WO2021033656A1 - Composition colorante, film, filtre optique, élément d'imagerie à semi-conducteurs et dispositif d'affichage d'image - Google Patents
Composition colorante, film, filtre optique, élément d'imagerie à semi-conducteurs et dispositif d'affichage d'image Download PDFInfo
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- WO2021033656A1 WO2021033656A1 PCT/JP2020/030936 JP2020030936W WO2021033656A1 WO 2021033656 A1 WO2021033656 A1 WO 2021033656A1 JP 2020030936 W JP2020030936 W JP 2020030936W WO 2021033656 A1 WO2021033656 A1 WO 2021033656A1
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- 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
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- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
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- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
- G02B5/22—Absorbing filters
Definitions
- color filters are used as key devices for displays and optical elements.
- a color filter usually includes pixels of the three primary colors of red, green, and blue, and plays a role of decomposing transmitted light into the three primary colors.
- Patent Document 1 describes an invention relating to a fluorescent diketopyrrolopyrrole compound.
- Patent Document 1 is an invention relating to a fluorescent diketopyrrolopyrrole compound, and by using this fluorescent diketopyrrolopyrrole compound as a light emitting element, a light emitting element having high efficiency of utilization of electric energy and high brightness can be obtained.
- this fluorescent diketopyrrolopyrrole compound as a light emitting element, a light emitting element having high efficiency of utilization of electric energy and high brightness can be obtained.
- the yellow colorant and the light resistance and moisture resistance of the film there is no description regarding the yellow colorant and the light resistance and moisture resistance of the film.
- a coloring composition for an optical filter containing a colorant, a curable compound, and a solvent contains a yellow colorant and contains The yellow colorant contains at least one compound (A) selected from the compound represented by the formula (I) and the compound represented by the formula (II).
- R 1 and R 2 independently represent a hydrocarbon group, a heterocyclic group, -OR 11 or -NR 12 R 13 , and R 11 to R 13 independently represent hydrogen. Representing an atom, hydrocarbon group or heterocyclic group, at least one of R 1 and R 2 represents an aliphatic hydrocarbon group, -OR 11 or -NR 12 R 13 , and R 3 and R 4 are independent of each other.
- R 5 and R 6 independently represent a hydrocarbon group, a heterocyclic group, -OR 21 or -NR 22 R 23 , and R 21 to R 23 independently represent hydrogen. Representing an atom, hydrocarbon group or heterocyclic group, at least one of R 5 and R 6 represents an aliphatic hydrocarbon group, -OR 21 or -NR 22 R 23 , and R 7 and R 8 are independent of each other. Represents a hydrogen atom, a metal atom or a substituent, and A 3 and A 4 independently represent O or S, respectively.
- R 1 and R 2 of the formula (I) are aliphatic hydrocarbon groups, and are The coloring composition according to ⁇ 1>, wherein R 5 and R 6 of the formula (II) are aliphatic hydrocarbon groups.
- R 3> The coloring composition according to ⁇ 1> or ⁇ 2>, wherein A 1 and A 2 of the formula (I) are O, and A 3 and A 4 of the formula (II) are O.
- ⁇ 4> The coloring composition according to any one of ⁇ 1> to ⁇ 3>, wherein the compound (A) is a pigment.
- ⁇ 5> The coloring composition according to any one of ⁇ 1> to ⁇ 4>, wherein the yellow colorant contains the compound (A) and a yellow colorant other than the compound (A).
- ⁇ 6> The coloring composition according to any one of ⁇ 1> to ⁇ 5>, wherein the coloring agent contains a coloring agent other than the yellow coloring agent.
- ⁇ 9> When a film having a thickness of 0.3 ⁇ m is formed using the coloring composition, the minimum value of the transmittance of the film in the wavelength region of 400 to 550 nm is 20% or less, ⁇ 1> to ⁇ 8. > The coloring composition according to any one of.
- ⁇ 10> The coloring composition according to any one of ⁇ 1> to ⁇ 9>, which is for a color filter or an infrared transmission filter.
- ⁇ 11> A film obtained from the coloring composition according to any one of ⁇ 1> to ⁇ 10>.
- ⁇ 12> An optical filter having the film according to ⁇ 11>.
- ⁇ 13> A solid-state image sensor having the film according to ⁇ 11>.
- ⁇ 14> An image display device having the film according to ⁇ 11>.
- a coloring composition capable of forming a film having excellent light resistance and moisture resistance. Further, it is possible to provide a film, an optical filter, a solid-state image sensor, and an image display device using the coloring composition.
- the contents of the present invention will be described in detail below.
- "-" is used to mean that the numerical values described before and after it are included as the lower limit value and the upper limit value.
- the notation not describing substitution and non-substitution also includes a group having a substituent (atomic group) as well as a group having no substituent (atomic group).
- the "alkyl group” includes not only an alkyl group having no substituent (unsubstituted alkyl group) but also an alkyl group having a substituent (substituted alkyl group).
- exposure includes not only exposure using light but also drawing using particle beams such as an electron beam and an ion beam.
- the light used for exposure include the emission line spectrum of a mercury lamp, far ultraviolet rays typified by an excimer laser, extreme ultraviolet rays (EUV light), X-rays, active rays such as electron beams, or radiation.
- EUV light extreme ultraviolet rays
- (meth) acrylate” represents both acrylate and methacrylate, or either
- (meth) acrylic represents both acrylic and methacrylic, or either.
- Acryloyl represents both acryloyl and / or methacryloyl.
- Me in the structural formula represents a methyl group
- Et represents an ethyl group
- Bu represents a butyl group
- Ph represents a phenyl group.
- the weight average molecular weight and the number average molecular weight are polystyrene-equivalent values measured by a GPC (gel permeation chromatography) method.
- the total solid content means the total mass of all the components of the composition excluding the solvent.
- the term pigment means a compound that is difficult to dissolve in a solvent.
- the term "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. ..
- the coloring composition of the present invention is a coloring composition for an optical filter containing a colorant, a curable compound, and a solvent.
- the colorant contains a yellow colorant and contains
- the yellow colorant contains at least one compound (A) selected from the compound represented by the formula (I) and the compound represented by the formula (II).
- the content of the compound (A) in the colorant is 3.5% by mass or more.
- a film having excellent light resistance and moisture resistance can be formed.
- compound (A) has a high flatness of the dye matrix and easily associates in the membrane. Therefore, it is presumed that an aggregate of the compound (A) was easily formed in the film, and a film having excellent light resistance and moisture resistance could be formed.
- the minimum value of the transmittance of the above-mentioned film in the wavelength region of 400 to 550 nm is preferably 20% or less, preferably 10% or less. Is more preferable, and 5% or less is further preferable.
- a coloring composition having such spectral characteristics is preferably used as a coloring composition for forming green pixels, red pixels or yellow pixels of a color filter, and a coloring composition for an infrared transmission filter.
- the coloring composition of the present invention contains a coloring agent.
- the colorant include a chromatic colorant such as a red colorant, a green colorant, a blue colorant, a yellow colorant, and a purple colorant, and a black colorant.
- the colorant may be a pigment or a dye. Pigments and dyes may be used in combination.
- the pigment may be either an inorganic pigment or an organic pigment.
- an inorganic pigment or a material in which a part of the organic-inorganic pigment is replaced with an organic chromophore can be used. Hue design can be facilitated by replacing inorganic pigments and organic-inorganic pigments with organic chromophores.
- the average primary particle size of the pigment is preferably 1 to 200 nm.
- the lower limit is preferably 5 nm or more, more preferably 10 nm or more.
- the upper limit is preferably 180 nm or less, more preferably 150 nm or less, and even more preferably 100 nm or less.
- the primary particle size of the pigment can be determined from the image photograph obtained by observing the primary particles of the pigment with a transmission electron microscope. Specifically, the projected area of the primary particles of the pigment is obtained, and the corresponding circle-equivalent diameter is calculated as the primary particle diameter of the pigment.
- the average primary particle size in the present invention is an arithmetic mean value of the primary particle size for the primary particles of 400 pigments.
- the primary particles of the pigment refer to independent particles without aggregation.
- the coloring composition of the present invention contains a yellow colorant.
- the coloring composition of the present invention contains at least one compound (A) selected from the compound represented by the formula (I) and the compound represented by the formula (II) as the yellow colorant.
- the compound (A) is preferably a compound represented by the formula (I) because a film having more excellent light resistance can be easily obtained.
- the compound (A) is preferably a compound having a maximum absorption wavelength in the wavelength range of 350 to 490 nm, more preferably a compound having a maximum absorption wavelength in the wavelength range of 375 to 485 nm, and a wavelength of 400 to 400. It is even more preferable that the compound has a maximum absorption wavelength in the range of 480 nm.
- compound A For the maximum absorption wavelength of compound (A), compound A is diluted with KBr to prepare a powder sample (compound A content 0.001% by mass), and a diffuse reflection spectrum of the powder sample is obtained using an integrating sphere. It can be measured and obtained.
- the measuring device include an absorption spectroscope V7200 (using an integrating sphere) manufactured by JASCO Corporation.
- R 1 and R 2 independently represent a hydrocarbon group, a heterocyclic group, -OR 11 or -NR 12 R 13 , and R 11 to R 13 independently represent hydrogen. Representing an atom, hydrocarbon group or heterocyclic group, at least one of R 1 and R 2 represents an aliphatic hydrocarbon group, -OR 11 or -NR 12 R 13 , and R 3 and R 4 are independent of each other. Represents a hydrogen atom, a metal atom or a substituent, and A 1 and A 2 independently represent O or S;
- R 5 and R 6 independently represent a hydrocarbon group, a heterocyclic group, -OR 21 or -NR 22 R 23 , and R 21 to R 23 independently represent hydrogen.
- R 5 and R 6 represents an aliphatic hydrocarbon group
- -OR 21 or -NR 22 R 23 and R 7 and R 8 are independent of each other.
- a 1 and A 2 of the formula (I) and A 3 and A 4 of the formula (II) are preferably O because the color value per unit weight increases as the molecular weight decreases.
- Hydrocarbon groups represented by R 1 and R 2 of the formula (I), hydrocarbon groups represented by R 11 to R 13 of the formula (I), hydrocarbon groups represented by R 5 and R 6 of the formula (II), and Examples of the hydrocarbon group represented by R 21 to R 23 in the formula (II) include an aliphatic hydrocarbon group and an aromatic hydrocarbon group.
- the aliphatic hydrocarbon group may be a saturated aliphatic hydrocarbon group or an unsaturated aliphatic hydrocarbon group.
- the aliphatic hydrocarbon group may be linear, cyclic or branched, but is preferably a linear or branched aliphatic hydrocarbon group because the dispersibility in the composition can be further improved. , A straight chain aliphatic hydrocarbon group is more preferable.
- Ra 1 to Ra 3 represent a hydrogen atom or a substituent.
- Examples of the substituent include a group described as a substituent T described later and a group represented by the formula (DP-1) described later, and an alkyl group is preferable.
- na1 represents an integer of 1 or more, preferably an integer of 1 to 10, more preferably an integer of 1 to 5, further preferably an integer of 1 to 3, and even more preferably 1 or 2.
- the number of carbon atoms of the aliphatic hydrocarbon group is preferably 1 to 50, more preferably 1 to 40, further preferably 1 to 30, and even more preferably 1 to 20. It is even more preferably 1 to 10, and even more preferably 1 to 5 from the viewpoint of the dispersibility of the compound (A) in the coloring composition and the light resistance and moisture resistance of the obtained film. It is particularly preferably 1 to 3, and most preferably 1.
- aromatic hydrocarbon group examples include an aryl group.
- the number of carbon atoms of the aromatic hydrocarbon group is preferably 6 to 50, more preferably 6 to 40, further preferably 6 to 30, and even more preferably 6 to 20. , 6 to 10 is even more preferable, and 6 is particularly preferable.
- the heterocyclic group represented by R 21 to R 23 in II) may be a monocyclic ring or a condensed ring.
