Pyrrole-based colorant compounds, resin compositions and layers thereof, color filters and applications thereof

Abstract

The present disclosure relates to a resin composition comprising a colorant, the colorant comprising a mixture of a blue pigment and a pyrrole-based colorant compound having a maximum absorption value at 500 nm to 600 nm and being a compound having the following general formula (1), a layer thereof, a color filter, and applications thereof. The resin composition is capable of solving the problems of existing color filter spectral characteristic defects and poor color reproducibility when used for a color filter.(1).

Description

Technical Field

[0001] This disclosure relates to the field of optics, and more specifically to a pyrrole-based pigment compound, a resin composition and its layer, a color filter and its application. Background Technology

[0002] In recent years, liquid crystal displays (LCDs) have been praised for their thinness, space-saving design, lightweight construction, and energy efficiency. They are rapidly gaining popularity, particularly in applications such as television receivers, where there is a growing demand for improved brightness, contrast, and overall visual clarity, as well as higher brightness and contrast ratios in the color filters used.

[0003] Traditionally, color filters have been made using pigment-containing photosensitive resin compositions. While these pigments exhibit high heat and light resistance and good dispersibility, their ability to improve spectral properties and transmittance is limited. Furthermore, due to the inherent depolarization properties of pigments, the improvement in contrast is also limited.

[0004] On the other hand, since pigment compounds have high transmittance, it has also been proposed to use photosensitive resin compositions containing pigment compounds to prepare color filters.

[0005] However, compared to conventional staining techniques, the color filters obtained by the above method have spectral defects. Furthermore, because some of the colorant used in the color filter is difficult to miniaturize, the color reproduction of solid-state imaging elements and image display elements using the obtained color filter is worse than that of conventional staining methods. Summary of the Invention

[0006] The purpose of this disclosure is to provide a resin composition with good spectral characteristics and excellent lightfastness and heat resistance, as well as its layer, color filter, and its application.

[0007] In a first aspect, this disclosure provides a resin composition comprising a colorant comprising a mixture of a blue pigment and a pyrrole pigment compound, wherein the pyrrole pigment compound has a maximum absorption value at 500 nm to 600 nm and is a compound having the following general formula (1):

[0008] (1),

[0009] In general formula (1):

[0010] R1 through R4 are each independently selected from substituted or unsubstituted C1-C. 10 Alkyl or substituted or unsubstituted C3-C 10 cycloalkyl;

[0011] R5 is selected from halogenated, substituted, or unsubstituted C6-C. 20 aryloxy, substituted or unsubstituted C1-C 10 Alkyl thio, substituted or unsubstituted C3-C 10 Cycloalkylthio, substituted or unsubstituted C6-C 20 Arylthio, substituted or unsubstituted C2-C 20 Heterocyclic thio groups, substituted or unsubstituted C1-C 20 Heteroarylthio, substituted or unsubstituted pyridinylthio, substituted or unsubstituted thiazolylthio, substituted or unsubstituted imidazolethio, substituted or unsubstituted triazolethio, substituted or unsubstituted tetrazolylthio, substituted or unsubstituted quinolinylthio, substituted or unsubstituted benzothiazolylthio, substituted or unsubstituted benzo[a]azolylthio, or substituted or unsubstituted benzo[a]imidazolylthio;

[0012] R6 is selected from substituted or unsubstituted alkoxycarbonyl, cyano, or carboxyl groups; and

[0013] R7 is selected from cyano, substituted, or unsubstituted di-C1-C 10 Alkylamino or substituted or unsubstituted C3-C 10 Cycloalkylamino;

[0014] R8 and R9 are each independently selected from halogens, C1-C 10 Alkyl, C1-C 10 Halogenated alkyl groups:

[0015] n is an integer selected from 0 to 5;

[0016] x and y are integers selected from 0 to 4;

[0017] "Substituted or unsubstituted" means unsubstituted or substituted by one or more substituents selected independently from the following: halogen, C1-C 10 Alkyl, hydroxyl, C1-C 10 Alkoxy, carboxyl, amide, cyano, nitro, or ester groups;

[0018] "Ester group" refers to -OCOR0 or -COOR0, where R0 is independently C1-C each time it appears. 10 alkyl.

[0019] This disclosure utilizes a combination of a blue pigment and a pyrrole-based pigment compound with a specific structure that has a maximum absorption value at 500 nm to 600 nm as a colorant to obtain a resin composition with specific optical properties, thereby solving the problems of spectral characteristic defects and poor color reproducibility in existing blue color filters. Furthermore, the resin composition exhibits good lightfastness and heat resistance. By using the above resin composition, color filters with good spectral transmittance and excellent heat and light resistance can be manufactured.

[0020] In one possible implementation, in general formula (1), R1 to R4 are each independently selected from substituted or unsubstituted C1-C6 alkyl or substituted or unsubstituted C3-C8 cycloalkyl.

[0021] In one possible implementation, in general formula (1), R1 to R4 are each independently selected from substituted or unsubstituted C1-C4 alkyl or substituted or unsubstituted C3-C5 cycloalkyl.

[0022] In one possible implementation, in general formula (1), R1 to R4 are methyl, ethyl, propyl or cyclopropylmethyl.

[0023] In one possible implementation, in general formula (1), R1 to R4 are methyl or ethyl.

[0024] In one possible implementation, in general formula (1), R1 to R4 are methyl groups.

[0025] In one possible implementation, in general formula (1), R5 is selected from halogenated, substituted, or unsubstituted C6-C. 10 Aryloxy group, substituted or unsubstituted C1-C6 alkyl thio group, substituted or unsubstituted C3-C8 cycloalkyl thio group, substituted or unsubstituted C6-C 10 Arylthio, substituted or unsubstituted C2-C 10 Heterocyclic thio groups, substituted or unsubstituted C1-C 10 Heteroarylthio, substituted or unsubstituted pyridinethio, substituted or unsubstituted thiazolethio, substituted or unsubstituted imidazolethio, substituted or unsubstituted triazolethio, substituted or unsubstituted tetrazoliumthio, substituted or unsubstituted quinolinylthio, substituted or unsubstituted benzothiazolylthio, substituted or unsubstituted benzo[a]azolylthio, or substituted or unsubstituted benzo[a]imidazolylthio.

[0026] In one possible embodiment, in general formula (1), R5 is selected from halogen, substituted or unsubstituted C6-C8 aryloxy, substituted or unsubstituted C1-C4 alkylthio, substituted or unsubstituted C3-C5 cycloalkylthio, substituted or unsubstituted C6-C8 arylthio, substituted or unsubstituted C2-C6 heterocyclic thio, substituted or unsubstituted C1-C6 heteroarylthio, substituted or unsubstituted pyridinethio, substituted or unsubstituted thiazolethio, substituted or unsubstituted imidazolethio, substituted or unsubstituted triazolethio, substituted or unsubstituted tetrazoliumthio, substituted or unsubstituted quinolinylthio, substituted or unsubstituted benzothiazolylthio, substituted or unsubstituted benzo[a]azolylthio, or substituted or unsubstituted benzimidazolylthio.

[0027] In one possible implementation, in general formula (1), R5 is selected from halogens, substituted or unsubstituted C6-C. 10 Aryloxy group, substituted or unsubstituted C1-C6 alkylthio group, substituted or unsubstituted C6-C 10 Arylthio, substituted or unsubstituted C2-C 10 Heterocyclic thio groups, substituted or unsubstituted C1-C 10 Heteroarylthio, substituted or unsubstituted pyridinethio, substituted or unsubstituted thiazolethio, substituted or unsubstituted imidazolethio, substituted or unsubstituted triazolethio, substituted or unsubstituted tetrazoliumthio, substituted or unsubstituted quinolinylthio, substituted or unsubstituted benzothiazolylthio, substituted or unsubstituted benzo[a]azolylthio, or substituted or unsubstituted benzo[a]imidazolylthio.

[0028] In one possible embodiment, in general formula (1), R5 is selected from halogen, substituted or unsubstituted C6-C8 aryloxy, substituted or unsubstituted C1-C4 alkyl thio, substituted or unsubstituted C6-C8 aryl thio, substituted or unsubstituted C2-C6 heterocyclic thio, substituted or unsubstituted C1-C6 heteroaryl thio, substituted or unsubstituted pyridine thio, substituted or unsubstituted thiazole thio, substituted or unsubstituted imidazole thio, substituted or unsubstituted triazole thio, substituted or unsubstituted tetrazolium thio, substituted or unsubstituted quinolinyl thio, substituted or unsubstituted benzothiazolyl thio, substituted or unsubstituted benzo[a]azolyl thio, or substituted or unsubstituted benzimidazolyl thio.

[0029] In one possible implementation, in general formula (1), R5 is selected from halogens or substituted or unsubstituted groups of the following: C6-C8 arylthio or C1-C6 heteroarylthio.

[0030] In one possible implementation, in general formula (1), R5 is selected from halogens or optionally C6-C8 arylthio groups substituted with carboxyl groups.

[0031] In one possible implementation, in general formula (1), R5 is selected from Cl, substituted or unsubstituted phenylthio, substituted or unsubstituted pyridinylthio, substituted or unsubstituted thiazolyl thio, substituted or unsubstituted imidazolyl thio, substituted or unsubstituted triazolyl thio, substituted or unsubstituted tetrazolyl thio, substituted or unsubstituted quinolinyl thio, substituted or unsubstituted benzothiazolyl thio, or substituted or unsubstituted benzimidazolyl thio.

[0032] In one possible implementation, in general formula (1), R5 is selected from Cl or optionally phenylthio groups substituted with carboxyl groups.

[0033] In one possible implementation, in general formula (1), R6 is selected from substituted or unsubstituted C1-C6 alkoxycarbonyl or carboxyl groups.

[0034] In one possible implementation, in general formula (1), R6 is selected from substituted or unsubstituted C1-C4 alkoxycarbonyl groups.

[0035] In one possible implementation, in general formula (1), R6 is selected from methoxycarbonyl or ethoxycarbonyl.

[0036] In one possible implementation, in general formula (1), R7 is selected from cyano, substituted or unsubstituted di-C1-C6 alkylamino or substituted or unsubstituted C3-C8 cycloalkylamino.

[0037] In one possible implementation, in general formula (1), R7 is selected from cyano, substituted or unsubstituted di-C1-C4 alkylamino or substituted or unsubstituted C3-C5 cycloalkylamino.

[0038] In one possible implementation, in general formula (1), R7 is selected from substituted or unsubstituted di-C1-C6 alkylamino or cyano groups.

[0039] In one possible implementation, in general formula (1), R7 is selected from substituted or unsubstituted di-C1-C4 alkylamino or cyano groups.

[0040] In one possible implementation, R7 is a cyano group in general formula (1).

[0041] In one possible implementation, in general formula (1), R8 and R9 are each independently selected from halogens, C1-C6 alkyl groups, or C1-C6 haloalkyl groups.

[0042] In one possible implementation, in general formula (1), R8 and R9 are each independently selected from halogens, C1-C4 alkyl groups, or C1-C4 haloalkyl groups.

[0043] In one possible implementation, in general formula (1), R8 and R9 are each independently selected from F, Cl, Br, methyl, ethyl, halomethyl or haloethyl.

[0044] In one possible implementation, in general formula (1), R8 and R9 are methyl groups.

[0045] In one possible implementation, in general formula (1), n ​​is an integer selected from 0 to 4.

[0046] In one possible implementation, n is 0, 1 or 2 in general formula (1).

[0047] In one possible implementation, n is 0 or 1 in general formula (1).

[0048] In one possible implementation, in general formula (1), x and y are independently selected from integers from 0 to 3.

[0049] In one possible implementation, in general formula (1), x and y are independently 0, 1, or 2.

[0050] In one possible implementation, in general formula (1), x and y are independently 0 or 1.

[0051] In one possible implementation, in general formula (1), both x and y are 0.

[0052] In one possible implementation, R0 is independently a C1-C6 alkyl or C1-C4 alkyl that is optionally substituted with a halogen atom each time it appears.

[0053] In one possible implementation, “substituted or unsubstituted” means unsubstituted or substituted by one or more substituents selected independently from the following: halogen, C1-C6 alkyl, hydroxyl, C1-C6 alkoxy, carboxyl, amide, cyano, nitro or ester.

[0054] In one possible implementation, “substituted or unsubstituted” means unsubstituted or substituted by one or more substituents selected independently from the following: cyano, halogen, or carboxyl.

[0055] In one possible implementation, "substituted or unsubstituted" means unsubstituted or substituted with a carboxyl group.

[0056] In one possible embodiment, the pyrrole pigment compound is selected from at least one of the compounds of formula 1(a) to formula 1(i):

[0057] 1(a) 1(b) 1(c) 1(d) 1(e) 1(f), 1(g), 1(h) 1(i).

[0058] In one possible embodiment, the cured film of the resin composition, with a thickness of less than 3.0 micrometers, has a spectral transmittance of more than 55% at a wavelength of 400 nm, a spectral transmittance of more than 85% in the wavelength range of 400 nm to 500 nm, a spectral transmittance of less than 20% in the wavelength range of 550 nm to 650 nm, and a maximum transmittance in the wavelength range of 400 nm to 500 nm.

[0059] In one possible embodiment, the cured film of the resin composition, with a thickness of less than 3.0 micrometers, has a spectral transmittance of more than 60% at a wavelength of 400 nm, a spectral transmittance of more than 90% in the wavelength range of 400 nm to 500 nm, a spectral transmittance of less than 20% in the wavelength range of 550 nm to 650 nm, and a maximum transmittance in the wavelength range of 400 nm to 450 nm.

[0060] In one possible embodiment, the cured film of the resin composition, with a thickness of less than 3.0 micrometers, has a spectral transmittance of more than 70% at a wavelength of 400 nm, a spectral transmittance of more than 90% in the wavelength range of 400 nm to 500 nm, a spectral transmittance of less than 20% in the wavelength range of 550 nm to 650 nm, and a maximum transmittance in the wavelength range of 420 nm to 450 nm.

[0061] In one possible implementation, the blue pigment is selected from at least one of CI Pigment Blue 15:6 or CI Pigment Blue 15:3.

[0062] In one possible implementation, the blue pigment is a mixture of CI Pigment Blue 15:6 and CI Pigment Blue 15:3.

[0063] In one possible implementation, the blue pigment is CI Pigment Blue 15:6.

[0064] In one possible implementation, the mass ratio of the blue pigment to the compound is 9:1 to 1:9.

[0065] In one possible implementation, the mass ratio of the blue pigment to the compound is 4:1 to 1:4.

[0066] In one possible implementation, the mass ratio of the blue pigment to the compound is 12:3 to 3:12.

[0067] This disclosure enables further improvement in the spectral characteristics and color reproducibility of the obtained color filter by using the specific compounds described above.

[0068] In one possible implementation, the resin composition contains 20% to 90% by mass of colorant based on the total solids mass of the resin composition.

