least one of X 2 to X 9 in formula (1) is CR x , and R x is a nitro group, a cyano group, —NR 101 R 102 , —OR 103 , —SR 104 , —COOR 105 , —OCOR 106 , —SO 2 R 107 , —SO 2 NR 108 R 109 , —SO 2 OR 110 , —CONR 111 R 112 or —NR 113 COR 114 , wherein R 101 and R 102 each independently represent , represents a hydrogen atom, an alkyl group or an aryl group, R 101 and R 102 may combine to form a ring, R 103 to R 114 each independently represent an alkyl group or an aryl group, The colored composition according to any one of ⁇ 1> to ⁇ 3>.
- ⁇ 9> The colored composition according to any one of ⁇ 1> to ⁇ 8>, further comprising a polymerizable compound and a photopolymerization initiator.
- ⁇ 10> The colored composition according to any one of ⁇ 1> to ⁇ 9>, which is used for color filters or infrared transmission filters.
- ⁇ 11> A film obtained from the colored composition according to any one of ⁇ 1> to ⁇ 10>.
- ⁇ 12> An optical filter comprising the film according to ⁇ 11>.
- ⁇ 13> A solid-state imaging device comprising the film according to ⁇ 11>.
- ⁇ 14> An image display device comprising the film according to ⁇ 11>.
- R 1 represents a hydrogen atom, an alkyl group or an aryl group
- X 2 to X 9 each independently represents a nitrogen atom, CH or CR x
- R x represents a substituent
- formula (1) satisfies any of the following requirements 1 to 4
- Requirement 1 Adjacent two of X 3 to X 5 are CR x , and the R x 's of the two adjacent CR x 's are bonded to form a ring
- Requirement 2 X 2 and X 3 are CR x
- R x of CR x represented by X 2 and R x of CR x represented by X 3 combine to form a heterocyclic ring
- Requirement 3 Adjacent two of X 3 to X 5 are CR x , and the R x 's of the two adjacent CR x 's are bonded to form a ring
- Requirement 2 X 2 and X 3 are CR
- exposure includes not only exposure using light but also drawing using particle beams such as electron beams and ion beams, unless otherwise specified.
- Light used for exposure includes actinic rays or radiation such as emission line spectra of mercury lamps, far ultraviolet rays represented by excimer lasers, extreme ultraviolet rays (EUV light), X-rays, and electron beams.
- (meth)acrylate represents both or either acrylate and methacrylate
- (meth)acryl represents both or either acrylic and methacrylic
- (meth) ) acryloyl refers to acryloyl and/or methacryloyl.
- the coloring composition of the present invention is a coloring composition containing a coloring agent and a resin,
- the coloring agent is characterized by containing a compound Y in which a compound represented by formula (1) is coordinated to a metal atom.
- the coloring composition of the present invention a film with excellent light resistance can be formed. Although the detailed reason why such an effect is obtained is unknown, it is presumed to be due to the following.
- Compound Y used as a colorant in the coloring composition of the present invention is easy to form an association in the film, also, since it is possible to efficiently transfer electrons between molecules, the coloring composition of the present invention It is presumed that a film with excellent light resistance could be formed by using
- the coloring composition of the present invention is preferably used as a coloring composition for color filters or infrared transmission filters. More specifically, it can be preferably used as a coloring composition for forming color filter pixels or as a coloring composition for forming infrared transmission filters, and is more preferably used as a coloring composition for forming color filter pixels.
- Pixel types include red pixels, green pixels, blue pixels, magenta pixels, cyan pixels, and yellow pixels. Red pixels, green pixels, and yellow pixels are preferred. More preferably, it is a green pixel.
- the wavelength at which the light transmittance of the film is 50% is preferably present in the wavelength range of 470 to 520 nm. More preferably in the wavelength range of 520 nm, even more preferably in the wavelength range of 480-520 nm. In particular, it is preferable that the wavelengths at which the light transmittance is 50% exist in both the wavelength range of 470 to 520 nm and the wavelength range of 575 to 625 nm. In this embodiment, the wavelength on the short wavelength side at which the light transmittance is 50% preferably exists in the wavelength range of 475 to 520 nm, more preferably in the wavelength range of 480 to 520 nm.
- the number of carbon atoms in the alkyl group represented by R 1 in formula (1) is preferably 1-30, more preferably 1-15, and even more preferably 1-8.
- the alkyl group may be linear, branched or cyclic, preferably linear or branched, more preferably linear.
- the alkyl group may have a substituent.
- Substituents include the substituent T described later.
- the aryl group represented by R 1 in formula (1) preferably has 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, and still more preferably 6 to 12 carbon atoms.
- the aryl group may have a substituent.
- Substituents include the substituent T described later.
- R 1 in formula (1) is preferably a hydrogen atom or an alkyl group, more preferably a hydrogen atom.
