Colored composition, cured film, structure, color filter and display device
The colored composition with specific pigments and additives addresses curing and color mixing issues in low-temperature processes, ensuring effective spectral characteristics and curing in color filters.
Patent Information
- Application Number
- JP2022551196
- Authority / Receiving Office
- JP · JP
- Patent Type
- Patents
- Current Assignee / Owner
- Priority Date
- 2021-01-05
- Filing Date
- 2021-08-19
- Publication Date
- 2025-01-23
- Estimated Expiration
- 2041-08-19
AI Technical Summary
Existing color filters face issues with insufficient curing at low temperatures and color mixing when forming pixels, particularly in low-heat-resistant materials like organic semiconductor elements, leading to fluctuations in spectral characteristics.
A colored composition containing Color Index Pigment Green 7, a yellow colorant, a polymerizable compound, a photopolymerization initiator, and a compound with a cyclic ether group, which is formulated to suppress color mixing and achieve sufficient curing at temperatures of 150°C or lower by optimizing spectral characteristics and interaction between pigments.
The composition forms a cured film with excellent color separation from other colors, ensuring proper spectral characteristics and sufficient curing even at low temperatures, thereby improving the quality of green pixels in color filters.
Smart Images

Figure 0007620639000001 
Figure 0007620639000002 
Figure 0007620639000003
Abstract
Description
[Technical field]
[0001] The present invention relates to a colored composition. More specifically, the present invention relates to a colored composition used for forming green pixels of a color filter. The present invention also relates to a cured film, a structure, a color filter, and a display device using the colored composition. [Background technology]
[0002] 2. Description of the Related Art In various display devices, color filters are generally used to colorize displayed images. In color filters, attempts have been made to adjust the spectrum by using a plurality of pigments in combination.
[0003] A coloring composition for forming green pixels of a color filter contains a green colorant as a colorant. For example, Examples 1 to 7 of Patent Document 1 describe the formation of green pixels using a coloring composition containing colorants including Color Index Pigment Green 7 and Color Index Pigment Yellow 150, a polymerizable compound, and a photopolymerization initiator. [Prior art documents] [Patent documents]
[0004] [Patent Document 1] JP 2014-041341 A Summary of the Invention [Problem to be solved by the invention]
[0005] Generally, a color filter has pixels of a plurality of colors. Such a color filter having pixels of a plurality of colors is manufactured by forming pixels of each color by sequentially forming a pattern of colored compositions for forming pixels of each color.
[0006] In recent years, color filters are sometimes formed on components with low heat resistance (for example, organic semiconductor elements such as organic electroluminescence display elements). Because such components have low heat resistance, it is desirable to form the pixels of the color filter in a low-temperature process at, for example, 150°C or less to prevent thermal damage to the support.
[0007] However, when pixels are formed by a low-temperature process, the degree of curing of the pixels may be insufficient, and when pixels of other colors are formed, color mixing with coloring compositions of other colors tends to occur, resulting in fluctuations in spectral characteristics.
[0008] Furthermore, according to the present inventors' investigations, it was found that even in the colored composition described in Patent Document 1, there is still room for further improvement in terms of color mixing with other colors.
[0009] Therefore, an object of the present invention is to provide a colored composition capable of forming a cured film in which mixing with other colors is suppressed. Another object of the present invention is to provide a cured film, a structure, a color filter, and a display device using the above-mentioned colored composition. [Means for solving the problem]
[0010] According to the present inventors' investigations, it was found that the above object can be achieved by using a coloring composition described below, and thus the present invention was completed. <1> A coloring composition comprising a colorant, a resin, a polymerizable compound, a photopolymerization initiator, and a compound having a cyclic ether group, The colorants include Color Index Pigment Green 7 and a yellow colorant; The coloring composition has an absorbance of 0.2 at a wavelength of 540 nm or more and 610 nm or less, when the absorbance of the coloring composition is 1 at a wavelength of 450 nm or more. Colored composition. <2> The compound having a cyclic ether group includes a compound having a weight average molecular weight of 1500 or more. <1> The coloring composition according to claim 1. <3> The compound having a cyclic ether group includes a compound having a repeating unit having a cyclic ether group. <1> or <2> The coloring composition according to claim 1. <4> The repeating unit having a cyclic ether group is a repeating unit having a polyether structure, a repeating unit having a novolak structure, or a repeating unit having a (meth)acrylic structure. <3> The coloring composition according to claim 1. <5> The repeating unit having a cyclic ether group contains an aliphatic hydrocarbon ring in the main chain structure. <3> or <4> The coloring composition according to claim 1. <6> The compound having a cyclic ether group includes a compound having an epoxy group and a compound having an oxetanyl group. <1> ~ <5> 13. The coloring composition according to claim 12, <7> The content of the compound having a cyclic ether group in the total solid content of the coloring composition is 1% by mass or more. <1> ~ <6> 13. The coloring composition according to claim 12, <8> The coloring composition has wavelengths in the wavelength range of 470 nm or more and 520 nm or less, and in the wavelength range of 540 nm or more and 610 nm or less, at which the absorbance of the coloring composition is 0.2 when the absorbance of the coloring composition is 1 for light having a wavelength of 450 nm. <1> ~ <7> 13. The coloring composition according to claim 12, <9> Contains 25 to 600 parts by mass of a yellow colorant per 100 parts by mass of Color Index Pigment Green 7; <1> ~ <8> 13. The coloring composition according to claim 12, <10> The yellow colorant includes at least one selected from Color Index Pigment Yellow 129, Color Index Pigment Yellow 139, Color Index Pigment Yellow 150, and Color Index Pigment Yellow 185; <1> ~ <9> 13. The coloring composition according to claim 12, <11> The colorant further comprises at least one selected from Color Index Pigment Green 36, Color Index Pigment Green 58 and Color Index Pigment Green 59; <1> ~ <10> 13. The coloring composition according to claim 12, <12> The content of the colorant in the total solid content of the coloring composition is 15% by mass or more. <1> ~ <11> 13. The coloring composition according to claim 12, <13> It is used to form a hardened film at a temperature of 150°C or less throughout the entire process. <1> ~ <12> 13. The coloring composition according to claim 12, <14> <1> ~ <13> 2. A cured film obtained by using the colored composition according to claim 1. <15> A structure having a green pixel, a red pixel and a blue pixel, the green pixel being <1> ~ <13> A structure obtained by using the coloring composition according to any one of the above items. <16> <14> A color filter having the cured film according to claim 1. <17> <14> A display device comprising the cured film according to claim 1. Effect of the Invention
[0011] According to the present invention, it is possible to provide a colored composition capable of forming a cured film in which mixing with other colors is suppressed. In addition, the present invention can provide a cured film, a structure, a color filter, and a display device using the colored composition. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS
[0012] The present invention will be described in detail below. In the description of groups (atomic groups) in this specification, the notation without indicating whether substituted or unsubstituted includes groups (atomic groups) that have no substituents as well as groups (atomic groups) that have a substituent. For example, "alkyl group" includes not only alkyl groups that have no substituents (unsubstituted alkyl groups) but also alkyl groups that have a substituent (substituted alkyl groups). In this specification, unless otherwise specified, "exposure" includes not only exposure using light but also drawing using particle beams such as electron beams and ion beams. In addition, examples of light used for exposure generally include actinic rays or radiation such as the bright line spectrum of a mercury lamp, far ultraviolet light represented by an excimer laser, extreme ultraviolet light (EUV light), X-rays, and electron beams. In this specification, a numerical range expressed using "to" means a range that includes the numerical values before and after "to" as the lower and upper limits. In this specification, the total solid content refers to the total mass of all components of the composition excluding the solvent. In this specification, "(meth)acrylate" refers to both or either of acrylate and methacrylate, "(meth)acrylic" refers to both or either of acrylic and methacrylic, "(meth)allyl" refers to both or either of allyl and methallyl, and "(meth)acryloyl" refers to both or either of acryloyl and methacryloyl. In this specification, the term "process" refers not only to an independent process, but also to a process that cannot be clearly distinguished from other processes, as long as the intended effect of the process is achieved. In this specification, the weight average molecular weight (Mw) and the number average molecular weight (Mn) are defined as values calculated in terms of polystyrene measured by gel permeation chromatography (GPC).
[0013] <Coloring composition> The coloring composition of the present invention is a coloring composition comprising a colorant, a resin, a polymerizable compound, a photopolymerization initiator, and a compound having a cyclic ether group, The colorants include Color Index Pigment Green 7 and a yellow colorant; The coloring composition is characterized in that, when the absorbance of light having a wavelength of 450 nm is taken as 1, the wavelength at which the absorbance becomes 0.2 is in the wavelength range of 540 nm or more and 610 nm or less.
[0014] According to the coloring composition of the present invention, a cured film in which color mixing with other colors is suppressed can be formed. In particular, even when the cured film is formed at a low temperature of 150° C. or less (preferably 120° C. or less, more preferably 100° C. or less), a cured film in which color mixing with other colors is suppressed can be formed.
[0015] Although the detailed reason why such an effect is obtained is unclear, it is presumed that by using a coloring composition having the above-mentioned specific spectral characteristics and containing Color Index Pigment Green 7 and a yellow coloring agent as a coloring agent, the interaction between the pigments makes it easier to transmit heat, and when the coloring composition is heated and cured, the curing of the coloring composition proceeds quickly, and as a result, a cured film that is sufficiently cured can be formed even by heating at a relatively low temperature. Therefore, it is presumed that the coloring composition of the present invention can form a cured film in which mixing with other colors is suppressed.
[0016] In addition, by satisfying the above-mentioned specific absorbance characteristics, the coloring composition can form a cured film suitable for a green pixel having spectral characteristics excellent in color separation from other colors such as red and blue.
[0017] The absorbance Aλ at a certain wavelength λ is defined by the following formula (Ab1). Aλ=-log(Tλ / 100) (Ab1) Aλ is the absorbance at wavelength λ, and Tλ is the transmittance (%) at wavelength λ.
[0018] In the present invention, the absorbance value may be a value measured in the state of a solution, or may be a value of a cured film formed using the coloring composition. When measuring the absorbance in the state of a film, the coloring composition is applied onto a glass substrate by a method such as spin coating, dried at 100°C for 2 minutes using a hot plate, and then measured with an ultra-high pressure mercury lamp at a light illuminance of 20 mW / cm. 2 , exposure dose 100mJ / cm 2 It is preferable to measure the absorbance using a film (cured film) having a thickness of 1.5 μm obtained by exposing the film under the above conditions, heating the film on a hot plate at 100° C. for 20 minutes, and allowing the film to cool to room temperature. The absorbance can be measured using a conventionally known spectrophotometer.
[0019] In the coloring composition of the present invention, when the absorbance of light having a wavelength of 450 nm is taken as 1, the wavelength at which the absorbance is 0.2 exists in the wavelength range of 540 nm or more and 610 nm or less. In the coloring composition of the present invention, when the absorbance of light having a wavelength of 450 nm is taken as 1, the wavelength at which the absorbance is 0.2 exists preferably in each of the wavelength ranges of 470 nm or more and 520 nm or less and the wavelength range of 540 nm or more and 610 nm or less.
[0020] The wavelength on the short wavelength side where the absorbance is 0.2 (hereinafter also referred to as wavelength λ1) is preferably in the wavelength range of 470 nm to 515 nm from the viewpoint of color separation, more preferably in the wavelength range of 475 nm to 500 nm, even more preferably in the wavelength range of 480 nm to 495 nm, and particularly preferably in the wavelength range of 480 nm to 490 nm. Also, the wavelength on the long wavelength side where the absorbance is 0.2 (hereinafter also referred to as wavelength λ2) is preferably in the wavelength range of 550 nm to 600 nm from the viewpoint of color separation, more preferably in the wavelength range of 555 nm to 600 nm, and even more preferably in the wavelength range of 570 nm to 590 nm.
[0021] From the viewpoint of color separation, the wavelength difference (λ2-λ1) between the wavelength λ2 and the wavelength λ1 is preferably 40 to 120 nm, more preferably 60 to 110 nm, and even more preferably 80 to 100 nm.
[0022] The coloring composition of the present invention preferably has a minimum absorbance value in the wavelength range of 495 nm to less than 550 nm among the absorbance values for light with wavelengths of 400 to 700 nm, more preferably has a minimum absorbance value in the wavelength range of 505 nm to 540 nm, and further preferably has a minimum absorbance value in the wavelength range of 515 nm to 530 nm. Hereinafter, the wavelength showing the minimum absorbance value among the absorbance values for light with wavelengths of 400 to 700 nm is also referred to as the wavelength λmin.
[0023] From the viewpoint of color separation, the wavelength difference between the wavelength λmin and the wavelength λ1 (wavelength λmin-λ1) is preferably 15 to 60 nm, more preferably 15 to 55 nm, and even more preferably 30 to 50 nm. Also, the wavelength difference between the wavelength λ2 and the wavelength λmin (wavelength λ2-wavelength λmin) is preferably 20 to 80 nm, more preferably 30 to 70 nm, and even more preferably 40 to 60 nm.