[0069] In one possible implementation, the resin composition contains 30% to 85% by mass of colorant based on the total solids mass of the resin composition.

[0070] In one possible implementation, the resin composition contains 30% to 80% by mass of colorant based on the total solids mass of the resin composition.

[0071] By adding the colorant in the above proportion to the resin composition, the image-forming properties of the resin composition can be improved.

[0072] In one possible embodiment, the resin composition further includes a curable resin and a solvent, the curable resin containing an alkali-soluble resin, a polymerizable monomer, and a photopolymerization initiator.

[0073] A curable resin containing an alkali-soluble resin, a polymerizable monomer, and a photopolymerization initiator is suitable for forming the color filter membrane of the color filter disclosed herein. The patterned color filter membrane has a good pattern outline and good membrane strength.

[0074] In one possible implementation, the resin composition comprises 10% to 90% by mass of curable resin based on the total solids mass of the resin composition.

[0075] In one possible implementation, the resin composition comprises 15% to 80% by mass of curable resin based on the total solids mass of the resin composition.

[0076] In one possible implementation, the resin composition comprises 20% to 70% by mass of curable resin based on the total solids mass of the resin composition.

[0077] In one possible implementation, the curable resin comprises 0 to 50% by weight of an alkali-soluble resin, based on the total weight of the curable resin.

[0078] By adding the above-mentioned proportion of alkali-soluble resin to a curable resin, a good pattern outline can be obtained.

[0079] In one possible implementation, the curable resin comprises 0 to 45% by weight of alkali-soluble resin, based on the total weight of the curable resin.

[0080] In one possible implementation, the curable resin comprises 0 to 40% by weight of alkali-soluble resin, based on the total weight of the curable resin.

[0081] In one possible implementation, the curable resin contains 0.1% to 100% by mass of polymeric monomers based on the total weight of the curable resin.

[0082] In one possible implementation, the curable resin contains 1% to 100% by mass of polymeric monomers based on the total weight of the curable resin.

[0083] In one possible implementation, the curable resin contains 2% to 100% by mass of polymeric monomers based on the total weight of the curable resin.

[0084] In one possible implementation, the curable resin contains 0.01% to 10% by mass of a photopolymerization initiator based on the total weight of the curable resin.

[0085] In one possible implementation, the curable resin contains 0.01% to 8% by mass of a photopolymerization initiator based on the total weight of the curable resin.

[0086] In one possible implementation, the curable resin contains 0.01% to 6% by mass of a photopolymerization initiator based on the total weight of the curable resin.

[0087] By adding the above proportions of polymerizable monomers and photopolymerization initiators to a curable resin, a film strength suitable for color filters can be obtained.

[0088] In one possible embodiment, the resin composition comprises, based on the total solids mass of the resin composition, 20% to 90% by mass of a coloring compound; 0% to 39% by mass of an alkali-soluble resin; 0.08% to 78% by mass of a polymerizable monomer; and 0.008% to 7.8% by mass of a photopolymerization initiator.

[0089] In one possible embodiment, the resin composition comprises, based on the total solids mass of the resin composition, 20% to 90% by mass of a coloring compound; 0% to 39% by mass of an alkali-soluble resin; 0.08% to 78% by mass of a polymerizable monomer; and 0.01% to 7.8% by mass of a photopolymerization initiator.

[0090] In one possible embodiment, the resin composition comprises, based on the total solids mass of the resin composition, 30% to 85% by mass of a coloring compound; 0% to 35% by mass of an alkali-soluble resin; 0.8% to 78% by mass of a polymerizable monomer; and 0.08% to 7.8% by mass of a photopolymerization initiator.

[0091] In one possible embodiment, the resin composition comprises, based on the total solids mass of the resin composition, 30% to 85% by mass of a coloring compound; 0% to 35% by mass of an alkali-soluble resin; 0.78% to 78% by mass of a polymerizable monomer; and 0.01% to 6.2% by mass of a photopolymerization initiator.

[0092] In one possible embodiment, the resin composition comprises, based on the total solids mass of the resin composition, 30% to 80% by mass of a coloring compound; 0% to 31% by mass of an alkali-soluble resin; 1.6% to 78% by mass of a polymerizable monomer; and 0.08% to 4.7% by mass of a photopolymerization initiator.

[0093] In one possible embodiment, the resin composition comprises, based on the total solids mass of the resin composition, 30% to 80% by mass of a coloring compound; 0% to 31% by mass of an alkali-soluble resin; 1.6% to 78% by mass of a polymerizable monomer; and 0.01% to 4.7% by mass of a photopolymerization initiator.

[0094] The above-described resin composition is suitable for forming the color filter disclosed herein, and the resulting color filter has improved spectral characteristics and color reproducibility.

[0095] Secondly, this disclosure provides a method for preparing a color filter layer, the method comprising:

[0096] The above-described resin composition is coated onto a substrate to form a resin composition layer; and

[0097] The resin composition layer is patterned to obtain the color filter layer.

[0098] In one possible implementation, the color filter layer is obtained by curing the resin composition described in this disclosure.

[0099] In one possible implementation, the color filter layer is obtained by photocuring the resin composition described in this disclosure.

[0100] In one possible implementation, the thickness of the color filter layer is 0.3 to 5.0 micrometers.

[0101] In one possible implementation, the thickness of the color filter layer is 0.3 to 4.5 micrometers.

[0102] Thirdly, this disclosure provides a color filter layer, which is prepared by the method for preparing a color filter layer as described above in this disclosure.

[0103] Fourthly, this disclosure provides a color filter, the color filter including a color filter layer according to this disclosure.

[0104] In one possible implementation, the color filter is a blue color filter.

[0105] In one possible implementation, the color filter further includes a substrate on which the resin composition layer or color filter layer is disposed.

[0106] Fifthly, this disclosure provides a solid-state imaging element, the solid-state imaging element comprising: a light-receiving element; and a color filter formed on the light-receiving element, the color filter being the color filter described in this disclosure.

[0107] In a sixth aspect, this disclosure provides an image display element comprising: a light-emitting element selected from at least one of OLED and LED; and a color filter formed on the light-emitting element, the color filter being the color filter described in this disclosure.

[0108] In a seventh aspect, this disclosure provides a display device, the display device comprising:

[0109] The color filter described in this disclosure;

[0110] The solid-state imaging element described in this disclosure; or

[0111] The image display element described in this disclosure.

[0112] In one possible implementation, the display device further includes display pixel units.

[0113] Eighthly, this disclosure provides an electronic device, the electronic device comprising:

[0114] The color filter described in this disclosure;

[0115] Solid-state imaging elements described in this disclosure;

[0116] The image display element described in this disclosure; or

[0117] The display device described in this disclosure.

[0118] In one possible implementation, the electronic device further includes at least one of a power supply unit, a drive circuit, and a control circuit.

[0119] In one possible implementation, the electronic device is selected from: flat panel displays, curved displays, computer monitors, medical monitors, televisions, billboards, indoor lights, outdoor lights, signal lights, head-up displays, fully transparent displays, partially transparent displays, flexible displays, rollable displays, foldable displays, retractable displays, laser printers, telephones, portable telephones, tablet PCs, tablet computers, personal digital assistants, wearable devices, laptop computers, digital cameras, camcorders, viewfinders, microdisplays, 3D displays, virtual reality displays, augmented reality displays, vehicle display panels, vehicle dashboards, aircraft display panels, aircraft dashboards, video walls with multiple displays spliced ​​together, theater screens, stadium screens, phototherapy devices, or signs. Attached Figure Description

[0120] To more clearly illustrate the technical solutions in the embodiments of this disclosure or the prior art, the drawings used in the description of the embodiments or the prior art will be briefly introduced below. Obviously, the drawings described below are only some embodiments of this disclosure. For those skilled in the art, other drawings can be obtained based on these drawings without creative effort.

[0121] Figure 1 This is a spectral transmittance curve of the blue color filter of Embodiment 1 of this disclosure in the wavelength range of 400 nm to 700 nm;

[0122] Figure 2 The graph shows the spectral transmittance of the blue filter of Comparative Example 1 of this disclosure in the wavelength range of 400 nm to 700 nm. Detailed Implementation

[0123] definition

[0124] The following definitions and methods are provided to better define this disclosure and to guide those skilled in the art in its practice. Unless otherwise stated, the terms are to be understood in accordance with their conventional usage by those skilled in the art. All patent documents, academic papers, and other publications cited herein are incorporated herein by reference in their entirety.

[0125] The terms “comprising” or “including” shall be interpreted herein as having a non-exhaustive meaning and allowing for the addition or reference to further elements, such as adding features or method steps or members or components to anything that includes the listed elements. “Comprising” may be replaced by “including” if the practice of a given language variant requires it, or may be limited to “consistently consisting of” if other elements besides those listed are not essential to the practice of this disclosure, or may be limited to “consisting of” in the absence of any other elements.

[0126] The term “optional” or “optionally” means that the event or situation described below may or may not occur, including both the occurrence and non-occurrence of the event or situation.

[0127] The numerical range representing the number of carbon atoms in this article refers to the integers within a given range, for example, "C1-C1". 20 "or "C 1-20 "" means that the group can have 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19 or 20 carbon atoms.

[0128] The terms “halogen,” “halogenated,” or “halogen” themselves or as part of another substituent represent fluorine (F), chlorine (Cl), bromine (Br), or iodine (I) atoms.

[0129] The term "pyrrole pigment compounds" refers to pigment compounds with a pyrrole group as the parent nucleus.

[0130] The term "alkyl" refers to a straight-chain or branched saturated hydrocarbon group, which can be monovalent (e.g., methyl), divalent (e.g., methylene), or polyvalent (e.g., methine). Examples of alkyl groups include C1-C4 alkyl, C1-C6 alkyl, C1-C8 alkyl, and C1-C6 alkyl groups. 10 Alkyl groups, such as methyl (Me), ethyl (Et), propyl (e.g., n-propyl and isopropyl), butyl (e.g., n-butyl, isobutyl, s-butyl, tert-butyl), pentyl (e.g., n-pentyl, isopentyl, neopentyl), etc.; for example, the term "C1-C6 alkyl" refers to alkyl groups containing 1 to 6 (e.g., 1, 2, 3, 4, 5, 6) carbon atoms (e.g., methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, neopentyl, hexyl, 2-methylpentyl, etc.).

[0131] The term "alkoxy" refers to -O-alkyl, where "alkyl" is defined as above. Examples of "alkoxy" include, but are not limited to, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, tert-butoxy, n-pentoxy, and isopentoxy. "Optionally substituted alkoxy" means that the alkyl group is substituted or unsubstituted.

[0132] The term "cycloalkyl" refers to a fully saturated non-aromatic ring consisting of carbon and hydrogen atoms, preferably comprising one or two rings. The cycloalkyl group can be monocyclic, fused polycyclic, bridged, or spirocyclic. Non-limiting examples of cycloalkyl groups include, but are not limited to, C1... 3-18 cycloalkyl, C 3-16 cycloalkyl, C 3-12 cycloalkyl, C 3-10 cycloalkyl, C 3-8 cycloalkyl, C 3-7 cycloalkyl, C 3-6 Cycloalkyl groups, such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, spiro[3.3]heptyl, norbornyl (bicyclo[2.2.1]heptyl), bicyclo[2.2.2]octyl, adamantyl, bicyclo[1.1.1]pent-1-yl, etc.

[0133] The term "heterocyclic alkyl" refers to a fully saturated cyclic group that may exist as a monocyclic, bridged, or spirocyclic ring. Unless otherwise indicated, the heterocycle is typically a ring containing 1 to 5 (e.g., 1, 2, 3, 4, 5) heteroatoms independently selected from sulfur, oxygen, and / or nitrogen. Examples of 3-membered heterocyclic alkyl groups include, but are not limited to, ethylene oxide, cyclothioethylene, and cycloazoethylene; non-limiting examples of 4-membered heterocyclic alkyl groups include, but are not limited to, acridine, thiobutyl, and thiobutyl; examples of 5-membered heterocyclic alkyl groups include, but are not limited to, tetrahydrofuranyl, tetrahydrothiophenyl, pyrrolidinyl, isozolyl, thiobutyl, isothiazolyl, thiazolyl, imidazolyl, and tetrahydropyrazolyl; examples of 6-membered heterocyclic alkyl groups include, but are not limited to, piperidinyl, tetrahydropyranyl, tetrahydrothiaranyl, morpholinyl, piperazine, 1,4-thiazolyl, 1,4-dioxane, thiomorpholinyl, 1,3-dithiaalkyl, and 1,4-dithiaalkyl; and examples of 7-membered heterocyclic alkyl groups include, but are not limited to, azirheptanyl, oxeheptyl, and thioheptyl.

[0134] The term "aryl" or "aromatic ring" refers to an aromatic ring or a ring system of aromatics or partially aromatics composed of carbon and hydrogen atoms. It can be a monocyclic ring or a polycyclic ring (such as a bicyclic ring or other rings with two or more rings) fused together or covalently linked. Non-limiting examples of aryl groups include, but are not limited to, phenyl, naphthyl, anthracene, and 1,2,3,4-tetrahydronaphthalene. Depending on its structure, an aryl group can be a monovalent or bivalent group, i.e., an aryl group.

[0135] The term "C6-C" 20"Aryl" or "aromatic ring" refers to an aryl or aromatic ring as defined above that has 6 to 20 carbon atoms (e.g., 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19 or 20 carbon atoms).

[0136] "Heteroaryl" or "heteroary ring" refers to an aromatic ring group consisting of a carbon atom and at least one (e.g., 1 to 5, such as 1, 2, 3, 4, 5) heteroatoms selected from nitrogen, oxygen, and sulfur. The heteroaryl group can be a monocyclic, bicyclic, tricyclic, or tetracyclic ring system, which may include fused or bridged ring systems; and the nitrogen, carbon, or sulfur atom in the heteroaryl group can be arbitrarily oxidized; the nitrogen atom can be arbitrarily quaternized. Examples include, but are not limited to, azirrolyl, acridine, benzimidazolyl, benzothiazolyl, benzoindolyl, benzothiadiazolyl, benzonaphthuronyl, benzo[2]azolyl, benzo[m]dioxanepentenyl, benzodioxinyl, benzopyranyl, benzopyranoneyl, benzofuranyl, benzofuranoneyl, benzothiopheneyl (benzobenzenethio), benzotriazolyl, benzo[4,6]imidazo[1,2-a]pyridyl, carbazole, cenolinyl, dibenzofuranyl, furanyl, thiopheneyl, furanoneyl, isothiazolyl, imidazolyl, indolyl, Indazole, isoindolyl, dihydroindolyl, isodihydroindolyl, indene, isozolyl, naphthidyl, diazolyl, 2-oxoazapyrrolyl, diazolyl, ethylene oxide, phenazinyl, phenothiazinyl, phenothiazinyl, 2,3-diazanaphthyl, pteridinyl, purine, pyrrolyl, pyrazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinazolinyl, quinoxalinyl, quinolinyl, quininecycloyl, isoquinolinyl, thiazolyl, thiadiazolyl, triazolyl, tetrazolyl, triazinyl, thiazolyl, imidazolyl, triazolyl, tetrazolyl, and phenylthio.