- Specific functional groups A include a nitro group, a cyano group, -NR 101 R 102 , -OR 103 , -SR 104 , -COOR 105 , -OCOR 106 , -SO 2 R 107 , -SO 2 NR 108 R 109 , - SO 2 OR 110 , —CONR 111 R 112 and —NR 113 COR 114 , preferably a nitro group, a cyano group, —NR 101 R 102 , —OR 103 , —SR 104 and —COOR 105 , — NR 101 R 102 and -OR 103 are more preferred.
- R 101 and R 102 each independently represent a hydrogen atom, an alkyl group or an aryl group, R 101 and R 102 may combine to form a ring, and R 103 to R 114 each independently , represents an alkyl group or an aryl group.
- the R x 's of the two adjacent CR x 's may combine to form a ring.
- the ring to be formed may be a hydrocarbon ring or a hetero ring.
- the hydrocarbon ring may be an aliphatic hydrocarbon ring or an aromatic hydrocarbon ring.
- Heteroatoms contained in the heterocycle include nitrogen, sulfur and oxygen atoms.
- the heterocycle is preferably a 5- or 6-membered ring.
- Formula (1) satisfies any one of requirements 1 to 4 above.
- At least one of X 6 to X 9 is CR x and R x is a heteroatom-containing group (preferably, the specific functional group A described above).
- Requirement 2 is that X 2 and X 3 are CR x , and R x of CR x represented by X 2 and R x of CR x represented by X 3 combine to form a heterocyclic ring.
- Examples of the heterocycle formed by combining R x include the heterocycles described above.
- the hetero ring formed by combining R x may further have a substituent.
- Substituents include the substituent T described below.
- the substituent is preferably a group containing a heteroatom, more preferably the specific functional group A described above.
- At least one of X 6 to X 9 is CR x and R x is a heteroatom-containing group (preferably the above-mentioned specific functional group A).
- Requirement 3 is that adjacent two of X 6 to X 9 are CR x , and the R x 's of the two adjacent CR x 's are bonded to form a ring.
- the ring formed by combining R x include the rings described above, preferably a benzene ring or a naphthalene ring, more preferably a benzene ring.
- the ring formed by combining R x may further have a substituent.
- Substituents include the substituent T described below.
- the substituent is preferably a group containing a heteroatom, more preferably the specific functional group A described above.
- X 6 and X 7 are each independently CR x , and R x of CR x represented by X 6 and R x of CR x represented by X 7 can be formed. are combined to form a ring, or X 7 and X 8 are each independently CR x , and R x of CR x represented by X 7 and R x of CR x represented by X 8 are preferably bonded to form a ring, X 7 and X 8 are each independently CR x , and R x of CR x represented by X 7 and R of CR x represented by X 8 It is more preferable that x is bonded to form a ring.
- Formula (1) preferably satisfies any one of requirements 1, 3 or 4 described above, more preferably satisfies requirement 3 or requirement 4, and satisfies requirement 3 More preferred.
- the compound represented by formula (1) is preferably a compound represented by formula (1-1).
- R 1 represents a hydrogen atom, an alkyl group or an aryl group
- R 2 to R 9 each independently represent a hydrogen atom or a substituent, adjacent two of R 2 to R 9 may combine to form a ring
- formula (1-1) satisfies any of the following requirements 1a to 4a; Requirement 1a adjacent two of R 3 to R 5 are bonded to form a ring; Requirement 2a R 2 and R 3 are combined to form a heterocycle; Requirement 3a adjacent two of R 6 to R 9 are bonded to form a ring; Requirement 4a At least one of R 2 and R 3 is a hydrogen atom, and at least one of R 2 to R 9 is a substituent.
- R 1 in formula (1-1) has the same definition as R 1 in formula (1).
- Substituents represented by R 2 to R 9 in formula (1-1) include the substituent T described later, preferably a group containing a heteroatom, more preferably the specific functional group A described above. preferable.
- adjacent two of R 2 to R 9 may combine to form a ring.
- the ring to be formed includes the rings described above.
- the ring thus formed may further have a substituent.
- Substituents include the substituent T described later.
- the substituent is preferably a group containing a heteroatom, more preferably the specific functional group A described above.
- Requirement 1a is that adjacent two of R 3 to R 5 are bonded to form a ring.
- the ring to be formed includes the rings described above, preferably a benzene ring or a naphthalene ring, more preferably a benzene ring.
- the ring formed above may further have a substituent.
- Substituents include the substituent T described below.
- the substituent is preferably a group containing a heteroatom, more preferably the specific functional group A described above.
- Requirement 3a is that adjacent two of R 6 to R 9 are bonded to form a ring.
- the ring to be formed includes the rings described above, preferably a benzene ring or a naphthalene ring, more preferably a benzene ring.
- the ring formed above may further have a substituent.
- Substituents include the substituent T described below.
- the substituent is preferably a group containing a heteroatom, more preferably the specific functional group A described above.