- the heterocyclic group is preferably a single ring or a condensed ring having 2 to 4 condensation numbers.
- the number of heteroatoms constituting the ring of the heterocyclic group is preferably 1 to 3.
- the hetero atom constituting the ring of the heterocyclic group is preferably a nitrogen atom, an oxygen atom or a sulfur atom.
- the number of carbon atoms constituting the ring of the heterocyclic group is preferably 3 to 30, more preferably 3 to 18, and even more preferably 3 to 12.
- R 11 to R 13 in the formula (I) and R 21 to R 23 in the formula (I) are preferably independent hydrocarbon groups, more preferably aliphatic hydrocarbon groups. It is more preferably an alkyl group.
- At least one of R 1 and R 2 is preferably an aliphatic hydrocarbon group or ⁇ NR 12 R 13 , and at least one of R 1 and R 2 is an aliphatic hydrocarbon from the viewpoint of moisture resistance. It is more preferable that it is a hydrogen group, and it is further preferable that both R 1 and R 2 are aliphatic hydrocarbon groups because it is easy to increase the color value of yellow.
- at least one of R 5 and R 6 is preferably an aliphatic hydrocarbon group or ⁇ NR 22 R 23 , and at least one of R 5 and R 6 is fat from the viewpoint of moisture resistance. It is more preferable that it is a group hydrocarbon group, and it is preferable that both R 5 and R 6 are aliphatic hydrocarbon groups because it is easier to increase the color value of yellow.
- the heterocyclic group represented by R 5 and R 6 of the formula (II) may have a substituent.
- substituents include a group listed as the substituent T described later and a group represented by the formula (DP-1) described later.
- Examples of the metal atom represented by R 3 and R 4 of the formula (I) and the metal atom represented by R 7 and R 8 of the formula (II) include lithium, sodium, potassium and silver.
- the substituents represented by R 3 and R 4 of the formula (I) and the substituents represented by R 7 and R 8 of the formula (II) include an alkyl group, an alkoxy group, an acyl group, an acyloxy group, an aryl group and a heterocyclic group.
- R 7A to R 7D independently represent a hydrogen atom or a substituent
- n represents an integer of 2 to 4
- M 1 represents an n + 1-valent metal atom.
- the number of carbon atoms of the alkyl group and the alkoxy group is preferably 1 to 50, more preferably 1 to 40, still more preferably 1 to 30, further preferably 1 to 20, and even more preferably 1 to 10.
- the alkyl group and the alkoxy group may be linear, branched or cyclic, but linear or branched is preferable.
- the aryl group preferably has 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, and even more preferably 6 to 12 carbon atoms.
- the heterocyclic group may be a monocyclic ring or a condensed ring.
- the heterocyclic group is preferably a single ring or a condensed ring having 2 to 4 condensation numbers.
- the number of heteroatoms constituting the ring of the heterocyclic group is preferably 1 to 3.
- the hetero atom constituting the ring of the heterocyclic group is preferably a nitrogen atom, an oxygen atom or a sulfur atom.
- the number of carbon atoms constituting the ring of the heterocyclic group is preferably 3 to 30, more preferably 3 to 18, and even more preferably 3 to 12.
- alkyl group, aryl group or heterocyclic group examples include the groups described above.
- the above-mentioned alkyl group, alkoxy group, acyl group, acyloxy group, aryl group and heterocyclic group may have a substituent.
- substituent examples include a group listed as the substituent T described later and a group represented by the formula (DP-1) described later.
- Examples of the substituent represented by R 7A to R 7D include a halogen atom, an alkyl group, an alkoxy group, an acyl group, an acyloxy group, an aryl group and a heterocyclic group, and a halogen atom, an alkyl group, an aryl group or a heterocyclic group can be used.
- a halogen atom, an alkyl group or an aryl group is more preferable, and an aryl group is even more preferable.
- the plurality of R 7A , R 7B , R 7C and R 7D may be the same or different. Further, a plurality of R 7A's , R 7B's , R 7C's and R 7D's may be connected to each other to form a ring.
- Examples of the halogen atom represented by R 7A to R 7D include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
- Examples of the alkyl group, alkoxy group, acyl group, acyloxy group, aryl group and heterocyclic group represented by R 7A to R 7D include the above-mentioned groups.
- n + 1-valent metal atom represented by M 1 examples include magnesium, aluminum, calcium, barium, zinc, tin, vanadium, iron, cobalt, nickel, copper, palladium, iridium, platinum, and gold.
- R 3 and R 4 are each independently preferably a hydrogen atom, an alkyl group, an alkoxy group, an acyl group, an acyloxy group, an aryl group or a heterocyclic group, and the association is improved.
- a hydrogen atom or an aryl group is more preferable because the light resistance and moisture resistance of the obtained film can be further improved.
- R 7 and R 8 are each independently preferably a hydrogen atom, an alkyl group, an alkoxy group, an acyl group, an acyloxy group, an aryl group or a heterocyclic group, and the association is improved.
- a hydrogen atom or an aryl group is more preferable because the light resistance and moisture resistance of the obtained film can be further improved.
- the substituent T includes a halogen atom, a cyano group, a nitro group, an alkyl group, an aryl group, a heterocyclic group, -ORt 1 , -CORt 1 , -COORt 1 , -OCORt 1 , -NRt 1 Rt 2 , and -NHCORt 1. , -CONRt 1 Rt 2 , -NHCONRt 1 Rt 2 , -NHCOORt 1 , -SRt 1 , -SO 2 Rt 1 , -SO 2 ORt 1 , -NHSO 2 Rt 1 or -SO 2 NRt 1 Rt 2 .
- Rt 1 and Rt 2 independently represent a hydrogen atom, an alkyl group, an aryl group or a heterocyclic group, respectively.
- Rt 1 and Rt 2 may be combined to form a ring.
- halogen atom examples include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.
- the number of carbon atoms of the alkyl group is preferably 1 to 30, more preferably 1 to 15, and even more preferably 1 to 8.
- the alkyl group may be linear, branched or cyclic, and is preferably linear or branched, more preferably linear.
- the aryl group preferably has 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, and even more preferably 6 to 12 carbon atoms.
- the heterocyclic group may be a monocyclic ring or a condensed ring.
- the heterocyclic group is preferably a single ring or a condensed ring having 2 to 4 condensation numbers.
- the number of heteroatoms constituting the ring of the heterocyclic group is preferably 1 to 3.
- the hetero atom constituting the ring of the heterocyclic group is preferably a nitrogen atom, an oxygen atom or a sulfur atom.
- the number of carbon atoms constituting the ring of the heterocyclic group is preferably 3 to 30, more preferably 3 to 18, and even more preferably 3 to 12.
- the alkyl group, aryl group and heterocyclic group may have a substituent or may be unsubstituted. Examples of the substituent include the substituent described by the above-mentioned Substituent T and the group represented by the following formula (DP-1).
- L T1 represents a single bond or a divalent linking group
- P T1 represents a group represented by the following formula (T1) or (T-II)
- R T100 is a hydrogen atom or It represents a substituent
- n1 represents an integer of 1 to 10.
- Examples of the divalent linking group L T1 represents an alkylene group (preferably an alkylene group having 1 to 12 carbon atoms), an arylene group (preferably an arylene group having 6 to 20 carbon atoms), a heterocyclic group, -NH-, Examples thereof include -SO-, -SO 2- , -CO-, -O-, -COO-, OCO-, -S-, and groups composed of a combination of two or more of these.
- Examples of the substituent represented by RT100 include the groups listed as the above-mentioned substituent T.
- n1 represents an integer of 1 to 10, preferably an integer of 1 to 9, more preferably an integer of 1 to 5, and even more preferably 1 or 2.
- R 1T and R 2T independently represent a hydrocarbon group and a heterocyclic group
- R 3T and R 4T independently represent a hydrogen atom, a metal atom or a substituent, respectively.
- a 1T and A 2T independently represent O or S, respectively.
- any of R 1T to R 4T includes a connecting hand with LT 1 or RT 100.
- a 1T and A 2T of the formula (TI ) and A 3T and A 4T of the formula (T-II) are preferably O.
- hydrocarbon groups represented by R 1T and R 2T of the formula (TI ) and the hydrocarbon groups represented by R 5T and R 6T of the formula (T-II) are represented by R 1 and R 2 of the formula (I).
- hydrocarbon group include the groups described as the hydrocarbon group R 5 and R 6 represents the formula (II).
- the heterocyclic groups represented by R 1T and R 2T of the formula (TI ) and the heterocyclic groups represented by R 5T and R 6T of the formula (T-II) include R 1 and R 2 of the formula (I). Examples thereof include the heterocyclic group represented by and the group described as the heterocyclic group represented by R 5 and R 6 of the formula (II).
- the metal atom represented by R 3T and R 4T of the formula (TI ) and the metal atom represented by R 7T and R 8T of the formula (T-II) include the metal atom represented by R 3 and R 4 of the formula (I).
- the metal atom described as the metal atom represented by R 7 and R 8 of the formula (II) can be mentioned.
- the substituents represented by R 3T and R 4T of the formula (TI ) and the substituents represented by R 7T and R 8T of the formula (T-II) include the substituents represented by R 3 and R 4 of the formula (I).
- the group described as the substituent represented by R 7 and R 8 of the formula (II) can be mentioned.
- the molecular weight of compound (A) is preferably 164 to 2000, and more preferably 164 to 1500, because the thixotropy of the coloring composition is likely to be lowered.
- the acid value of compound (A) is preferably 510 mgKOH / g or less, more preferably 100 mgKOH / g or less, and 50 mgKOH / g or less because it is easy to form a film having more excellent moisture resistance. It is more preferably present, and particularly preferably 0 mgKOH / g.
- Me represents a methyl group
- Et represents an ethyl group
- n Pr represents a normal propyl group
- n Bu represents a normal butyl group
- n Hex represents a normal hexyl group
- n Hep represents a normal.
- n Oct represents a n-octyl group
- i Pr denotes an isopropyl group
- t Bu represents a tert- butyl group
- Cy represents a cyclohexyl group
- Ph represents a phenyl group
- the wavy line represents a bond Represents.
- the yellow colorant used in the present invention may contain a yellow colorant other than the above-mentioned compound (A) (hereinafter, also referred to as another yellow colorant). According to this aspect, the crystallinity of the compound (A) in the coloring composition can be lowered, and the thixotropy property of the coloring composition can be further lowered.
- pigments used as yellow colorants include Color Index (CI) Pigment Yellow 1,2,3,4,5,6,10,11,12,13,14,15,16,17, 18, 20, 24, 31, 32, 34, 35, 35: 1,36,36: 1,37,37: 1,40,42,43,53,55,60,61,62,63,65, 73,74,77,81,83,86,93,94,95,97,98,100,101,104,106,108,109,110,113,114,115,116,117,118,119, 120, 123, 125, 126, 127, 128, 129, 137, 138, 139, 147, 148, 150, 151, 152, 153, 154, 155, 156, 161, 162, 164, 166, 167, 168, 169,170,171,172,173,174,175,176,177,179,180,181,182,185,187,188,193,194,199,213,214,215,228,231,232
- dyes used as other yellow colorants include C.I. I. Acid Yellow 1,3,7,9,11,17,23,25,29,34,36,42,54,72,73,76,79,98,99,111,112,114,116,184,200 And so on.
- X 1 to X 16 independently represent a hydrogen atom or a halogen atom, and Z 1 represents an alkylene group having 1 to 3 carbon atoms.
- Specific examples of the compound represented by the formula (QP1) include the compounds described in paragraph No. 0016 of Japanese Patent No. 6443711.
- Y 1 ⁇ Y 3 represents a halogen atom independently.
- n and m represent integers of 0 to 6, and p represents an integer of 0 to 5.
- N + m is 1 or more.
- Specific examples of the compound represented by the formula (QP2) include the compounds described in paragraphs 0047 to 0048 of Japanese Patent No. 6432077.