[0137] The term "C1-C" 20 "Heteroaryl" refers to an aromatic ring group having, in addition to 1 to 20 carbon atoms (e.g., 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19 or 20 carbon atoms), at least one heteroatom selected from N, O, and S as a cyclic atom (e.g., 1, 2, 3, 4, 5 heteroatoms).

[0138] Unless otherwise specified, the term "heterocyclic group" or "heterocycle" refers to a non-aromatic cyclic structure that may be saturated or unsaturated, wherein the cyclic structure contains at least one carbon and at least one heteroatom selected from O, N, and S, examples of which include heterocyclic alkyl, heterocyclic alkenyl, and heterocyclic alkynyl groups.

[0139] The term "C2-C" 20A "heterocyclic group" is a heterocyclic group as defined above that has, in addition to 2 to 20 carbon atoms (e.g., 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19 or 20 carbon atoms), at least one heteroatom selected from N, O, and S as a cyclic atom (e.g., 1, 2, 3, 4 or 5 heteroatoms).

[0140] The term "carboxyalkyl" refers to a group having an alkyl-COOH structure, wherein the alkyl group is as defined above. Representative examples of carboxyalkyl groups include, but are not limited to, carboxymethyl (-CH2CO2H), 2-carboxyethyl, etc. "Optionally substituted carboxyalkyl" means that the alkyl portion of the group is substituted or unsubstituted.

[0141] The term "amino" refers to -NH2.

[0142] The term "ester group" as used in this article refers to a group having a -OCOR0 or -COOR0 structure, where R0 is independently C1-C each time it appears. 10 Alkyl group. A substituted ester group refers to an ester group in which the R0 group is replaced.

[0143] The term "C1-C" as used in this article 10 "alkyl thio" refers to a group with C1-C2 groups. 10 Alkyl-S-structure groups. Similarly, the term "C3-C" refers to... 10 "Cycloalkylthio" refers to a group with C3-C6 groups. 10 Cycloalkyl-S-structure groups, termed "C6-C" 20 "Arylthio" refers to a group with C6-C... 20 Aryl-S-structure groups, termed "C2-C" 20 "Heterocyclic thio" refers to a group with C2-C... 20 Heterocyclic -S-structure groups, and the term "C1-C" 20 "Heteroarylthio" refers to a group with C1-C... 20 A heteroaryl-S-structure group.

[0144] The term "amide group" as used in this article refers to a group having a -NR'COR0 structure, where R0 is independently C1-C each time it appears. 10 Alkyl group, where R' is hydrogen or C1-C 10 Alkyl group. A substituted amide group refers to an amide group in which R0 is substituted.

[0145] The term "cyano" as used in this article refers to a group having a -CN structure.

[0146] The term "substituted or unsubstituted" means that a group is substituted or unsubstituted by one or more substituents (e.g., 1 to 4, 1 to 3, or 1 to 2), and when substituted, the substituent is individually and independently selected from one or more of the following groups: halogen, hydroxyl, C1-C. 10 Alkyl, haloalkyl, hydroxyalkyl, alkenyl, alkynyl, cycloalkyl, aryl, heteroaryl, heterocyclic, alkoxy, aryloxy, heteroaryloxy, mercapto, alkylthio, arylthio, cyano, carbonyl, thiocarbonyl, O-carbamoyl, N-carbamoyl, O-thiocarbamoyl, N-thiocarbamoyl, C-amide, N-amide, S-sulfinylamide, N-sulfinylamide, carboxyl, C-carboxyl, O-carboxyl, isocyanate, cyanothio, isothiocyanate, nitro, ester, cyano, silyl, trihalomethanesulfonyl, or amino groups including mono- and di-substituted amino groups, and their protected derivatives, etc. Whenever a substituent is described as "substituted," the substituent can be substituted by one of the substituents listed above.

[0147] When a group is replaced by more than one substituent, the substituents can be the same or different. Any substituted functional group in this article can be substituted at 1 to 4 different positions, and those 1 to 4 substituted groups can be substituted independently at 1 to 4 positions.

[0148] The H atom is typically not shown in the general formula of the specification; however, those skilled in the art can understand the formula and identify the complete structure.

[0149] The term “color masterbatch” as used in this article refers to a mixture of resin and a large amount of pigment or dye to form a high concentration of color. It is generally composed of three basic elements: pigment or dye, carrier and additives. It is an aggregate made by uniformly loading an extraordinary amount of pigment into the resin.

[0150] Throughout the specification, optional terms are used, such as optional embodiments or variations, where “specific” refers to embodiments or variations of particular interest, and “preferred” refers to embodiments or variations preferred for some reason.

[0151] Unless the context clearly specifies otherwise, the singular forms “a” and “the”, or at least “one”, include plural references.

[0152] <Color Filter>

[0153] To address the spectral defects and poor color reproducibility of color filters prepared using pigments, this disclosure provides a color filter comprising a resin composition layer (hereinafter also referred to as a color filter layer) prepared using a resin composition described below. The resin composition may contain components such as pigment compounds, pigments, and curable resins, the various components of which will be described in detail below.

[0154] [Pigment compound]

[0155] To address the spectral defects and poor color reproducibility of color filters, pigments such as diphenylmethane, triphenylmethane, anthocyanin, melocyanine, pyrrole, and perimidine can generally be used. From a lightfastness perspective, anthocyanin, melocyanine, pyrrole, and perimidine pigments are preferred.

[0156] However, the inventors have discovered that the following pigment compounds can effectively solve the problems of spectral characteristic defects and poor color reproducibility of color filters. Specifically, this disclosure provides a resin composition comprising a pigment compound represented by the following general formula (1):

[0157] (1),

[0158] in,

[0159] R1 through R4 are each independently selected from substituted or unsubstituted C1-C. 10 Alkyl or substituted or unsubstituted C3-C 10 cycloalkyl;

[0160] R5 is selected from halogenated, substituted, or unsubstituted C6-C. 20 aryloxy, substituted or unsubstituted C1-C 10 Alkyl thio, substituted or unsubstituted C3-C 10 Cycloalkylthio, substituted or unsubstituted C6-C 20 Arylthio, substituted or unsubstituted C2-C 20 Heterocyclic thio groups, substituted or unsubstituted C1-C 20 Heteroarylthio, substituted or unsubstituted pyridinylthio, substituted or unsubstituted thiazolylthio, substituted or unsubstituted imidazolethio, substituted or unsubstituted triazolethio, substituted or unsubstituted tetrazolylthio, substituted or unsubstituted quinolinylthio, substituted or unsubstituted benzothiazolylthio, substituted or unsubstituted benzo[a]azolylthio, or substituted or unsubstituted benzo[a]imidazolylthio;

[0161] R6 is selected from substituted or unsubstituted alkoxycarbonyl, cyano, carboxyl, or nitro groups; and

[0162] R7 is selected from cyano, substituted, or unsubstituted di-C1-C 10 Alkylamino or substituted or unsubstituted C3-C 10 Cycloalkylamino;

[0163] R8 and R9 are each independently selected from halogens, C1-C 10 Alkyl, C1-C 10 Halogenated alkyl groups:

[0164] n is an integer selected from 0 to 5;

[0165] x and y are integers selected from 0 to 4.

[0166] In one possible implementation, in general formula (1), R1 to R4 are each independently selected from substituted or unsubstituted C1-C6 alkyl or substituted or unsubstituted C3-C8 cycloalkyl.

[0167] In one possible implementation, in general formula (1), R1 to R4 are each independently selected from substituted or unsubstituted C1-C4 alkyl or substituted or unsubstituted C3-C5 cycloalkyl.

[0168] In one possible implementation, in general formula (1), R1 to R4 are methyl, ethyl, propyl or cyclopropylmethyl.

[0169] In one possible implementation, in general formula (1), R1 to R4 are methyl or ethyl.

[0170] In one possible implementation, in general formula (1), R1 to R4 are methyl groups.

[0171] In one possible implementation, in general formula (1), R5 is selected from halogenated, substituted, or unsubstituted C6-C. 10 Aryloxy group, substituted or unsubstituted C1-C6 alkyl thio group, substituted or unsubstituted C3-C8 cycloalkyl thio group, substituted or unsubstituted C6-C 10 Arylthio, substituted or unsubstituted C2-C 10 Heterocyclic thio groups, substituted or unsubstituted C1-C 10 Heteroarylthio, substituted or unsubstituted pyridinethio, substituted or unsubstituted thiazolethio, substituted or unsubstituted imidazolethio, substituted or unsubstituted triazolethio, substituted or unsubstituted tetrazoliumthio, substituted or unsubstituted quinolinylthio, substituted or unsubstituted benzothiazolylthio, substituted or unsubstituted benzo[a]azolylthio, or substituted or unsubstituted benzo[a]imidazolylthio.

[0172] In one possible embodiment, in general formula (1), R5 is selected from halogen, substituted or unsubstituted C6-C8 aryloxy, substituted or unsubstituted C1-C4 alkylthio, substituted or unsubstituted C3-C5 cycloalkylthio, substituted or unsubstituted C6-C8 arylthio, substituted or unsubstituted C2-C6 heterocyclic thio, substituted or unsubstituted C1-C6 heteroarylthio, substituted or unsubstituted pyridinethio, substituted or unsubstituted thiazolethio, substituted or unsubstituted imidazolethio, substituted or unsubstituted triazolethio, substituted or unsubstituted tetrazoliumthio, substituted or unsubstituted quinolinylthio, substituted or unsubstituted benzothiazolylthio, substituted or unsubstituted benzo[a]azolylthio, or substituted or unsubstituted benzimidazolylthio.

[0173] In one possible implementation, in general formula (1), R5 is selected from halogenated, substituted, or unsubstituted C6-C. 10 Aryloxy group, substituted or unsubstituted C1-C6 alkylthio group, substituted or unsubstituted C6-C 10 Arylthio, substituted or unsubstituted C2-C 10 Heterocyclic thio groups, substituted or unsubstituted C1-C 10 Heteroarylthio, substituted or unsubstituted pyridinylthio, substituted or unsubstituted thiazolethio, substituted or unsubstituted imidazolethio, substituted or unsubstituted triazolethio, substituted or unsubstituted tetrazoliumthio, substituted or unsubstituted quinolinylthio, substituted or unsubstituted benzothiazolylthio, substituted or unsubstituted benzo[a]azolylthio, substituted or unsubstituted benzo[a]azolylthio, substituted or unsubstituted benzo[a]imidazolylthio.

[0174] In one possible embodiment, in general formula (1), R5 is selected from halogen, substituted or unsubstituted C6-C8 aryloxy, substituted or unsubstituted C1-C4 alkyl thio, substituted or unsubstituted C6-C8 aryl thio, substituted or unsubstituted C2-C6 heterocyclic thio, substituted or unsubstituted C1-C6 heteroaryl thio, substituted or unsubstituted pyridine thio, substituted or unsubstituted thiazole thio, substituted or unsubstituted imidazole thio, substituted or unsubstituted triazole thio, substituted or unsubstituted tetrazolium thio, substituted or unsubstituted quinolinyl thio, substituted or unsubstituted benzothiazolyl thio, substituted or unsubstituted benzo[a]azolyl thio, substituted or unsubstituted benzo[a]azolyl thio, substituted or unsubstituted benzo[a]imidazolyl thio.

[0175] In one possible implementation, in general formula (1), R5 is selected from halogens or substituted or unsubstituted groups of the following: C6-C8 arylthio or C1-C6 heteroarylthio.

[0176] In one possible implementation, in general formula (1), R5 is selected from halogens or optionally C6-C8 arylthio groups substituted with carboxyl groups.

[0177] In one possible implementation, in general formula (1), R5 is selected from Cl, substituted or unsubstituted pyridinyl thio, substituted or unsubstituted thiazolyl thio, substituted or unsubstituted imidazolyl thio, substituted or unsubstituted triazolyl thio, substituted or unsubstituted tetrazolyl thio, substituted or unsubstituted quinolinyl thio, substituted or unsubstituted benzothiazolyl thio, or substituted or unsubstituted benzimidazolyl thio.

[0178] In one possible implementation, in general formula (1), R5 is selected from Cl or optionally phenylthio groups substituted with carboxyl groups.

[0179] In one possible implementation, in general formula (1), R6 is selected from substituted or unsubstituted C1-C6 alkoxycarbonyl or carboxyl groups.

[0180] In one possible implementation, in general formula (1), R6 is selected from substituted or unsubstituted C1-C4 alkoxycarbonyl groups.

[0181] In one possible implementation, in general formula (1), R6 is selected from methoxycarbonyl or ethoxycarbonyl.

[0182] In one possible implementation, in general formula (1), R7 is selected from halogens, substituted or unsubstituted di-C1-C6 alkylamino groups or substituted or unsubstituted C3-C8 cycloalkylamino groups.

[0183] In one possible implementation, in general formula (1), R7 is selected from cyano, substituted or unsubstituted di-C1-C4 alkylamino or substituted or unsubstituted C3-C5 cycloalkylamino.

[0184] In one possible implementation, in general formula (1), R7 is selected from substituted or unsubstituted di-C1-C6 alkylamino or cyano groups.

[0185] In one possible implementation, in general formula (1), R7 is selected from substituted or unsubstituted di-C1-C4 alkylamino or cyano groups.

[0186] In one possible implementation, R7 is a cyano group in general formula (1).

[0187] In one possible implementation, in general formula (1), R8 and R9 are each independently selected from halogens, C1-C6 alkyl groups, or C1-C6 haloalkyl groups.

[0188] In one possible implementation, in general formula (1), R8 and R9 are each independently selected from halogens, C1-C4 alkyl groups, or C1-C4 haloalkyl groups.

[0189] In one possible implementation, in general formula (1), R8 and R9 are each independently selected from F, Cl, Br, methyl, ethyl, halomethyl or haloethyl.

[0190] In one possible implementation, in general formula (1), R8 and R9 are methyl groups.

[0191] In one possible implementation, in general formula (1), n ​​is an integer selected from 0 to 4.

[0192] In one possible implementation, n is 0, 1 or 2 in general formula (1).

[0193] In one possible implementation, n is 0 in general formula (1).

[0194] In one possible implementation, n is 1 in general formula (1).

[0195] In one possible implementation, in general formula (1), x and y are integers selected from 0 to 3.

[0196] In one possible implementation, x and y are 0, 1 or 2 in general formula (1).

[0197] In one possible implementation, x and y are 0 or 1 in general formula (1).

[0198] In one possible implementation, x and y are 0 in general formula (1).