- Requirement 4a is that at least one of R 2 and R 3 is a hydrogen atom, and at least one of R 2 to R 9 is a substituent.
- 1 to 4 of R 2 to R 9 are preferably substituents, more preferably 1 or 2 are substituents.
- Substituents include the substituent T described below.
- the substituent is preferably a group containing a heteroatom, more preferably the specific functional group A described above.
- the metal atoms coordinated by the compound represented by formula (1) include copper atom, zinc atom, iron atom, titanium atom, aluminum atom, tin atom, magnesium atom, chromium atom, calcium atom and silicon atom. Atoms can be mentioned, preferably a copper atom and a zinc atom, more preferably a copper atom.
- one compound represented by formula (1) may be coordinated to the metal atom, or two or more compounds may be coordinated. Further, the metal atom may be further coordinated with a ligand other than the compound represented by formula (1).
- a red colorant a diketopyrrolopyrrole compound in which at least one bromine atom is substituted in the structure described in JP-A-2017-201384, a diketopyrrolopyrrole described in paragraphs 0016 to 0022 of Japanese Patent No.
- green colorants include C.I. I. Green pigments such as Pigment Green 7, 10, 36, 37, 58, 59, 62, 63, 64, 65, 66 are included. Further, as a green colorant, a halogenated zinc phthalocyanine having an average number of halogen atoms of 10 to 14, an average number of bromine atoms of 8 to 12, and an average number of chlorine atoms of 2 to 5 per molecule. Pigments can also be used. Specific examples include compounds described in International Publication No. 2015/118720. In addition, as a green colorant, the compound described in Chinese Patent Application No.
- C.I. I. Pigment Green 7, 36, 58, 62 and 63 are preferred, C.I. I. Pigment Greens 36 and 58 are more preferred.
- chromatic colorants triarylmethane dye polymers described in Korean Patent Publication No. 10-2020-0028160, xanthene compounds described in JP-A-2020-117638, and International Publication No. 2020/174991.
- the phthalocyanine compound described, the isoindoline compound described in JP-A-2020-160279, or a salt thereof can be used.
- the coloring composition of the present invention contains a green coloring agent, it is preferably used as a coloring composition for forming green pixels of color filters. Moreover, when the coloring composition of the present invention contains a red coloring agent, it is preferably used as a coloring composition for forming red pixels of a color filter.
- the coloring composition of the present invention contains a resin.
- the resin is blended, for example, for dispersing a pigment or the like in a coloring composition or as a binder.
- a resin mainly used for dispersing a pigment or the like in a coloring composition is also called a dispersant.
- such uses of the resin are only examples, and the resin can be used for purposes other than such uses.
- the acid value of the resin having acid groups is preferably 30-500 mgKOH/g.
- the lower limit is more preferably 40 mgKOH/g or more, particularly preferably 50 mgKOH/g or more.
- the upper limit is more preferably 400 mgKOH/g or less, still more preferably 300 mgKOH/g or less, and particularly preferably 200 mgKOH/g or less.
- the weight average molecular weight (Mw) of the acid group-containing resin is preferably 5,000 to 100,000, more preferably 5,000 to 50,000.
- the number average molecular weight (Mn) of the resin having an acid group is preferably 1,000 to 20,000.
- Examples of the compound represented by formula (X) include ethylene oxide- or propylene oxide-modified (meth)acrylate of paracumylphenol.
- Commercially available products include Aronix M-110 (manufactured by Toagosei Co., Ltd.).
- the cyclic ether group is preferably at least one selected from the group represented by the formula (e-1) and the group represented by the formula (e-2), and the group represented by the formula (e-2) It is more preferable that the group is When n in formula (e-1) is 0, the group represented by formula (e-1) is an epoxy group, and when n is 1, it is represented by formula (e-1) The group is an oxetanyl group. Also, the group represented by formula (e-2) is an alicyclic epoxy group.
- X a1 represents a trivalent linking group
- L a1 represents a single bond or a divalent linking group
- Z a1 represents a cyclic ether group.
- Examples of the trivalent linking group represented by X a1 in the formula (A1) include a poly(meth)acrylic linking group, a polyalkyleneimine linking group, a polyester linking group, a polyurethane linking group, a polyurea linking group, and a polyamide linking group.
- Linking groups, polyether-based linking groups, polystyrene-based linking groups, bisphenol-based linking groups, novolac-based linking groups, etc. poly(meth)acrylic-based linking groups, polyether-based linking groups, polyester-based linking groups, bisphenol-based linking groups, etc.
- a linking group and a novolac linking group are preferred, a polyether linking group, a novolak linking group and a poly(meth)acrylic linking group are more preferred, and a poly(meth)acrylic linking group is even more preferred.
- the content of repeating units having a cyclic ether group in the resin having a cyclic ether group is preferably 1 to 100 mol% of the total repeating units of the resin having a cyclic ether group.