- the coloring composition of the present invention may further contain a coloring agent other than the yellow coloring agent.
- a coloring agent other than the yellow coloring agent According to this aspect, the crystallinity of the compound (A) in the coloring composition can be lowered, and the thixotropy property of the coloring composition can be further lowered.
- other colorants used in combination include chromatic colorants such as green colorants, red colorants, purple colorants, blue colorants, and orange colorants, and black colorants. As other colorants, green colorants and red colorants are preferable.
- a green colorant is contained as another colorant, it is preferably used as a coloring composition for forming green pixels of a color filter.
- red colorant When a red colorant is contained as another colorant, it is preferably used as a coloring composition for forming red pixels of a color filter. It is also preferable to use a black colorant as another colorant. When a black colorant is contained as another colorant, it is preferably used as a color composition for forming an infrared transmission filter.
- the other colorant may be a pigment or a dye.
- the colorant contained in the coloring composition may contain two or more kinds of chromatic colorants, and a combination of two or more kinds of chromatic colorants may form black.
- a coloring composition is preferably used as a coloring composition for forming an infrared transmission filter.
- the following are examples of combinations of chromatic colorants when black is formed by a combination of two or more chromatic colorants.
- An embodiment containing a red colorant, a blue colorant, and a yellow colorant. An embodiment containing a red colorant, a blue colorant, a yellow colorant, and a purple colorant.
- An embodiment containing a red colorant, a blue colorant, a yellow colorant, a purple colorant, and a green colorant An embodiment containing a red colorant, a blue colorant, a yellow colorant, and a green colorant.
- An embodiment containing a red colorant, a blue colorant, a yellow colorant, and a green colorant. An embodiment containing a
- pigments used as other colorants include those shown below.
- a halogenated zinc phthalocyanine having an average number of halogen atoms in one molecule of 10 to 14, a bromine atom number of 8 to 12, and a chlorine atom number of 2 to 5 on average. Pigments can also be used. Specific examples include the compounds described in International Publication No. 2015/118720. Further, as a green colorant, a compound described in Chinese Patent Application No. 106909027, a phthalocyanine compound having a phosphate ester described in International Publication No. 2012/10395 as a ligand, and Japanese Patent Application Laid-Open No. 2019-008014. The phthalocyanine compound of JP-A-2018-180023, the compound described in JP-A-2019-038958, and the like can also be used.
- an aluminum phthalocyanine compound having a phosphorus atom can also be used. Specific examples include the compounds described in paragraphs 0022 to 0030 of JP2012-247591A and paragraph numbers 0047 of JP2011-157478A.
- a red colorant As a red colorant, a diketopyrrolopyrrole compound in which at least one bromine atom is substituted in the structure described in JP-A-2017-2013384, and a diketopyrrolopyrrole compound described in paragraphs 0016 to 0022 of Patent No. 6248838. , Diketopyrrolopyrrole compound described in WO2012 / 102399, diketopyrrolopyrrole compound described in WO2012 / 117965, naphtholazo compound described in JP2012-229344, patent No. 6516119.
- the red colorant described in JP-A, the red colorant described in Patent No. 6525101, and the like can also be used.
- red colorant a compound having a structure in which an aromatic ring group having an oxygen atom, a sulfur atom or a nitrogen atom bonded to the aromatic ring is bonded to a diketopyrrolopyrrole skeleton is used. You can also.
- Examples of the black colorant include bisbenzofuranone compounds, azomethine compounds, perylene compounds, azo compounds and the like, and bisbenzofuranone compounds and perylene compounds are preferable.
- Examples of the bisbenzofuranone compound include the compounds described in Japanese Patent Publication No. 2010-534726, Japanese Patent Publication No. 2012-515233, Japanese Patent Publication No. 2012-515234, and the like. It is available.
- Examples of the perylene compound include the compounds described in paragraphs 0016 to 0020 of JP-A-2017-226821, C.I. I. Pigment Black 31, 32 and the like can be mentioned.
- Examples of the azomethine compound include the compounds described in JP-A-01-17601 and JP-A-02-0346664, and are available as, for example, "Chromofine Black A1103" manufactured by Dainichiseika.
- Pigment derivatives can also be used as other colorants.
- the pigment derivative used as the colorant include compounds having coloration in the visible region among the pigment derivatives described later.
- pigment derivatives used as colorants include compounds having a maximum molar extinction coefficient ( ⁇ max) of more than 3000 L ⁇ mol -1 ⁇ cm -1 in the wavelength region of 400 to 700 nm.
- the content of the colorant in the total solid content of the coloring composition is preferably 10 to 80% by mass.
- the lower limit is preferably 15% by mass or more, and more preferably 20% by mass or more.
- the upper limit is preferably 70% by mass or less, and more preferably 60% by mass or less.
- the content of the compound (A) in the yellow colorant is preferably 3.5% by mass or more, more preferably 4.0% by mass or more, and preferably 4.5% by mass or more. More preferred.
- the upper limit can be 100% by mass, 95% by mass or less, or 90% by mass or less.
- the yellow colorant may be substantially only compound (A).
- the ratio of the compound (A) in the total amount of the yellow colorant is 99% by mass or more, and 99.5% by mass or more. It is preferably present, and more preferably only compound (A).
- the content of the compound (A) in the total solid content of the coloring composition is preferably 0.35% by mass or more, more preferably 1.0% by mass or more, and 2.0% by mass. The above is more preferable.
- the upper limit is preferably 80% by mass or less, more preferably 70% by mass or less, and further preferably 60% by mass or less.
- the content of the compound (A) in the colorant is 3.5 mass by mass from the viewpoint of spectral characteristics, light resistance and moisture resistance. % Or more, more preferably 4.5% by mass or more, and even more preferably 5.0% by mass or more.
- the content of the compound (A) in the colorant is 3.5 to 3.5 from the viewpoint of spectral characteristics, light resistance and moisture resistance. It is preferably 60% by mass, more preferably 4.5 to 55% by mass, and even more preferably 5.0 to 50% by mass.
- the colorant used in combination with compound (A) is preferably a green colorant.
- the content of the compound (A) in the colorant is 3.5 from the viewpoint of spectral characteristics, light resistance and moisture resistance. It is preferably to 60% by mass, more preferably 4.5 to 55% by mass, and even more preferably 5.0 to 50% by mass.
- the colorant used in combination with compound (A) is preferably a red colorant.
- the content of the compound (A) in the colorant is 3.5 to 60 from the viewpoint of spectral characteristics, light resistance and moisture resistance. It is preferably by mass, more preferably 4.5 to 55% by mass, and even more preferably 5.0 to 50% by mass.
- examples of the colorant used in combination with the compound (A) include a red colorant, a blue colorant, a purple colorant, a green colorant, and a black colorant.
- the coloring composition of the present invention contains a curable compound.
- the curable compound include polymerizable compounds and resins.
- the resin may be a non-polymerizable resin (a resin having no polymerizable group) or a polymerizable resin (a resin having a polymerizable group).
- the polymerizable group include an ethylenically unsaturated bond-containing group, a cyclic ether group, a methylol group, and an alkoxymethyl group.
- Examples of the ethylenically unsaturated bond-containing group include a vinyl group, an allyl group, and a (meth) acryloyl group.
- the cyclic ether group include an epoxy group and an oxetanyl group, and an epoxy group is preferable.
- the resin having a polymerizable group is also a polymerizable compound.
- the curable compound preferably contains at least a resin, more preferably a resin and a monomer-type polymerizable compound, and has a resin and a group having an ethylenically unsaturated bond. It is more preferable to use a monomer type polymerizable compound.
- the content of the curable compound in the total solid content of the coloring composition is preferably 0.1 to 80% by mass.
- the lower limit is preferably 0.5% by mass or more, more preferably 1% by mass or more, and further preferably 5% by mass or more.
- the upper limit is preferably 75% by mass or less, more preferably 70% by mass or less.
- the curable compound 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.
- polymerizable compound examples include a compound having an ethylenically unsaturated bond-containing group, a compound having a cyclic ether group, a compound having a methylol group, and a compound having an alkoxymethyl group.
- the polymerizable compound may be a monomer or a resin.
- a monomer-type polymerizable compound having an ethylenically unsaturated bond-containing group can be preferably used as a radically polymerizable compound.
- a compound having a cyclic ether group, a compound having a methylol group, and a compound having an alkoxymethyl group can be preferably used as the cationically polymerizable compound.
- the molecular weight of the monomer-type polymerizable compound is preferably less than 2000, more preferably 100 or more and less than 2000, and further preferably 200 or more and less than 2000.
- the upper limit of the molecular weight is preferably 1500 or less.
- the weight average molecular weight (Mw) of the resin-type polymerizable compound is preferably 2000 to 2000000.
- the upper limit of the weight average molecular weight is preferably 1,000,000 or less, and more preferably 500,000 or less.
- the lower limit of the weight average molecular weight is preferably 3000 or more, and more preferably 5000 or more.
- the compound containing an ethylenically unsaturated bond-containing group as a monomer-type polymerizable compound is preferably a 3- to 15-functional (meth) acrylate compound, and is preferably a 3- to 6-functional (meth) acrylate. More preferably, it is a compound.
- Compounds containing an ethylenically unsaturated bond-containing group include dipentaerythritol triacrylate (commercially available KAYARAD D-330; manufactured by Nippon Kayaku Co., Ltd.) and dipentaerythritol tetraacrylate (commercially available KAYARAD D-).
- Examples thereof include compounds having a structure bound to each other (for example, SR454 and SR499 commercially available from Sartmer).
- Examples of the compound containing an ethylenically unsaturated bond-containing group include diglycerin EO (ethylene oxide) modified (meth) acrylate (commercially available M-460; manufactured by Toa Synthetic) and pentaerythritol tetraacrylate (Shin-Nakamura Chemical Industry Co., Ltd.).
- NK ester A-TMMT (manufactured by Nippon Kayaku Co., Ltd.), 1,6-hexanediol diacrylate (manufactured by Nippon Kayaku Co., Ltd., KAYARAD HDDA), RP-1040 (manufactured by Nippon Kayaku Co., Ltd.), Aronix TO-2349 (manufactured by Nippon Kayaku Co., Ltd.)
- NK Oligo UA-7200 Shin-Nakamura Chemical Co., Ltd.
- 8UH-1006 8UH-1012
- Light Acrylate POB-A0 (Kyoeisha Chemical Co., Ltd.)
- Etc. can also be used.
- Examples of the compound containing 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. It is also preferable to use a trifunctional (meth) acrylate compound such as an ethyleneoxy-modified trimethylolpropane or pentaerythritol tri (meth) acrylate.
- trifunctional (meth) acrylate compounds include Aronix M-309, M-310, M-321, M-350, M-360, M-313, M-315, M-306, and M-305. , M-303, M-452, M-450 (manufactured by Toa Synthetic Co., Ltd.), NK ester A9300, A-GLY-9E, A-GLY-20E, A-TMM-3, A-TMM-3L, A -TMM-3LM-N, A-TMPT, TMPT (manufactured by Shin Nakamura Chemical Industry Co., Ltd.), KAYARAD GPO-303, TMPTA, THE-330, TPA-330, PET-30 (manufactured by Nippon Kayaku Co., Ltd.) And so on.
- the compound containing an ethylenically unsaturated bond-containing group may further have an acid group such as a carboxy group, a sulfo group, and a phosphoric acid group.
- an acid group such as a carboxy group, a sulfo group, and a phosphoric acid group.
- Examples of commercially available products of such compounds include Aronix M-305, M-510, M-520, Aronix TO-2349 (manufactured by Toagosei Co., Ltd.) and the like.
- a compound having a caprolactone structure can also be used.
- the description in paragraphs 0042 to 0045 of JP2013-253224A can be referred to, and the content thereof is incorporated in the present specification.