[0199] In one possible implementation, R0 is independently a C1-C6 alkyl or C1-C4 alkyl that is optionally substituted with a halogen atom each time it appears.

[0200] In one possible implementation, “substituted or unsubstituted” means unsubstituted or substituted by one or more substituents selected independently from the following: halogen, C1-C6 alkyl, hydroxyl, C1-C6 alkoxy, carboxyl, amide, cyano, nitro or ester.

[0201] In one possible implementation, “substituted or unsubstituted” means unsubstituted or substituted by one or more substituents selected independently from the following: cyano, halogen, or carboxyl.

[0202] In one possible implementation, "substituted or unsubstituted" means unsubstituted or substituted with a carboxyl group.

[0203] In a specific embodiment, the pigment compound is one of the compounds of formula (1a) to formula (1i):

[0204] 1(a) 1(b)

[0205] 1(c) 1(d)

[0206] 1(e) 1(f),

[0207] 1(g), 1(h), or

[0208] 1(i).

[0209] In one possible implementation, the pigment compound has a maximum absorption value at 500 nm to 600 nm.

[0210] By using these pigment compounds, color filters with good spectral transmittance and excellent heat and light resistance can be made.

[0211] [pigment]

[0212] The resin compositions disclosed herein also comprise pigments. In some embodiments, the pigment is a blue pigment, which may be at least one of CI Pigment Blue 15:6, CI Pigment Blue 15:3, and CI Pigment Violet 23.

[0213] The pigment used as a first method of the resin composition disclosed herein contains a blue pigment of CI Pigment Blue 15:6.

[0214] The pigment used in a second embodiment of the resin composition of this disclosure comprises a mixture of CI Pigment Blue 15:6 and CI Pigment Blue 15:3 as a blue pigment. The pigment used in a third embodiment of the resin composition of this disclosure comprises a mixture of CI Pigment Blue 15:6 and CI Pigment Violet 23 as a blue pigment.

[0215] Considering the solubility of pigments and pigment compounds, it is preferable in this disclosure to pretreat the pigments with various masterbatch resins. As an example, the treatment process typically involves supplying the pigment or pigment compound by various methods, typically in the form of a powder after drying in an aqueous medium. However, water drying requires a large latent heat of vaporization, thus requiring a large latent heat to form the dried powder. Consequently, the pigment or pigment compound usually forms aggregates (secondary particles) composed of primary particles, which are not easily dispersed into microparticles. Therefore, pretreating with a masterbatch resin to prepare the masterbatch is ideal. As an example, the masterbatch resin used to prepare the masterbatch can be a microdispersed acrylic resin, a maleic acid resin, a vinyl chloride-vinyl acetate copolymer, an ethyl cellulose resin, etc.

[0216] As processing methods, common methods include washing, mixing, extrusion, ball mills, and roller mills (e.g., those with two or three rollers). Among these, washing or mixing with roller mills is suitable for micronization.

[0217] The aforementioned rinsing process typically includes: mixing an aqueous dispersion of the pigment or pigment compound with a masterbatch resin solution dissolved in a water-immiscible medium; extracting the pigment or pigment compound from the aqueous medium into an organic medium; and treating the pigment or pigment compound with the masterbatch resin. According to this method, since the pigment or pigment compound is not dried, it is easier to prevent agglomeration and dispersion. Furthermore, in the mixing process using the aforementioned tumbling mill, after mixing the pigment or pigment compound with the masterbatch resin or masterbatch resin solution, the pigment and masterbatch resin are mixed while applying high shear force, thereby forming a masterbatch resin layer on the pigment surface. This is a method of treating pigment or pigment compounds by coating. In this process, agglomerated pigment or pigment compound particles are dispersed from lower-level agglomerates into primary particles.

[0218] Furthermore, the pigments or pigment compounds treated as described above can also be used as pigment masterbatches pretreated with acrylic resin, vinyl chloride-vinyl acetate resin, maleic acid resin, ethyl cellulose resin, nitrocellulose resin, etc. The preferred form of this pigment masterbatch is a powder, paste, or granules in which the masterbatch resin and the pigment or pigment compound are uniformly mixed. It should be noted that unevenly formed lumps of gelled masterbatch resin are undesirable.

[0219] To improve the dispersibility of the aforementioned pigments or color compounds, conventionally known pigment dispersants and surfactants can be used.

[0220] As a pigment dispersant or surfactant, it can be, for example, but not limited to: organosiloxane polymer KP341 (manufactured by Shin-Etsu Chemical Co., Ltd.), (meth)acrylic (co)polymer Polyflow No. 75. Cationic surfactants such as No. 90, No. 95 (manufactured by Kyoei-sha Oil & Chemical Industry Co., Ltd.), and W001 (manufactured by Yusho Co., Ltd.); nonionic surfactants such as polyoxyethylene dodecyl ether, polyoxyethylene stearyl ether, polyoxyethylene oil-based ether, polyoxyethylene octylphenyl ether, polyoxyethylene nonylphenyl ether, polyethylene glycol dilaurate, polyethylene glycol distearate, sorbitan fatty acid esters, etc.; anionic surfactants such as W004, W005, W017 (manufactured by Yusho Co., Ltd.); polymeric dispersants such as EFKA-46, EFKA-47, EFKA-47EA, EFKA polymer 100, EFKA polymer 400, EFKA polymer 401, EFKA polymer 450 (and above, manufactured by Morishita Sangyo Co., Ltd.), dispersing aid 6, dispersing aid 8, dispersing aid 15, dispersing aid 9100 (manufactured by Sanopco Co., Ltd.); solution dispersants such as Solsperse 3000, 5000, 9000, 12000, 13240, 13940, 17000, 24000, 26000, 28000 (Lubrizol), Adkapronik L31, Adkapronik F38, Adkapronik L42, Adkapronik L44, Polyether L61, Polyether L64, Polyether F68, Polyether L72, Polyether P95, Polyether F77, Polyether P84, Polyether F87, Polyether P94, Polyether L101, Polyether P103, Polyether F108, Polyether L121, Polyether P-123 (Adeka), and Isonet S-20 (Sanyo Chemicals), etc.

[0221] As an example, based on the total mass of the pigment masterbatch disclosed herein, the pigment masterbatch comprises 20 to 70% by mass of masterbatch resin, 30 to 80% by mass of pigment / pigment compound, and 10 to 40% by mass of dispersant or surfactant.

[0222] There is no particular limitation on the mass ratio of the blue pigment to the pigment compound. Generally, the mass ratio of the blue pigment to the pigment compound is 9:1 to 1:9. From the viewpoint of spectral characteristics, specifically, the mass ratio of the blue pigment to the pigment compound is preferably 4:1 to 1:4, and more preferably 12:3 to 3:12.

[0223] The total mass of the pigments and pigment compounds in the resin composition disclosed herein can be 20 to 90% by mass relative to the total solid content (mass) of the resin composition. From the viewpoint of pattern formation, the total mass of the pigments and pigment compounds is preferably 30 to 85% by mass, more preferably 30 to 80% by mass.

[0224] As an example, the total mass of the pigments and pigment compounds mentioned above can be 35 wt%, 40 wt%, 45 wt%, 50 wt%, 55 wt%, 60 wt%, 61 wt%, 62 wt%, 63 wt%, 64 wt%, 65 wt%, 66 wt%, 67 wt%, 68 wt%, 69 wt%, 70 wt%, 71 wt%, 72 wt%, 73 wt%, 74 wt%, 75 wt%, 76 wt%, 77 wt%, 78 wt%, 79 wt%, 80 wt%, 81 wt%, 82 wt%, 83 wt%, 84 wt%, 85 wt%, 86 wt%, 87 wt%, 88 wt%, 89 wt%, 90 wt%, and any value between any two of the above values.

[0225] [Cureable Resin]

[0226] The resin composition disclosed herein contains a curable resin, but there is no particular limitation on the curable resin, as long as it can form the shape of a color filter, preferably selected according to the method of manufacturing the color filter.

[0227] As a method for manufacturing the aforementioned color filters, any previously known color filter forming method can be used, such as negative photolithography, positive photolithography, printing, or inkjet printing. From the perspective of obtaining fine and well-shaped color filters, negative photolithography is preferred.

[0228] The following description of the resin composition disclosed herein will focus on the curable resin using negative photolithography, but is not limited thereto.

[0229] The resin composition disclosed herein contains at least a curable resin, a pigment, and a pigment compound. When the color filter is manufactured using the aforementioned negative photolithography method, the curable resin may include an alkali-soluble resin, a polymerizable monomer, and a photopolymerizable initiator. The curable resin may also generally further include a solvent, and may use other components such as additives as needed.

[0230] -Alkali-soluble resin-

[0231] As a resin used in the preparation of color filters using negative photolithography, an alkali-soluble resin generally needs to be able to undergo an alkaline developing step. Therefore, the alkali-soluble resin disclosed herein needs to have acidic functional groups such as carboxyl groups and phenolic hydroxyl groups for alkaline developing. As an example, the acid value of the alkali-soluble resin is in the range of 100 to 250 mg KOH / g.

[0232] As an example, the acid value of the alkali-soluble resin can be 110 mgKOH / g, 120 mgKOH / g, 130 mgKOH / g, 140 mgKOH / g, 150 mgKOH / g, 160 mgKOH / g, 170 mgKOH / g, 180 mgKOH / g, 190 mgKOH / g, 200 mgKOH / g, 210 mgKOH / g, 220 mgKOH / g, 230 mgKOH / g, 240 mgKOH / g, and any value between any two of the above.

[0233] As a specific example, linear organic polymers that are soluble in organic solvents and can be developed using weakly alkaline aqueous solutions are preferred. Examples of such linear organic polymers include polymers with carboxylic acids in their side chains, such as methacrylic acid copolymers, acrylic acid copolymers, itaconic acid copolymers, crotonic acid copolymers, maleic acid copolymers, and partially esterified maleic acid copolymers described in patents JP 1984-44615A, JP 1979-34327B, JP 1983-12577B, JP 1979-25957B, JP 1984-53836B, and JP 1984-71048A. Acid cellulose containing carboxylic acids can also be used as an alkali-soluble resin. In addition, polymers obtained by adding an anhydrous acid to a polymer having hydroxyl groups can also be cited, such as polyhydroxystyrene resins, polysiloxane resins, poly(meth)acrylate 2-hydroxyethyl ester, polyvinylpyrrolidone or polyethylene oxide, polyvinyl alcohol, etc.

[0234] The above-mentioned alkali-soluble resins can also be copolymerized with hydrophilic monomers. Examples of hydrophilic monomers include (meth)acrylate hydroxyalkyl esters, glyceryl acrylates, (meth)acrylamide, N-hydroxymethylacrylamide, secondary and tertiary alkylacrylamides, dialkylaminoalkyl acrylates, morpholine (meth)acrylates, N-vinylpyrrolidone, N-vinylcaprolactam, vinylimidazole, vinyltriazole, methyl acrylate, ethyl acrylate, branched or linear propyl acrylate, branched or linear butyl acrylate, etc.

[0235] Other available hydrophilic monomers include those containing tetrahydrofurfuryl, phosphoric acid, phosphate esters, quaternary ammonium salts, ethylene oxide chains, propylene oxide chains, sulfonic acids and salts, morpholinoethyl, etc.

[0236] Furthermore, alkali-soluble resins including polymers containing polymeric double bonds (olefinic unsaturated groups) are suitable. Any polymer containing polymeric double bonds in the aforementioned molecules can be used, as long as it has olefinic unsaturated double bonds, such as polymers with olefinic unsaturated bonds. Additionally, any alkali-soluble polymer containing polymeric double bonds that has olefinic unsaturated double bonds can be used, such as polymers with olefinic unsaturated bonds.

[0237] At this point, the proportion of the "polymer containing polymeric double bonds" in the total mass of the alkali-soluble resin can be 10% by mass or more, preferably 20% by mass or more, and particularly preferably 30% by mass or more. If this proportion is less than 10% by mass, the pattern distribution of the pixels may sometimes deviate from a rectangle. In addition, the amount of double bonds in the alkali-soluble resin, expressed in millimoles per gram of resin, is preferably 1 to 5 mmol / g, more preferably 1 to 4.5 mmol / g, and most preferably 1.5 to 4.0 mmol / g.

[0238] As an example, the amount of double bonds in an alkali-soluble resin can be 1.6 mmol / g, 1.7 mmol / g, 1.8 mmol / g, 1.9 mmol / g, 2.0 mmol / g, 2.5 mmol / g, 3.0 mmol / g, 3.1 mmol / g, 3.2 mmol / g, 3.3 mmol / g, 3.4 mmol / g, 3.5 mmol / g, 3.6 mmol / g, 3.7 mmol / g, 3.8 mmol / g, 3.9 mmol / g, or any value between any two of the above.

[0239] Below are examples of polymers containing polymeric double bonds. However, the following substances are not the only examples that contain carbon-carbon unsaturated bonds.

[0240] Examples of polymers containing polymerizable double bonds include polymers with OH groups (e.g., 2-hydroxyethyl acrylate), polymers with COOH groups (e.g., methacrylic acid), and polymers of acrylic or vinyl compounds that can copolymerize with them. Polymers with OH groups are obtained, for example, by reacting a compound having an epoxy ring and carbon-carbon unsaturated bond groups that are reactive with OH groups (e.g., glycidyl acrylate compounds) with a monomer. Besides epoxy rings, anhydrous acid compounds, compounds with isocyanate groups, and compounds with acryloyl groups can also be used as compounds reactive with OH groups. Furthermore, as described in JP 1994-102669 A and JP 1994-1938 A, reaction products obtained by reacting a saturated or unsaturated polyacid anhydride with a compound containing an epoxy ring and an unsaturated carboxylic acid such as acrylic acid can be used. Examples of compounds possessing both alkali-soluble COOH and OH groups and carbon-carbon unsaturated groups include the Dianal NR series (manufactured by Mitsubishi Rayon), Photomer 6173 (a COOH-containing polyurethane acrylic oligomer manufactured by Diamond Shamrock), Viscoat R-264, KS Resist 106 (all manufactured by Osaka Organic Chemicals Co., Ltd.), Cyclomer P series, Plaxel CF200 series (all manufactured by Daicel Chemical Co., Ltd.), and Ebecryl 3800 (manufactured by Daicel UCB). Polymers having at least one of crotonyl, acrylate, methacrylate, allyl, propyl, vinyl ester, and allyloxyalkyl groups in their side chains are preferred, and polymers having at least one of acrylate, methacrylate, and allyl groups in their side chains are particularly preferred.

[0241] The weight-average molecular weight M of the alkali-soluble resin in this disclosure is... w It can be 3,000 to 300,000, more preferably 5,000 to 100,000, and most preferably 10,000 to 80,000.

[0242] As an example, the weight-average molecular weight M of alkali-soluble resins w It can be 20,000, 30,000, 40,000, 50,000, 60,000, 70,000, 75,000, or any value between any two of the above.