- the upper limit is preferably 90 mol % or less, more preferably 80 mol % or less.
- the lower limit is preferably 2 mol % or more, more preferably 3 mol % or more.
- the resin having a cyclic ether group may have other repeating units in addition to the repeating unit having a cyclic ether group.
- Other repeating units include a repeating unit having an acid group (hereinafter also referred to as repeating unit B-1) and a repeating unit having a group in which the acid group is protected with a protecting group (hereinafter also referred to as repeating unit B-2). , a repeating unit having an ethylenically unsaturated bond-containing group (hereinafter also referred to as repeating unit B-3).
- Examples of the protecting group for protecting the acid group in the repeating unit B-2 include groups that are decomposed and eliminated by the action of an acid or base.
- the protecting group is preferably a group represented by any one of formulas (Y1) to (Y5), and is a group represented by formula (Y3) or formula (Y5) because it is easy to deprotect. is more preferred.
- R Y1 to R Y3 each independently represent an alkyl group, and two of R Y1 to R Y3 may combine to form a ring;
- R Y4 to R Y6 each independently represent an alkyl group, and two of R Y4 to R Y6 may combine to form a ring;
- R Y7 and R Y8 each independently represent a hydrogen atom, an alkyl group or an aryl group, at least one of R Y7 and R Y8 is an alkyl group or an aryl group, and R Y9 is an alkyl group.
- the number of carbon atoms in the alkyl groups represented by R Y1 to R Y3 in formula (Y1) is preferably 1 to 12, more preferably 1 to 6, even more preferably 1 to 4.
- the alkyl group may be linear, branched, or cyclic, but preferably linear or branched. In formula (Y1), two of R Y1 to R Y3 may combine to form a ring.
- R Y7 and R Y8 each independently represent a hydrogen atom, an alkyl group or an aryl group, at least one of R Y7 and R Y8 is an alkyl group or an aryl group, and R Y9 is an alkyl represents a group or an aryl group, and R Y7 or R Y8 and R Y9 may combine to form a ring.
- Alkyl groups may be linear, branched, or cyclic.
- the number of carbon atoms in the alkyl group is preferably 1-12, more preferably 1-6, even more preferably 1-4.
- the aryl group preferably has 6 to 20 carbon atoms, more preferably 6 to 12 carbon atoms.
- the molecular weight of the protective group is preferably 40-200, more preferably 40-150, even more preferably 40-120. If the molecular weight of the protective group is within the above range, a colored composition having excellent storage stability and excellent curability at low temperatures can be obtained.
- Examples of the ethylenically unsaturated bond-containing group possessed by the repeating unit B-3 include a vinyl group, a styrene group, a (meth)allyl group, and a (meth)acryloyl group.
- Examples of the group in which the acid group represented by Z b2 of the formula (B2) is protected by a protecting group include groups in which the acid group is protected by a group represented by any one of the formulas (Y1) to (Y5) described above. It is preferable that the acid group is a group protected by a group represented by formula (Y3) or formula (Y5).
- Examples of the acid group include a phenolic hydroxy group, a carboxyl group, a sulfo group and a phosphoric acid group, preferably a phenolic hydroxy group or a carboxyl group, more preferably a carboxyl group.
- Examples of the ethylenically unsaturated bond-containing group represented by Zb3 in formula (B3) include a vinyl group, a styrene group, a (meth)allyl group, and a (meth)acryloyl group.
- the content of the unit B-3 in the resin having a cyclic ether group is 1 to 65 mol% of the total repeating units of the resin having a cyclic ether group.
- the upper limit is preferably 45 mol % or less, more preferably 30 mol % or less.
- the lower limit is preferably 2 mol % or more, more preferably 3 mol % or more.
- aromatic carboxy group-containing group represented by Ar 1 in formula (Ac-1) examples include structures derived from aromatic tricarboxylic acid anhydrides, structures derived from aromatic tetracarboxylic acid anhydrides, and the like.
- Aromatic tricarboxylic anhydrides and aromatic tetracarboxylic anhydrides include compounds having the following structures.
- the divalent linking group represented by L 2 is preferably a group represented by -L 2a -O-.
- L 2a is an alkylene group; an arylene group; a group in which an alkylene group and an arylene group are combined; at least one selected from an alkylene group and an arylene group; Examples include groups in which at least one selected from —NH— and —S— are combined, and alkylene groups are preferred.
- the number of carbon atoms in the alkylene group is preferably 1-30, more preferably 1-20, and even more preferably 1-15.
- the alkylene group may be linear, branched or cyclic. An alkylene group and an arylene group may have a substituent. A hydroxy group etc. are mentioned as a substituent.
- L 12c represents a trivalent linking group
- X 1 represents S
- *1 represents the bonding position with L 11 of formula (Ac-2)
- *2 represents formula ( The binding position of Ac- 2 ) with P10 is shown.