[0024] When the coloring composition of the present invention forms a cured film having a thickness of 0.6 to 3.0 μm, the maximum transmittance in the thickness direction of the film for light having a wavelength of 495 nm or more and less than 550 nm is preferably 65% or more, more preferably 70% or more, and even more preferably 75% or more. Furthermore, the average transmittance of the film to light having a wavelength of 495 nm or more and less than 550 nm is preferably 60% or more, more preferably 65% or more, and even more preferably 70% or more. Furthermore, the transmittance of the above film to light with a wavelength of 450 nm is preferably 10% or less, more preferably 5% or less, and even more preferably 2% or less. Furthermore, the average transmittance of the film for light having a wavelength of 400 nm or more and 450 nm or less is preferably 10% or less, more preferably 5% or less, and even more preferably 1% or less. Furthermore, the average transmittance of the film for light with a wavelength of 540 nm or more and 610 nm or less is preferably 60% or less, more preferably 50% or less, and even more preferably 40% or less.
[0025] In order to adjust the values of the absorbance and the like of the coloring composition to the above-mentioned range, the content of Color Index Pigment Green 7 in the total solid content of the coloring composition, the type and content of the yellow colorant, the ratio of Color Index Pigment Green 7 and the yellow colorant in the colorant, the content of the colorant in the coloring composition, etc. can be appropriately adjusted by changing the amount.
[0026] The colored composition of the present invention can be preferably used as a colored composition for forming pixels of a color filter, and more preferably used as a colored composition for forming green pixels of a color filter.
[0027] The coloring composition of the present invention can be preferably used as a coloring composition for a display device. More specifically, it can be preferably used as a coloring composition for forming pixels of a color filter for a display device, and more preferably used as a coloring composition for forming green pixels of a color filter for a display device. The type of the display device is not particularly limited, and examples thereof include display devices having an organic semiconductor element as a light source, such as an organic electroluminescence display device.
[0028] The coloring composition of the present invention can also be used as a coloring composition for a solid-state imaging device. More specifically, it can be preferably used as a coloring composition for forming pixels of a color filter for a solid-state imaging device, and more preferably used as a coloring composition for forming green pixels of a color filter for a solid-state imaging device.
[0029] It is also preferable that the coloring composition of the present invention is used to form a cured film at a temperature of 150° C. or less (preferably, a temperature of 120° C. or less) throughout all steps. In this specification, forming a cured film at a temperature of 150° C. or less throughout all steps means that all steps of forming a cured film using the coloring composition are performed at a temperature of 150° C. or less.
[0030] The thickness of the cured film and pixels formed by the colored composition of the present invention is preferably 0.5 to 3.0 μm. The lower limit is preferably 0.8 μm or more, more preferably 1.0 μm or more, and even more preferably 1.1 μm or more. The upper limit is preferably 2.5 μm or less, more preferably 2.0 μm or less, and even more preferably 1.8 μm or less.
[0031] The line width (pattern size) of the pixel formed by the coloring composition of the present invention is preferably 2.0 to 10.0 μm. The upper limit is preferably 7.5 μm or less, more preferably 5.0 μm or less, and even more preferably 4.0 μm or less. The lower limit is preferably 2.25 μm or more, more preferably 2.5 μm or more, and even more preferably 2.75 μm or more.
[0032] The colored composition of the present invention will be described in detail below.
[0033] <<Coloring agent>> The coloring composition of the present invention contains a colorant. The colorant used in the coloring composition of the present invention includes Color Index (CI) Pigment Green 7 and a yellow colorant. CI Pigment Green 7 is a green colorant.
[0034] The average primary particle diameter of CI Pigment Green 7 is preferably 30 to 200 nm, more preferably 30 to 150 nm, and even more preferably 30 to 100 nm. In this specification, the primary particle diameter of a pigment such as CI Pigment Green 7 can be obtained by observing the primary particles of the pigment with a transmission electron microscope and taking an image. Specifically, the projected area of the primary particles of the pigment is obtained, and the corresponding circle equivalent diameter is calculated as the primary particle diameter of the pigment. In this specification, the average primary particle diameter is the arithmetic mean value of the primary particle diameters of 400 primary particles of the pigment. In addition, the primary particles of the pigment refer to independent particles without aggregation.
[0035] The yellow colorant may be either a pigment or a dye, but is preferably a pigment. The average primary particle size of the pigment is preferably 30 to 200 nm, more preferably 30 to 150 nm, and even more preferably 30 to 100 nm.
[0036] Specific examples of yellow colorants include CI Pigment Yellow 1, 2, 3, 4, 5, 6, 10, 11, 12, 13, 14, 15, 16, 17, 18, 20, 24, 31, 32, 34, 35, 35:1, 36, 36:1, 37, 37:1, 40, 42, 43, 53, 55, 60, 61, 62, 63, 65, 73, 74, 77, 81, 83, 86, 93, 94, 95, 97, 98, 100, 101, 104, 106, 108, 109, 110, 113, 114, 115, 116, 117, 118, 119, 120, 123, 125, 126, 127, 128, 129, 137, 138, 139, 147, 148, 150, 151, 152, 153, 154, 155, 156, 161, 162, 164, 166, 167, 168, 169, 170, 171, 172, 173, 174, 175, 176, 177, 179, 180, 181, 182, 185, 187, 188, 193, 194, 199, 213, 214, 215, 228, 231, 232, 233, 234, 235, 236, etc.
[0037] Furthermore, as the yellow colorant, an azobarbituric acid nickel complex having the following structure can also be used. [ka]
[0038] In addition, as the yellow colorant, compounds described in JP-A-2017-201003, compounds described in JP-A-2017-197719, compounds described in paragraphs 0011 to 0062 and 0137 to 0276 of JP-A-2017-171912, compounds described in paragraphs 0010 to 0062 and 0138 to 0295 of JP-A-2017-171913, compounds described in paragraphs 0011 to 0062 and 0139 to 0190 of JP-A-2017-171914, compounds described in paragraphs 0010 to 0065 and 0142 to 0222 of JP-A-2017-171915, , quinophthalone compounds described in paragraphs 0011 to 0034 of JP 2013-054339 A, quinophthalone compounds described in paragraphs 0013 to 0058 of JP 2014-026228 A, isoindoline compounds described in JP 2018-062644 A, quinophthalone compounds described in JP 2018-203798 A, quinophthalone compounds described in JP 2018-062578 A, quinophthalone compounds described in Japanese Patent No. 6432076, quinophthalone compounds described in JP 2018-155881 A, JP 2018-1117 57, quinophthalone compounds described in JP 2018-040835 A, quinophthalone compounds described in JP 2017-197640 A, quinophthalone compounds described in JP 2016-145282 A, quinophthalone compounds described in JP 2014-085565 A, quinophthalone compounds described in JP 2014-021139 A, quinophthalone compounds described in JP 2013-209614 A, quinophthalone compounds described in JP 2013-209435 A, quinophthalone compounds described in JP 2013-181015 A Quinophthalone compounds, quinophthalone compounds described in JP 2013-061622 A, quinophthalone compounds described in JP 2013-032486 A, quinophthalone compounds described in JP 2012-226110 A, quinophthalone compounds described in JP 2008-074987 A, quinophthalone compounds described in JP 2008-081565 A, quinophthalone compounds described in JP 2008-074986 A, quinophthalone compounds described in JP 2008-074985 A, quinophthalone compounds described in JP 2008-050420 A,Quinophthalone compounds described in JP 2008-031281 A, JP 48-032765 A, JP 2019-008014 A, JP 6607427 A, methine dyes described in JP 2019-073695 A, methine dyes described in JP 2019-073696 A, methine dyes described in JP 2019-073697 A, JP 201 Methine dyes described in JP 9-073698 A, compounds described in Korean Patent Publication No. 10-2014-0034963 A, compounds described in JP 2017-095706 A, compounds described in Taiwan Patent Application Publication No. 201920495 A, compounds described in Japanese Patent No. 6607427 A, quinophthalone dimers described in JP 2020-033521 A, and isoindoline compounds described in JP 2020-023652 A can also be used. In addition, oligomers of these compounds are also preferably used from the viewpoint of improving color value. As a yellow colorant, a compound represented by the following formula (QP1) and a compound represented by the following formula (QP2) can also be used. , [ka]
[0039] In formula (QP1), X 1 ~X 16 each independently represents a hydrogen atom or a halogen atom; Z 1 represents an alkylene group having 1 to 3 carbon atoms. Specific examples of the compound represented by formula (QP1) include the compounds described in paragraph 0016 of Japanese Patent No. 6443711. [ka]
[0040] In formula (QP2), Y 1 ~Y 3each independently represents a halogen atom. n and m represent integers of 0 to 6, and p represents an integer of 0 to 5. (n+m) is 1 or more. Specific examples of the compound represented by formula (QP2) include the compounds described in paragraphs 0047 to 0048 of Japanese Patent No. 6432077.
[0041] The yellow colorant is preferably at least one selected from CI Pigment Yellow 129, CI Pigment Yellow 138, CI Pigment Yellow 139, CI Pigment Yellow 150, and CI Pigment Yellow 185, more preferably at least one selected from CI Pigment Yellow 129, CI Pigment Yellow 139, CI Pigment Yellow 150, and CI Pigment Yellow 185, and from the viewpoint of light fastness, further preferably CI Pigment Yellow 150. It is also preferable to use CI Pigment Yellow 185 as the yellow colorant from the viewpoint of color separation from other colors.
[0042] The yellow colorant may be used alone or in combination of two or more. When only one yellow colorant is used, the storage stability of the colored composition can be improved. When two or more yellow colorants are used in combination, the color can be easily adjusted.
[0043] Preferred aspects of the yellow colorant used in the present invention include the following aspects Y1, Y2, and Y3. From the viewpoints of suppressing color mixing and storage stability, the following aspect Y1 is preferred. Also, from the viewpoint of color separation from other colors, the following aspect Y3 is preferred.
[0044] Embodiment Y1: An embodiment in which the yellow colorant is substantially only CI Pigment Yellow 150. Embodiment Y2: An embodiment in which the yellow colorant includes CI Pigment Yellow 150 and a yellow colorant other than CI Pigment Yellow 150. Embodiment Y3: An embodiment in which the yellow colorant is substantially only CI Pigment Yellow 185.
[0045] In addition, when the yellow colorant is substantially only CI Pigment Yellow 150, it means that the content of CI Pigment Yellow 150 in the yellow colorant is 99.5% by mass or more, and preferably 99.9% by mass or more. In addition, when the yellow colorant is substantially only CI Pigment Yellow 185, it means that the content of CI Pigment Yellow 185 in the yellow colorant is 99.5% by mass or more, and preferably 99.9% by mass or more.
[0046] In the yellow colorant of Aspect Y2 above, examples of the yellow colorant other than CI Pigment Yellow 150 include CI Pigment Yellow 129, Pigment Yellow 138, CI Pigment Yellow 139, and CI Pigment Yellow 185. From the viewpoints of color separation properties and light fastness, at least one selected from CI Pigment Yellow 129, CI Pigment Yellow 139, and CI Pigment Yellow 185 is preferable.
[0047] In the yellow colorant of Aspect Y2, the content of the yellow colorant other than CI Pigment Yellow 150 is preferably 0.1 to 200 parts by mass, more preferably 1 to 50 parts by mass, and even more preferably 10 to 125 parts by mass, relative to 100 parts by mass of CI Pigment Yellow 150.
[0048] The colored composition of the present invention may further contain a green colorant other than CI Pigment Green 7 (hereinafter also referred to as other green colorant).
[0049] Other green colorants include CI Pigment Green 10, 36, 37, 58, 59, 62, 63, 64, 65, and 66. Other green colorants include halogenated zinc phthalocyanine pigments having an average of 10 to 14 halogen atoms, an average of 8 to 12 bromine atoms, and an average of 2 to 5 chlorine atoms in one molecule. Specific examples include compounds described in International Publication No. 2015 / 118720. Other green colorants include compounds described in Chinese Patent Application No. 106909027, phthalocyanine compounds having phosphoric acid esters as ligands described in International Publication No. 2012 / 102395, phthalocyanine compounds described in JP-A-2019-008014, phthalocyanine compounds described in JP-A-2018-180023, and compounds described in JP-A-2019-038958. In addition, as another green colorant, the core-shell type dye described in JP-A-2020-076995 can also be used.
[0050] The other green colorant is preferably at least one selected from CI Pigment Green 36, CI Pigment Green 58, and CI Pigment Green 59, and more preferably CI Pigment Green 36.
[0051] Preferred embodiments of the green colorant used in the present invention include the following embodiments G1 and G2, and from the viewpoint of color separation, the following embodiment G1 is preferred.
[0052] Embodiment G1: An embodiment in which the green colorant is substantially only CI Pigment Green 7. Embodiment G2: An embodiment in which the green colorant includes CI Pigment Green 7 and a green colorant other than CI Pigment Green 7.
[0053] Incidentally, when the green colorant is substantially only CI Pigment Green 7, this means that the content of CI Pigment Green 7 in the green colorant is 99.5% by mass or more, and preferably 99.9% by mass or more.
[0054] In the green colorant of the above-mentioned embodiment G2, the green colorant other than CI Pigment Green 7 is preferably at least one selected from CI Pigment Green 36, CI Pigment Green 58, and CI Pigment Green 59, and more preferably CI Pigment Green 36. The other green colorant is preferably only CI Pigment Green 36 from the viewpoint of fastness and stability. That is, the green colorant of the above-mentioned embodiment G2 is preferably substantially composed of CI Pigment Green 7 and CI Pigment Green 36. Note that when the green colorant is substantially composed of CI Pigment Green 7 and CI Pigment Green 36, the total content of CI Pigment Green 7 and CI Pigment Green 36 in the green colorant is 99.5% by mass or more, and preferably 99.9% by mass or more.