[0243] The curable resin comprises 0 to 50% by mass of alkali-soluble resin, based on the total weight of the curable resin. If it exceeds 50% by mass, a good pattern outline may not always be obtained.

[0244] As an example, the content of alkali-soluble resin can be 0.5% by mass, 1% by mass, 3% by mass, 4% by mass, 5% by mass, 6% by mass, 7% by mass, 8% by mass, 9% by mass, 10% by mass, 11% by mass, 12% by mass, 13% by mass, 14% by mass, 15% by mass, 16% by mass, 17% by mass, 18% by mass, 19% by mass, 20% by mass, 25% by mass, 30% by mass, 35% by mass, 40% by mass, 45% by mass, 50% by mass, and any value between the above two.

[0245] -polymerizable monomers-

[0246] The aforementioned curable resin contains at least one polymerizable monomer. Preferably, the polymerizable monomer is a compound having at least one addition-polymerizable vinyl group and an olefinic unsaturated group having a boiling point of 100°C or higher at normal pressure. As examples, polymerizable monomers may be, but are not limited to: monofunctional acrylates or methacrylates, such as polyethylene glycol mono(meth)acrylate, polypropylene glycol mono(methyl)acrylate, phenoxyethyl(meth)acrylate, etc.; substances obtained by adding ethylene oxide or propylene oxide to polyfunctional alcohols such as glycerol or trimethylolpropane and then subjecting them to (meth)acrylate, such as polyethylene glycol di(meth)acrylate, trimethylol(meth)acrylate, neopentyl glycol di(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth) ester, dipentaerythritol penta(meth)acrylate, dipentaerythritol hexa(meth)acetate, hexanediol (meth)acrylate, trimethylolpropane tri(acryloyloxypropyl) ether, tri(acryloyloxyethyl)isocyanurate, etc.; polyurethane acrylates, such as those described in JP 1973-41708B, JP The following are listed in JP 1975-6034B and JP 1976-37193A: including polyfunctional acrylates or methacrylates such as polyester acrylates, epoxy acrylates (results of the reaction of epoxy resin and (meth)acrylic acid), as described in JP 1973-64183A, JP 1974-43191B, and JP 1977-30490B; and mixtures thereof. Furthermore, substances described as photocurable monomers and oligomers in the "Journal of the Japan Association for Adhesion, Vol. 20, No. 7, 300-308" can also be cited.

[0247] The content of polymerizable monomers in the curable resin disclosed herein is preferably 0.1 to 90% by mass, more preferably 1.0 to 80% by mass, and even more preferably 2.0 to 70% by mass, relative to the solid content of the curable resin.

[0248] As an example, the content of polymerizable monomers can be 5% by mass, 10% by mass, 15% by mass, 20% by mass, 25% by mass, 30% by mass, 35% by mass, 40% by mass, 45% by mass, 50% by mass, 55% by mass, 60% by mass, 65% by mass, and any value between the two of the above.

[0249] In one embodiment, the curable resin contains 0.1 to 100% by mass of polymeric monomers based on the total weight of the curable resin.

[0250] In one embodiment, the curable resin contains 1.0 to 100% by mass of polymeric monomers based on the total weight of the curable resin.

[0251] In one embodiment, the curable resin contains 2.0 to 100% by mass of polymeric monomers based on the total weight of the curable resin.

[0252] -Photopolymerization initiator-

[0253] The aforementioned curable resin contains at least one photopolymerization initiator. The photopolymerization initiator is any substance capable of polymerizing the aforementioned polymerizable monomers and alkali-soluble resins containing polymerizable double bonds in their molecules; there are no particular limitations. From the viewpoints of polymerization characteristics, initiation efficiency, absorption wavelength, availability, and cost, at least one photopolymerization initiator selected from halomethyl-S-triazine compounds, oxime compounds, or α-aminoketone compounds can be used.

[0254] Examples of halomethyl-s-triazine compounds include, for example, the ethylene-halomethyl-s-triamine compound described in JP 1984-1281 B, and the 2-(naphtho-1-yl)-4,6-bis-halomethyl-s-triazine and 4-(p-aminophenyl)-2,6-di-halomethyl-s-triazine compounds described in JP 1978-133428 A. Other commercially available examples include the TAZ series manufactured by Green Chemicals (e.g., TAZ-107, TAZ-110, TAZ-104, TAZ-109, TAZ-140, TAZ-204, TAZ-113, TAZ-123, etc.).

[0255] As oxime compounds, there are no particular limitations. Examples include 2-(o-benzoyl oxime)-1-[4-(phenylthio)phenyl]-1,2-octanedione, 1-(4-methylsulfonylphenyl)-butane-1,2-butane 2-oxime-O-acetate, 1-(4-methylsulfonylphenyl)-butane-1-oxime-O-acetate, hydroxyimino-(4-methylsulfonylphenyl)-ethyl acetate-O-acetate, and hydroxyimino-(4-methylsulfonylphenyl)-ethyl acetate-O-benzoate, etc.

[0256] As α-aminoketone compounds, there are no particular limitations. Examples include the Irgacure series manufactured by Ciba-Geigy (e.g., Irgacure 907, Irgacure 369, etc.), 2-methyl-1-phenyl-2-morpholinopropane-1-one, 2-methyl-1-[4-(hexyl)phenyl]-2-morpholinopropane-1-one, 2-ethyl-2-dimethylamino-1-(4-morpholinophenyl)-butanone-1, etc.

[0257] These photopolymerization initiators can be used in conjunction with sensitizers or light stabilizers. Specific examples of sensitizers or light stabilizers include benzoin, benzoin methyl ether, 9-fluorenone, 2-chloro-9-fluorenone, 2-methyl-9-fluorenone, 9-anthrone, 2-bromo-9-anthrone, 2-ethyl-9-anthrone, 9,10-anthraquinone, 2-ethyl-9,10-anthraquinone, 2-tert-butyl-9,10-anthraquinone, 2,6-dichloro-9,10-anthraquinone, flavonoids, 2-methylflavonoids, and 2-methoxyflavonoids. Ketones, 2-methoxyflavones, 2-methoxyflavones, thioflavones, 2,4-diethylthioanthrone, acridinones, 10-butyl-2-chloroacridinone benzyl, dibenzocyclophenone, p-(dimethylamino)phenylstyrene ketone, p-(dimethylamino)phenyl-p-methylbenzyl ketone, benzophenone, p-(dimethylamino)benzophenone (or michleone), p-(diethylamino)benzophenone, benzanthrone, and benzothiazole compounds as described in JP 1976-48516B, Chinubin 1130, 400, etc.

[0258] In addition to the photopolymerization initiators described above, other known photopolymerization initiators, as shown below, can also be used. Specifically, these include vicinal polyketolaldonyl compounds as described in U.S. Patent No. 2,367,660; α-carbonyl compounds as described in U.S. Patent Nos. 2,367,661 and 2,367,670; alanine ethers as described in U.S. Patent No. 2,448,828; aromatic azo compounds substituted with α-hydrocarbons as described in U.S. Patent No. 2,722,512; quinone compounds as described in U.S. Patent Nos. 3,046,127 and 2,951,758; combinations of triallyl imidazole dimers and p-aminobenzophenone as described in U.S. Patent No. 3,549,367; and benzothiazole compounds / trihalomethyl-s-triazine compounds as described in JP 1,976-48516 B.

[0259] In addition, examples include activated halogen compounds selected from halomethyl diazoles, at least one activated halogen compound selected from halomethyl-s-triazine compounds, halomethyl-s-triazine, rofen dimers, benzophenone compounds, acetophenone compounds and their compounds, cyclopentadiene-benzene-iron complexes and their salts, oxime compounds, etc.

[0260] Examples of activated halogen compounds such as halomethyl diazoles include 2-halomethyl-5-vinyl-1,3,4-diazole compounds as described in JP 1982-6096 B, or 2-trichloromethyl-5-phenylethyl-1,3,4-diazole, 2-trichloromethyl-5-(p-cyano)-1,3,4-diazole, 2-trichloromethyl-5-(p-methoxyphenylethyl)-1,3,4-diazole, etc.

[0261] In addition, Panchim's T-series (e.g., T-OMS, T-BMP, TR, TB, etc.), Ciba Geigy's Irgacure series (e.g., Irgacure 651, Irgacure 184, Irgacure 500, Irgacure 1000, Irgacure 149, Irgacure 819, Irgacure 261, etc.), and Darocure series (e.g., Darocure 1173, etc.) are also valid.

[0262] Other examples can be 4,4-bis(diethylamino)-benzophenone, 2-O-benzoyl oxime-1-[4-(phenylthio)phenyl]-1,2-octanedione, 2-benzyl-2-dimethylamino-4-morpholinobutanol 2,2-dimethoxy-2-phenylacetophenone, 2-(o-chlorophenyl)-4,5-diphenylimidazolyl dimer, 2-(o-fluorophenyl)-4,5-diphenylimidazolyl dimer, 2-(o-methoxyphenyl)-4,5-diphenylimidazolyl dimer, 2-(p-methoxyphenyl)-4,5-diphenylimidazolium dimer, 2-(p-methoxyphenyl)-4,5-diphenylimidazolium dimer, 2-(p-methoxyphenyl)-4,5-diphenylimidazolium dimer, 2-(p-dimethoxyphenyl)-4,5-diphenylimidazolium dimer, 2-(2,4-dimethoxyphenyl)-4,5-diphenylimidazolium dimer, 2-(p-methylmercaptophenyl)-4,5-diphenylimidazolium dimer, benzoisopropyl ether, etc.

[0263] In this disclosure, the aforementioned photopolymerization initiator can also be used in conjunction with a photopolymerization initiator that has maximum absorption in the ultraviolet band.

[0264] In this case, it is particularly beneficial to use ultraviolet light for appropriate post-curing irradiation. Using ultraviolet light allows for a shorter processing time. Even with subsequent post-baking, deformation caused by thermal collapse and trailing in the pixels can be effectively prevented, resulting in rectangular pixels with well-defined cross-sectional profiles.

[0265] As specific examples, one can cite at least one photopolymerization initiator having a maximum absorption wavelength in the ultraviolet region below 300 nm and at least two or more photopolymerization initiators having a maximum absorption wavelength in the ultraviolet region above 300 nm (e.g., 310 nm to 420 nm). In this case, not only are two or more photopolymerization initiators contained, but also a photopolymerization initiator with a maximum absorption wavelength exceeding 300 nm is included. Simultaneously containing a photopolymerization initiator with a maximum absorption wavelength less than or equal to 300 nm, pattern exposure can be performed using light with a wavelength exceeding 300 nm (particularly 310 to 420 nm), and post-curing can be performed using short-wavelength light below 300 nm.

[0266] In the configuration described above, the photopolymerization initiator having the maximum absorption wavelength in a band exceeding 300 nm (e.g., 310 nm to 420 nm) can be selected from the photopolymerization initiators described above. In addition, examples of photopolymerization initiators with the maximum absorption wavelength in the ultraviolet region below 300 nm include carbonyl compounds such as Epacure TZT (manufactured by Fatelli Lambert), Kayacure BTC, and Kayacure ITX (manufactured by Nippon Kayaku Co., Ltd.); dicarbonyl compounds such as Vicure55 (manufactured by Stauffer AKZO); acetophenone compounds such as Esacure KIP100F, Esacure KT37 (manufactured by Siebel Hegner), and FIRST DEAP (manufactured by FIRST CHEMICAL); benzoin compounds such as BENZOIN B and BENZOIN PS-8A (manufactured by Fujifilm and Koujun Pharmaceutical Co., Ltd.); aminocarbonyl compounds such as Kayacure EPA and Kayacure DMBI (manufactured by Nippon Kayaku Co., Ltd.); and halides such as Triazine A, Triazine PP, and Triazine B (manufactured by Panchim Co., Ltd.).

[0267] The content of the photopolymerization initiator in the aforementioned curable resin, relative to the total solids content of the polymerizable monomer and the alkali-soluble resin having polymerizable double bonds in its molecules, is preferably 0.01 to 50% by mass, more preferably 1 to 30% by mass, and most preferably 1 to 20% by mass. When the content of the photopolymerization initiator is less than 0.01% by mass, the polymerization reaction is difficult to proceed. When the content of the photopolymerization initiator exceeds 50% by mass, although the polymerization rate increases, the molecular weight decreases, and sometimes the film strength weakens.

[0268] As an example, the content of photopolymerization initiator can be 5% by mass, 7% by mass, 9% by mass, 10% by mass, 12% by mass, 14% by mass, 15% by mass, 16% by mass, 17% by mass, 18% by mass, 19% by mass, and any value between the two of the above.

[0269] In one embodiment, the curable resin contains 0.01 to 5% by mass of a photopolymerization initiator based on the total weight of the curable resin.

[0270] In one embodiment, the curable resin contains 0.01 to 4.5% by weight of a photopolymerization initiator based on the total weight of the curable resin.

[0271] In one embodiment, the curable resin contains 0.01 to 4% by mass of a photopolymerization initiator based on the total weight of the curable resin.

[0272] In addition to the aforementioned components, a heat polymerization inhibitor may be pre-added to the curable resin described above. Examples of heat polymerization inhibitors include, but are not limited to, hydroquinone, p-methoxyphenol, di-tert-butyl-p-cresol, pyrogallol, tert-butylcatechol, benzoquinone, 4,4'-thiobis(3-methyl-6-tert-butylphenol), 2,2'-methylenebis(4-methyl-6-tert-butylphenol), and 2-mercaptobenzimidazole.

[0273] -Organic solvents-

[0274] The aforementioned curable resins may, generally speaking, further include solvents as needed. There are no limitations on the solvent, as long as the solubility of the various components and the spreadability of the resulting composition are satisfied. In particular, it is ideal to select solvents that take into account the solubility, spreadability, and safety of alkali-soluble resins.

[0275] As examples of the aforementioned organic solvents, ester solvents can be used, such as, but not limited to, ethyl acetate, n-butyl acetate, isobutyl acetate, amyl formate, isoamyl acetate, isobutyl acetate, butyl propionate, isopropyl butyrate, ethyl butyrate, butyl butyrate, alkyl esters, methyl lactate, ethyl lactate, methyl acetate, ethyl acetate, methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, ethyl ethoxyacetate, ethyl ethoxyacetate, ethyl ethoxyacetate, γ-butyrolactone, etc.