- the trivalent linking group represented by L 12c includes a hydrocarbon group; and at least one selected from -O-, -CO-, -COO-, -OCO-, -NH- and -S- and the like, preferably a hydrocarbon group.
- the resin used as the dispersant is also preferably a polyimine-based dispersant containing nitrogen atoms in at least one of its main chain and side chains.
- the polyimine-based dispersant has a main chain having a partial structure having a functional group with a pKa of 14 or less and a side chain having 40 to 10,000 atoms, and at least one of the main chain and the side chain has a basic nitrogen atom.
- a resin having The basic nitrogen atom is not particularly limited as long as it is a nitrogen atom exhibiting basicity.
- the description in paragraphs 0102 to 0166 of JP-A-2012-255128 can be referred to, and the contents thereof are incorporated herein.
- the resin used as the dispersant is also preferably a resin containing a repeating unit having an ethylenically unsaturated bond-containing group in its side chain.
- the content of repeating units having an ethylenically unsaturated bond-containing group in the side chain is preferably 10 mol% or more, more preferably 10 to 80 mol%, more preferably 20 to 70, of the total repeating units of the resin. More preferably, it is mol %.
- the coloring composition of the present invention preferably contains a polymerizable compound.
- the polymerizable compound include compounds having an ethylenically unsaturated bond-containing group.
- ethylenically unsaturated bond-containing groups include vinyl groups, (meth)allyl groups, and (meth)acryloyl groups.
- the polymerizable compound used in the present invention is preferably a radically polymerizable compound.
- E is each independently -((CH 2 ) y CH 2 O)- or -((CH 2 ) y CH(CH 3 )O)- , y each independently represents an integer of 0 to 10, and each X independently represents a (meth)acryloyl group, a hydrogen atom, or a carboxy group.
- the total number of (meth)acryloyl groups is 3 or 4
- the sum of m is an integer of 0 to 40.
- the total number of (meth)acryloyl groups is 5 or 6
- each n independently represents an integer of 0-10, and the sum of each n is an integer of 0-60.
- m is preferably an integer of 0-6, more preferably an integer of 0-4.
- the sum of m is preferably an integer of 2 to 40, more preferably an integer of 2 to 16, and particularly preferably an integer of 4 to 8.
- n is preferably an integer of 0-6, more preferably an integer of 0-4.
- the sum of n is preferably an integer of 3-60, more preferably an integer of 3-24, and particularly preferably an integer of 6-12.
- diglycerin EO ethylene oxide modified (meth) acrylate
- pentaerythritol tetra (meth) acrylate manufactured by Shin-Nakamura Chemical Co., Ltd., NK ester A-TMMT
- 1,6-hexanediol diacrylate manufactured by Nippon Kayaku Co., Ltd., KAYARAD HDDA
- RP-1040 manufactured by Nippon Kayaku Co., Ltd.
- Aronix TO-2349 Toagosei Co., Ltd.
- a polymerizable compound having a fluorene skeleton can also be used.
- Commercially available products include Ogsol EA-0200 and EA-0300 (manufactured by Osaka Gas Chemicals Co., Ltd., (meth)acrylate monomer having a fluorene skeleton).
- photopolymerization initiators include trihalomethyltriazine compounds, benzyldimethylketal compounds, ⁇ -hydroxyketone compounds, ⁇ -aminoketone compounds, acylphosphine compounds, phosphine oxide compounds, metallocene compounds, oxime compounds, hexaarylbi imidazole compounds, onium compounds, benzothiazole compounds, benzophenone compounds, acetophenone compounds, cyclopentadiene-benzene-iron complexes, halomethyloxadiazole compounds and 3-aryl-substituted coumarin compounds, oxime compounds, ⁇ -hydroxyketones compounds, ⁇ -aminoketone compounds, and acylphosphine compounds, more preferably oxime compounds.
- hexaarylbiimidazole compounds include 2,2′,4-tris(2-chlorophenyl)-5-(3,4-dimethoxyphenyl)-4,5-diphenyl-1,1′-biimidazole, etc. are mentioned.
- a benzoyl group may have a substituent.
- substituents include halogen atoms, cyano groups, nitro groups, hydroxy groups, alkyl groups, alkoxy groups, aryl groups, aryloxy groups, heterocyclic groups, heterocyclicoxy groups, alkenyl groups, alkylsulfanyl groups, arylsulfanyl groups, It is preferably an acyl group or an amino group, more preferably an alkyl group, an alkoxy group, an aryl group, an aryloxy group, a heterocyclic oxy group, an alkylsulfanyl group, an arylsulfanyl group or an amino group.
- a sulfanyl group or an amino group is more preferred.
- R X12 is an electron-withdrawing group
- R X10 , R X11 , R X13 and R X14 are preferably hydrogen atoms.