- Examples of the compound having a caprolactone structure include DPCA-20, DPCA-30, DPCA-60, DPCA-120, etc., which are commercially available from Nippon Kayaku Co., Ltd. as the KAYARAD DPCA series.
- a compound having an ethylenically unsaturated bond-containing group and an alkyleneoxy group can also be used.
- Such a compound is preferably a compound having an ethylenically unsaturated bond-containing group and an ethyleneoxy group and / or a propyleneoxy group, and is a compound having an ethylenically unsaturated bond-containing group and an ethyleneoxy group. It is more preferable that the compound is a 3 to 6 functional (meth) acrylate compound having 4 to 20 ethyleneoxy groups.
- SR-494 which is a tetrafunctional (meth) acrylate having four ethyleneoxy groups manufactured by Sartmer
- KAYARAD TPA-330 which is a trifunctional (meth) acrylate having three isobutyleneoxy groups.
- a polymerizable compound having a fluorene skeleton can also be used.
- examples of commercially available products include Ogsol EA-0200 and EA-0300 (manufactured by Osaka Gas Chemical Co., Ltd., (meth) acrylate monomer having a fluorene skeleton).
- the compound containing an ethylenically unsaturated bond-containing group it is also preferable to use a compound that does not substantially contain an environmentally regulatory substance such as toluene.
- an environmentally regulatory substance such as toluene.
- commercially available products of such compounds include KAYARAD DPHA LT and KAYARAD DPEA-12 LT (manufactured by Nippon Kayaku Co., Ltd.).
- the content of the compound containing an ethylenically unsaturated bond-containing group in the total solid content of the coloring composition is 0.1 to 50% by mass is preferable.
- the lower limit is preferably 0.5% by mass or more, and more preferably 1% by mass or more.
- the upper limit is preferably 40% by mass or less, more preferably 30% by mass or less.
- the content of the compound containing the monomer-type ethylenically unsaturated bond-containing group is preferably 0.1 to 50% by mass based on the total solid content of the coloring composition.
- the lower limit is preferably 0.5% by mass or more, and more preferably 1% by mass or more.
- the upper limit is preferably 40% by mass or less, more preferably 30% by mass or less.
- Examples of the compound having a cyclic ether group include a compound having an epoxy group, a compound having an oxetanyl group, and the like, and a compound having an epoxy group is preferable.
- Examples of the compound having an epoxy group include 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 compound having an epoxy group include paragraph numbers 0034 to 0036 of JP2013-011869A, paragraph numbers 0147 to 0156 of JP2014-043556, and paragraph numbers 805 to 0092 of JP2014-089408.
- the described compound, the compound described in JP-A-2017-179172 can also be used, and the contents thereof are incorporated in the present specification.
- the compound having an epoxy group may be either a low molecular weight compound (for example, 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).
- the weight average molecular weight of the compound having an epoxy group 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 Corporation
- EPICLON N-695 manufactured by DIC Corporation
- 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 compound having a cyclic ether group in the total solid content of the coloring composition is preferably 0.1 to 50% 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 40% by mass or less, more preferably 30% by mass or less.
- Examples of the compound having a methylol group include a compound in which the methylol group is bonded to a nitrogen atom or a carbon atom forming an aromatic ring.
- Examples of the compound having an alkoxymethyl group include a compound in which an alkoxymethyl group is bonded to a nitrogen atom or a carbon atom forming an aromatic ring.
- the content of the methylol compound in the total solid content of the coloring composition is preferably 0.1 to 50% 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 40% by mass or less, more preferably 30% by mass or less.
- the coloring composition of the present invention contains an alkoxymethyl compound, the content of the alkoxymethyl compound in the total solid content of the coloring composition is preferably 0.1 to 50% 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 40% by mass or less, more preferably 30% by mass or less.
- a resin in the coloring composition of the present invention, can be used as the curable compound. It is preferable to use a curable compound containing at least a resin.
- the resin is blended, for example, for the purpose of dispersing a pigment or the like in a resin composition or for the purpose of a binder.
- a resin mainly used for dispersing a pigment or the like in a resin composition is also referred to as 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 resin having a polymerizable group also corresponds to a polymerizable compound.
- the weight average molecular weight (Mw) of the 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, and more preferably 5000 or more.
- the resin examples include (meth) acrylic resin, epoxy resin, en-thiol resin, polycarbonate resin, polyether resin, polyarylate resin, polysulfone resin, polyethersulfone resin, polyphenylene resin, polyarylene ether phosphine oxide resin, and polyimide resin.
- examples thereof include polyamideimide resin, polyolefin resin, cyclic olefin resin, polyester resin, and styrene resin. One of these resins may be used alone, or two or more of these resins may be mixed and used.
- the resin used in the present invention may have an acid group.
- the acid group include a carboxy group, a phosphoric acid group, a sulfo group, a phenolic hydroxy group and the like. These acid groups may be only one type or two or more types.
- a resin having an acid group can be preferably used as an alkali-soluble resin. Since the coloring composition of the present invention contains an alkali-soluble resin, a desired pattern can be formed by alkaline development.
- the acid value of the resin having an acid group 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 resin contains 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”). Is also preferable.
- 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.
- the description of JP-A-2010-168539 can be referred to.
- paragraph number 0317 of JP2013-209760A can be referred to, and this content is incorporated in the present specification.
- the resin is also preferably a resin containing a repeating unit having a polymerizable group.
- the resin preferably contains a resin containing a repeating unit derived from the compound represented by the formula (X).
- R 1 represents a hydrogen atom or a methyl group
- R 21 and R 22 each independently represent an alkylene group
- n represents an integer of 0 to 15.
- the alkylene group represented by R 21 and R 22 preferably has 1 to 10 carbon atoms, more preferably 1 to 5 carbon atoms, further preferably 1 to 3 carbon atoms, and particularly preferably 2 or 3 carbon atoms.
- n represents an integer of 0 to 15, preferably an integer of 0 to 5, more preferably an integer of 0 to 4, and even more preferably an integer of 0 to 3.
- Examples of the compound represented by the formula (X) include ethylene oxide of paracumylphenol or propylene oxide-modified (meth) acrylate.
- Examples of commercially available products include Aronix M-110 (manufactured by Toagosei Co., Ltd.).
- the coloring composition of the present invention may also contain a resin as a dispersant.
- the dispersant include an acidic dispersant (acidic resin) and a basic dispersant (basic resin).
- the acidic dispersant (acidic resin) represents a resin in which the amount of acid groups is larger than the amount of basic groups.
- the acidic dispersant (acidic resin) is preferably a resin in which the amount of acid groups accounts for 70 mol% or more when the total amount of the amount of acid groups and the amount of basic groups is 100 mol%, and is substantially an acid. A resin consisting only of groups is more preferable.
- the acid group of the acidic dispersant (acidic resin) is preferably a carboxy group.
- the acid value of the acidic dispersant (acidic resin) is preferably 40 to 105 mgKOH / g, more preferably 50 to 105 mgKOH / g, and even more preferably 60 to 105 mgKOH / g.
- the basic dispersant (basic resin) represents a resin in which the amount of basic groups is larger than the amount of acid groups.
- the basic dispersant (basic resin) is preferably a resin in which the amount of basic groups exceeds 50 mol% when the total amount of the amount of acid groups and the amount of basic groups is 100 mol%.
- the basic group contained in the basic dispersant is preferably an amino group.
- the resin used as the dispersant preferably contains a repeating unit having an acid group. Since the resin used as the dispersant contains a repeating unit having an acid group, the generation of development residue can be further suppressed when the pattern is formed by the photolithography method.
- the resin used as the dispersant is also preferably a graft resin.
- graft resin the description in paragraphs 0025 to 0094 of JP2012-255128A can be referred to, and the content thereof is incorporated in the present specification.
- the resin used as the dispersant is a polyimine-based dispersant containing a nitrogen atom in at least one of the main chain and the side chain.
- the polyimine-based dispersant has a main chain having a partial structure having a functional group of pKa14 or less, a side chain having 40 to 10,000 atoms, and a basic nitrogen atom in at least one of the main chain and the side chain.
- the resin to have is preferable.
- the basic nitrogen atom is not particularly limited as long as it is a nitrogen atom exhibiting basicity.
- the description in paragraphs 0102 to 0166 of JP2012-255128A can be referred to, and this content is incorporated in the present specification.
- the resin used as the dispersant is also preferably a resin having a structure in which a plurality of polymer chains are bonded to the core portion.
- resins include dendrimers (including star-shaped polymers).
- specific examples of the dendrimer include polymer compounds C-1 to C-31 described in paragraphs 0196 to 0209 of JP2013-043962.
- the resin used as the dispersant is also preferably a resin containing a repeating unit having a polymerizable group in the side chain.
- the content of the repeating unit having a polymerizable group in the side chain is preferably 10 mol% or more, more preferably 10 to 80 mol%, and 20 to 70 mol% in all the repeating units of the resin. Is even more preferable.
- the resin used as the dispersant is also preferably a resin having an aromatic carboxy group (hereinafter, also referred to as resin Ac).
- resin Ac the aromatic carboxy group may be contained in the main chain of the repeating unit or may be contained in the side chain of the repeating unit, but the aromatic carboxy group is contained in the main chain of the repeating unit. It is preferable to have.
- the number of carboxy groups bonded to the aromatic ring is preferably 1 to 4, and more preferably 1 to 2.
- the resin Ac is preferably a resin containing at least one repeating unit selected from the repeating unit represented by the formula (b-101) and the repeating unit represented by the formula (b-110).
- Ar 101 represents a group containing an aromatic carboxy group
- L 101 represents -COO- or -CONH-
- L 102 represents a divalent linking group.
- Ar 110 represents a group containing an aromatic carboxy group
- L 111 represents -COO- or -CONH-
- L 112 represents a trivalent linking group
- P 110 is a polymer. Represents a chain.
- resin Ac examples include the compounds described in JP-A-2017-156652, the contents of which are incorporated in the present specification.
- the block copolymers (EB-1) to (EB-9) described in paragraphs 0219 to 0221 of Japanese Patent No. 6432077 can also be used.
- Dispersants are also available as commercial products, and specific examples thereof include DISPERBYK series manufactured by BYK Chemie (for example, DISPERBYK-111, 142, 161 etc.) and sparse sparse manufactured by Japan Lubrizol K.K. Examples include series (eg, Solsparse 76500). Further, the pigment dispersant described in paragraphs 0041 to 0130 of JP2014-130338A can also be used, and the contents thereof are incorporated in the present specification. The resin described as the dispersant can also be used for purposes other than the dispersant. For example, it can also be used as a binder.
- the content of the resin in the total solid content of the coloring composition is preferably 1 to 80% by mass.
- the lower limit is preferably 5% by mass or more, more preferably 10% by mass or more, further preferably 15% by mass or more, and particularly preferably 20% by mass or more.
- the upper limit is preferably 70% by mass or less, more preferably 60% by mass or less, further preferably 50% by mass or less, and particularly preferably 40% by mass or less.
- the content of the resin containing an acid group is preferably 0.1 to 50% by mass based on the total solid content of the coloring composition.
- the lower limit is preferably 0.5% by mass or more, more preferably 1% by mass or more, further preferably 2% by mass or more, and particularly preferably 3% by mass or more.
- the upper limit is more preferably 30% by mass or less, and further preferably 20% by mass or less.
- the content of the dispersant is preferably 0.1 to 40% by mass based on the total solid content of the coloring composition.
- the upper limit is preferably 20% by mass or less, and more preferably 10% by mass or less.
- the lower limit is preferably 0.5% by mass or more, and more preferably 1% by mass or more.
- the content of the dispersant is preferably 1 to 100 parts by mass with respect to 100 parts by mass of the pigment.
- the upper limit is preferably 80 parts by mass or less, and more preferably 75 parts by mass or less.
- the lower limit is preferably 2.5 parts by mass or more, and more preferably 5 parts by mass or more.