[0055] It is also preferred that the green colorant of the above-mentioned embodiment G2 is substantially composed of CI Pigment Green 7 and CI Pigment Green 59. According to this embodiment, the peak transmittance is increased, and a cured film having higher brightness can be formed. Note that, when the green colorant is substantially composed of CI Pigment Green 7 and CI Pigment Green 59, the total content of CI Pigment Green 7 and CI Pigment Green 59 in the green colorant is 99.5% by mass or more, and preferably 99.9% by mass or more.
[0056] In the green colorant of the above-mentioned Aspect G2, the content of the green colorant other than CI Pigment Green 7 is preferably 0.1 to 5000 parts by mass, more preferably 0.1 to 3000 parts by mass, even more preferably 0.1 to 2000 parts by mass, still more preferably 0.1 to 500 parts by mass, even more preferably 10 to 300 parts by mass, and particularly preferably 25 to 200 parts by mass, relative to 100 parts by mass of CI Pigment Green 7. In addition, when CI Pigment Green 36 is used as the green colorant other than CI Pigment Green 7, the content of CI Pigment Green 36 is preferably 0.1 to 500 parts by mass, more preferably 10 to 300 parts by mass, and even more preferably 25 to 200 parts by mass, relative to 100 parts by mass of CI Pigment Green 7. Furthermore, when CI Pigment Green 59 is used as a green colorant other than CI Pigment Green 7, the content of CI Pigment Green 59 is preferably 0.1 to 5000 parts by mass relative to 100 parts by mass of CI Pigment Green 7. The lower limit is more preferably 10 parts by mass or more, and even more preferably 25 parts by mass or more. The upper limit is more preferably 3000 parts by mass or less, and even more preferably 1500 parts by mass or less.
[0057] The coloring composition of the present invention may contain a colorant other than the green colorant and the yellow colorant (hereinafter, also referred to as other colorants). The content of the other colorant in the colorant is preferably 30% by mass or less, more preferably 25% by mass or less, and even more preferably 10% by mass or less, and from the viewpoint of color separation, it is particularly preferable that the colorant does not substantially contain other colorants. Note that, when the colorant used in the coloring composition of the present invention does not substantially contain other colorants, the content of the other colorant in the colorant is less than 0.5% by mass, preferably less than 0.1% by mass, and more preferably does not contain other colorants.
[0058] The other colorants include chromatic colorants such as red colorants, blue colorants, purple colorants, and orange colorants. The other colorants may be pigments or dyes. Pigments and dyes may be used in combination. Examples of pigments include the following.
[0059] CI Pigment Orange 2, 5, 13, 16, 17:1, 31, 34, 36, 38, 43, 46, 48, 49, 51, 52, 55, 59, 60, 61, 62, 64, 71, 73, etc. (orange pigments) CI Pigment Red 1, 2, 3, 4, 5, 6, 7, 9, 10, 14, 17, 22, 23, 31, 38, 41, 48:1, 48:2, 48:3, 48:4, 49, 49:1, 49:2, 52:1, 52:2, 53:1, 57:1, 60:1, 63:1, 66, 67, 81:1, 81:2, 81:3, 83, 88, 90, 105, 112, 119, 122, 123, 144, 146, 149, 150 ,155,166,168,169,170,171,172,175,176,177,178,179,184,185,187,188,190,200,202,206,207,208,209,210,216,220,224,226,242,246,254,255,264,269,270,272,279,291,294,295,296,297 etc. (above, red pigments), CI Pigment Violet 1, 19, 23, 27, 32, 37, 42, 60, 61, etc. (above, purple pigments), CI Pigment Blue 1, 2, 15, 15:1, 15:2, 15:3, 15:4, 15:6, 16, 22, 29, 60, 64, 66, 79, 80, 87, 88, etc. (above, blue pigments).
[0060] In addition, an aluminum phthalocyanine compound having a phosphorus atom can also be used as the blue colorant. Specific examples include the compounds described in paragraphs 0022 to 0030 of JP-A No. 2012-247591 and paragraph 0047 of JP-A No. 2011-157478.
[0061] As red colorants, diketopyrrolopyrrole compounds having at least one bromine atom substituted in the structure described in JP 2017-201384 A, diketopyrrolopyrrole compounds described in paragraphs 0016 to 0022 of Japanese Patent No. 6248838 A, diketopyrrolopyrrole compounds described in WO 2012 / 102399 A, diketopyrrolopyrrole compounds described in WO 2012 / 117965 A, naphthol azo compounds described in JP 2012-229344 A, Red colorants described in JP 6516119 A, red colorants described in JP 6525101 A, brominated diketopyrrolopyrrole compounds described in paragraph number 0229 of JP 2020-090632 A, anthraquinone compounds described in Korean Patent Publication No. 10-2019-0140741 A, anthraquinone compounds described in Korean Patent Publication No. 10-2019-0140744 A, perylene compounds described in JP 2020-079396 A, etc. can also be used. In addition, as a red colorant, a compound having a structure in which an aromatic ring group in which a group in which an oxygen atom, a sulfur atom or a nitrogen atom is bonded to an aromatic ring is bonded to a diketopyrrolopyrrole skeleton can also be used.
[0062] In addition, as another colorant, the phthalocyanine compounds described in WO 2020 / 174991 can also be used.
[0063] The dye is not particularly limited, and known dyes can be used, such as pyrazole azo dyes, anilino azo dyes, triarylmethane dyes, anthraquinone dyes, anthrapyridone dyes, benzylidene dyes, oxonol dyes, pyrazolotriazole azo dyes, pyridone azo dyes, cyanine dyes, phenothiazine dyes, pyrrolopyrazole azomethine dyes, xanthene dyes, phthalocyanine dyes, benzopyran dyes, indigo dyes, and pyrromethene dyes. In addition, as dyes, the thiazole compounds described in JP 2012-158649 A, the azo compounds described in JP 2011-184493 A, the azo compounds described in JP 2011-145540 A, the triarylmethane dye polymers described in Korean Patent Publication No. 10-2020-0028160, and the xanthene compounds described in JP 2020-117638 A can also be preferably used.
[0064] The other colorant may be a dye multimer. The dye multimer has two or more dye structures in one molecule, and preferably has three or more dye structures. The upper limit is not particularly limited, but may be 100 or less. The multiple dye structures in one molecule may be the same dye structure or different dye structures. The weight average molecular weight (Mw) of the dye multimer is preferably 2000 to 50000. The lower limit is more preferably 3000 or more, and even more preferably 6000 or more. The upper limit is more preferably 30000 or less, and even more preferably 20000 or less. As the dye multimer, compounds described in JP2011-213925A, JP2013-041097A, JP2015-028144A, JP2015-030742A, WO2016 / 031442, etc. may also be used.
[0065] The content of the colorant in the total solid content of the coloring composition is preferably 15% by mass or more, more preferably 20% by mass or more, and even more preferably 25% by mass or more. The upper limit is preferably 60% by mass or less, more preferably 50% by mass or less, and even more preferably 40% by mass or less.
[0066] The content of CI Pigment Green 7 in the colorant contained in the coloring composition of the present invention is preferably 1 to 80 mass%, more preferably 3 to 80 mass%, even more preferably 5 to 80 mass%, still more preferably 15 to 65 mass%, and particularly preferably 25 to 50 mass%, from the viewpoint of achieving both brightness and color separation. Furthermore, the content of CI Pigment Green 7 in the total solid content of the colored composition is preferably from 1 to 50 mass %, more preferably from 5 to 40 mass %, and even more preferably from 10 to 30 mass %.
[0067] The content of the yellow colorant in the colorant contained in the colored composition of the present invention is preferably from 5 to 85% by mass, more preferably from 15 to 75% by mass, and even more preferably from 30 to 65% by mass. Furthermore, the content of the yellow colorant in the total solid content of the colored composition is preferably from 1 to 50 mass %, more preferably from 5 to 40 mass %, and even more preferably from 10 to 30 mass %. The content of the yellow colorant is preferably 25 to 2000 parts by mass, more preferably 25 to 1000 parts by mass, and even more preferably 25 to 600 parts by mass, relative to 100 parts by mass of CI Pigment Green 7. The upper limit is more preferably 450 parts by mass or less, even more preferably 300 parts by mass or less, and even more preferably 240 parts by mass or less. The lower limit is more preferably 50 parts by mass or more, and even more preferably 100 parts by mass or more. When the ratio of CI Pigment Green 7 to the yellow colorant is within the above range, better storage stability is likely to be obtained.
[0068] The content of CI Pigment Yellow 150 in the colorant contained in the coloring composition of the present invention is preferably 0.1 to 85 mass%, more preferably 10 to 75 mass%, and even more preferably 20 to 65 mass%. The content of CI Pigment Yellow 150 in the total solid content of the coloring composition is preferably 1 to 50 mass%, more preferably 5 to 40 mass%, and even more preferably 10 to 30 mass%. The content of CI Pigment Yellow 150 is preferably 25 to 2000 mass parts, more preferably 25 to 1000 mass parts, and even more preferably 25 to 600 mass parts, relative to 100 mass parts of CI Pigment Green 7. The upper limit is more preferably 450 mass parts or less, more preferably 300 mass parts or less, and even more preferably 240 mass parts or less. The lower limit is more preferably 50 mass parts or more, and even more preferably 100 mass parts or more. If the ratio of CI Pigment Green 7 to CI Pigment Yellow 150 is within the above range, better storage stability is likely to be obtained.
[0069] In addition, when CI Pigment Yellow 185 is used as the yellow colorant, the content of CI Pigment Yellow 185 in the colorant contained in the coloring composition of the present invention is preferably 0.1 to 85 mass%, more preferably 10 to 75 mass%, and even more preferably 20 to 65 mass%. In addition, the content of CI Pigment Yellow 185 in the total solid content of the coloring composition is preferably 1 to 50 mass%, more preferably 5 to 40 mass%, and even more preferably 10 to 30 mass%. In addition, the content of CI Pigment Yellow 185 is preferably 25 to 2000 mass parts, more preferably 25 to 1000 mass parts, and even more preferably 25 to 600 mass parts, relative to 100 mass parts of CI Pigment Green 7. The upper limit is more preferably 450 mass parts or less, more preferably 300 mass parts or less, and even more preferably 240 mass parts or less. The lower limit is more preferably 50 mass parts or more, and even more preferably 100 mass parts or more. If the ratio of CI Pigment Green 7 to CI Pigment Yellow 185 is within the above range, better storage stability is likely to be obtained.
[0070] The total content of CI Pigment Green 7 and the yellow colorant in the total amount of the colorants contained in the coloring composition of the present invention is preferably 30 to 100 mass%, more preferably 40 to 100 mass%, even more preferably 50 to 100 mass%, even more preferably 60 to 100 mass%, even more preferably 75 to 100 mass%, and particularly preferably 90 to 100 mass%.
[0071] In addition, as a preferred embodiment, the total content of CI Pigment Green 7 and CI Pigment Yellow 150 in the total amount of the colorant contained in the coloring composition of the present invention is preferably 30 to 100 mass%, more preferably 40 to 100 mass%, even more preferably 50 to 100 mass%, even more preferably 60 to 100 mass%, even more preferably 75 to 100 mass%, and particularly preferably 90 to 100 mass%.
[0072] In addition, as another preferred embodiment, the total content of CI Pigment Green 7 and CI Pigment Yellow 185 in the total amount of the colorant contained in the coloring composition of the present invention is preferably 30 to 100 mass%, more preferably 40 to 100 mass%, even more preferably 50 to 100 mass%, even more preferably 60 to 100 mass%, even more preferably 75 to 100 mass%, and particularly preferably 90 to 100 mass%.
[0073] In addition, when the coloring composition of the present invention further contains a green colorant other than CI Pigment Green 7, the total content of CI Pigment Green 7, the yellow colorant, and the green colorant other than CI Pigment Green 7 in the total amount of the colorants contained in the coloring composition of the present invention is preferably 50 to 100 mass%, more preferably 75 to 100 mass%, and even more preferably 90 to 100 mass%.
[0074] <<Resin>> The coloring composition of the present invention contains a resin. The resin is blended, for example, for dispersing a pigment (such as CI Pigment Green 7) in the coloring composition or for use as a binder. A resin used mainly for dispersing a pigment in a coloring composition is also called a dispersant. The resin as a dispersant can be used when preparing a pigment dispersion. However, such uses of the resin are only examples, and the resin can also be used for purposes other than such uses. In this specification, a resin having a cyclic ether group is a component that corresponds to a compound having a cyclic ether group.
[0075] The weight average molecular weight (Mw) of the resin is preferably 2000 to 2000000. The upper limit is more preferably 1000000 or less, and even more preferably 500000 or less. The lower limit is more preferably 3000 or more, more preferably 4000 or more, and even more preferably 5000 or more.