[0276] Alkyl esters of 3-hydroxypropionate, such as methyl 3-hydroxypropionate, ethyl 3-hydroxypropionate, methyl 3-ethoxypropionate, and ethyl 3-ethoxypropionate, can be used; alkyl esters of 2-hydroxypropionate, such as methyl 2-hydroxypropionate, ethyl 2-hydroxypropionate, propyl 2-hydroxypropionate, methyl 2-ethoxypropionate, methyl 2-ethoxypropionate, methyl 2-oxy-2-methylpropionate, methyl 2-oxy-2-methylpropionate, methyl 2-oxy-2-methylpropionate, methyl 2-oxy-2-methylpropionate, ethyl 2-oxy-2-methylpropionate, ethyl 2-oxy-2-methylpropionate, ethyl 2-oxy-2-methylpropionate, ethyl pyruvate, propyl pyruvate, methyl acetoacetate, ethyl acetoacetate, methyl 2-oxobutyrate, and ethyl 2-oxobutyrate, can also be used.

[0277] Ethers can be used, such as diethylene glycol dimethyl ether, tetrahydrofuran, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, methyl acetate, ethylene glycol ethyl ether, ethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, propylene glycol methyl ether, propylene glycol methyl ether acetate, propylene glycol ethyl ether acetate, propylene glycol ethyl ether acetate, propylene glycol propyl ether acetate, dipropylene glycol methyl acetate, dipropylene glycol ethyl ether acetate, etc.

[0278] Ketones, such as methyl ethyl ketone, cyclohexanone, 2-heptanone, 3-heptanone, etc., can be used.

[0279] Alternatively, aromatic hydrocarbons, such as toluene and xylene, can also be cited.

[0280] In addition, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, ethyl lactate, diethylene glycol dimethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, butyl acetate, methyl 3-methoxypropionate, 2-heptanone, cyclohexanone, ethyl acetate, ethyl acetate, butyl carbiol acetate, propylene glycol methyl ether, and propylene glycol methyl ether are more suitable.

[0281] -Other ingredients-

[0282] Various additives can be added to the above-mentioned curable resin as needed, such as fillers, polymers other than those mentioned above, surfactants, adhesion promoters, antioxidants, ultraviolet absorbers, anti-coagulation agents, etc.

[0283] Specific examples of these additives include fillers such as glass and alumina; polymers other than adhesive resins such as polyvinyl alcohol, polyacrylic acid, polyethylene glycol monoalkyl ethers, and polyfluoroalkyl acrylates; and surfactants such as neutral ionic, anionic, and cationic surfactants: vinyltrimethoxysilane, vinyltriethoxysilane, vinyltri(2-methoxyethoxy)silane, N-(2-aminoethyl)-3-aminopropylmethyldimethoxysilane, N-(2-aminoethyl)-3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, 3-aminopropyltriethoxysilane, 3-... Clumping promoters such as glyceryl oxypropyltrimethoxysilane, 3-glycidyl oxypropylmethyldimethoxysilane, 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, 3-chloropropylmethyldimethoxysilane, 3-chloropropyltrimethoxysilane, and 3-mercaptopropyltrimethoxysilane; antioxidants such as 2,2-thio(4-methyl-6-tert-butylphenol) and 2,6-di-tert-butylphenol; ultraviolet absorbers such as 2-(3-tert-butyl-5-methyl-2-hydroxyphenyl)-5-chlorobenzotriazole and alkoxybenzophenone; and anti-coagulants such as sodium polyacrylate.

[0284] In addition, in order to promote the alkali solubility of the uncured part and further improve the development of the curable resin, the curable resin is further contained in an organic carboxylic acid, preferably a low molecular weight organic carboxylic acid with a molecular weight of less than 1000. Specific examples include aliphatic monocarboxylic acids such as formic acid, acetic acid, propionic acid, butyric acid, valeric acid, valproic acid, hexanoic acid, diacetic acid, heptaacetic acid ester, and octanoic acid; aliphatic dicarboxylic acids such as oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid, pyruvic acid, paraic acid, azelaic acid, sebacic acid, brassic acid, methylmalonic acid, ethylmalonic acid, dimethylmalonic acid, methylsuccinic acid, tetramethylsuccinic acid, and citric acid; aliphatic tricarboxylic acids such as trimethylcarboxylic acid, aconitic acid, and canlolinic acid; aromatic monocarboxylic acids such as benzoic acid, toluenesulfonic acid, aniseic acid, and trimellitic acid; and other carboxylic acids such as phenylacetic acid, hydrogenated aromatic acid, hydrogenated cinnamic acid, mandelic acid, phenylsuccinic acid, denatured acid, cinnamic acid, methylcinnamic acid, benzylcinnamylacetic acid, coumaric acid, and umbelliferous acid.

[0285] The curable resin content (by mass) in the resin composition disclosed herein, relative to the total solids content of the resin composition, can be 10 to 90% by mass, wherein preferably 15 to 80% by mass and more preferably 20 to 70% by mass.

[0286] As an example, the content of curable resin can be 35% by mass, 40% by mass, 45% by mass, 50% by mass, 55% by mass, 60% by mass, 65% by mass, 66% by mass, 67% by mass, 68% by mass, 69% by mass, 70% by mass, 75% by mass, 80% by mass, 85% by mass, 90% by mass, and any value between the two of the above.

[0287] [Resin Composition Characteristics]

[0288] The film thickness of the resin composition disclosed herein is not particularly limited, but may be 0.3 to 5.0 micrometers, 0.3 to 4.5 micrometers, 0.3 to 3.0 micrometers, or 0.3 to 1.5 micrometers.

[0289] As for the spectral characteristics of the resin composition disclosed herein, for example, the film with a thickness of 3.0 micrometers or less after curing of the resin composition disclosed herein has a spectral transmittance of 55% or more at a wavelength of 400 nm (e.g., 60% or more, 65% or more, 70% or more, 75% or more, or even 80% or more), has the maximum transmittance in the wavelength range of 400 nm to 500 nm, and its spectral transmittance is 85% or more (e.g., 86% or more, 87% or more, 88% or more, 89% or more, 90% or more, 91% or more, or even 92% or more), and its spectral transmittance in the wavelength range of 550 nm to 650 nm is 20% or less (e.g., 19% or less, 17% or less, 15% or less, 13% or less, 11% or less, 10% or less, or even 5% or less).

[0290] More ideally, the spectral transmittance at a wavelength of 400 nm is greater than 60% (e.g., greater than 65%, 70%, 75%, or even greater than 80%), the maximum transmittance is in the wavelength range of 400 nm to 500 nm, the spectral transmittance is greater than 90% (e.g., greater than 91%, or even greater than 92%), and the spectral transmittance in the wavelength range of 550 nm to 650 nm is less than 20% (e.g., less than 19%, less than 17%, less than 15%, less than 13%, less than 11%, less than 10%, or even less than 5%).

[0291] The spectral characteristics mentioned here can be either the inherent spectral characteristics of the resin composition itself or the spectral characteristics of the resin composition after curing. The lightfastness of the resin composition of this invention was tested using a Soga Testing Machine Co., Ltd. SX75F with a xenon lamp as the light source, an illuminance of 100,000 lux, and irradiation for 50 hours. The color difference (ΔE) before and after irradiation was measured using an Otsuka Electronics Co., Ltd. MCPD-2000. ab). The color difference (i.e., ΔE) of the resin composition disclosed herein before and after irradiation. (ab) is below 3 (e.g., below 2.5, below 2, below 1.5, below 1, or even below 0.5).

[0292] The heat resistance of the resin composition of the present invention was tested by heating on a hot plate at 220°C for 1 hour. The color difference (ΔE) before and after heating was measured using an MCPD-2000 manufactured by Otsuka Electronics Co., Ltd. The color difference before and after heating of the resin composition disclosed herein (i.e., ΔE) is as follows: (ab) is below 3 (e.g., below 2.5, below 2, below 1.5, below 1, or even below 0.5).

[0293] [Manufacturing method of color filter layer]

[0294] The method for manufacturing the color filter layer disclosed herein includes:

[0295] The resin composition of this disclosure is coated onto a substrate to form a resin composition layer; and

[0296] The resin composition layer is patterned to obtain the color filter layer.

[0297] [Manufacturing method of color filters]

[0298] Regarding the manufacturing method of the color filter disclosed herein, the following description uses the negative photolithography method as an example, but is not limited to this method.

[0299] The above manufacturing method includes:

[0300] The above resin composition is coated onto the substrate directly or in between other layers, and then dried (pre-baked) to form a resin composition layer;

[0301] A specific pattern is exposed on the formed resin composition layer, and the exposed resin composition layer is developed using an alkaline developer; and

[0302] A color filter is formed by post-baking the developed resin composition layer.

[0303] More specifically, the resin composition layer described above is formed by coating the resin composition onto a substrate using coating methods such as spin coating, cast coating, roller coating, and slot coating. The coating can be performed directly on the substrate or in between other layers.

[0304] As the aforementioned substrate, imaging elements and the like can be used. The substrate used for photoelectric conversion elements can be, for example, silicon substrates, sodium glass, pyroxene glass, quartz glass, etc., used in CCD (charge-coupled device), CMOS (complementary metal oxide semiconductor), liquid crystal display elements, etc., as well as materials on which a transparent conductive film is adhered. These substrates sometimes also have a black background formed to isolate each pixel.

[0305] Additionally, if necessary, a base coating may be applied to these substrates to improve adhesion to the upper layer, prevent material diffusion, or make the substrate surface smooth.

[0306] The above-described exposure process involves exposing a specific pattern onto the resin composition layer formed above using, for example, a mask. As the radiation used during exposure, ultraviolet light such as g-line, h-line, or i-line can be used in particular.

[0307] The above-described developing process involves treating the exposed resin composition layer with an alkaline developing solution. As for the alkaline developing solution, any alkaline developing solution can be used, as long as it dissolves the resin composition disclosed herein without dissolving the exposed portion (radiation irradiation portion). Specifically, various organic solvents and combinations thereof, or alkaline aqueous solutions, can be used.

[0308] Examples of organic solvents used in preparing the resin compositions disclosed herein include those used in the preparation of the aforementioned organic solvents. Additionally, examples of alkaline aqueous solutions include aqueous solutions of sodium hydroxide, potassium hydroxide, sodium carbonate, sodium silicate, sodium metasilicate, ammonia, ethylamine, diethylamine, monoethanolamine, diethanolamine, dimethylethanolamine, tetramethylammonium hydroxide, tetraethylammonium hydroxide, choline, pyrrole, piperidine, and 1,8-diazabicyclo-[5.4.0]-7-undecene.

[0309] The alkaline developing solution used in this disclosure is preferably an alkaline aqueous solution with an alkaline concentration adjusted to pH 11 to 13, more preferably pH 11.5 to 12.5. If the alkaline concentration exceeds pH 13, pattern cracking, peeling, and a decrease in residual film yield may sometimes occur. If the pH is less than 11, the developing speed may sometimes slow down, and residue may be generated. In the preparation method of this disclosure, a developing solution composed of such an alkaline aqueous solution can be used for appropriate developing treatment. For example, dip coating, spraying, or stirring methods can be used as developing methods. The developing temperature is preferably 15 to 40°C. Furthermore, washing with running water is usually performed after developing.

[0310] Furthermore, the aforementioned post-baking is performed, for example, using a hot plate. The post-baking temperature is 150 to 300°C, preferably 180 to 250°C. Additionally, the heating time is typically 2 to 10 minutes.

[0311] The resin composition disclosed herein can be used as a color filter for OLEDs or LEDs, and is even more suitable for high-resolution CCD elements, CMOS elements, etc.

[0312] Solid-state imaging elements

[0313] The solid-state imaging element disclosed herein has a light-receiving element and a color filter formed thereon. By manufacturing an element using a color filter containing the specific resin composition described above, the solid-state imaging element of this disclosure can achieve good color reproduction.

[0314] Furthermore, in addition to the color filters containing the resin composition described above, the solid-state imaging element disclosed herein also contains other color filters in its structure.

[0315] Color filters other than those described in the resin composition can be prepared using the methods described in this disclosure. For example, pigments corresponding to other colors can be used instead of the pigments and color compounds in the resin composition. Thus, color filters composed of three or four corresponding colors can be obtained.

[0316] The following describes the color filter described above in the solid-state imaging element of this disclosure, as well as the pigment other than blue used in the color filter having three colors or hues.

[0317] -Yellow filter-

[0318] The yellow color filter used in the solid-state imaging element disclosed herein contains at least CI pigment yellow 150 or 139 as a yellow pigment.

[0319] Furthermore, without hindering the purpose of this disclosure, appropriate selections can be made from conventionally known inorganic or organic yellow pigments, such as diazo yellow pigments, quinoline phthalide yellow pigments, methylimine yellow pigments, and isoisinin yellow pigments. Specifically, CI pigments 11, 24, 31, 53, 83, 93, 99, 108, 109, 110, 138, 147, 151, 154, 155, 167, 180, and 199 are preferred examples.

[0320] These yellow pigments can be used in one or more ways.

[0321] In the yellow color filter, the content (mass%) of the pigment used in the yellow color filter can be from 10% to 80% by mass, preferably from 20% to 70% by mass, and particularly from 30% to 60% by mass.

[0322] From the viewpoint of the transmittance of the color filter, the average particle size of the yellow pigment can be 0.01 to 0.2 micrometers, preferably 0.01 to 0.1 micrometers, and particularly 0.1 to 0.05 micrometers.

[0323] The film thickness of the yellow filter is not particularly limited and can be 0.3 to 3.0 micrometers, preferably 0.3 to 1.5 micrometers, and particularly 0.3 to 1.0 micrometers.

[0324] The spectral characteristics (transmittance) of this yellow filter are preferably below 20% in the wavelength range of 400 nm to 460 nm, and preferably above 80% in the wavelength range of 510 nm to 700 nm.

[0325] The lightfastness of this yellow filter, after being exposed to a 100,000 lux cesium lamp for 50 hours, is such that its ΔEab can be less than 3.

[0326] The heat resistance of this yellow filter is such that after being placed on a hot plate at 220°C for 1 hour, the ΔEab can be less than 3.

[0327] -Red Filter-

[0328] The red color filter used in the solid-state imaging element disclosed herein contains at least CI Pigment Red 254 as a pigment.

[0329] Furthermore, without prejudice to the purpose of this disclosure, appropriate selections can be made from conventionally known inorganic or organic red pigments, such as CI pigments 22, 44, 169, and 177, which are preferred examples.

[0330] These red pigments can be used not only with one type, but also with two or more types combined.

[0331] In the red filter, the content (mass%) of the pigment used as the red filter can be 10 to 80% by mass, preferably 20 to 70% by mass, and particularly 30 to 60% by mass.

[0332] From the viewpoint of the transmittance of the color filter, the average particle size of the red pigment can be 0.01 to 0.2 micrometers, preferably 0.01 to 0.1 micrometers, and particularly 0.1 to 0.05 micrometers.

[0333] The film thickness of the red filter is not particularly limited and can be 0.3 to 3.0 micrometers, preferably 0.3 to 1.5 micrometers, and particularly 0.3 to 1.0 micrometers.

[0334] The spectral characteristics (transmittance) of this red color filter are less than 20% in the wavelength range of 400 nm to 560 nm, and can be more than 70% in the wavelength range of 600 nm to 700 nm.