- the coloring composition of the present invention may contain only one type of resin, or may contain two or more types of resin. When two or more kinds of resins are contained, it is preferable that the total amount thereof is within the above range.
- the coloring composition of the present invention contains a solvent.
- the solvent include organic solvents.
- the type of solvent is basically not particularly limited as long as it satisfies the solubility of each component and the coatability of the composition.
- the organic solvent include ester solvents, ketone solvents, alcohol solvents, amide solvents, ether solvents, hydrocarbon solvents and the like.
- paragraph number 0223 of WO 2015/166779 can be referred to, the contents of which are incorporated herein by reference.
- an ester solvent substituted with a cyclic alkyl group and a ketone solvent substituted with a cyclic alkyl group can also be preferably used.
- organic solvent examples include polyethylene glycol monomethyl ether, dichloromethane, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, ethyl cellosolve acetate, ethyl lactate, diethylene glycol dimethyl ether, butyl acetate, methyl 3-methoxypropionate, 2 -Heptanone, cyclohexanone, cyclohexyl acetate, cyclopentanone, ethyl carbitol acetate, butyl carbitol acetate, propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, 3-methoxy-N, N-dimethylpropanamide, 3-butoxy-N , N-Dimethylpropanamide and the like.
- aromatic hydrocarbons (benzene, toluene, xylene, ethylbenzene, etc.) as organic solvents may need to be reduced for environmental reasons (for example, 50 mass ppm (parts) with respect to the total amount of organic solvent. Per million) or less, 10 mass ppm or less, or 1 mass ppm or less).
- an organic solvent having a low metal content it is preferable to use an organic solvent having a low metal content, and the metal content of the organic solvent is preferably, for example, 10 mass ppb (parts per parts) or less. If necessary, an organic solvent at the mass ppt (parts per trillion) level may be used, and such an organic solvent is provided by, for example, Toyo Synthetic Co., Ltd. (The Chemical Daily, November 13, 2015).
- Examples of the method for removing impurities such as metals from the organic solvent include distillation (molecular distillation, thin film distillation, etc.) and filtration using a filter.
- the filter pore diameter of the filter used for filtration is preferably 10 ⁇ m or less, more preferably 5 ⁇ m or less, and even more preferably 3 ⁇ m or less.
- the filter material is preferably polytetrafluoroethylene, polyethylene or nylon.
- the organic solvent may contain isomers (compounds having the same number of atoms but different structures). Further, only one kind of isomer may be contained, or a plurality of kinds may be contained.
- the content of peroxide in the organic solvent is preferably 0.8 mmol / L or less, and more preferably substantially free of peroxide.
- the content of the solvent in the coloring composition is preferably 10 to 95% by mass, more preferably 20 to 90% by mass, and even more preferably 30 to 90% by mass.
- the coloring composition of the present invention does not substantially contain an environmentally regulated substance from the viewpoint of environmental regulation.
- substantially free of the environmentally regulated substance means that the content of the environmentally regulated substance in the coloring composition is 50 mass ppm or less, and preferably 30 mass ppm or less. It is more preferably 10 mass ppm or less, and particularly preferably 1 mass ppm or less.
- the environmentally regulated substance include benzene; alkylbenzenes such as toluene and xylene; and halogenated benzenes such as chlorobenzene.
- Examples of the method for reducing the environmentally regulated substance include a method of heating or depressurizing the inside of the system to raise the boiling point of the environmentally regulated substance to the boiling point or higher, and distilling off the environmentally regulated substance from the system to reduce the amount. Further, when distilling off a small amount of an environmentally regulated substance, it is also useful to azeotrope with a solvent having a boiling point equivalent to that of the solvent in order to improve efficiency.
- a polymerization inhibitor or the like is added and distilled under reduced pressure in order to prevent the radical polymerization reaction from proceeding and cross-linking between molecules during distillation under reduced pressure. You may.
- These distillation methods include a raw material stage, a product obtained by reacting the raw materials (for example, a resin solution after polymerization or a polyfunctional monomer solution), or a coloring composition stage prepared by mixing these compounds. It is possible at any stage of.
- the coloring composition of the present invention can further contain an infrared absorber.
- an infrared transmission filter is formed using the coloring composition of the present invention, the wavelength of light transmitted through the film obtained by containing an infrared absorber in the coloring composition is shifted to a longer wavelength side.
- the infrared absorber used in the present invention is preferably a compound having a maximum absorption wavelength on the longer wavelength side than the wavelength of 700 nm.
- the infrared absorber is preferably a compound having a maximum absorption wavelength in the range of more than 700 nm and 1800 nm or less.
- the ratio A 1 / A 2 between the absorbance A 2 in the absorbance A 1 and the maximum absorption wavelength in the wavelength 500nm of the infrared absorbing agent is preferably 0.08 or less, and more preferably 0.04 or less ..
- infrared absorbers examples include pyrolopyrrole compounds, cyanine compounds, squarylium compounds, phthalocyanine compounds, naphthalocyanine compounds, quaterylene compounds, merocyanine compounds, croconium compounds, oxonor compounds, iminium compounds, dithiol compounds, triarylmethane compounds, pyromethene compounds and azomethine.
- examples thereof include compounds, anthraquinone compounds, dibenzofuranone compounds, dithiolene metal complexes, metal oxides, and metal boroides.
- Examples of the pyrrolopyrrole compound include the compounds described in paragraphs 0016 to 0058 of JP2009-263614, the compounds described in paragraphs 0037-0052 of JP2011-066731, and International Publication No. 2015/166783. Examples thereof include the compounds described in paragraphs 0010 to 0033.
- Examples of the squarylium compound include the compounds described in paragraphs 0044 to 0049 of JP2011-208101A, the compounds described in paragraphs 0060 to 0061 of Patent No. 6065169, and paragraph numbers 0040 of International Publication No. 2016/181987. , The compound described in JP-A-2015-176046, the compound described in paragraph number 0072 of International Publication No.
- JP2012-077153 the oxytitanium phthalocyanine described in JP2006-343631, and paragraphs 0013 to 0029 of JP2013-195480.
- Examples of the naphthalocyanine compound include the compounds described in paragraph No. 0093 of JP2012-077153.
- Examples of the dithiolene metal complex include the compounds described in Japanese Patent No. 5733804.
- the metal oxide include indium tin oxide, antimonthine oxide, zinc oxide, Al-doped zinc oxide, fluorine-doped tin dioxide, niobium-doped titanium dioxide, and tungsten oxide.
- tungsten oxide paragraph number 0080 of JP-A-2016-006476 can be referred to, and the contents thereof are incorporated in the present specification.
- the metal boride include lanthanum hexaboride. Examples of commercially available lanthanum boride, LaB 6 -F (manufactured by Japan New Metals Co., Ltd.), and the like. Further, as the metal boride, the compound described in International Publication No. 2017/119394 can also be used. Examples of commercially available indium tin oxide products include F-ITO (manufactured by DOWA Hi-Tech Co., Ltd.).
- Examples of the infrared absorber 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. 5884953.
- Squalylium compounds described in Japanese Patent Publication No. 6036689 Squalylium compounds described in Japanese Patent No. 581604, Squalylium compounds described in International Publication No. 2017/213047, paragraph numbers 0090 to 0107, Pyrrole ring-containing compounds described in paragraphs 0019 to 0075 of Japanese Patent Application Laid-Open No.
- Concatenated squalylium compound compound having a pyrrolbis type squalylium skeleton or croconium skeleton described in JP-A-2017-141215, dihydrocarbazolebis-type squalylium compound described in JP-A-2017-082029, JP-A-2017-068120
- the asymmetric compound described in paragraphs 0027 to 0114 of Japanese Patent Application Laid-Open No. 2017, the pyrrole ring-containing compound (carbazole type) described in JP-A-2017-067963, the phthalocyanine compound described in Japanese Patent No. 6251530, and the like are used. You can also do it.
- the content of the infrared absorber in the total solid content of the coloring composition is preferably 50% by mass or less, more preferably 40% by mass or less, still more preferably 30% by mass or less.
- the lower limit is preferably 1% by mass or more, more preferably 3% by mass or more, and further preferably 5% by mass or more.
- the total content of the infrared absorber and the colorant in the total solid content of the coloring composition is preferably 10 to 80% by mass.
- the lower limit is preferably 20% by mass or more, more preferably 30% by mass or more.
- the content of the infrared absorber is preferably 5 to 50 parts by mass with respect to 100 parts by mass of the colorant.
- the upper limit is preferably 45 parts by mass or less, and more preferably 40 parts by mass or less.
- the lower limit is preferably 10 parts by mass or more, and more preferably 15 parts by mass or more.
- the coloring composition of the present invention can contain 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, oxonor pigment skeleton, and pyrolopyrrolop pigment.
- Examples of the acid group include a sulfo group, a carboxy group, a phosphoric acid group and salts thereof.
- 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.
- a pigment derivative having excellent visible transparency (hereinafter, also referred to as a transparent pigment derivative) can be contained as the pigment derivative.
- the maximum value of the molar extinction coefficient in the wavelength region of 400 ⁇ 700 nm of the transparent pigment derivative (.epsilon.max) is that it is preferable, 1000L ⁇ mol -1 ⁇ cm -1 or less is not more than 3000L ⁇ mol -1 ⁇ cm -1 Is more preferable, and 100 L ⁇ mol -1 ⁇ cm -1 or less is further preferable.
- the lower limit of ⁇ max is, for example, 1 L ⁇ mol -1 ⁇ cm -1 or more, and may be 10 L ⁇ mol -1 ⁇ cm -1 or more.
- 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 kinds are used in combination, the total amount thereof is preferably in the above range.
- the coloring composition of the present invention can contain a photopolymerization initiator.
- a photopolymerization initiator is not particularly limited and may be appropriately selected from known photopolymerization initiators.
- 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 includes trihalomethyltriazine compound, benzyldimethylketal compound, ⁇ -hydroxyketone compound, ⁇ -aminoketone compound, acylphosphine compound, phosphine oxide compound, metallocene compound, oxime compound, and 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 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. 19, No. 3, 2019 Peroxide-based Photopolymerization Initiator, International Publication No. 2018/221177, Photopolymerization Initiator, International Publication No. 2018/110179, Photopolymerization Initiator, JP-A-2019-043864 Examples thereof include the photopolymerization initiator described in Japanese Patent Application Laid-Open No. 2019-044030, and the contents thereof are incorporated in the present specification.
- ⁇ -hydroxyketone compounds include Omnirad 184, Omnirad 1173, Omnirad 2959, Omnirad 127 (all manufactured by IGM Resins BV), Irgacure 184, Irgacure 1173, Irgacure 1173, Irgacure29. (Made by the company) and so on.
- Commercially available ⁇ -aminoketone compounds include Omnirad 907, Omnirad 369, Omnirad 369E, Omnirad 379EG (above, IGM Resins BV), Irgacare 907, Irgacare 369, Irgacure 369, Irgacure 369, Irgacure 369, Irgar (Made) and so on.
- acylphosphine compounds examples include Omnirad 819, Omnirad TPO (above, manufactured by IGM Resins BV), Irgacure 819, 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, the compounds described in JP-A-2006-342166, and J. Am. C. S. The compound according to Perkin II (1979, pp. 1653-1660), J. Mol. C. S. The compound described in Perkin II (1979, pp. 156-162), the compound described in Journal of Photopolymer Science and Technology (1995, pp. 202-232), the compound described in JP-A-2000-066385.
- oxime compound examples include 3-benzoyloxyiminobutane-2-one, 3-acetoxyiminovtan-2-one, 3-propionyloxyiminovtan-2-one, 2-acetoxyimiminopentane-3-one, 2-acetoxyimino-1-phenylpropan-1-one, 2-benzoyloxyimino-1-phenylpropane-1-one, 3- (4-toluenesulfonyloxy) iminobutane-2-one, and 2-ethoxycarbonyloxy Examples thereof include imino-1-phenylpropane-1-one.
- an oxime compound having a fluorene ring can also be used.