[0076] Examples of the resin include (meth)acrylic resins, (meth)acrylamide resins, ene-thiol resins, polycarbonate resins, polyether resins, polyarylate resins, polysulfone resins, polyethersulfone resins, polyphenylene resins, polyarylene ether phosphine oxide resins, polyimide resins, polyamideimide resins, polyolefin resins, cyclic olefin resins, polyester resins, styrene resins, and siloxane resins. In addition, the resins described in paragraphs 0041 to 0060 of JP 2017-206689 A, the resins described in paragraphs 0022 to 0071 of JP 2018-010856 A, the resins described in JP 2017-057265 A, the resins described in JP 2017-032685 A, the resins described in JP 2017-075248 A, the resins described in JP 2017-066240 A, and the resins described in JP 2020-1 Resins described in JP 2020-111656 A, resins described in JP 2020-139021 A, alkali-soluble resins having a urea functional group described in JP 2020-139021 A, and resins containing a structural unit having a ring structure in the main chain and a structural unit having a biphenyl group in the side chain described in JP 2017-138503 A can be used.
[0077] The resin used in the present invention may have an acid group. Examples of the acid group include a carboxy group, a phosphoric acid group, a sulfo group, and a phenolic hydroxy group. These acid groups may be of one type or of two or more types. The resin having an acid group preferably contains a repeating unit having an acid group in a side chain. The resin having an acid group may also be used as an alkali-soluble resin or a dispersant.
[0078] The acid value of the resin having an acid group is preferably 30 to 500 mgKOH / g. The lower limit is more preferably 50 mgKOH / g or more, and even more preferably 70 mgKOH / g or more. The upper limit is more preferably 400 mgKOH / g or less, even more preferably 200 mgKOH / g or less, particularly preferably 150 mgKOH / g or less, and most preferably 120 mgKOH / g or less.
[0079] The resin having an acid group may have a repeating unit derived from a maleimide compound. Examples of the maleimide compound include N-alkylmaleimide, N-arylmaleimide, etc. Examples of the repeating unit derived from the maleimide compound include a repeating unit represented by the formula (C-mi). [ka]
[0080] In formula (C-mi), Rmi represents an alkyl group or an aryl group. The alkyl group preferably has 1 to 20 carbon atoms. The alkyl group may be linear, branched, or cyclic. The aryl group preferably has 6 to 20 carbon atoms, more preferably 6 to 15, and even more preferably 6 to 10. Rmi is preferably an aryl group.
[0081] It is also preferable that the resin having an acid group is a resin containing a repeating unit derived from a compound represented by the following formula (ED1) and / or a compound represented by the following formula (ED2) (hereinafter, these compounds may be referred to as "ether dimers").
[0082] [ka]
[0083] In formula (ED1), R 1 and R 2 each independently represents a hydrogen atom or a hydrocarbon group having 1 to 25 carbon atoms which may have a substituent. [ka] In formula (ED2), R represents a hydrogen atom or an organic group having 1 to 30 carbon atoms. For details of formula (ED2), refer to the description in JP2010-168539A, the contents of which are incorporated herein by reference. For specific examples of ether dimers, refer to paragraph 0317 of JP2013-029760A, the contents of which are incorporated herein by reference.
[0084] An example of a resin containing a repeating unit derived from an ether dimer is a resin having the following structure: In the following structural formula, Me represents a methyl group. [ka]
[0085] The coloring composition of the present invention also preferably contains a resin having a basic group. The resin having a basic group is preferably a resin containing a repeating unit having a basic group in a side chain, more preferably a copolymer having a repeating unit having a basic group in a side chain and a repeating unit not having a basic group, and even more preferably a block copolymer having a repeating unit having a basic group in a side chain and a repeating unit not having a basic group. The resin having a basic group can also be used as a dispersant. The amine value of the resin having a basic group is preferably 5 to 300 mgKOH / g. The lower limit is more preferably 10 mgKOH / g or more, and even more preferably 20 mgKOH / g or more. The upper limit is more preferably 200 mgKOH / g or less, and even more preferably 100 mgKOH / g or less.
[0086] Commercially available resins having basic groups include DISPERBYK-161, 162, 163, 164, 166, 167, 168, 174, 182, 183, 184, 185, 2000, 2001, 2050, 2150, 2163, 2164, and BYK-LPN6919 (all manufactured by BYK-Chemie), and Solsperse 112. 00, 13240, 13650, 13940, 24000, 26000, 28000, 32000, 32500, 32550, 32600, 33000, 34750, 35100, 35200, 37500, 38500, 39000, 53095, 56000, 7100 (all manufactured by Lubrizol Japan), Efka PX 4300, 4330, 4046, 4060, 4080 (all manufactured by BASF), and the like. In addition, the resin having a basic group may be the block copolymer (B) described in paragraphs 0063 to 0112 of JP 2014-219665 A, the block copolymer A1 described in paragraphs 0046 to 0076 of JP 2018-156021 A, or the vinyl resin having a basic group described in paragraphs 0150 to 0153 of JP 2019-184763 A, the contents of which are incorporated herein by reference.
[0087] It is also preferable that the coloring composition of the present invention contains a resin having an acid group and a resin having a basic group. According to this embodiment, the storage stability of the coloring composition can be further improved. When a resin having an acid group and a resin having a basic group are used in combination, the content of the resin having a basic group is preferably 20 to 500 parts by mass, more preferably 30 to 300 parts by mass, and further preferably 50 to 200 parts by mass, relative to 100 parts by mass of the resin having an acid group.
[0088] The resin used in the present invention may have a polymerizable group. Examples of the polymerizable group include ethylenically unsaturated bond-containing groups such as vinyl, (meth)allyl, and (meth)acryloyl groups. Commercially available resins having a polymerizable group include Dianale NR series (manufactured by Mitsubishi Rayon Co., Ltd.), Photomer 6173 (carboxyl group-containing polyurethane acrylate oligomer, manufactured by Diamond Shamrock Co., Ltd.), Viscoat R-264, KS Resist 106 (all manufactured by Osaka Organic Chemical Industry Co., Ltd.), Cyclomer P series (e.g., ACA230AA), Plaxel CF200 series (all manufactured by Daicel Corporation), Ebecryl 3800 (manufactured by Daicel UCB Co., Ltd.), Acricur RD-F8 (manufactured by Nippon Shokubai Co., Ltd.), and DP-1305 (manufactured by Fujifilm Fine Chemicals Co., Ltd.).
[0089] The resin used in the present invention preferably contains a resin b1 containing a repeating unit derived from a compound represented by formula (III). By using the resin b1, a cured film having excellent low-temperature curing properties and sufficiently cured even when heated at a relatively low temperature can be formed. Furthermore, a cured film having excellent spectral characteristics can be easily formed. [ka]
[0090] In the formula, R 1 represents a hydrogen atom or a methyl group, and R 21 and R 22 each independently represents an alkylene group, and n represents an integer of 0 to 15. 21 and R 22 The number of carbon atoms in the alkylene group represented by is preferably 1 to 10, more preferably 1 to 5, even more preferably 1 to 3, and particularly preferably 2 or 3. n represents an integer of 0 to 15, preferably an integer of 0 to 5, more preferably an integer of 0 to 4, and even more preferably an integer of 0 to 3.
[0091] Examples of the compound represented by formula (III) include ethylene oxide or propylene oxide modified (meth)acrylate of paracumylphenol, etc. Examples of commercially available products include Aronix M-110 (manufactured by Toagosei Co., Ltd.).
[0092] The proportion of the repeating units derived from the compound represented by formula (III) in all repeating units of resin b1 is preferably 1 to 99 mol %. The lower limit is more preferably 3 mol % or more, and even more preferably 5 mol % or more. The upper limit is more preferably 95 mol % or less, and even more preferably 90 mol % or less.
[0093] Resin b1 may further contain a repeating unit other than the repeating unit derived from the compound represented by formula (III). For example, resin b1 may contain a repeating unit derived from a (meth)acrylate, and preferably contains a repeating unit derived from an alkyl (meth)acrylate. The number of carbon atoms in the alkyl moiety of the alkyl (meth)acrylate is preferably 3 to 10, more preferably 3 to 8, and even more preferably 3 to 6. A preferred example of the alkyl (meth)acrylate is n-butyl (meth)acrylate. In addition, resin b1 preferably contains a repeating unit having an acid group.
[0094] The resin used in the present invention preferably contains a resin having a repeating unit containing a blocked isocyanate group (hereinafter, also referred to as resin BI). According to this embodiment, better low-temperature curing properties can be obtained, and a sufficiently cured film can be formed even by heating at a relatively low temperature.
[0095] The blocked isocyanate group of the resin BI is preferably a group capable of generating an isocyanate group by heat, and more preferably a group capable of generating an isocyanate group by heat at 70 to 150° C. Examples of the blocked isocyanate group include a group having a structure in which an isocyanate group is chemically protected by a blocking agent. The blocked isocyanate group is a group having a structure in which an isocyanate group is protected by a compound called a blocking agent, and is a group having a structure in which the isocyanate group does not show reactivity as an isocyanate group at room temperature (for example, 10 to 30° C.), but when heated or the like, the blocking agent is detached from the blocked isocyanate group to generate an isocyanate group.
[0096] The blocked isocyanate group in the resin BI is preferably a group capable of generating an isocyanate group by heat at 70 to 150° C. That is, the isocyanate generation temperature of the blocked isocyanate group (the elimination temperature of the blocking agent) is preferably 70 to 150° C. The lower limit of the isocyanate generation temperature is preferably 75° C. or higher, more preferably 80° C. or higher, from the viewpoint of storage stability. The upper limit of the isocyanate generation temperature is preferably 130° C. or lower, more preferably 120° C. or lower, from the viewpoint of curability.
[0097] Examples of blocking agents that protect the isocyanate group of the blocked isocyanate group include oxime compounds, lactam compounds, phenol compounds, alcohol compounds, amine compounds, active methylene compounds, pyrazole compounds, mercaptan compounds, imidazole compounds, and imide compounds. From the viewpoint of ease of the protection reaction and the deprotection reaction, oxime compounds, lactam compounds, active methylene compounds, and pyrazole compounds are preferred, oxime compounds, active methylene compounds, and pyrazole compounds are more preferred, and oxime compounds are even more preferred.
[0098] The coloring composition of the present invention may contain a resin as a dispersant. Examples of dispersants include acidic dispersants (acidic resins) and basic dispersants (basic resins). Here, the acidic dispersant (acidic resin) refers to a resin in which the amount of acid groups is greater than the amount of basic groups. As the acidic dispersant (acidic resin), a resin in which the amount of acid groups is 70 mol% or more is preferable when the total amount of the acid groups and the amount of the basic groups is 100 mol%, and a resin consisting essentially of only acid groups is more preferable. The acid group possessed by the acidic dispersant (acidic resin) is preferably a carboxy group. The acid value of the acidic dispersant (acidic resin) is preferably 10 to 105 mgKOH / g. In addition, the basic dispersant (basic resin) refers to a resin in which the amount of basic groups is greater than the amount of acid groups. As the basic dispersant (basic resin), a resin in which the amount of basic groups is greater than the amount of acid groups is preferable when the total amount of the acid groups and the amount of the basic groups is 100 mol% is preferable when the total amount of the acid groups and the amount of the basic groups is 100 mol%. The basic group possessed by the basic dispersant is preferably an amino group.
[0099] Examples of dispersants include polymer dispersants (e.g., polyamidoamines and their salts, polycarboxylic acids and their salts, high molecular weight unsaturated acid esters, modified polyurethanes, modified polyesters, modified poly(meth)acrylates, (meth)acrylic copolymers, naphthalenesulfonic acid formalin condensates), polyoxyethylene alkyl phosphates, polyoxyethylene alkylamines, alkanolamines, etc. Polymer dispersants can be further classified into linear polymers, terminal modified polymers, graft polymers, and block polymers based on their structure. Polymer dispersants act to adsorb to the particle surface of pigments and the like and prevent reaggregation. For this reason, terminal modified polymers, graft polymers, and block polymers having anchor sites to the particle surface of pigments and the like can be cited as preferred structures. In addition, dispersants described in paragraphs 0028 to 0124 of JP-A-2011-070156 and dispersants described in JP-A-2007-277514 are also preferably used.
[0100] The dispersant may be a graft copolymer. For details of the graft copolymer, see paragraphs 0131 to 0160 of JP 2012-137564 A, the contents of which are incorporated herein by reference. For the dispersant, an oligoimine copolymer containing a nitrogen atom in at least one of the main chain and the side chain may be used. For the oligoimine copolymer, see paragraphs 0102 to 0174 of JP 2012-255128 A, the contents of which are incorporated herein by reference. For the dispersant, a resin having a structure in which a plurality of polymer chains are bonded to a core part may be used. Examples of such resins include dendrimers (including star-shaped polymers). Specific examples of dendrimers include polymer compounds C-1 to C-31 described in paragraphs 0196 to 0209 of JP 2013-043962 A. In addition, the dispersant may be a polyethyleneimine having a polyester side chain as described in WO 2016 / 104803, a block copolymer as described in WO 2019 / 125940, a block polymer having an acrylamide structural unit as described in JP 2020-066687 A, or a block polymer having an acrylamide structural unit as described in JP 2020-066688 A.
[0101] Dispersants are also available as commercially available products, and specific examples thereof include the Disperbyk series (e.g., Disperbyk-111, 2001, etc.) and BYK series manufactured by BYK-Chemie, the Solsperse series (e.g., Solsperse 20000, 76500, etc.) manufactured by Nippon Lubrizol Co., Ltd., and the Ajisper series manufactured by Ajinomoto Fine-Techno Co., Ltd. In addition, the products described in paragraph number 0129 of JP 2012-137564 A and the products described in paragraph number 0235 of JP 2017-194662 A can also be used as dispersants.