[0335] The lightfastness of this red filter, after being exposed to a 100,000 lux meteorite lamp for 50 hours, is ΔEab below 3.

[0336] The heat resistance of the red color filter used in the solid-state imaging element disclosed herein is preferably ΔEab of 3 or less after being placed on a hot plate at 220°C for 1 hour.

[0337] -Green Filter-

[0338] The green color filter used in the solid-state imaging element of this disclosure, as a green pigment, may also be appropriately selected from conventionally known inorganic or organic green pigments, without prejudice to the purpose of this disclosure. For example, combinations of CI pigments Green 7, 36, 37, 58, 59, Zinc Phthalocyanine, Aluminum Phthalocyanine, Titanium Phthalocyanine, etc., and CI pigments Yellow 11, 24, 108, 109, 110, 138, 139, 150, 151, 154, 167, 180, and 185 may be used.

[0339] Combinations of CI pigments 7, 36, 58, and 59 and CI pigments 139, 150, and 185 are preferred. For green filters used in solid-state imaging elements, combinations of one or both of CI pigments 58 and 59, and one or both of CI pigments 139 and 150 are particularly preferred.

[0340] In the green filter, the content (mass%) of the pigment used as the green filter can be 10 to 80% by mass, preferably 20 to 70% by mass, and particularly 30 to 60% by mass.

[0341] From the viewpoint of the transmittance of the color filter, the average particle size of the green pigment can be 0.01 to 0.2 micrometers, preferably 0.01 to 0.1 micrometers, and particularly 0 to 0.05 micrometers.

[0342] The thickness of the green filter is not particularly limited, but can be 0.3 to 3.0 micrometers, preferably 0.3 to 1.5 micrometers, and especially 0.3 to 1.0 micrometers.

[0343] The spectral characteristics (transmittance) of this green filter have a maximum peak value of over 80% in the wavelength range of 500 nm to 570 nm, less than 30% in the wavelength range of 400 nm to 460 nm, and preferably less than 30% in the wavelength range of 620 nm to 660 nm.

[0344] The lightfastness of this green filter, when exposed to a 100,000 lux cesium lamp for 50 hours, is such that its ΔEab can be less than 3.

[0345] The heat resistance of this green filter is such that after being placed on a hot plate at 220°C for 1 hour, the ΔEab can be less than 3.

[0346] The red, yellow, and green color filters used in the solid-state imaging elements and image display elements disclosed herein can be manufactured using the same method as the blue filter, except that a resin composition containing red, yellow, or even green pigments is used instead of a resin composition containing blue pigments.

[0347] [Methods for Manufacturing Solid-State Imaging Elements]

[0348] The method for manufacturing the solid-state imaging element disclosed herein is not particularly limited, and known methods for manufacturing solid-state imaging elements may be used. The following description, as an example, illustrates the method for manufacturing the solid-state imaging element of this disclosure, but this disclosure is not limited thereto.

[0349] The above-described method for manufacturing a color filter is performed on a light-receiving element (e.g., a CMOS element) arranged on a two-dimensional plane, and a color filter having a red pixel (R pixel) is formed on the light-receiving element.

[0350] Secondly, except for using a resin composition in which the pigment in the resin composition used to form the above-mentioned red pixel is replaced with a yellow pigment, yellow pixels (Y pixels) are formed in the areas where no red pixels are formed in the same manner as the formation operation of the red filter.

[0351] Next, except that a resin composition in which the pigment used to form the red pixel is replaced with a green pigment is used, green pixels are formed in the areas where no red or yellow pixels are formed, in the same manner as the red filter formation operation.

[0352] Finally, except for using a resin composition in which the pigment in the resin composition used to form the above-mentioned red pixel is replaced with a blue pigment, blue pixels are formed in the areas where no red, yellow, and green pixels are formed in the same way as the red color filter formation operation, thereby obtaining a (CMOS) solid-state imaging element.

[0353] In addition, CCD solid-state imaging elements can be manufactured in the same way by using CCD light-receiving elements instead of CMOS light-receiving elements.

[0354] The light-receiving element disclosed herein is not particularly limited, and well-known light-receiving elements may be used.

[0355] Alternatively, if the same color filter as described above is formed on the OLED or LED image display element, then each image display element can be manufactured.

[0356] <Display Device>

[0357] The color filter and the solid-state imaging element or image display element including thereof can be included in one or more suitable display devices. For example, the display device including the color filter and the solid-state imaging element or image display element including thereof can be a display, an instrument (e.g., an instrument for a vehicle, aircraft, or ship) and / or a projection device, etc.

[0358] The display device disclosed herein may further include display pixel units. In some embodiments, the color separation unit of the color filter corresponds one-to-one with the display pixel unit of the display device and is located in the outgoing light path of the display pixel unit.

[0359] <Electronic Devices>

[0360] The color filter and the solid-state imaging element, image display element or display device including the color filter may be included in one or more suitable electronic devices.

[0361] The electronic device may further include at least one of a power supply unit, a drive circuit, and a control circuit.

[0362] The electronic devices may include, for example, flat panel displays, curved displays, computer monitors, medical monitors, televisions, billboards, indoor lights, outdoor lights, signal lights, head-up displays, fully transparent displays, partially transparent displays, flexible displays, rollable displays, foldable displays, retractable displays, laser printers, telephones, portable telephones, tablet PCs, tablet computers, personal digital assistants, wearable devices, laptop computers, digital cameras, camcorders, viewfinders, microdisplays, 3D displays, virtual reality displays, augmented reality displays, vehicle display panels, vehicle dashboards, aircraft display panels, aircraft dashboards, video walls with multiple displays spliced ​​together, theater screens, stadium screens, phototherapy devices, or signs.

[0363] Consumer Goods

[0364] This application provides a consumer product that includes the color filter, solid-state imaging element, image display element, display device, or electronic device described above.

[0365] In some implementations, the consumer product can be a portable consumer product, such as a mobile phone, smartphone, tablet PC, mobile communication terminal, electronic notebook computer, e-book, portable multimedia player (PMP), navigation or ultra-mobile PC (UMPC), and one or more suitable products or parts thereof, such as a television, laptop computer, monitor, billboard or Internet of Things (IoT) device.

[0366] In some implementations, the consumer product may be a wearable device or part thereof, such as a smartwatch, a watch phone, an eyeglass-type or similar display, or a head-mounted display (HMD). However, the implementation is not limited to this.

[0367] In some embodiments, the consumer product may further include a vehicle display panel, a vehicle dashboard, an aircraft display panel, or an aircraft dashboard, such as a vehicle's instrument panel, a vehicle's center console, a central information display disposed on a vehicle's instrument panel, an interior rearview mirror display replacing a vehicle's side mirrors, an entertainment display for a vehicle's rear seats, a display disposed on the back of a front seat, a head-up display (HUD) mounted on the front of a vehicle or projected onto the windshield, and a computer-generated holographic augmented reality head-up display (CGH AR HUD). In some embodiments, the consumer product may also be a vehicle and an aircraft (e.g., a car and an airplane) that includes the aforementioned devices that can be used in the vehicle and aircraft.

[0368] To make the embodiments of this disclosure easier to understand, the present disclosure will be described in detail below with reference to the embodiments. These embodiments are for illustrative purposes only and are not limited to the application scope of this disclosure.

[0369] Unless otherwise specified, the specific operations and processing methods or conditions not described in the following embodiments are conventional methods in the art or are performed in accordance with the techniques or conditions described in the literature in the art or in accordance with the product manual.

[0370] Unless otherwise specified, all reagents or instruments used in the following examples that do not specify the manufacturer are commercially available products and conventional instruments in the field.

[0371] In the following examples, unless otherwise specified, all percentages are mass percentages.

[0372] Preparation Example 1

[0373] Add 500 ml of phosphoryl chloride and 61 g of 3-ethoxycarboxy-2-phenyl-5-oxo-4,5-dihydro-1H-pyrrole to the reaction vessel: Compound A and 71 g of 4,4'-bis(dimethylamino)benzophenone were stirred at 50–60 °C for 4 hours. Heating was then stopped, and the reaction mixture was added dropwise to 3 L of cold water in another container. Tetramethylammonium hydroxide (TMAH) aqueous solution was then added for neutralization, and the mixture was stirred for 3 hours before extraction with trifluoromethane. The organic layer was washed with water, dehydrated, and concentrated. A mixed solution of toluene and hexane was added to the resulting tar-like substance, and the mixture was stirred. The supernatant was removed by decantation, and hexane was added to the residue to obtain crystals. After precipitation, the filtered crystals were heated and stirred in a mixed solution of hexane and toluene for a period of time, then cooled, filtered, and dried to obtain 73 g of blackish-green crystalline compound 1.

[0374] (Compound 1).

[0375] Preparation Example 2

[0376] 100g of compound 1, 200ml of DMF, and 55g of potassium carbonate were added to a reaction vessel. While stirring, 32g of 4-sulfobenzoic acid was added over 1 hour. After further stirring for 1 hour, the reaction solution was filtered, and the filtrate was concentrated using an evaporator. Brine was added to the residue, and the precipitated crystals were filtered off, followed by washing with a small amount of water. After drying the crystals, they were dissolved in a mixture of acetone and methanol, and the insoluble matter was filtered off. The filtrate was concentrated, and the resulting crystals were decomposed in hexane, filtered off, and dried to obtain 110g of dark green crystalline compound 2.

[0377] (Compound 2).

[0378] Preparation Example 3

[0379] Except for replacing compound A in Synthetic Example 1 with the same molar amount of 3-methoxycarbonyl-2-(4-cyanophenyl)-5-oxo-4,5-dihydro-1-pyrrole, all other compounds were synthesized. Following the same procedure as in Preparation Example 1, 67 g of crystalline compound 3 was obtained.

[0380] (Compound 3).

[0381] Example 1

[0382] <The Formation of Blue Filters>

[0383] 1) Preparation of resin composition

[0384] After kneading each component of composition A for 30 minutes in a kneading machine, further high-viscosity dispersion treatment is carried out using a twin-shaft roller.

[0385] (Component A, blue pigment masterbatch)

[0386] ● Pigment (CI Pigment Blue 15:6) 30 parts

[0387] ● Dispersant (Disper 163, BYK) 3 parts

[0388] ● 20 parts of a propylene glycol monomethyl ether acetate solution (50% solids) of resin (a copolymer of (benzyl) methacrylate (BzMA) / methacrylic acid (MAA)).

[0389] The components of composition B below were added to the dispersion obtained above, and the mixture was stirred for 3 hours using a homogenizer. Then, a 4-hour micro-dispersion treatment was carried out using a 0.3 mm zirconia bead disperser (trade name: Dispermat, manufactured by GETZMZNN).

[0390] (Component B, pigment compound, colorant)

[0391] ● 130 parts of compound

[0392] ● 20 parts of a propylene glycol monomethyl ether acetate solution (50% solids) of resin (a copolymer of (benzyl) methacrylate (BzMA) / methacrylic acid (MAA)).

[0393] ● 200 parts of propylene glycol monomethyl ether acetate

[0394] The resin composition of the present invention is prepared by adding the components of composition C below to the dispersion obtained above and stirring and mixing.

[0395] (Composition C, curable resin)

[0396] ● 65 parts of propylene glycol monomethyl ether acetate

[0397] ● Polymerizing monomer (dipentaerythritol hexaacrylate, manufactured by Daicel Allnex) 20 parts

[0398] ● UV polymerization initiator (Irgacure OXE01, Ciba Special Chemicals) 3 parts

[0399] 2) Fabrication of wafer substrates with an undercoat

[0400] A 6-inch channel quartz wafer substrate was heated in an oven at 120°C for at least 30 minutes. Then, a primer resin Caut200 (manufactured by TOK Corporation) was coated onto the substrate, and it was then heated and dried in an oven at 230°C for 1 minute to obtain a quartz wafer substrate with a primer coating.

[0401] 3) Exposure and development of the resin composition layer

[0402] The resin composition prepared in 1) above is coated onto the base coating of the quartz wafer substrate with the base coating obtained in 2) above to form a photocurable resin composition layer. Then, it is subjected to a heat treatment (pre-baking) for 60 seconds using a hot plate at 100°C.

[0403] Next, using an i-line stepper exposure unit FPA-3000i5+ (manufactured by Canon), at a wavelength of 365 nm, the formed resin composition layer was subjected to exposure at 300 mJ / cm² using a blue island-patterned mask. 2The wafer substrate was irradiated with the specified exposure amount. Then, the wafer substrate with the irradiated resin composition layer formed was placed on the horizontal rotating stage of a rotary spray developing machine (DW-30 model; manufactured by Chemitronics). Paddle development was performed for 60 seconds at 23°C using a developing solution (2.38% by mass TMAH). Next, while rotating at 50 rpm, pure water was sprayed from a nozzle above the center of rotation to provide rinsing. Finally, spray drying was performed to form a blue pattern on the wafer substrate.

[0404] 4) Post-baking

[0405] The dried quartz wafer substrate is then baked for another 5 minutes on the aforementioned hot plate, which is set to 220°C. This forms a blue filter with blue pixels (B pixels).

[0406] Example 2

[0407] The blue filter was obtained in the same manner as in Example 1, except that compound 2 was used instead of compound 1.

[0408] Example 3

[0409] The blue filter was obtained in the same manner as in Example 1, except that compound 3 was used instead of compound 1.

[0410] Example 4

[0411] The blue filter was obtained in the same manner as in Example 1, except that components D and E were used instead of components A and B in Example 1.

[0412] (Composition D, blue pigment masterbatch)

[0413] ● Pigment (CI Pigment Blue 15:6) 30 parts

[0414] ● Pigment (CI Pigment Violet 23) 15 parts

[0415] ● Dispersant (Disper 163, BYK) 4.5 parts

[0416] ● 30 parts of a propylene glycol monomethyl ether acetate solution (50% solids) of resin (a copolymer of (benzyl) methacrylate (BzMA) / methacrylic acid (MAA)).

[0417] (Composition E, pigment compound, colorant)

[0418] ● 115 parts of compound

[0419] ● 10 parts of a propylene glycol monomethyl ether acetate solution (50% solids) of resin (a copolymer of (benzyl) methacrylate (BzMA) / methacrylic acid (MAA)).

[0420] ● 200 parts of propylene glycol monomethyl ether acetate

[0421] Comparative Example 1

[0422] The blue filter was obtained in the same manner as in Example 1, except that CI pigment violet 23 was used instead of compound 1 in Example 1.

[0423] Test case

[0424] The color filters formed by the above method were subjected to the following measurements and evaluations. The results of the measurements and evaluations are shown in Table 1 below.

[0425] -Spectral transmittance measurement-

[0426] The maximum peak and spectral transmittance in the wavelength range of 400 nm, 400 nm to 500 nm, and 550 nm to 650 nm were measured using an MCPD-2000 manufactured by Otsuka Electronics Co., Ltd.