- 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, from the viewpoint of sensitivity. It is particularly preferable to have.
- the molar extinction coefficient of a compound can be measured using a known method. For example, it is preferable to measure at a concentration of 0.01 g / L using 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.
- a photoradical polymerization initiator two or more radicals are generated from one molecule of the photoradical polymerization initiator, so that good sensitivity can be obtained.
- the crystallinity is lowered, the solubility in a solvent or the like is improved, the precipitation is less likely to occur with time, and the stability of the coloring 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 coloring 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 kinds are used, it is preferable that the total amount thereof is within the above range.
- the coloring composition of the present invention may contain a curing accelerator.
- the curing accelerator include thiol compounds, methylol compounds, amine compounds, phosphonium salt compounds, amidin salt compounds, amide compounds, base generators, isocyanate compounds, alkoxysilane compounds, and onium salt compounds.
- Specific examples of the curing accelerator include the compounds described in paragraphs 0094 to 0097 of International Publication No. 2018/056189, the compounds described in paragraphs 0246 to 0253 of JP2015-034963, and JP2013-014165. Compounds described in paragraphs 0186 to 0251 of Japanese Patent Application Laid-Open No.
- the curing accelerator when the curing accelerator is contained, 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.
- the coloring composition of the present invention can contain an ultraviolet absorber.
- an ultraviolet absorber a conjugated diene compound, an aminodiene compound, a salicylate compound, a benzophenone compound, a benzotriazole compound, an acrylonitrile compound, a hydroxyphenyltriazine compound, an indol compound, a triazine compound and the like can be used. 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.
- Specific examples of the ultraviolet absorber include compounds having the following structures. Examples of commercially available ultraviolet absorbers include UV-503 (manufactured by Daito Kagaku Co., Ltd.). Examples of the benzotriazole compound include the MYUA series made by Miyoshi Oil & Fat Co., Ltd. (The Chemical Daily, February 1, 2016). 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 coloring composition is preferably 0.01 to 10% by mass, more preferably 0.01 to 5% by mass.
- the content of the ultraviolet absorber in the total solid content of the coloring composition is preferably 0.01 to 10% by mass, more preferably 0.01 to 5% by mass.
- only one type of ultraviolet absorber may be used, or two or more types may be used.
- the total amount is preferably in the above range.
- the coloring composition of the present invention can contain a polymerization inhibitor.
- the polymerization inhibitor include hydroquinone, p-methoxyphenol, di-tert-butyl-p-cresol, pyrogallol, tert-butylcatechol, benzoquinone, 4,4'-thiobis (3-methyl-6-tert-butylphenol), and the like.
- examples thereof include 2,2'-methylenebis (4-methyl-6-t-butylphenol) and N-nitrosophenylhydroxyamine salts (ammonium salt, primary cerium salt, etc.). Of these, p-methoxyphenol is preferable.
- the content of the polymerization inhibitor in the total solid content of the coloring composition is preferably 0.0001 to 5% by mass.
- the polymerization inhibitor may be only one type or two or more types. In the case of two or more types, the total amount is preferably in the above range.
- the coloring composition of the present invention can contain a silane coupling agent.
- the silane coupling agent means a silane compound having a hydrolyzable group and other functional groups.
- the hydrolyzable group refers to a substituent that is directly linked to a silicon atom and can form a siloxane bond by at least one of a hydrolysis reaction and a condensation reaction.
- the hydrolyzable group include a halogen atom, an alkoxy group, an acyloxy group and the like, and an alkoxy group is preferable. That is, the silane coupling agent is preferably a compound having an alkoxysilyl group.
- Examples of the functional group other than the hydrolyzable group include a vinyl group, a (meth) allyl group, a (meth) acryloyl group, a mercapto group, an epoxy group, an oxetanyl group, an amino group, a ureido group, a sulfide group and an isocyanate group.
- a phenyl group and the like preferably an amino group, a (meth) acryloyl group and an epoxy group.
- silane coupling agent examples include N- ⁇ -aminoethyl- ⁇ -aminopropylmethyldimethoxysilane (manufactured by Shinetsu Chemical Industry Co., Ltd., trade name KBM-602), N- ⁇ -aminoethyl- ⁇ -amino.
- Propyltrimethoxysilane (manufactured by Shinetsu Chemical Industry Co., Ltd., trade name KBM-603), N- ⁇ -aminoethyl- ⁇ -aminopropyltriethoxysilane (manufactured by Shinetsu Chemical Industry Co., Ltd., trade name KBE-602), ⁇ -Aminopropyltrimethoxysilane (manufactured by Shinetsu Chemical Industry Co., Ltd., trade name KBM-903), ⁇ -aminopropyltriethoxysilane (manufactured by Shinetsu Chemical Industry Co., Ltd., trade name KBE-903), 3-methacryloxy There are propylmethyldimethoxysilane (manufactured by Shinetsu Chemical Industry Co., Ltd., trade name KBM-502), 3-methacryloxypropyltrimethoxysilane (manufactured by Shinetsu Chemical Industry Co., Ltd., trade
- the silane coupling agent include the compounds described in paragraphs 0018 to 0036 of JP2009-288703 and the compounds described in paragraphs 0056 to 0066 of JP2009-242604A. , These contents are incorporated herein by reference.
- the content of the silane coupling agent in the total solid content of the coloring composition is preferably 0.01 to 15.0% by mass, more preferably 0.05 to 10.0% by mass. preferable.
- the silane coupling agent may be only one type or two or more types. In the case of two or more types, the total amount is preferably in the above range.
- the coloring composition of the present invention can contain a surfactant.
- a surfactant various surfactants such as a fluorine-based surfactant, a nonionic surfactant, a cationic surfactant, an anionic surfactant, and a silicone-based surfactant can be used.
- the surfactant 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 fluorine content in the fluorine-based surfactant is preferably 3 to 40% by mass, more preferably 5 to 30% by mass, and particularly preferably 7 to 25% by mass.
- a fluorine-based surfactant having a fluorine content within this range is effective in terms of uniformity of coating film thickness and liquid saving property, and has good solubility in a coloring composition.
- 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.
- 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.
- silicone-based surfactant examples 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 (all, 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, (Shin-Etsu 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 coloring composition is preferably 0.001% by mass to 5.0% by mass, more preferably 0.005 to 3.0% by mass. preferable.
- the surfactant may be only one kind or two or more kinds. In the case of two or more types, the total amount is preferably in the above range.
- the coloring composition of the present invention can contain an antioxidant.
- the antioxidant include phenol compounds, phosphite ester compounds, thioether compounds and the like.
- the phenol compound any phenol compound known as a phenolic antioxidant can be used.
- Preferred phenolic compounds include hindered phenolic compounds.
- a compound having a substituent at a site (ortho position) adjacent to the phenolic hydroxy group is preferable.
- a substituted or unsubstituted alkyl group having 1 to 22 carbon atoms is preferable.
- the antioxidant a compound having a phenol group and a phosphite ester group in the same molecule is also preferable.
- a phosphorus-based antioxidant can also be preferably used.
- the content of the antioxidant in the total solid content of the coloring composition is preferably 0.01 to 20% by mass, more preferably 0.3 to 15% by mass.
- containing an antioxidant only one type of antioxidant may be used, or two or more types may be used. When two or more types are used, the total amount is preferably in the above range.
- the coloring compositions of the present invention include sensitizers, curing accelerators, fillers, thermosetting accelerators, plasticizers and other auxiliaries (eg, conductive particles, fillers, defoamers, etc.). It may contain a flame retardant, a leveling agent, a peeling accelerator, a fragrance, a surface tension modifier, a chain transfer agent, etc.). By appropriately containing these components, properties such as film physical characteristics can be adjusted. These components are described in, for example, paragraph No. 0183 and subsequent paragraphs of JP2012-003225A (paragraph number 0237 of the corresponding US Patent Application Publication No. 2013/0034812), paragraphs of JP-A-2008-250074. The descriptions of Nos.
- the coloring composition of the present invention may contain a latent antioxidant, if necessary.
- the latent antioxidant is a compound in which the site that functions as an antioxidant is protected by a protecting group, and is heated at 100 to 250 ° C. or at 80 to 200 ° C. in the presence of an acid / base catalyst.
- a compound in which the protecting group is eliminated and functions as an antioxidant can be mentioned.
- Examples of the latent antioxidant include compounds described in International Publication No. 2014/021023, International Publication No. 2017/030005, and JP-A-2017-008219.
- Examples of commercially available products of latent antioxidants include ADEKA ARKULS GPA-5001 (manufactured by ADEKA Corporation). Further, as described in JP-A-2018-155881, C.I. I. Pigment Yellow 129 may be added for the purpose of improving weather resistance.
- the coloring composition of the present invention may contain a metal oxide in order to adjust the refractive index of the obtained film.
- the metal oxide include TiO 2 , ZrO 2 , Al 2 O 3 , SiO 2 and the like.
- the primary particle size of the metal oxide is preferably 1 to 100 nm, more preferably 3 to 70 nm, and even more preferably 5 to 50 nm.
- the metal oxide may have a core-shell structure. Further, in this case, the core portion may be hollow.
- the coloring composition of the present invention may contain a light resistance improving agent.
- the light resistance improving agent include the compounds described in paragraphs 0036 to 0037 of JP-A-2017-198787, the compounds described in paragraphs 0029 to 0034 of JP-A-2017-146350, and JP-A-2017-129774.
- the 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, and more preferably 0.1 to 1.0% by mass.
- the water content can be measured by the Karl Fischer method.
- the coloring composition of the present invention can be used by adjusting the viscosity for the purpose of adjusting the film surface (flatness, etc.), adjusting the film thickness, and the like.
- the viscosity value can be appropriately selected as needed, but for example, at 25 ° C., 0.3 mPa ⁇ s to 50 mPa ⁇ s is preferable, and 0.5 mPa ⁇ s to 20 mPa ⁇ s is more preferable.
- a method for measuring the viscosity for example, a cone plate type viscometer can be used, and the viscosity can be measured in a state where the temperature is adjusted to 25 ° C.
- the container for the colored composition of the present invention is not particularly limited, and a known 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 coloring composition of the present invention can be prepared by mixing the above-mentioned components. In preparing the coloring composition, all the components may be dissolved and / or dispersed in a solvent at the same time to prepare the coloring composition, or each component may be appropriately used as two or more solutions or dispersions, if necessary. Then, these may be mixed at the time of use (at the time of application) to prepare a coloring composition.
- the mechanical force used for dispersing the pigment includes compression, squeezing, impact, shearing, cavitation and the like.
- Specific examples of these processes include bead mills, sand mills, roll mills, ball mills, paint shakers, microfluidizers, high speed impellers, sand grinders, flow jet mixers, high pressure wet atomization, ultrasonic dispersion and the like.
- 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.
- a fluororesin such as polytetrafluoroethylene (PTFE), a polyamide resin such as nylon (for example, nylon-6, nylon-6,6), and a polyolefin resin such as polyethylene and polypropylene (PP) (high density, ultrahigh molecular weight).
- PP polypropylene
- a filter using a material such as (including a polyolefin resin) can be mentioned.
- polypropylene (including high-density polypropylene) and nylon are preferable.
- the pore size of the filter is preferably 0.01 to 7.0 ⁇ m, more preferably 0.01 to 3.0 ⁇ m, and even more preferably 0.05 to 0.5 ⁇ m. If the pore size of the filter is within the above range, fine foreign matter can be removed more reliably.
- the nominal value of the filter manufacturer can be referred to.
- various filters provided by Nippon Pole Co., Ltd. (DFA4201NIEY, etc.), Advantech Toyo Co., Ltd., Japan Integris Co., Ltd. (formerly Nippon Microlith Co., Ltd.), KITZ Microfilter Co., Ltd., etc. can be used.
- a fibrous filter medium examples include polypropylene fiber, nylon fiber, glass fiber and the like.