- aromatic hydrocarbons (benzene, toluene, xylene, ethylbenzene, etc.) as organic solvents may be better reduced for environmental reasons (for example, 50 mass ppm (parts per million), 10 mass ppm or less, or 1 mass ppm or less).
- an organic solvent with a low metal content it is preferable to use an organic solvent with a low metal content.
- the metal content of the organic solvent is preferably, for example, 10 mass ppb (parts per billion) or less. If necessary, an organic solvent at a ppt (parts per trillion) level by mass may be used, and such an organic solvent is provided, for example, by Toyo Gosei Co., Ltd. (Chemical Daily, November 13, 2015). .
- Examples of methods for removing impurities such as metals from organic solvents include distillation (molecular distillation, thin film distillation, etc.) and filtration using a filter.
- the filter pore size 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 material of the filter is preferably polytetrafluoroethylene, polyethylene or nylon.
- the content of peroxide in the organic solvent is preferably 0.8 mmol/L or less, and more preferably substantially free of peroxide.
- the colored composition of the present invention does not substantially contain environmentally regulated substances.
- substantially free of environmentally regulated substances means that the content of environmentally regulated substances in the colored composition is 50 ppm by mass or less, preferably 30 ppm by mass or less. , is more preferably 10 mass ppm or less, and particularly preferably 1 mass ppm or less.
- Environmental control substances include, for example, benzene; alkylbenzenes such as toluene and xylene; and halogenated benzenes such as chlorobenzene.
- lanthanum boride products include LaB 6 -F (manufactured by Nippon New Metal Co., Ltd.). Moreover, as a metal boride, the compound as described in international publication 2017/119394 can also be used.
- commercially available products of indium tin oxide include F-ITO (manufactured by DOWA Hitech Co., Ltd.).
- the value of the number average molecular weight measured by the viscosity method is used.
- the value of the number average molecular weight in terms of polystyrene measured by the GPC (gel permeation chromatography) method is used.
- alkyleneimine examples include ethyleneimine, propyleneimine, 1,2-butyleneimine, 2,3-butyleneimine and the like, preferably ethyleneimine or propyleneimine, more preferably ethyleneimine. preferable. It is particularly preferred that the polyalkyleneimine is polyethyleneimine. In addition, the polyethyleneimine preferably contains 10 mol% or more, more preferably 20 mol% or more, of the primary amino group with respect to the total of the primary amino group, the secondary amino group and the tertiary amino group. , more preferably 30 mol % or more.
- Commercial products of polyethyleneimine include Epomin SP-003, SP-006, SP-012, SP-018, SP-200, P-1000 (manufactured by Nippon Shokubai Co., Ltd.).
- the content of polyalkyleneimine in the total solid content of the coloring composition is preferably 0.1 to 5% by mass.
- the lower limit is preferably 0.2% by mass or more, more preferably 0.5% by mass or more, and even more preferably 1% by mass or more.
- the upper limit is preferably 4.5% by mass or less, more preferably 4% by mass or less, and even more preferably 3% by mass or less.
- the content of the polyalkyleneimine is preferably 0.5 to 20 parts by mass with respect to 100 parts by mass of the pigment.
- the lower limit is preferably 0.6 parts by mass or more, more preferably 1 part by mass or more, and even more preferably 2 parts by mass or more.
- the upper limit is preferably 10 parts by mass or less, more preferably 8 parts by mass or less. Only one kind of polyalkyleneimine may be used, or two or more kinds thereof may be used. When two or more types are used, the total amount thereof is preferably within the above range.
- the coloring composition of the present invention may contain a curing accelerator.
- Curing accelerators include thiol compounds, methylol compounds, amine compounds, phosphonium salt compounds, amidine salt compounds, amide compounds, base generators, isocyanate compounds, alkoxysilane compounds, onium salt compounds and the like.
- the curing accelerator include compounds described in paragraph numbers 0094 to 0097 of WO 2018/056189, compounds described in paragraph numbers 0246 to 0253 of JP 2015-034963, JP 2013-041165 Compounds described in paragraphs 0186 to 0251 of the publication, ionic compounds described in JP 2014-055114, compounds described in paragraphs 0071 to 0080 of JP 2012-150180, JP 2011-253054 Alkoxysilane compounds having an epoxy group described in JP-A-2005-200557, compounds described in paragraphs 0085 to 0092 of Japanese Patent No. 5765059, and carboxy group-containing epoxy curing agents described in JP-A-2017-036379.
- the content of the curing accelerator in the total solid content of the coloring composition is preferably 0.3 to 8.9% by mass, more preferably 0.8 to 6.4% by mass.
- Examples of functional groups other than hydrolyzable groups include vinyl group, (meth)allyl group, (meth)acryloyl group, mercapto group, epoxy group, oxetanyl group, amino group, ureido group, sulfide group and isocyanate group. , phenyl group, etc., and amino group, (meth)acryloyl group and epoxy group are preferred.