[0102] The content of the resin is preferably 5 to 50% by mass based on the total solid content of the coloring composition. The upper limit is more preferably 40% by mass or less, and even more preferably 30% by mass or less. The lower limit is more preferably 10% by mass or more, and even more preferably 20% by mass or more. The coloring composition of the present invention may contain only one type of resin, or may contain two or more types of resin. When two or more types of resins are contained, the total amount thereof is preferably within the above range.
[0103] <<Polymerizable compounds>> The coloring composition of the present invention contains a polymerizable compound. Examples of the polymerizable compound include a compound having an ethylenically unsaturated bond-containing group. Examples of the ethylenically unsaturated bond-containing group include a vinyl group, a (meth)allyl group, and a (meth)acryloyl group. The polymerizable compound used in the present invention is preferably a radical polymerizable compound.
[0104] The polymerizable compound may be in any chemical form such as a monomer, a prepolymer, or an oligomer, but is preferably a monomer. The molecular weight of the polymerizable compound is preferably 100 to 3000. The upper limit is more preferably 2000 or less, and even more preferably 1500 or less. The lower limit is more preferably 150 or more, and even more preferably 250 or more.
[0105] The ethylenically unsaturated bond-containing group value (hereinafter referred to as C=C value) of the polymerizable compound is preferably 2 to 14 mmol / g from the viewpoint of the stability over time of the coloring composition. The lower limit is more preferably 3 mmol / g or more, even more preferably 4 mmol / g or more, and even more preferably 5 mmol / g or more. The upper limit is more preferably 12 mmol / g or less, even more preferably 10 mmol / g or less, and even more preferably 8 mmol / g or less. The C=C value of the polymerizable compound is a value calculated by dividing the number of ethylenically unsaturated bond-containing groups contained in one molecule of the polymerizable compound by the molecular weight of the polymerizable compound.
[0106] The polymerizable compound is preferably a compound containing 3 or more ethylenically unsaturated bond-containing groups, and more preferably a compound containing 4 or more ethylenically unsaturated bond-containing groups. According to this embodiment, the curability of the colored composition by exposure is good. From the viewpoint of the stability over time of the colored composition, the upper limit of the ethylenically unsaturated bond-containing groups is preferably 15 or less, more preferably 10 or less, and even more preferably 6 or less. In addition, the polymerizable compound is preferably a trifunctional or higher (meth)acrylate compound, more preferably a 3-15 functional (meth)acrylate compound, even more preferably a 3-10 functional (meth)acrylate compound, and particularly preferably a 3-6 functional (meth)acrylate compound.
[0107] The polymerizable compound is also preferably a compound containing an ethylenically unsaturated bond-containing group and an alkyleneoxy group. Such a polymerizable compound has high flexibility, and the ethylenically unsaturated bond-containing group is easily movable, so that the polymerizable compounds react with each other during exposure, and a cured film (pixel) having excellent adhesion to the support or the like can be formed. In addition, when a hydroxyalkylphenone compound is used as a photopolymerization initiator, it is presumed that the polymerizable compound and the photopolymerization initiator are close to each other, so that the polymerizable compound can be reacted more effectively by generating radicals in the vicinity of the polymerizable compound, and it is easy to form a cured film (pixel) in which the mixing of colors with other colors is more suppressed.
[0108] The number of alkyleneoxy groups contained in one molecule of the polymerizable compound is preferably 3 or more, and more preferably 4 or more. The upper limit is preferably 20 or less, from the viewpoint of the stability over time of the colored composition.
[0109] In addition, the SP value (Solubility Parameter) of the compound containing an ethylenically unsaturated bond-containing group and an alkyleneoxy group is preferably 9.0 to 11.0 from the viewpoint of compatibility with other components in the coloring composition. The upper limit is more preferably 10.75 or less, and even more preferably 10.5 or less. The lower limit is more preferably 9.25 or more, and even more preferably 9.5 or more. In this specification, the SP value is a calculated value based on the Fedors method.
[0110] An example of the compound having an ethylenically unsaturated bond-containing group and an alkyleneoxy group is a compound represented by the following formula (M-1). Formula (M-1) [ka] A in the formula 1 represents an ethylenically unsaturated bond-containing group, L 1 represents a single bond or a divalent linking group, R 1 represents an alkylene group, m represents an integer of 1 to 30, n represents an integer of 3 or more, L 2 represents an n-valent linking group.
[0111] A 1 Examples of the ethylenically unsaturated bond-containing group represented by the formula (I) include a vinyl group, a (meth)allyl group, and a (meth)acryloyl group, and a (meth)acryloyl group is preferred.
[0112] L 1 Examples of the divalent linking group represented by include an alkylene group, an arylene group, -O-, -CO-, -COO-, -OCO-, -NH-, and a group combining two or more of these. The number of carbon atoms in the alkylene group is preferably 1 to 30, more preferably 1 to 20, and even more preferably 1 to 15. The alkylene group may be linear, branched, or cyclic. The number of carbon atoms in the arylene group is preferably 6 to 30, more preferably 6 to 20, and even more preferably 6 to 10.
[0113] R 1The number of carbon atoms in the alkylene group represented by R is preferably 1 to 10, more preferably 1 to 5, further preferably 1 to 3, particularly preferably 2 or 3, and most preferably 2. 1 The alkylene group represented by R is preferably linear or branched, and more preferably linear. 1 Specific examples of the alkylene group represented by the formula (I) include an ethylene group and a linear or branched propylene group, with an ethylene group being preferred.
[0114] m represents an integer of 1 to 30, preferably an integer of 1 to 20, more preferably an integer of 1 to 10, and further preferably 1 to 5.
[0115] n represents an integer of 3 or more, and preferably an integer of 4 or more. The upper limit of n is preferably an integer of 15 or less, more preferably an integer of 10 or less, and even more preferably an integer of 6 or less.
[0116] L 2 Examples of the n-valent linking group represented by include an aliphatic hydrocarbon group, an aromatic hydrocarbon group, a heterocyclic group, and a group consisting of a combination thereof, and a group consisting of at least one selected from an aliphatic hydrocarbon group, an aromatic hydrocarbon group, and a heterocyclic group, and at least one selected from -O-, -CO-, -COO-, -OCO-, and -NH-. The number of carbon atoms in the aliphatic hydrocarbon group is preferably 1 to 30, more preferably 1 to 20, and even more preferably 1 to 15. The aliphatic hydrocarbon group may be linear, branched, or cyclic, and is preferably linear or branched. The number of carbon atoms in the aromatic hydrocarbon group is preferably 6 to 30, more preferably 6 to 20, and even more preferably 6 to 10. The heterocyclic group may be a non-aromatic heterocyclic group or an aromatic heterocyclic group. The heterocyclic group is preferably a 5-membered or 6-membered ring. The types of heteroatoms constituting the heterocyclic group include a nitrogen atom, an oxygen atom, and a sulfur atom. The number of heteroatoms constituting the heterocyclic group is preferably 1 to 3. The heterocyclic group may be a monocyclic ring or a condensed ring. 2 The n-valent linking group represented by the formula (I) is also preferably a group derived from a polyfunctional alcohol.
[0117] As the compound having an ethylenically unsaturated bond-containing group and an alkyleneoxy group, a compound represented by the following formula (M-2) is more preferable. Formula (M-2) [ka] R in the formula 2 represents a hydrogen atom or a methyl group, and R 1 represents an alkylene group, m represents an integer of 1 to 30, n represents an integer of 3 or more, L 2 R in formula (M-2) represents a linking group having a valence of n. 1 , L 2 , m, n are R in formula (M-1) 1 , L 2 , m, and n have the same meanings and preferred ranges.
[0118] Commercially available products of the compound having an ethylenically unsaturated bond-containing group and an alkyleneoxy group include KAYARAD T-1420(T) and RP-1040 (manufactured by Nippon Kayaku Co., Ltd.).
[0119] As the polymerizable compound, dipentaerythritol tri(meth)acrylate (commercially available product is KAYARAD D-330, manufactured by Nippon Kayaku Co., Ltd.), dipentaerythritol tetra(meth)acrylate (commercially available product is KAYARAD D-320, manufactured by Nippon Kayaku Co., Ltd.), dipentaerythritol penta(meth)acrylate (commercially available product is KAYARAD D-310, manufactured by Nippon Kayaku Co., Ltd.), dipentaerythritol hexa(meth)acrylate (commercially available products are KAYARAD DPHA, manufactured by Nippon Kayaku Co., Ltd., and NK Ester A-DPH-12E, manufactured by Shin-Nakamura Chemical Co., Ltd.), and compounds having a structure in which these (meth)acryloyl groups are bonded via ethylene glycol and / or propylene glycol residues (for example, SR454, SR499, commercially available from Sartomer Co., Ltd.) are preferred. Examples of polymerizable compounds include diglycerol EO (ethylene oxide) modified (meth)acrylate (commercially available product is M-460, manufactured by Toagosei Co., Ltd.), pentaerythritol tetraacrylate (NK Ester A-TMMT, manufactured by Shin-Nakamura Chemical Co., Ltd.), 1,6-hexanediol diacrylate (KAYARAD HDDA, manufactured by Nippon Kayaku Co., Ltd.), RP-1040 (manufactured by Nippon Kayaku Co., Ltd.), and Aronix. M-402 (manufactured by Toagosei Co., Ltd., a mixture of dipentaerythritol hexaacrylate and dipentaerythritol pentaacrylate), Aronix TO-2349 (manufactured by Toagosei Co., Ltd.), NK Oligo UA-7200 (manufactured by Shin-Nakamura Chemical Co., Ltd.), 8UH-1006, 8UH-1012 (manufactured by Taisei Fine Chemical Co., Ltd.), Light Acrylate POB-A0 (manufactured by Kyoeisha Chemical Co., Ltd.), and the like can also be used.
[0120] As the polymerizable compound, it is also preferable to use a trifunctional (meth)acrylate compound such as trimethylolpropane tri(meth)acrylate, trimethylolpropane propylene oxide modified tri(meth)acrylate, trimethylolpropane ethylene oxide modified tri(meth)acrylate, isocyanuric acid ethylene oxide modified tri(meth)acrylate, or pentaerythritol tri(meth)acrylate. Commercially available trifunctional (meth)acrylate compounds include ARONIX M-309, M-310, M-321, M-350, M-360, M-313, M-315, M-306, M-305, M-303, M-452, and M-450 (manufactured by Toagosei Co., Ltd.), NK Ester A9300, A-GLY-9E, A-GLY-20E, A-TMM-3, A-TMM-3L, A-TMM-3LM-N, A-TMPT, and TMPT (manufactured by Shin-Nakamura Chemical Co., Ltd.), KAYARAD GPO-303, TMPTA, THE-330, TPA-330, and PET-30 (manufactured by Nippon Kayaku Co., Ltd.).
[0121] As the polymerizable compound, a polymerizable compound having an acid group can also be used. By using a polymerizable compound having an acid group, the colored composition in the unexposed area is easily removed during development, and the generation of development residues can be suppressed. Examples of the acid group include a carboxy group, a sulfo group, and a phosphate group, and a carboxy group is preferred. Examples of commercially available polymerizable compounds having an acid group include ARONIX M-305, M-510, M-520, and ARONIX TO-2349 (manufactured by Toagosei Co., Ltd.). The preferred acid value of the polymerizable compound having an acid group is 0.1 to 40 mgKOH / g, and more preferably 5 to 30 mgKOH / g. If the acid value of the polymerizable compound is 0.1 mgKOH / g or more, the solubility in the developer is good, and if it is 40 mgKOH / g or less, it is advantageous in terms of production and handling.
[0122] As the polymerizable compound, a polymerizable compound having a caprolactone structure can also be used. Polymerizable compounds having a caprolactone structure are commercially available as the KAYARAD DPCA series from Nippon Kayaku Co., Ltd., and examples thereof include DPCA-20, DPCA-30, DPCA-60, and DPCA-120.
[0123] As the polymerizable compound, a polymerizable compound having a fluorene skeleton can also be used. Commercially available polymerizable compounds having a fluorene skeleton include OGSOL EA-0200 and EA-0300 (manufactured by Osaka Gas Chemicals Co., Ltd., (meth)acrylate monomers having a fluorene skeleton).
[0124] It is also preferable to use a polymerizable compound that does not substantially contain environmentally regulated substances such as toluene. Examples of commercially available products of such compounds include KAYARAD DPHA LT and KAYARAD DPEA-12 LT (manufactured by Nippon Kayaku Co., Ltd.).
[0125] As the polymerizable compound, urethane acrylates as described in JP-B-48-041708, JP-A-51-037193, JP-B-02-032293, and JP-B-02-016765, and urethane compounds having an ethylene oxide skeleton as described in JP-B-58-049860, JP-B-56-017654, JP-B-62-039417, and JP-B-62-039418 are also suitable. In addition, it is also preferable to use polymerizable compounds having an amino structure or a sulfide structure in the molecule as described in JP-A-63-277653, JP-A-63-260909, and JP-A-01-105238. In addition, commercially available polymerizable compounds such as UA-7200 (manufactured by Shin-Nakamura Chemical Co., Ltd.), DPHA-40H (manufactured by Nippon Kayaku Co., Ltd.), UA-306H, UA-306T, UA-306I, AH-600, T-600, AI-600, and LINC-202UA (manufactured by Kyoeisha Chemical Co., Ltd.) can also be used.