[0427] The evaluation criteria are: transmittance of 55% or higher in the 400 nm wavelength range, maximum transmittance of 85% or higher in the wavelength range between 400 nm and 550 nm, and transmittance of 20% or lower in the wavelength range between 550 nm and 650 nm. A transmittance within these ranges is considered good; any other ranges are considered poor.

[0428] Furthermore, the spectral transmittance curves for Example 1 and Comparative Example 1 in the wavelength range of 400 nm to 700 nm are shown below. Figure 1 and Figure 2 As shown. Among them, the spectral characteristics of the color filter in Example 1 are as follows: spectral transmittance at a wavelength of 400 nm is 82%, with the maximum transmittance in the wavelength range of 445 nm, spectral transmittance in the wavelength range of 400 nm to 500 nm is 93%, and spectral transmittance in the wavelength range of 550 nm to 650 nm is less than 20%.

[0429] However, the spectral characteristics of the color filter in Comparative Example 1 are as follows: spectral transmittance at 400 nm wavelength is 58%, with maximum transmittance at 450 nm wavelength, spectral transmittance in the wavelength range of 400 nm to 500 nm is 77%, and spectral transmittance in the wavelength range of 550 nm to 650 nm is less than 20%.

[0430] -Lightfastness-

[0431] Lightfastness tests were conducted using a Suga SX75F testing machine with a meteorite lamp as the light source, irradiated at 100,000 lux for 50 hours. The color difference (ΔE) before and after irradiation was measured using an Otsuka Electronics MCPD-2000. (ab) Color difference of less than 3 is rated as good, and color difference of more than 3 is rated as bad.

[0432] -Heat resistance-

[0433] Heated on a hot plate at 220°C for 1 hour. The color difference (ΔE) before and after heating was measured using an MCPD-2000 instrument manufactured by Otsuka Electronics Co., Ltd. (ab) Color difference of less than 3 is rated as good and color difference of more than 3 is rated as bad.

[0434] Table 1

[0435] pigment Spectral characteristics Lightfastness Heat resistance Example 1 Compound 1 good good good Example 2 Compound 2 good good good Example 3 Compound 3 good good good Example 4 Compound 1 + P.I. Pigment Violet 23 good good good Comparative Example 1 PI Pigment Purple 23 bad good good

[0436] As shown in Table 1, the spectral characteristics of Comparative Example 1 are poor. On the other hand, the color filters of Examples 1 to 4 all exhibit good spectral characteristics (spectral transmittance) as blue color filters, and also have excellent lightfastness and heat resistance.

[0437] Application examples

[0438] CMOS solid-state imaging element

[0439] Except that a CMOS light-receiving element arranged on a two-dimensional plane is used instead of the quartz wafer transparent substrate of Example 1, a color filter with blue pixels (B pixels) is formed on the element in the same manner as in Example 1.

[0440] Next, the pigments in the resin composition B used to form the blue pixels were changed to CI pigment red 254 and CI pigment yellow 139 to obtain resin composition R. Otherwise, the same operation as in Example 1 was performed to form red pixels (R pixels) in the areas on the above-mentioned element where B pixels were not formed. Additionally, a red island pattern mask with a pattern of 2 micrometers was used during i-line irradiation.

[0441] Next, except that the pigment in the resin composition B used to form the blue pixel was changed to CI Pigment Yellow 150, resin composition Y was obtained. Otherwise, the same operation as in Example 1 was performed to form yellow pixels (Y pixels) in areas where the B and R pixels were not formed. Furthermore, a yellow island pattern mask with a pattern of 2 micrometers was used during i-line irradiation.

[0442] Furthermore, the pigments in resin composition B used to form the aforementioned blue-green pixels were changed to CI pigment ratio 58 and CI pigment yellow 150 to obtain resin composition G. Otherwise, the same operation as in Example 1 was performed to form green pixels (G pixels) in areas where the aforementioned B, R, and Y pixels were not formed, in order to fabricate a CMOS solid-state imaging element. Additionally, a green island pattern mask with a pattern of 2 micrometers was used during i-line illumination.

[0443] The CMOS solid-state imaging element obtained in the corresponding application case was visually tested using a color palette. The results show that the solid-state imaging element in the application case exhibits good color reproduction.

[0444] The foregoing preferred embodiments have further illustrated the objectives, technical solutions, and advantages of the present invention. It should be understood that the above descriptions are merely preferred embodiments of the present invention and are not intended to limit the present invention. Any modifications, equivalent substitutions, improvements, etc., made within the spirit and principles of the present invention should be included within the protection scope of the present invention.

Claims

1. A pyrrole-based pigment compound, characterized in that, The pyrrole pigment compound has a maximum absorbance at 500 nm to 600 nm and is a compound having the following general formula (1): (1)， In general formula (1): R1 through R4 are each independently selected from substituted or unsubstituted C1-C. 10 Alkyl or substituted or unsubstituted C3-C 10 cycloalkyl; R5 is selected from halogenated, substituted, or unsubstituted C6-C. 20 aryloxy, substituted or unsubstituted C1-C 10 Alkyl thio, substituted or unsubstituted C3-C 10 Cycloalkylthio, substituted or unsubstituted C6-C 20 Arylthio, substituted or unsubstituted C2-C 20 Heterocyclic thio groups, substituted or unsubstituted C1-C 20 Heteroarylthio, substituted or unsubstituted pyridinylthio, substituted or unsubstituted thiazolylthio, substituted or unsubstituted imidazolethio, substituted or unsubstituted triazolethio, substituted or unsubstituted tetrazolylthio, substituted or unsubstituted quinolinylthio, substituted or unsubstituted benzothiazolylthio, substituted or unsubstituted benzo[a]azolylthio, or substituted or unsubstituted benzo[a]imidazolylthio; R6 is selected from substituted or unsubstituted alkoxycarbonyl, cyano, or carboxyl groups; and R7 is selected from cyano, substituted, or unsubstituted di-C1-C 10 Alkylamino or substituted or unsubstituted C3-C 10 Cycloalkylamino; R8 and R9 are each independently selected from halogens, C1-C 10 Alkyl, C1-C 10 Halogenated alkyl groups: n is an integer selected from 0 to 5; x and y are integers selected from 0 to 4; Wherein, "substituted or unsubstituted" means unsubstituted or substituted by one or more substituents independently selected from the following: halogen, C1-C 10 Alkyl, hydroxyl, C1-C 10 Alkoxy, carboxyl, amide, cyano, nitro, or ester groups; "Ester group" refers to -OCOR0 or -COOR0, where R0 is independently C1-C each time it appears. 10 alkyl.

2. The pyrrole-based pigment compound according to claim 1, characterized in that, In general formula (1): R1 to R4 are each independently selected from substituted or unsubstituted C1-C6 alkyl or substituted or unsubstituted C3-C8 cycloalkyl.

3. The pyrrole pigment compound according to claim 1 or 2, characterized in that, In general formula (1): R1 to R4 are methyl or ethyl.

4. The pyrrole-based pigment compound according to claim 1 or 2, characterized in that, In general formula (1): R5 is selected from Cl, substituted or unsubstituted phenylthio, substituted or unsubstituted pyridinylthio, substituted or unsubstituted thiazolyl thio, substituted or unsubstituted imidazolyl thio, substituted or unsubstituted triazolyl thio, substituted or unsubstituted tetrazolyl thio, substituted or unsubstituted quinolinyl thio, substituted or unsubstituted benzothiazolyl thio, or substituted or unsubstituted benzimidazolyl thio.

5. The pyrrole pigment compound according to claim 1 or 2, characterized in that, In general formula (1): R5 is selected from Cl or phenylthio group which is optionally substituted with a carboxyl group.

6. The pyrrole-based pigment compound according to claim 1 or 2, characterized in that, In general formula (1): R6 is selected from substituted or unsubstituted C1-C6 alkoxycarbonyl groups.

7. The pyrrole pigment compound according to claim 1 or 2, characterized in that, In general formula (1): R6 is selected from methoxycarbonyl or ethoxycarbonyl.

8. The pyrrole pigment compound according to claim 1 or 2, characterized in that, In general formula (1): R7 is selected from substituted or unsubstituted di-C1-C6 alkylamino or cyano groups.

9. The pyrrole pigment compound according to claim 1 or 2, characterized in that, In general formula (1): R7 is a cyano group.

10. The pyrrole pigment compound according to claim 1 or 2, characterized in that, In general formula (1): R8 and R9 are each independently selected from halogens, C1-C6 alkyl groups or C1-C6 haloalkyl groups.

11. The pyrrole-based pigment compound according to claim 1 or 2, characterized in that, In general formula (1): R8 and R9 are methyl groups.

12. The pyrrole pigment compound according to claim 1 or 2, characterized in that, In general formula (1): n is 0, 1 or 2; And / or, x and y are independently 0, 1, or 2.

13. The pyrrole pigment compound according to claim 1 or 2, characterized in that, In general formula (1): R0 is independently a C1-C6 alkyl group that is optionally substituted with a halogen atom each time it appears; And / or, "substituted or unsubstituted" means unsubstituted or substituted by one or more substituents selected independently from the following: halogen, C1-C6 alkyl, hydroxyl, C1-C6 alkoxy, carboxyl, amide, cyano, nitro or ester.

14. The pyrrole-based pigment compound according to claim 1 or 2, characterized in that, In general formula (1): "substituted or unsubstituted" means unsubstituted or substituted by a carboxyl group.

15. The pyrrole pigment compound according to claim 1, characterized in that, The pyrrole pigment compound is selected from at least one of the compounds of formula 1(a) to formula 1(i): 1(a)、 1(b)、 1(c)、 1(d)、 1(e)、 1(f)、 1(g)、 1(h)、 1(i)。 16. A resin composition, characterized in that, The resin composition comprises a colorant comprising a mixture of a blue pigment and a pyrrole pigment compound, wherein the pyrrole pigment compound is any one of claims 1-15.

17. The resin composition according to claim 16, characterized in that, The cured film of the resin composition, with a thickness of less than 3.0 micrometers, has a spectral transmittance of more than 55% at a wavelength of 400 nm, a spectral transmittance of more than 85% in the wavelength range of 400 nm to 500 nm, a spectral transmittance of less than 20% in the wavelength range of 550 nm to 650 nm, and / or a maximum transmittance in the wavelength range of 400 nm to 500 nm.

18. The resin composition according to claim 16, characterized in that, The cured film of the resin composition, with a thickness of less than 3.0 micrometers, has a spectral transmittance of more than 60% at a wavelength of 400 nm, a spectral transmittance of more than 90% in the wavelength range of 400 nm to 500 nm, a spectral transmittance of less than 20% in the wavelength range of 550 nm to 650 nm, and / or a maximum transmittance in the wavelength range of 400 nm to 450 nm.

19. The resin composition according to claim 16, characterized in that, The cured film of the resin composition, with a thickness of less than 3.0 micrometers, has a spectral transmittance of more than 70% at a wavelength of 400 nm, a spectral transmittance of more than 90% in the wavelength range of 400 nm to 500 nm, a spectral transmittance of less than 20% in the wavelength range of 550 nm to 650 nm, and / or a maximum transmittance in the wavelength range of 420 nm to 450 nm.

20. The resin composition according to claim 16, characterized in that, The blue pigment is selected from at least one of CI Pigment Blue 15:6 or CI Pigment Blue 15:

3.

21. The resin composition according to any one of claims 16 to 20, characterized in that, The blue pigment is a mixture of CI Pigment Blue 15:6 and CI Pigment Blue 15:3; Alternatively, the blue pigment is CI Pigment Blue 15:

6.

22. The resin composition according to any one of claims 16 to 20, characterized in that, The mass ratio of the blue pigment to the compound is 1:9 to 9:

1.

23. The resin composition according to any one of claims 16 to 20, characterized in that, The mass ratio of the blue pigment to the pyrrole pigment compound is 1:4 to 4:

1.

24. The resin composition according to any one of claims 16 to 20, characterized in that, The resin composition contains 20% to 90% by mass of colorant based on the total solids mass of the resin composition.

25. The resin composition according to any one of claims 16 to 20, characterized in that, The resin composition further includes a curable resin and a solvent, wherein the curable resin contains an alkali-soluble resin, a polymerizable monomer, and a photopolymerization initiator.

26. The resin composition according to claim 25, characterized in that, The resin composition comprises 10% to 90% by mass of curable resin based on the total solids mass of the resin composition; And / or, based on the total weight of the curable resin, the curable resin comprises 0 to 50% by mass of an alkali-soluble resin; And / or, based on the total weight of the curable resin, the curable resin contains 0.1% to 78% by mass of polymerizable monomers; And / or, based on the total weight of the curable resin, the curable resin contains 0.01% to 10% by mass of a photopolymerization initiator.

27. A method for preparing a color filter layer, characterized in that, The method includes: Coating a resin composition according to any one of claims 16 to 26 onto a substrate to form a resin composition layer; and The resin composition layer is patterned to obtain the color filter layer.

28. A color filter layer, characterized in that, The color filter layer is prepared by the method according to claim 27.

29. A color filter, characterized in that, The color filter includes the color filter layer according to claim 28, wherein the color filter is a blue color filter.

30. A solid-state imaging element, characterized in that, The solid-state imaging element includes: Light-receiving element; and A color filter, the color filter being formed on the light-receiving element, The color filter is the color filter according to claim 29.

31. An image display element, characterized in that, The image display element includes: Light-emitting element, wherein the light-emitting element is selected from at least one of OLED and LED; and A color filter is formed on the light-emitting element. The color filter is the color filter according to claim 29.

32. A display device, characterized in that, The display device includes: The color filter according to claim 29; The solid-state imaging element according to claim 30; or The image display element according to claim 31.

33. The display device according to claim 32, characterized in that, The display device further includes: a display pixel unit.

34. An electronic device, characterized in that, The electronic device includes: The color filter according to claim 29; The solid-state imaging element according to claim 30; The image display element according to claim 31; or The display device according to claim 32 or 33.

35. The electronic device according to claim 34, characterized in that, The electronic device further includes at least one of a power supply unit, a drive circuit, and a control circuit.

36. The electronic device according to claim 34 or 35, characterized in that, The electronic device is selected from: flat panel displays, curved displays, computer monitors, medical monitors, televisions, billboards, indoor lights, outdoor lights, signal lights, head-up displays, fully transparent displays, partially transparent displays, flexible displays, rollable displays, foldable displays, retractable displays, laser printers, telephones, portable telephones, tablet PCs, tablet computers, personal digital assistants, wearable devices, laptop computers, digital cameras, camcorders, viewfinders, miniature displays, 3D displays, virtual reality displays, augmented reality displays, vehicle display panels, vehicle dashboards, aircraft display panels, aircraft dashboards, video walls with multiple displays spliced ​​together, theater screens, stadium screens, phototherapy devices, or signs.

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