- a block polymer can also be used as the fluorosurfactant.
- the fluorosurfactant has 2 or more (preferably 5 or more) repeating units derived from a (meth)acrylate compound having a fluorine atom and an alkyleneoxy group (preferably an ethyleneoxy group or a propyleneoxy group) (meta).
- 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 fluorine-based surfactants used in the present invention.
- the weight average molecular weight of the above compound is preferably 3000-50000, for example 14000. In the above compounds, % indicating the ratio of repeating units is mol%.
- a fluoropolymer having an ethylenically unsaturated bond-containing group in a side chain can also be used as the fluorosurfactant.
- Specific examples include compounds described in paragraph numbers 0050 to 0090 and paragraph numbers 0289 to 0295 of JP-A-2010-164965, MEGAFACE RS-101, RS-102 and RS-718K manufactured by DIC Corporation, and RS-72-K.
- compounds described in paragraphs 0015 to 0158 of JP-A-2015-117327 can also be used.
- antioxidants examples include 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 (manufactured by ADEKA Corporation) and the like.
- antioxidants are compounds described in paragraphs 0023 to 0048 of Japanese Patent No. 6268967, compounds described in WO 2017/006600, compounds described in WO 2017/164024, Compounds described in Korean Patent Publication No. 10-2019-0059371 can also be used.
- the water content of the coloring composition of the present invention is usually 3% by mass or less, preferably 0.01 to 1.5% by mass, more preferably 0.1 to 1.0% by mass.
- the water content can be measured by the Karl Fischer method.
- the pore size of the filter is preferably 0.01-7.0 ⁇ m, more preferably 0.01-3.0 ⁇ m, and even more preferably 0.05-0.5 ⁇ m. If the pore diameter of the filter is within the above range, fine foreign matter can be removed more reliably.
- the pore size value of the filter reference can be made to the filter manufacturer's nominal value.
- Various filters provided by Nippon Pall Co., Ltd. (DFA4201NXEY, DFA4201NAEY, DFA4201J006P, etc.), Advantech Toyo Co., Ltd., Nihon Entegris Co., Ltd. (former Japan Microlith Co., Ltd.), Kitz Micro Filter Co., Ltd., etc. can be used as filters. .
- the wavelength at which the light transmittance is 50% is preferably in the wavelength range of 470 to 520 nm, more preferably in the wavelength range of 475 to 520 nm, and more preferably in the wavelength range of 480 to 520 nm. It is even more preferred to be present in the wavelength range. In particular, it is preferable that the wavelengths at which the light transmittance is 50% exist in both the wavelength range of 470 to 520 nm and the wavelength range of 575 to 625 nm. In this embodiment, the wavelength on the short wavelength side at which the light transmittance is 50% preferably exists in the wavelength range of 475 to 520 nm, more preferably in the wavelength range of 480 to 520 nm.
- Pattern formation by photolithography includes the steps of forming a colored composition layer on a support using the colored composition of the present invention, a step of patternwise exposing the colored composition layer, and a step of exposing the colored composition layer. forming a pattern (pixels) by developing and removing the exposed portion. If necessary, a step of baking the coloring composition layer (pre-baking step) and a step of baking the developed pattern (pixels) (post-baking step) may be provided.
- the underlayer may be formed using a composition obtained by removing the coloring agent from the colored composition described herein, or a composition containing the curable compound described herein, a surfactant, and the like.
- the surface contact angle of the underlayer is preferably 20 to 70° when measured with diiodomethane. Further, it is preferably 30 to 80° when measured with water.
- the colored composition layer formed on the support may be dried (pre-baked). Pre-baking may not be performed when the film is manufactured by a low-temperature process.
- the pre-baking temperature is preferably 150° C. or lower, more preferably 120° C. or lower, and even more preferably 110° C. or lower.
- the lower limit can be, for example, 50° C. or higher, and can also be 80° C. or higher.
- the pre-bake time is preferably 10 to 300 seconds, more preferably 40 to 250 seconds, even more preferably 80 to 220 seconds. Pre-baking can be performed using a hot plate, an oven, or the like.
- the colored composition layer is exposed in a pattern (exposure step).
- the colored composition layer can be exposed in a pattern by exposing through a mask having a predetermined mask pattern using a stepper exposure machine, a scanner exposure machine, or the like. Thereby, the exposed portion can be cured.
- the irradiation amount is, for example, preferably 0.03 to 2.5 J/cm 2 , more preferably 0.05 to 1.0 J/cm 2 .
- the oxygen concentration at the time of exposure can be selected as appropriate.
- the exposure may be in an oxygen-free atmosphere, or in a high-oxygen atmosphere with an oxygen concentration exceeding 21% by volume (for example, 22% by volume, 30% by volume, or 50% by volume).