[0126] The content of the polymerizable compound is preferably 5 to 35% by mass in the total solid content of the coloring composition. The upper limit is more preferably 30% by mass or less, and even more preferably 25% by mass or less. The lower limit is more preferably 10% by mass or more, and even more preferably 15% by mass or more. The coloring composition of the present invention may contain only one type of polymerizable compound, or may contain two or more types. When two or more types of polymerizable compounds are contained, the total amount thereof is preferably within the above range.
[0127] <<Photopolymerization initiator>> The coloring composition of the present invention contains a photopolymerization initiator. The photopolymerization initiator is not particularly limited and can be appropriately selected from known photopolymerization initiators. For example, a compound having photosensitivity to light rays in the ultraviolet to visible regions is preferred. The photopolymerization initiator is preferably a photoradical polymerization initiator.
[0128] Examples of the photopolymerization initiator include halogenated hydrocarbon derivatives (e.g., compounds having a triazine skeleton, compounds having an oxadiazole skeleton, etc.), acylphosphine compounds, hexaarylbiimidazole, oxime compounds, organic peroxides, thio compounds, ketone compounds, aromatic onium salts, hydroxyalkylphenone compounds, aminoalkylphenone compounds, phenylglyoxylate compounds, etc. From the viewpoint of exposure sensitivity, the photopolymerization initiator is preferably at least one selected from oxime compounds, hydroxyalkylphenone compounds, aminoalkylphenone compounds, and acylphosphine compounds, and more preferably an oxime compound. Further, as the photopolymerization initiator, the compounds described in paragraphs 0065 to 0111 of JP 2014-130173 A and JP Patent No. 6301489 A, the peroxide-based photopolymerization initiator described in MATERIAL STAGE 37 to 60p, vol. 19, No. 3, 2019, the photopolymerization initiator described in WO 2018 / 221177 A, the photopolymerization initiator described in WO 2018 / 110179 A, the photopolymerization initiator described in JP 2019-043864 A, the photopolymerization initiator described in JP 2019-044030 A, and the peroxide-based initiator described in JP 2019-167313 A can be mentioned, the contents of which are incorporated herein by reference.
[0129] Examples of the phenyl glyoxylate compound include phenyl glyoxylic acid methyl ester, etc. Examples of commercially available products include Omnirad MBF (manufactured by IGM Resins BV) and Irgacure MBF (manufactured by BASF).
[0130] Examples of the acylphosphine compound include the acylphosphine compounds described in Japanese Patent No. 4225898. Specific examples include bis(2,4,6-trimethylbenzoyl)-phenylphosphine oxide. Commercially available acylphosphine compounds include Omnirad 819, Omnirad TPO (both manufactured by IGM Resins BV), Irgacure 819, Irgacure TPO (both manufactured by BASF), and the like.
[0131] Examples of the aminoalkylphenone compound include the aminoalkylphenone compounds described in JP-A-10-291969. Examples of commercially available aminoalkylphenone compounds include Omnirad 907, Omnirad 369, Omnirad 369E, Omnirad 379, Omnirad 379EG (all manufactured by IGM Resins BV), Irgacure 907, Irgacure 369, Irgacure 369E, Irgacure 379, Irgacure 379EG (all manufactured by BASF), and the like.
[0132] The hydroxyalkylphenone compound includes a compound represented by the following formula (V). Formula (V) [ka] Rv in the formula 1 represents a substituent, Rv 2 and Rv 3 each independently represents a hydrogen atom or a substituent; Rv 2 and Rv 3 and may be bonded to each other to form a ring, and m represents an integer of 0 to 5.
[0133] Rv 1 Examples of the substituent represented by Rv include an alkyl group (preferably an alkyl group having 1 to 10 carbon atoms) and an alkoxy group (preferably an alkoxy group having 1 to 10 carbon atoms). The alkyl group and the alkoxy group are preferably linear or branched, and more preferably linear.1 The alkyl group and alkoxy group represented by may be unsubstituted or may have a substituent. Examples of the substituent include a hydroxy group and a group having a hydroxyalkylphenone structure. Examples of the group having a hydroxyalkylphenone structure include Rv in formula (V). 1 or Rv 1 Examples of groups include those with a structure in which one hydrogen atom has been removed from the above.
[0134] Rv 2 and Rv 3 Each of Rv independently represents a hydrogen atom or a substituent. The substituent is preferably an alkyl group (preferably an alkyl group having 1 to 10 carbon atoms). 2 and Rv 3 may be bonded to each other to form a ring (preferably a ring having 4 to 8 carbon atoms, more preferably an aliphatic ring having 4 to 8 carbon atoms). The alkyl group is preferably linear or branched, more preferably linear.
[0135] Specific examples of the compound represented by formula (V) include the following compounds. [ka]
[0136] Commercially available hydroxyalkylphenone compounds include Omnirad 184, Omnirad 1173, Omnirad 2959, Omnirad 127 (all manufactured by IGM Resins BV), Irgacure 184, Irgacure 1173, Irgacure 2959, Irgacure 127 (all manufactured by BASF), and the like.
[0137] Examples of the oxime compound include compounds described in JP-A-2001-233842, compounds described in JP-A-2000-080068, compounds described in JP-A-2006-342166, compounds described in J.C.S. Perkin II (1979, pp. 1653-1660), compounds described in J.C.S. Perkin II (1979, pp. 156-162), compounds described in Journal of Photopolymer Science and Technology (1995, pp. 202-232), compounds described in JP 2000-066385 A, compounds described in JP-T-2004-534797 A, compounds described in JP-A-2017-019766 A, compounds described in Japanese Patent No. 6065596 A, compounds described in WO 2015 / 152153 A, compounds described in WO 2017 / 051680 A, compounds described in JP 2017-198865 A, compounds described in paragraphs 0025 to 0038 of WO 2017 / 164127 A, compounds described in WO 2013 / 167515 A, and the like. Specific examples of the oxime compound include 3-benzoyloxyiminobutan-2-one, 3-acetoxyiminobutan-2-one, 3-propionyloxyiminobutan-2-one, 2-acetoxyiminopentan-3-one, 2-acetoxyimino-1-phenylpropan-1-one, 2-benzoyloxyimino-1-phenylpropan-1-one, 3-(4-toluenesulfonyloxy)iminobutan-2-one, and 2-ethoxycarbonyloxyimino-1-phenylpropan-1-one. Examples of commercially available products include Irgacure OXE01, Irgacure OXE02, Irgacure OXE03, and Irgacure OXE04 (all manufactured by BASF), TR-PBG-304 (manufactured by Changzhou Strong Electronic New Materials Co., Ltd.), and Adeka Optomer N-1919 (manufactured by ADEKA Corporation, photopolymerization initiator 2 described in JP 2012-014052 A). In addition, it is also preferable to use a compound that is not colorable or a compound that is highly transparent and does not easily discolor as the oxime compound. Examples of commercially available products include Adeka Arcles NCI-730, NCI-831, and NCI-930 (all manufactured by ADEKA Corporation).
[0138] As the photopolymerization initiator, an oxime compound having a fluorene ring can also be used.Specific examples of the oxime compound having a fluorene ring include the compounds described in JP 2014-137466 A, the compounds described in JP 6636081 A, and the compounds described in KP 10-2016-0109444 A.
[0139] As the photopolymerization initiator, an oxime compound having a skeleton in which at least one benzene ring of a carbazole ring is replaced with a naphthalene ring can also be used. Specific examples of such oxime compounds include the compounds described in WO 2013 / 083505.
[0140] As the photopolymerization initiator, an oxime compound having a fluorine atom can also be used. The oxime compound having a fluorine atom is preferably a compound represented by the formula (OX-1). (OX-1) [ka] In formula (OX-1), Ar 1 and Ar 2 each independently represents an aromatic hydrocarbon ring which may have a substituent; R 1 represents an aryl group having a group containing a fluorine atom, R 2 and R 3 each independently represents an alkyl group or an aryl group.
[0141] Ar of formula (OX-1) 1 and Ar 2 The aromatic hydrocarbon ring represented by may be a single ring or a condensed ring. The number of carbon atoms constituting the ring of the aromatic hydrocarbon ring is preferably 6 to 20, more preferably 6 to 15, and particularly preferably 6 to 10. The aromatic hydrocarbon ring is preferably a benzene ring or a naphthalene ring. Among them, Ar 1 is preferably a benzene ring. 2is preferably a benzene ring or a naphthalene ring, and more preferably a naphthalene ring.
[0142] Ar 1 and Ar 2 The substituents which may be substituted include an alkyl group, an aryl group, a heterocyclic group, a nitro group, a cyano group, a halogen atom, -OR X1 , -SR X1 , -COR X1 , -COOR X1 , -OCOR X1 , -NR X1 R X2 , -NHCOR X1 , -CONR X1 R X2 , -NHCONR X1 R X2 , -NHCOOR X1 , -SO2R X1 , -SO2OR X1 , -NHSO2R X1 R X1 and R X2 each independently represents a hydrogen atom, an alkyl group, an aryl group, or a heterocyclic group. Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom, and a fluorine atom is preferable. X1 and R X2 The number of carbon atoms in the alkyl group represented by is preferably 1 to 30. The alkyl group may be linear, branched, or cyclic, but is preferably linear or branched. The alkyl group may have some or all of the hydrogen atoms substituted with halogen atoms (preferably fluorine atoms). The alkyl group may have some or all of the hydrogen atoms substituted with the above-mentioned substituents. The aryl group and R X1 and R X2 The number of carbon atoms in the aryl group represented by is preferably 6 to 20, more preferably 6 to 15, and even more preferably 6 to 10. The aryl group may be a monocyclic ring or a condensed ring. In addition, the aryl group may have some or all of the hydrogen atoms substituted with the above-mentioned substituents. The heterocyclic group as a substituent and R X1 and RX2 The heterocyclic group represented by is preferably a 5-membered ring or a 6-membered ring. The heterocyclic group may be a single ring or a condensed ring. The number of carbon atoms constituting the heterocyclic group is preferably 3 to 30, more preferably 3 to 18, and more preferably 3 to 12. The number of heteroatoms constituting the heterocyclic group is preferably 1 to 3. The heteroatom constituting the heterocyclic group is preferably a nitrogen atom, an oxygen atom, or a sulfur atom. In addition, the heterocyclic group may have some or all of the hydrogen atoms substituted with the above-mentioned substituents.
[0143] Ar 1 The aromatic hydrocarbon ring represented by Ar is preferably an unsubstituted aromatic hydrocarbon ring. 2 The aromatic hydrocarbon ring represented by the formula (I) preferably has a substituent. The substituent may be, for example, -COR X1 is preferred. X1 is preferably an alkyl group, an aryl group or a heterocyclic group, and more preferably an aryl group. The aryl group may have a substituent or may be unsubstituted. Examples of the substituent include an alkyl group having 1 to 10 carbon atoms.
[0144] R in formula (OX-1) 1 represents an aryl group having a group containing a fluorine atom. The number of carbon atoms in the aryl group is preferably 6 to 20, more preferably 6 to 15, and even more preferably 6 to 10. The group containing a fluorine atom is preferably an alkyl group having a fluorine atom (hereinafter also referred to as a fluorine-containing alkyl group) or a group containing an alkyl group having a fluorine atom (hereinafter also referred to as a fluorine-containing group). Examples of the fluorine-containing group include -OR F1 , -SR F1 , -COR F1 , -COOR F1 , -OCOR F1 , -NR F1 R F2 , -NHCOR F1 , -CONR F1 R F2 , -NHCONR F1 R F2 , -NHCOOR F1 , -SO2R F1 , -SO2OR F1and -NHSO2R F1 At least one group selected from the following is preferred. F1 represents a fluorine-containing alkyl group, R F2 represents a hydrogen atom, an alkyl group, a fluorine-containing alkyl group, an aryl group or a heterocyclic group. F1 is preferred.
[0145] R F1 and R F2 Fluorine-containing alkyl group represented by R F2 The number of carbon atoms in the alkyl group represented by is preferably 1 to 20, more preferably 1 to 15, further preferably 1 to 10, and particularly preferably 1 to 4. The fluorine-containing alkyl group and the alkyl group may be linear, branched, or cyclic, but linear or branched is preferred. In the fluorine-containing alkyl group, the substitution rate of fluorine atoms is preferably 40 to 100%, more preferably 50 to 100%, and further preferably 60 to 100%. The substitution rate of fluorine atoms refers to the ratio (%) of the number of fluorine atoms substituted with fluorine atoms to the number of all hydrogen atoms in the alkyl group.
[0146] R F2 The aryl group represented by the formula (I) preferably has 6 to 20 carbon atoms, more preferably 6 to 15 carbon atoms, and further preferably 6 to 10 carbon atoms.
[0147] R F2 The heterocyclic group represented by is preferably a 5-membered ring or a 6-membered ring. The heterocyclic group may be a monocyclic ring or a condensed ring. The number of condensed rings is preferably 2 to 8, more preferably 2 to 6, further preferably 3 to 5, and particularly preferably 3 to 4. The number of carbon atoms constituting the heterocyclic group is preferably 3 to 40, more preferably 3 to 30, and more preferably 3 to 20. The number of heteroatoms constituting the heterocyclic group is preferably 1 to 3. The heteroatom constituting the heterocyclic group is preferably a nitrogen atom, an oxygen atom, or a sulfur atom, and more preferably a nitrogen atom.