- examples of commercially available products include SBP type series (SBP008, etc.), TPR type series (TPR002, TPR005, etc.), and SHPX type series (SHPX003, etc.) manufactured by Loki Techno Co., Ltd.
- filters different filters (eg, first filter and second filter, etc.) may be combined. At that time, the filtration with each filter may be performed only once or twice or more. Further, filters having different pore diameters may be combined within the above-mentioned range. Further, the filtration with the first filter may be performed only on the dispersion liquid, and after mixing the other components, the filtration with the second filter may be performed.
- the film of the present invention is a film obtained from the above-mentioned coloring composition of the present invention.
- the film of the present invention can be used for an optical filter such as a color filter or a near infrared transmission filter.
- the film thickness of the film of the present invention can be appropriately adjusted according to the purpose.
- the film thickness is preferably 20 ⁇ m or less, more preferably 10 ⁇ m or less, and even more preferably 5 ⁇ m or less.
- the lower limit of the film thickness is preferably 0.1 ⁇ m or more, more preferably 0.2 ⁇ m or more, and further preferably 0.3 ⁇ m or more.
- the film of the present invention When the film of the present invention is used as a color filter, the film of the present invention preferably has a hue of green, red, blue, cyan, magenta or yellow, and more preferably has a hue of green, red or yellow. preferable. Further, the film of the present invention can be preferably used as a colored pixel of a color filter. Examples of the colored pixel include a red pixel, a green pixel, a blue pixel, a magenta color pixel, a cyan color pixel, a yellow pixel and the like, and are preferably a red pixel, a green pixel and a yellow pixel.
- the film of the present invention preferably has, for example, any of the following spectral characteristics (1) to (4).
- the maximum value of the light transmittance in the film thickness direction in the wavelength range of 400 to 640 nm is 20% or less (preferably 15% or less, more preferably 10% or less), and the light in the film thickness direction.
- the minimum value of the transmittance in the wavelength range of 800 to 1300 nm is 70% or more (preferably 75% or more, more preferably 80% or more).
- a film having such spectral characteristics can block light in the wavelength range of 400 to 640 nm and transmit light having a wavelength exceeding 700 nm.
- a film having such spectral characteristics can block light in the wavelength range of 400 to 830 nm and transmit light having a wavelength exceeding 940 nm.
- the maximum value of the light transmittance in the film thickness direction in the wavelength range of 400 to 950 nm is 20% or less (preferably 15% or less, more preferably 10% or less), and the light in the film thickness direction.
- a film having such spectral characteristics can block light in the wavelength range of 400 to 950 nm and transmit light having a wavelength exceeding 1040 nm.
- the film of the present invention can be produced through a step of applying the coloring composition of the present invention.
- the film manufacturing method preferably further includes a step of forming a pattern (pixel). Examples of the pattern (pixel) forming method include a photolithography method and a dry etching method, and the photolithography method is preferable.
- Pattern formation by the photolithography method includes a step of forming a coloring composition layer on a support using the coloring composition of the present invention, a step of exposing the coloring composition layer in a pattern, and a step of exposing the coloring composition layer in a pattern. It is preferable to include a step of developing and removing the exposed portion to form a pattern (pixel). If necessary, a step of baking the coloring composition layer (pre-baking step) and a step of baking the developed pattern (pixels) (post-baking step) may be provided.
- the coloring composition layer of the present invention is used to form the coloring composition layer on the support.
- the support is not particularly limited and may be appropriately selected depending on the intended use.
- a glass substrate, a silicon substrate, and the like can be mentioned, and a silicon substrate is preferable.
- a charge coupling element (CCD), a complementary metal oxide film semiconductor (CMOS), a transparent conductive film, or the like may be formed on the silicon substrate.
- CMOS complementary metal oxide film semiconductor
- a black matrix that separates each pixel may be formed on the silicon substrate.
- the silicon substrate may be provided with a base layer for improving the adhesion with the upper layer, preventing the diffusion of substances, or flattening the surface of the substrate.
- the base layer may be formed by using a composition obtained by removing a colorant from the coloring composition described in the present specification, a composition containing a curable compound, a surfactant or the like described in the present specification, or the like.
- the surface contact angle of the base layer is preferably 20 to 70 ° when measured with diiodomethane. Further, it is preferably 30 to 80 ° when measured with water. When the surface contact angle of the base layer is within the above range, the coating property of the resin composition is good.
- the surface contact angle of the base layer can be adjusted by, for example, adding a surfactant.
- a known method can be used as a method for applying the coloring composition.
- a dropping method drop casting
- a slit coating method for example, a spray method; a roll coating method; a rotary coating method (spin coating); a casting coating method; a slit and spin method; a pre-wet method (for example, JP-A-2009-145395).
- Methods described in the publication Inkjet (for example, on-demand method, piezo method, thermal method), ejection system printing such as nozzle jet, flexographic printing, screen printing, gravure printing, reverse offset printing, metal mask printing, etc.
- Various printing methods; transfer method using a mold or the like; nanoimprint method and the like can be mentioned.
- the application method for inkjet is not particularly limited, and for example, the method shown in "Expandable / Usable Inkjet-Infinite Possibilities Seen in Patents-, Issued 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 coloring 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 colored composition layer formed on the support may be dried (prebaked).
- prebaking may not be performed.
- the prebaking temperature is preferably 150 ° C. or lower, more preferably 120 ° C. or lower, and even more preferably 110 ° C. or lower.
- the lower limit can be, for example, 50 ° C. or higher, or 80 ° C. or higher.
- the prebaking time is preferably 10 to 300 seconds, more preferably 40 to 250 seconds, and even more preferably 80 to 220 seconds. Pre-baking can be performed on a hot plate, an oven, or the like.
- the colored composition layer is exposed in a pattern (exposure step).
- the colored composition layer can be exposed in a pattern by exposing it through a mask having a predetermined mask pattern using a stepper exposure machine, a scanner exposure machine, or the like. As a result, the exposed portion can be cured.
- Examples of radiation (light) that can be used for exposure include g-line and i-line. Further, light having a wavelength of 300 nm or less (preferably light having a wavelength of 180 to 300 nm) can also be used. Examples of the light having a wavelength of 300 nm or less include KrF line (wavelength 248 nm), ArF line (wavelength 193 nm), and KrF line (wavelength 248 nm) is preferable. Further, a long wave light source having a diameter of 300 nm or more can also be used.
- pulse exposure is an exposure method of a method in which light irradiation and pause are repeated in a short cycle (for example, millisecond level or less).
- Irradiation dose for example, preferably 0.03 ⁇ 2.5J / cm 2, more preferably 0.05 ⁇ 1.0J / cm 2.
- the oxygen concentration at the time of exposure can be appropriately selected, and in addition to the operation in the atmosphere, for example, in a low oxygen atmosphere having an oxygen concentration of 19% by volume or less (for example, 15% by volume, 5% by volume, or substantially). It may be exposed in an oxygen-free environment) or in a high oxygen atmosphere (for example, 22% by volume, 30% by volume, or 50% by volume) in which the oxygen concentration exceeds 21% by volume.
- the exposure illuminance can be set as appropriate, and is usually selected from the range of 1000 W / m 2 to 100,000 W / m 2 (for example, 5000 W / m 2 , 15,000 W / m 2 , or 35,000 W / m 2). Can be done. Oxygen concentration and exposure illuminance may appropriately combined conditions, for example, illuminance 10000 W / m 2 at an oxygen concentration of 10 vol%, oxygen concentration of 35 vol% can be such illuminance 20000W / m 2.
- the unexposed portion of the coloring composition layer is developed and removed to form a pattern (pixel).
- Development and removal of the unexposed portion of the coloring composition layer can be performed using a developing solution.
- the colored composition layer of the unexposed portion in the exposure step is eluted in the developing solution, and only the photocured portion remains.
- the temperature of the developing solution is preferably, for example, 20 to 30 ° C.
- the development time is preferably 20 to 180 seconds. Further, in order to improve the residue removability, the steps of shaking off the developing solution every 60 seconds and further supplying a new developing solution may be repeated several times.
- Examples of the developing solution include organic solvents and alkaline developing solutions, and alkaline developing solutions are preferably used.
- the alkaline developer an alkaline aqueous solution (alkaline developer) obtained by diluting an alkaline agent with pure water is preferable.
- the alkaline agent include ammonia, ethylamine, diethylamine, dimethylethanolamine, diglycolamine, diethanolamine, hydroxyamine, ethylenediamine, tetramethylammonium hydroxide, tetraethylammonium hydroxide, tetrapropylammonium hydroxide, and tetrabutylammonium hydroxide.
- Ethyltrimethylammonium hydroxide Ethyltrimethylammonium hydroxide, benzyltrimethylammonium hydroxide, dimethylbis (2-hydroxyethyl) ammonium hydroxide, choline, pyrrole, piperidine, 1,8-diazabicyclo- [5.4.0] -7-undecene, etc.
- examples thereof include organic alkaline compounds and inorganic alkaline compounds such as sodium hydroxide, potassium hydroxide, sodium carbonate, sodium hydrogencarbonate, sodium silicate and sodium metasilicate.
- the alkaline agent a compound having a large molecular weight is preferable in terms of environment and safety.
- the concentration of the alkaline agent in the alkaline aqueous solution is preferably 0.001 to 10% by mass, more preferably 0.01 to 1% by mass.
- the developer may further contain a surfactant. From the viewpoint of convenience of transfer and storage, the developer may be once produced as a concentrated solution and diluted to a concentration required for use.
- the dilution ratio is not particularly limited, but can be set in the range of, for example, 1.5 to 100 times. It is also preferable to wash (rinse) with pure water after development. Further, it is preferable that the rinsing is performed by supplying the rinsing liquid to the developed colored composition layer while rotating the support on which the developed colored composition layer is formed.
- the nozzle for discharging the rinse liquid from the central portion of the support it is also preferable to move the nozzle for discharging the rinse liquid from the central portion of the support to the peripheral edge of the support.
- the nozzle may be moved while gradually reducing the moving speed.
- Additional exposure treatment and post-baking are post-development curing treatments to complete the curing.
- the heating temperature in the post-bake is, for example, preferably 100 to 240 ° C, more preferably 200 to 240 ° C.
- Post-baking can be performed on the developed film in a continuous or batch manner by using a heating means such as a hot plate, a convection oven (hot air circulation dryer), or a high frequency heater so as to meet the above conditions. ..
- the light used for the exposure is preferably light having a wavelength of 400 nm or less. Further, the additional exposure process may be performed by the method described in Korean Patent Publication No. 10-2017-0122130.
- Pattern formation by the dry etching method includes a step of forming a colored composition layer on a support using the colored composition of the present invention and curing the entire colored composition layer to form a cured product layer.
- the optical filter of the present invention has the above-mentioned film of the present invention.
- Examples of the type of optical filter include a color filter and an infrared transmission filter, and a color filter is preferable.
- As the color filter it is preferable to have the film of the present invention as the colored pixels of the color filter.
- the optical filter may be provided with a protective layer on the surface of the film of the present invention.
- a protective layer By providing the protective layer, various functions such as oxygen blocking, low reflection, hydrophobicization, and shielding of light of a specific wavelength (ultraviolet rays, near infrared rays, etc.) can be imparted.
- the thickness of the protective layer is preferably 0.01 to 10 ⁇ m, more preferably 0.1 to 5 ⁇ m.
- Examples of the method for forming the protective layer include a method of applying a resin composition dissolved in an organic solvent to form the protective layer, a chemical vapor deposition method, and a method of attaching the molded resin with an adhesive.
- the components constituting the protective layer include (meth) acrylic resin, en-thiol resin, polycarbonate resin, polyether resin, polyarylate resin, polysulfone resin, polyethersulfone resin, polyphenylene resin, polyarylene ether phosphine oxide resin, and polyimide.