- the exposure illuminance can be set as appropriate, and is usually selected from a range of 1000 W/m 2 to 100000 W/m 2 (eg, 5000 W/m 2 , 15000 W/m 2 or 35000 W/m 2 ). can be done.
- the oxygen concentration and exposure illuminance may be appropriately combined.
- the illuminance may be 10000 W/m 2 at an oxygen concentration of 10% by volume and 20000 W/m 2 at an oxygen concentration of 35% by volume.
- the concentration of the alkaline agent in the alkaline aqueous solution is preferably 0.001 to 10% by mass, more preferably 0.01 to 1% by mass.
- the developer may further contain a surfactant. From the viewpoint of transportation and storage convenience, the developer may be produced once as a concentrated solution and then diluted to the required concentration when used. Although the dilution ratio is not particularly limited, it can be set, for example, in the range of 1.5 to 100 times. It is also preferable to wash (rinse) with pure water after development. Rinsing is preferably carried out by supplying a rinsing solution to the developed colored composition layer while rotating the support on which the developed colored composition layer is formed.
- optical filter of the present invention has the film of the present invention as described above.
- Types of optical filters include color filters and infrared transmission filters, with color filters being preferred.
- color filters it is preferable to have the film of the present invention as a colored pixel of the color filter.
- the solid-state imaging device of the present invention has the film of the present invention described above.
- the configuration of the solid-state imaging device is not particularly limited as long as it has the film of the present invention and functions as a solid-state imaging device.
- G-1 compound having the following structure (ultraviolet absorber)
- G-2 compound having the following structure (compound having an epoxy group, weight average molecular weight: 3500)
- G-3 EHPE3150 (manufactured by Daicel Corporation, 1,2-epoxy-4-(2-oxiranyl)cyclohexane adduct of 2,2′-bis(hydroxymethyl)-1-butanol)
- G-4 A compound having the following structure (silane coupling agent)
- G-5 3-methacryloxypropyltrimethoxysilane (KBM-503, manufactured by Shin-Etsu Chemical Co., Ltd., silane coupling agent)
- G-6 p-methoxyphenol (polymerization inhibitor)
- G-7 Adekastab AO-80 (manufactured by ADEKA Corporation, antioxidant)
- the film prepared above was irradiated with light of 100,000 Lux for 2,000 hours using a light resistance tester (super xenon weather meter SX75, manufactured by Suga Test Instruments Co., Ltd.) (total irradiation amount: 200 million Lux hr. ).
- the transmittance of the film after light irradiation was measured, and the light resistance was evaluated according to the following criteria.
- B The viscosity increase rate of the coloring composition exceeds 5% and is 7.5% or less.
- C The viscosity increase rate of the coloring composition exceeds 7.5% and is 10% or less.
- D The viscosity increase rate of the coloring composition exceeds 10%.
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| KR1020237024306A KR20230121861A (ko) | 2021-02-03 | 2022-01-28 | 착색 조성물, 막, 광학 필터, 고체 촬상 소자, 화상표시 장치 및 화합물 |
| JP2022579503A JPWO2022168741A1 (https=) | 2021-02-03 | 2022-01-28 | |
| CN202280010528.XA CN116848199B (zh) | 2021-02-03 | 2022-01-28 | 着色组合物、膜、滤光器、固体摄像元件、图像显示装置及化合物 |
| CN202510843618.2A CN120775398A (zh) | 2021-02-03 | 2022-01-28 | 着色组合物、膜、滤光器、固体摄像元件、图像显示装置及化合物 |
| CN202510843609.3A CN120775397A (zh) | 2021-02-03 | 2022-01-28 | 着色组合物、膜、滤光器、固体摄像元件、图像显示装置及化合物 |
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| JP2021146671 | 2021-09-09 | ||
| JP2021-146671 | 2021-09-09 | ||
| JP2021-212012 | 2021-12-27 | ||
| JP2021212012 | 2021-12-27 |
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| WO2024010025A1 (ja) * | 2022-07-07 | 2024-01-11 | 富士フイルム株式会社 | 着色組成物、膜、カラーフィルタ、固体撮像素子、画像表示装置及び化合物 |
| WO2024150571A1 (ja) * | 2023-01-11 | 2024-07-18 | 富士フイルム株式会社 | パターン形成方法、電子デバイスの製造方法 |
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| CN118955324B (zh) * | 2024-07-24 | 2026-01-27 | 南京林业大学 | 一种三苯胺基席夫碱类Hg2+荧光探针的制备方法及其应用 |
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| CN116848199B (zh) | 2025-07-25 |
| CN120775397A (zh) | 2025-10-14 |
| JPWO2022168741A1 (https=) | 2022-08-11 |
| CN116848199A (zh) | 2023-10-03 |
| CN120775398A (zh) | 2025-10-14 |
| TW202231790A (zh) | 2022-08-16 |
| KR20230121861A (ko) | 2023-08-21 |
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