[0148] The group containing a fluorine atom preferably has a terminal structure represented by formula (1) or (2), in which * represents a linking hand. *-CHF2(1) *-CF3(2)
[0149] R in formula (OX-1) 2 represents an alkyl group or an aryl group, and preferably an alkyl group. The alkyl group and the aryl group may be unsubstituted or may have a substituent. The substituent may be any of the above-mentioned Ar 1 and Ar 2 Examples of the substituents that may be possessed by the aryl group include the substituents described above. The number of carbon atoms in the alkyl group is preferably 1 to 20, more preferably 1 to 15, still more preferably 1 to 10, and particularly preferably 1 to 4. The alkyl group may be linear, branched, or cyclic, but is preferably linear or branched. The number of carbon atoms in the aryl group is preferably 6 to 20, more preferably 6 to 15, and still more preferably 6 to 10.
[0150] R in formula (OX-1) 3 represents an alkyl group or an aryl group, and preferably an alkyl group. The alkyl group and the aryl group may be unsubstituted or may have a substituent. The substituent may be any of the above-mentioned Ar 1 and Ar 2 Examples of the substituent that may be possessed by R include the substituents described above. 3 The number of carbon atoms in the alkyl group represented by R is preferably 1 to 20, more preferably 1 to 15, and even more preferably 1 to 10. The alkyl group may be linear, branched, or cyclic, but is preferably linear or branched. 3 The aryl group represented by the formula (I) preferably has 6 to 20 carbon atoms, more preferably 6 to 15 carbon atoms, and further preferably 6 to 10 carbon atoms.
[0151] Specific examples of oxime compounds having a fluorine atom include the compounds described in JP-A-2010-262028, compounds 24 and 36 to 40 described in JP-A-2014-500852, and compound (C-3) described in JP-A-2013-164471.
[0152] As the photopolymerization initiator, an oxime compound having a nitro group can be used. It is also preferable that the oxime compound having a nitro group is a dimer. Specific examples of the oxime compound having a nitro group include the compounds described in paragraphs 0031 to 0047 of JP 2013-114249 A, paragraphs 0008 to 0012, and 0070 to 0079 of JP 2014-137466 A, the compounds described in paragraphs 0007 to 0025 of Japanese Patent No. 4223071 A, and Adeka Arcles NCI-831 (manufactured by ADEKA Corporation).
[0153] As the photopolymerization initiator, an oxime compound having a benzofuran skeleton can also be used. Specific examples include OE-01 to OE-75 described in WO 2015 / 036910.
[0154] As the photopolymerization initiator, an oxime compound in which a substituent having a hydroxyl group is bonded to a carbazole skeleton can also be used. Examples of such photopolymerization initiators include the compounds described in WO 2019 / 088055.
[0155] Specific examples of oxime compounds that can be preferably used in the present invention are shown below, but the present invention is not limited to these.
[0156] [ka] [ka]
[0157] In the present invention, a photopolymerization initiator having an absorption coefficient of 1.0×10 at a wavelength of 365 nm in methanol is used. 3 Photopolymerization initiator A1 with a concentration of 1.0×10 at 365 nm in methanol and a concentration of 1.0×10 2 mL / gcm or less and an extinction coefficient at a wavelength of 254 nm of 1.0 x 10 3It is also preferable to use in combination with a photopolymerization initiator A2 having a concentration of mL / gcm or more. According to this embodiment, the coloring composition can be sufficiently cured by exposure to light, and pixels having good flatness and excellent properties such as light resistance and solvent resistance can be formed in a low-temperature process (for example, a process at a temperature of 150°C or less throughout the entire process, preferably 120°C or less). As the photopolymerization initiator A1 and the photopolymerization initiator A2, it is preferable to select and use a compound having the above-mentioned absorption coefficient from the above-mentioned compounds.
[0158] In the present invention, the absorption coefficient of the photopolymerization initiator at the above wavelength is a value measured as follows. That is, the photopolymerization initiator is dissolved in methanol to prepare a measurement solution, and the absorbance of the measurement solution is measured to calculate the absorption coefficient. Specifically, the measurement solution is placed in a glass cell with a width of 1 cm, and the absorbance is measured using a UV-Vis-NIR spectrometer (Cary5000) manufactured by Agilent Technologies. The absorption coefficient (mL / gcm) at wavelengths of 365 nm and 254 nm is calculated by applying the following formula.
number
[0159] The absorption coefficient of photopolymerization initiator A1 in methanol at a wavelength of 365 nm is 1.0 × 10 3 mL / gcm or more, 1.0×10 4 mL / gcm or more is preferable, and 1.1×10 4 mL / gcm or more is more preferable, and 1.2×10 4 ~1.0×10 5 More preferably, the ratio is 1.3×10 4 ~5.0×10 4 mL / gcm is even more preferable, and 1.5×10 4 ~3.0×10 4 mL / gcm is particularly preferred. The absorption coefficient of the photopolymerization initiator A1 in methanol at a wavelength of 254 nm is 1.0 × 10 4 ~1.0×10 5 mL / gcm is preferred, and 1.5×10 4 ~9.5×10 4 mL / gcm is more preferable, and 3.0×10 4 ~8.0×10 4 It is more preferably mL / gcm.
[0160] As the photopolymerization initiator A1, an oxime compound, an aminoalkylphenone compound, or an acylphosphine compound is preferred, an oxime compound or an acylphosphine compound is more preferred, an oxime compound is even more preferred, and an oxime compound containing a fluorine atom is particularly preferred from the viewpoint of compatibility with other components contained in the composition. As the oxime compound containing a fluorine atom, a compound represented by the above formula (OX-1) is preferred. Specific examples of the photopolymerization initiator A1 include 1,2-octanedione, 1-[4-(phenylthio)-, 2-(O-benzoyloxime)] (commercially available products include, for example, Irgacure OXE01, manufactured by BASF), ethanone, 1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]-, 1-(O-acetyloxime) (commercially available products include, for example, Irgacure OXE02, manufactured by BASF), and the specific examples of the oxime compounds (C-13), (C-14), and (C-17) shown above.
[0161] The absorption coefficient of photopolymerization initiator A2 in methanol at 365 nm is 1.0×10 2 mL / gcm or less, 10 to 1.0 × 10 2 mL / gcm is preferable, and 20 to 1.0×10 2 The difference between the absorption coefficient of the photopolymerization initiator A1 at a wavelength of 365 nm in methanol and the absorption coefficient of the photopolymerization initiator A2 at a wavelength of 365 nm in methanol is preferably 9.0×10 2 mL / gcm or more, 1.0×10 3mL / gcm or more is preferable, and 5.0×10 3 ~3.0×10 4 mL / gcm is more preferable, and 1.0×10 4 ~2.0×10 4 The absorption coefficient of the photopolymerization initiator A2 in methanol at a wavelength of 254 nm is preferably 1.0×10 3 mL / gcm or more, 1.0×10 3 ~1.0×10 6 mL / gcm is preferred, and 5.0×10 3 ~1.0×10 5 mL / gcm is more preferred.
[0162] As the photopolymerization initiator A2, a hydroxyalkylphenone compound, a phenylglyoxylate compound, an aminoalkylphenone compound, and an acylphosphine compound are preferred, a hydroxyalkylphenone compound and a phenylglyoxylate compound are more preferred, and a hydroxyalkylphenone compound is even more preferred. As the hydroxyalkylphenone compound, a compound represented by the above formula (V) is preferred. Specific examples of the photopolymerization initiator A2 include 1-hydroxy-cyclohexyl-phenyl-ketone, 1-[4-(2-hydroxyethoxy)-phenyl]-2-hydroxy-2-methyl-1-propan-1-one, and the like. As a commercially available product of the photopolymerization initiator A2, Omnirad 2959 (manufactured by IGM Resins BV, a hydroxyalkylphenone compound) and the like are given.
[0163] As a combination of the photopolymerization initiator A1 and the photopolymerization initiator A2, a combination in which the photopolymerization initiator A1 is an oxime compound and the photopolymerization initiator A2 is a hydroxyalkylphenone compound is preferred, a combination in which the photopolymerization initiator A1 is an oxime compound and the photopolymerization initiator A2 is a compound represented by the above-mentioned formula (V) is more preferred, and a combination in which the photopolymerization initiator A1 is an oxime compound containing a fluorine atom and the photopolymerization initiator A2 is a compound represented by the above-mentioned formula (V) is particularly preferred.
[0164] The content of the photopolymerization initiator is preferably 3 to 25% by mass in the total solid content of the coloring composition. The lower limit is more preferably 5% by mass or more, even more preferably 7.5% by mass or more, even more preferably 8% by mass or more, even more preferably 9% by mass or more, and particularly preferably 10% by mass or more. The upper limit is more preferably 20% by mass or less, even more preferably 17.5% by mass or less, and even more preferably 15% by mass or less. The photopolymerization initiator may be used alone or in combination of two or more types. When two or more types are used in combination, the total amount thereof is preferably within the above range.
[0165] In the coloring composition of the present invention, the ratio (M / I) of the content M of the polymerizable compound in the total solid content of the coloring composition to the content I of the photopolymerization initiator in the total solid content of the coloring composition, based on mass%, is preferably 20 or less. The upper limit of the ratio is more preferably 10 or less, even more preferably 5 or less, even more preferably 3 or less, and particularly preferably 2 or less. The lower limit of the ratio is preferably 0.1 or more, and more preferably 0.5 or more.
[0166] In the coloring composition of the present invention, when the above-mentioned oxime compound is used as a photopolymerization initiator, the content of the oxime compound is preferably 3 to 25 mass% of the total solid content of the coloring composition. The lower limit is more preferably 5 mass% or more, more preferably 7.5 mass% or more, even more preferably 8 mass% or more, even more preferably 9 mass% or more, and particularly preferably 10 mass% or more. The upper limit is more preferably 20 mass% or less, even more preferably 17.5 mass% or less, and even more preferably 15 mass% or less. By the content of the oxime compound being in the above range, the adhesion of the cured film to the support after development can be improved. The oxime compound may be used alone or in combination of two or more. When two or more types are used in combination, the total amount thereof is preferably in the above range.
[0167] In addition, in the coloring composition of the present invention, the content M of the polymerizable compound in the total solid content of the coloring composition and the content I of the oxime compound in the total solid content of the coloring composition are, based on mass%, O Ratio to (M / I O ) is preferably 20 or less. The upper limit of the above ratio is more preferably 10 or less, even more preferably 5 or less, even more preferably 3 or less, and particularly preferably 2 or less. The lower limit of the above ratio is preferably 0.1 or more, and more preferably 0.5 or more.
[0168] In the colored composition of the present invention, when the above-mentioned photopolymerization initiator A1 is used as the photopolymerization initiator, the content of the photopolymerization initiator A1 is preferably 3 to 25 mass% in the total solid content of the colored composition. The lower limit is more preferably 5 mass% or more, even more preferably 7.5 mass% or more, even more preferably 8 mass% or more, even more preferably 9 mass% or more, and particularly preferably 10 mass% or more. The upper limit is more preferably 20 mass% or less, even more preferably 17.5 mass% or less, and even more preferably 15 mass% or less. By having the content of the photopolymerization initiator A1 in the above range, the adhesion of the cured film to the support after development can be improved.
[0169] In the coloring composition of the present invention, the content M of the polymerizable compound in the total solid content of the coloring composition and the content I of the photopolymerization initiator A1 in the total solid content of the coloring composition are, based on mass %, A1 Ratio to (M / I A1 ) is preferably 20 or less. The upper limit of the above ratio is more preferably 10 or less, even more preferably 5 or less, even more preferably 3 or less, and particularly preferably 2 or less. The lower limit of the above ratio is preferably 0.1 or more, and more preferably 0.5 or more.
[0170] In the colored composition of the present invention, when the above-mentioned photopolymerization initiator A2 is used as the photopolymerization initiator, the content of the photopolymerization initiator A2 is preferably 0.1 to 10.0 mass% of the total solid content of the colored composition. The lower limit is more preferably 0.5 mass% or more, even more preferably 1.0 mass% or more, and even more preferably 1.5 mass% or more. The upper limit is more preferably 9.0 mass% or less, even more preferably 8.0 mass% or less, and even more preferably 7.0 mass% or less. If the content of the photopolymerization initiator A2 is within the above range, the solvent resistance of the cured film after development can be improved.
[0171] In the coloring composition of the present invention, when the above-mentioned photopolymerization initiator A1 and photopolymerization initiator A2 are used as photopolymerization initiators, the coloring composition of the present invention preferably contains 50 to 200 parts by mass of the photopolymerization initiator A2 relative to 100 parts by mass of the photopolymerization initiator A1. The upper limit is more preferably 175 parts by mass or less, and even more preferably 150 parts by mass or less. The lower limit is more preferably 60 parts by mass or more, and even more preferably 70 parts by mass or more. According to this embodiment, a cured film having excellent properties such as solvent resistance can be formed in a low-temperature process (for example, a process at a temperature of 150°C or less, preferably 120°C or less throughout the entire process). When two or more types of photopolymerization initiator A1 and photopolymerization initiator A2 are used in combination, it is preferable that the total amount of each of them satisfies the above requirement.
[0172] In the coloring composition of the present invention, when the above-mentioned photopolymerization initiator A1 and photopolymerization initiator A2 are used as photopolymerization initiators, the total content of the photopolymerization initiator A1 and the photopolymerization initiator A2 in the total solid content of the coloring composition is preferably 3.1 to 25 mass%. The lower limit is more preferably 4 mass% or more, even more preferably 5 mass% or more, even more preferably 7.5 mass% or more, even more preferably 8 mass% or more, even more preferably 9 mass% or more, and particularly preferably 10 mass% or more. The upper limit is more preferably 20 mass% or less, even more preferably 17.5 mass% or less, and even more preferably 15 mass% or less.