- Resin polyamideimide resin, polyolefin resin, cyclic olefin resin, polyester resin, styrene resin, polyol resin, polyvinylidene chloride resin, melamine resin, urethane resin, aramid resin, polyamide resin, alkyd resin, epoxy resin, modified silicone resin, fluorine Examples thereof include resins, polycarbonate resins, polyacrylonitrile resins, cellulose resins, Si, C, W, Al 2 O 3 , Mo, SiO 2 , and Si 2 N 4, and two or more of these components may be contained.
- the protective layer preferably contains a polyol resin, SiO 2 , and Si 2 N 4 .
- the protective layer preferably contains a (meth) acrylic resin and a fluororesin.
- the resin composition When the resin composition is applied to form the protective layer, a known method such as a spin coating method, a casting method, a screen printing method, or an inkjet method can be used as the application method of the resin composition.
- a known method such as a spin coating method, a casting method, a screen printing method, or an inkjet method can be used as the application method of the resin composition.
- a known organic solvent for example, propylene glycol 1-monomethyl ether 2-acetate, cyclopentanone, ethyl lactate, etc.
- the protective layer is formed by a chemical vapor deposition method
- the chemical vapor deposition method is a known chemical vapor deposition method (thermochemical vapor deposition method, plasma chemical vapor deposition method, photochemical vapor deposition method). Can be used.
- the protective layer may be an additive such as organic / inorganic fine particles, an absorber of light of a specific wavelength (for example, ultraviolet rays, near infrared rays, etc.), a refractive index adjuster, an antioxidant, an adhesive, a surfactant, etc., if necessary. May be contained.
- organic / inorganic fine particles include high molecular weight fine particles (for example, silicone resin fine particles, polystyrene fine particles, melamine resin fine particles), titanium oxide, zinc oxide, zirconium oxide, indium oxide, aluminum oxide, titanium nitride, and titanium oxynitride.
- a known absorbent can be used as the light absorber of a specific wavelength.
- the content of these additives can be adjusted as appropriate, but is preferably 0.1 to 70% by mass, more preferably 1 to 60% by mass, based on the total mass of the protective layer.
- the protective layer described in paragraphs 0073 to 0092 of JP-A-2017-151176 can also be used.
- the optical filter may have a structure in which each pixel is embedded in a space partitioned by a partition wall, for example, in a grid pattern.
- the solid-state image sensor of the present invention has the above-mentioned film of the present invention.
- the configuration of the solid-state image sensor is not particularly limited as long as it includes the film of the present invention and functions as a solid-state image sensor, and examples thereof include the following configurations.
- a solid-state image sensor CCD (charge-coupled device) image sensor, CMOS (complementary metal oxide semiconductor) image sensor, etc.
- a transfer electrode made of polysilicon or the like.
- the configuration has a color filter on the device protective film.
- the color filter may have a structure in which each colored pixel is embedded in a space partitioned by a partition wall, for example, in a grid pattern.
- the partition wall preferably has a low refractive index for each colored pixel.
- Examples of the imaging apparatus having such a structure include the apparatus described in JP-A-2012-227478, JP-A-2014-179757, and International Publication No. 2018/043654.
- the image pickup device provided with the solid-state image pickup device of the present invention can be used not only for digital cameras and electronic devices having an image pickup function (mobile phones and the like), but also for in-vehicle cameras and surveillance cameras.
- the image display device of the present invention has the above-mentioned film of the present invention.
- the image display device include a liquid crystal display device and an organic electroluminescence display device.
- the liquid crystal display device is described in, for example, “Next Generation Liquid Crystal Display Technology (edited by Tatsuo Uchida, Kogyo Chosakai Co., Ltd., published in 1994)”.
- the liquid crystal display device to which the present invention can be applied is not particularly limited, and for example, it can be applied to various types of liquid crystal display devices described in the above-mentioned "next-generation liquid crystal display technology".
- coloring and polishing conditions 5.3 parts by mass of coloring material, 74.7 parts by mass of grinding agent and 14 parts by mass of binder were added to Laboplast Mill (manufactured by Toyo Seiki Seisakusho Co., Ltd.), and the temperature of the kneaded product in the apparatus was 70 ° C. The temperature was controlled so as to be, and the mixture was kneaded for 2 hours.
- the coloring material the material described in the column of the type of yellow colorant described in the table below, or the material described in the column of the type of other colorant and infrared absorber described in the table below was used.
- Diethylene glycol was used as the binder.
- the kneaded product after kneading and polishing was washed with 10 L of water at 24 ° C. to remove the grinding agent and the binder, and treated in a heating oven at 80 ° C. for 24 hours.
- Pigment Violet23 (purple colorant) IB Compound with the following structure (black colorant)
- PBk32 Compound with the following structure (black colorant)
- IR1 A compound having the following structure (infrared absorber. In the following structural formula, Me represents a methyl group and Ph represents a phenyl group).
- (Pigment derivative) B1 Compound with the following structure
- B2 Compounds with the following structure (transparent derivatives, compounds that do not have coloring in the visible region)
- B3 Compound with the following structure
- B4 A compound having the following structure (in the following structural formula, Me represents a methyl group and Ph represents a phenyl group).
- B5 Compound with the following structure
- D5 Resin having the following structure (the numerical value added to the main chain is the molar ratio, and the numerical value added to the side chain is the number of repeating units.
- the viscosity of the dispersion liquid is 1 mPa ⁇ s or more and 15 mPa ⁇ s or less
- TI value thixotropy index
- Dispersions 1 to 80, a1 to a3, b1 to b8 Dispersions 1 to 80, a1 to a3, b1 to b8 described above.
- M1 A mixture of compounds having the following structure (a mixture of a left-side compound (6-functional (meth) acrylate compound) and a right-side compound (5-functional (meth) acrylate compound) having a molar ratio of 7: 3)
- M2 Compound with the following structure
- M3 Compound with the following structure
- M4 Aronix TO-2349 (manufactured by Toagosei Co., Ltd.)
- M5 Compound with the following structure
- M6 Compound with the following structure
- UV absorber UV1, UV2: Compounds with the following structure
- Each coloring composition was applied onto soda glass (75 mm ⁇ 75 mm square, thickness 1.1 mm) by a spin coating method at a rotation speed at which the film thickness after exposure was 0.6 ⁇ m, and a hot plate was used.
- a coating film was obtained by prebaking at 100 ° C. for 2 minutes.
- the obtained coating film was exposed to an exposure amount of 1000 mJ / cm 2 using an ultra-high pressure mercury lamp (“USH-500BY” (trade name)) manufactured by Ushio, Inc.
- USH-500BY ultra-high pressure mercury lamp
- the coating film after exposure was heated at 200 ° C. for 5 minutes using a hot plate in an air atmosphere to obtain a film.
- the transmittance in the wavelength range of 400 to 700 nm was measured using "MCPD-3000" (trade name) manufactured by Otsuka Electronics Co., Ltd.
- the amount of change in the transmittance compared is the amount of change for the wavelength with the largest change in transmittance in the wavelength range of 400 to 700 nm (
- the examples were able to form a film having excellent light resistance and moisture resistance.
- the comparative example at least one of the light resistance and the moisture resistance was inferior to that of the example.
- the coloring composition of the example can also be patterned by a dry etching method.
- Example 1001 A cyan coloring composition was applied onto a silicon wafer by a spin coating method so that the film thickness after film formation was 1.0 ⁇ 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 with an exposure amount of 1000 mJ / cm 2 through a mask with a 2 ⁇ m square dot pattern. Then, paddle development was carried out at 23 ° C. for 60 seconds using a 0.3% by mass aqueous solution of tetramethylammonium hydroxide (TMAH). Then, it was rinsed with a spin shower and further washed with pure water.
- TMAH tetramethylammonium hydroxide
- the cyan-colored composition was patterned to form cyan-colored pixels by heating at 200 ° C. for 5 minutes using a hot plate.
- the magenta coloring composition and the yellow coloring composition were patterned by the same process to sequentially form magenta color pixels and yellow pixels to form a color filter having cyan color pixels, magenta color pixels and yellow pixels. ..
- cyan pixels are formed in a Bayer pattern, and magenta pixels and yellow pixels are formed in an island pattern in an adjacent region thereof.
- the coloring composition of Example 57 was used as the yellow coloring composition.
- the cyan coloring composition and the magenta coloring composition will be described later.
- the obtained color filter was incorporated into a solid-state image sensor according to a known method. This solid-state image sensor had a suitable image recognition ability.
- ⁇ Preparation of cyan coloring composition and magenta coloring composition> Mix the colorants of the types listed in the table below, the dispersants of the types listed in the table below, and some of the solvents listed in the table below, and add 230 parts by mass of zirconia beads with a diameter of 0.3 mm.
- the dispersion treatment was carried out for 5 hours using a paint shaker, and the beads were separated by filtration to produce a pigment dispersion having a solid content of 20% by mass.
- a photosensitive resin composition was prepared by mixing the above-mentioned type of photopolymerization initiator and the types of ultraviolet absorbers described in the table below.
- the table below shows the blending amount of each component in each coloring composition.
- the numerical value of each component is a mass part.
- D1, D3, D6, M1, M6, F2, UV1, W1, G1 and S1S5 are the above-mentioned materials.
- PB15: 4 is C.I. I. Pigment Blue 15: 4.
- PR122 is C.I. I. Pigment Red122.
- the dispersant D11 is Efka PX 4300 (made by BASF, acrylic resin).
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- Compositions Of Macromolecular Compounds (AREA)
Abstract
L'invention concerne une composition colorante pour filtres optiques qui contient un agent colorant, un composé durcissable et un solvant, caractérisée en ce que : l'agent colorant contient un agent colorant jaune ; l'agent colorant jaune contient au moins un composé (A) qui est choisi parmi des composés représentés par la formule (I) et des composés représentés par la formule (II) ; et la teneur du composé (A) dans l'agent colorant est de 3,5 % en masse ou plus. L'invention concerne également un film, un filtre optique, un élément d'imagerie à semi-conducteurs et un dispositif d'affichage d'image dans chacun desquels la composition colorante est utilisée. Dans les formules, R1 et/ou R2 représentent un groupe hydrocarboné aliphatique ou similaire ; et R5 et/ou R6 représentent un groupe hydrocarboné aliphatique ou similaire.
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PCT/JP2020/030936 WO2021033656A1 (fr) | 2019-08-21 | 2020-08-17 | Composition colorante, film, filtre optique, élément d'imagerie à semi-conducteurs et dispositif d'affichage d'image |
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Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS61115960A (ja) * | 1984-11-07 | 1986-06-03 | チバ・ガイギー・アクチエンゲゼルシヤフト | ピロロ[3,4―c]ピロール類の製造方法 |
WO2007003520A1 (fr) * | 2005-07-05 | 2007-01-11 | Ciba Specialty Chemicals Holding Inc. | Dicétopyrrolopyrroles et dérivés fluorescents |
CN106896642A (zh) * | 2017-01-17 | 2017-06-27 | 住华科技股份有限公司 | 感旋光性树脂组成物、及应用其的彩色光刻胶结构和显示器 |
-
2020
- 2020-08-17 TW TW109127844A patent/TW202108703A/zh unknown
- 2020-08-17 JP JP2021540934A patent/JP7290731B2/ja active Active
- 2020-08-17 WO PCT/JP2020/030936 patent/WO2021033656A1/fr active Application Filing
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS61115960A (ja) * | 1984-11-07 | 1986-06-03 | チバ・ガイギー・アクチエンゲゼルシヤフト | ピロロ[3,4―c]ピロール類の製造方法 |
WO2007003520A1 (fr) * | 2005-07-05 | 2007-01-11 | Ciba Specialty Chemicals Holding Inc. | Dicétopyrrolopyrroles et dérivés fluorescents |
CN106896642A (zh) * | 2017-01-17 | 2017-06-27 | 住华科技股份有限公司 | 感旋光性树脂组成物、及应用其的彩色光刻胶结构和显示器 |
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JPWO2021033656A1 (fr) | 2021-02-25 |
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