[0173] The coloring composition of the present invention may contain a photopolymerization initiator other than the photopolymerization initiator A1 and the photopolymerization initiator A2 (hereinafter also referred to as other photopolymerization initiators) as a photopolymerization initiator, but it is preferable that the coloring composition does not substantially contain other photopolymerization initiators. When the coloring composition does not substantially contain other photopolymerization initiators, it means that the content of the other photopolymerization initiator is 1 part by mass or less relative to 100 parts by mass of the total of the photopolymerization initiator A1 and the photopolymerization initiator A2, more preferably 0.5 parts by mass or less, even more preferably 0.1 parts by mass or less, and even more preferably does not contain other photopolymerization initiators.
[0174] <<Compounds containing cyclic ether groups>> The coloring composition of the present invention contains a compound having a cyclic ether group. Examples of the cyclic ether group include an epoxy group and an oxetanyl group, and the epoxy group is preferred. The epoxy group may be an alicyclic epoxy group. The alicyclic epoxy group means a monovalent functional group having a cyclic structure in which an epoxy ring and a saturated hydrocarbon ring are condensed.
[0175] The cyclic ether group is preferably at least one selected from the group represented by formula (e-1), the group represented by formula (e-2), the group represented by formula (e-3) and the group represented by formula (e-4), and more preferably the group represented by formula (e-1). When n in formula (e-1) is 0, the group represented by formula (e-1) is an epoxy group, and when n is 1, the group represented by formula (e-1) is an oxetanyl group. In addition, the group represented by formula (e-2), the group represented by formula (e-3) and the group represented by formula (e-4) are alicyclic epoxy groups. [ka] In formula (e-1), R E1 represents a hydrogen atom or an alkyl group, n represents 0 or 1, and * represents a bond; In formula (e-2), ring A E1 represents a monocyclic aliphatic hydrocarbon ring, and * represents a bond; In formula (e-3) and formula (e-4), * represents a bond.
[0176] R E1 The number of carbon atoms in the alkyl group represented by R is preferably 1 to 20, more preferably 1 to 10, further preferably 1 to 5, and particularly preferably 1 to 3. E1 The alkyl group represented by is preferably linear or branched, and more preferably linear.
[0177] When n is 0, R E1 is preferably a hydrogen atom. When n is 1, R E1 is preferably a hydrogen atom or an alkyl group having 1 to 3 carbon atoms.
[0178] Here, when n in formula (e-1) is 0, formula (e-1) is a group represented by the following formula (e-1a). [ka]
[0179] Ring A of formula (e-2) E1The monocyclic aliphatic hydrocarbon ring represented by is preferably a 5- to 7-membered aliphatic hydrocarbon ring, more preferably a 5- or 6-membered aliphatic hydrocarbon ring, and even more preferably a 6-membered aliphatic hydrocarbon ring. Specific examples include a cyclopentane ring, a cyclohexane ring, and a cycloheptane ring, preferably a cyclopentane ring or a cyclohexane ring, and more preferably a cyclohexane ring. Specific examples of the group represented by formula (e-2) include the groups shown below. [ka]
[0180] As the compound having a cyclic ether group, it is also preferable to use a compound having an epoxy group and a compound having an oxetanyl group in combination. According to this embodiment, a sufficiently cured film can be formed even by heating at a relatively low temperature, and the occurrence of color mixing can be more effectively suppressed. When a compound having an epoxy group and a compound having an oxetanyl group are used in combination, the mass ratio of the compound having an epoxy group to the compound having an oxetanyl group is preferably 10 to 300 parts by mass, more preferably 20 to 200 parts by mass, and even more preferably 50 to 150 parts by mass, of the compound having an oxetanyl group relative to 100 parts by mass of the compound having an epoxy group.
[0181] The compound having a cyclic ether group may be a monomer or a macromolecule. When the compound having a cyclic ether group is a monomer, its molecular weight is preferably less than 1500, more preferably 100 to 1250, and even more preferably 300 to 1000. When the compound having a cyclic ether group is a macromolecular compound, its weight average molecular weight is preferably 1500 or more, more preferably 1750 or more, and even more preferably 2000 or more. The upper limit is preferably 30000 or less, more preferably 20000 or less, and even more preferably 10000 or less.
[0182] As the compound having a cyclic ether group, it is preferable to use a compound having a weight average molecular weight of 1500 or more. According to this embodiment, a sufficiently cured film can be formed even by heating at a relatively low temperature, and the occurrence of color mixing can be more effectively suppressed. In addition, as the compound having a cyclic ether group, it is also preferable to use a compound having a weight average molecular weight of 1500 or more in combination with a compound having a molecular weight of less than 1500. The mass ratio of the compound having a weight average molecular weight of 1500 or more to the compound having a molecular weight of less than 1500 is preferably 5 to 200 parts by mass, more preferably 10 to 100 parts by mass, and even more preferably 25 to 75 parts by mass, per 100 parts by mass of the compound having a weight average molecular weight of 1500 or more.
[0183] The content of the cyclic ether group in the compound having a cyclic ether group is preferably 2.0 to 6.5 mmol / g, more preferably 2.5 to 6.3 mmol / g, and even more preferably 3.0 to 6.0 mmol / g. In addition, when the compound having a cyclic ether group is a compound having a molecular weight of less than 1500, the content of the cyclic ether group is preferably 2.0 to 7.0 mmol / g, more preferably 3.0 to 6.5 mmol / g, and even more preferably 3.5 to 6.0 mmol / g. In addition, when the compound having a cyclic ether group is a compound having a weight molecular weight of 1500 or more, the content of the cyclic ether group is preferably 2.5 to 6.5 mmol / g, more preferably 3.0 to 6.3 mmol / g, and even more preferably 3.5 to 6.0 mmol / g. The content of the cyclic ether group in the compound having a cyclic ether group is a value calculated by dividing the number of cyclic ether groups contained in the compound having a cyclic ether group by the molecular weight of the compound having a cyclic ether group.
[0184] In the coloring composition of the present invention, it is preferable to use a compound having a repeating unit having a cyclic ether group as the compound having a cyclic ether group. Examples of the repeating unit having a cyclic ether group include a repeating unit represented by formula (A1). [ka]
[0185] In formula (A1), X a1 represents a trivalent linking group, L a1 represents a single bond or a divalent linking group; Z a1 represents a cyclic ether group.
[0186] X in formula (A1) a1 Examples of the trivalent linking group represented by the formula (I) include a poly(meth)acrylic linking group, a polyalkyleneimine linking group, a polyester linking group, a polyurethane linking group, a polyurea linking group, a polyamide linking group, a polyether linking group, a polystyrene linking group, a bisphenol linking group, and a novolac linking group. Of these, a poly(meth)acrylic linking group, a polyether linking group, a polyester linking group, a bisphenol linking group, and a novolac linking group are preferred, a polyether linking group, a novolac linking group, and a poly(meth)acrylic linking group are more preferred, a polyether linking group and a poly(meth)acrylic linking group are even more preferred, and a polyether linking group is particularly preferred.
[0187] L in formula (A1) a1 Examples of the divalent linking group represented by include an alkylene group (preferably an alkylene group having 1 to 12 carbon atoms), an arylene group (preferably an arylene group having 6 to 20 carbon atoms), -NH-, -SO-, -SO2-, -CO-, -O-, -COO-, -OCO-, -S-, and a group formed by combining two or more of these. The alkylene group may be linear, branched, or cyclic, and is preferably linear or branched. The alkylene group may have a substituent or may be unsubstituted. Examples of the substituent include a hydroxy group and an alkoxy group.
[0188] Z in formula (A1) a1 Examples of the cyclic ether group represented by Z include an epoxy group and an oxetanyl group, and the epoxy group is preferable. a1The cyclic ether group represented by is preferably a group represented by formula (e-1) or a group represented by formula (e-2), and more preferably a group represented by formula (e-1).
[0189] The repeating unit having a cyclic ether group is preferably a repeating unit of a polyether structure, a repeating unit of a novolac structure, or a repeating unit of a (meth)acrylic structure, more preferably a repeating unit of a polyether structure or a repeating unit of a (meth)acrylic structure, and even more preferably a repeating unit of a polyether structure.
[0190] In addition, the repeating unit having a cyclic ether group preferably contains an aliphatic hydrocarbon ring in the main chain structure. The aliphatic hydrocarbon ring contained in the main chain structure is preferably a saturated aliphatic hydrocarbon ring. According to this embodiment, the hydrophobicity of the main chain makes it easier for the compound having a cyclic ether group to exist in the vicinity of the pigment, and it is easier to form a cured film in which mixing with other colors is more suppressed. In addition, the aliphatic hydrocarbon ring contained in the main chain structure may be any of a monocyclic ring, a condensed ring, and a crosslinked ring, but is preferably a monocyclic ring. Specific examples of the aliphatic hydrocarbon ring include a cyclohexane ring, a cyclopentane ring, and a cycloheptane ring, and the like, and the cyclohexane ring is preferable.
[0191] The repeating unit having a cyclic ether group is preferably a repeating unit of a polyether structure containing an aliphatic hydrocarbon ring. An example of the repeating unit of the polyether structure containing an aliphatic hydrocarbon ring is a repeating unit represented by formula (A2). [ka]
[0192] In formula (A2), X a2 represents a trivalent aliphatic hydrocarbon ring group, L a2 represents a single bond or a divalent linking group; Z a2 represents a cyclic ether group.
[0193] Xa2 Examples of the trivalent aliphatic hydrocarbon ring group represented by include a cyclohexane ring group, a cyclopentane ring, and a cycloheptane ring, and a cyclohexane ring group is preferable.
[0194] L a2 Examples of the divalent linking group represented by include an alkylene group (preferably an alkylene group having 1 to 12 carbon atoms), an arylene group (preferably an arylene group having 6 to 20 carbon atoms), -NH-, -SO-, -SO2-, -CO-, -O-, -COO-, -OCO-, -S-, and a group formed by combining two or more of these. The alkylene group may be linear, branched, or cyclic, and is preferably linear or branched. The alkylene group may have a substituent or may be unsubstituted. Examples of the substituent include a hydroxy group and an alkoxy group. L a2 is preferably a single bond.
[0195] Z a2 Examples of the cyclic ether group represented by Z include an epoxy group and an oxetanyl group, and the epoxy group is preferable. a2 The cyclic ether group represented by is preferably a group represented by formula (e-1) or a group represented by formula (e-2), and more preferably a group represented by formula (e-1).
[0196] The compound having a cyclic ether group may have other repeating units in addition to the repeating unit having a cyclic ether group. The other repeating units include a repeating unit having an acid group (hereinafter, also referred to as repeating unit B-1), a repeating unit having a group in which the acid group is protected by a protecting group (hereinafter, also referred to as repeating unit B-2), and a repeating unit having a polymerizable group (hereinafter, also referred to as repeating unit B-3).
[0197] When the compound having a cyclic ether group has a repeating unit B-1, it can form a cured film that is sufficiently cured even when heated at a relatively low temperature, and can form a cured film that is more suppressed from mixing with other colors. Furthermore, when the coloring composition is used for patternwise exposure, the unexposed part is easily developed and removed with a developer, and the developability is also excellent, and the generation of residues in the unexposed part can be more suppressed. In addition, when the compound having a cyclic ether group contains a repeating unit B-2, the storage stability of the coloring composition can be further improved.
[0198] Examples of the acid group in the repeating unit B-1 and the acid group protected by the protecting group in the repeating unit B-2 include a phenolic hydroxy group, a carboxy group, a sulfo group, and a phosphate group. A phenolic hydroxy group or a carboxy group is preferable, and a carboxy group is more preferable.
[0199] The protecting group for protecting the acid group in the repeating unit B-2 includes a group that is decomposed and eliminated by the action of an acid or a base. The protecting group is preferably a group represented by any one of formulae (Y1) to (Y5), and more preferably a group represented by formula (Y3) or formula (Y5) because it is easy to remove the protecting group.
[0200] Formula (Y1):-C(R Y1 )(R Y2 )(R Y3 ) Formula (Y2):-C(=O)OC(R Y4 )(R Y5 )(R Y6 ) Formula (Y3):-C(R Y7 )(R Y8 )(OR Y9 ) Formula (Y4): -C(R Y10 )(H)(Ar Y1 ) Formula (Y5):-C(=O)(R Y11 )
[0201] In formula (Y1), R Y1 ~R Y3each independently represents an alkyl group; R Y1 ~R Y3 two of which may be linked to form a ring; In formula (Y2), R Y4 ~R Y6 each independently represents an alkyl group; R Y4 ~R Y6 two of which may be linked to form a ring; In formula (Y3), R Y7 and R Y8 each independently represents a hydrogen atom, an alkyl group, or an aryl group; R Y7 and R Y8 At least one of R is an alkyl group or an aryl group, Y9 represents an alkyl group or an aryl group, R Y7 or R Y8 And, R Y9 and may be linked to form a ring; In formula (Y4), Ar Y1 represents an aryl group, R Y10 represents an alkyl group or an aryl group; In formula (Y5), R Y11 represents an alkyl group or an aryl group.
[0202] R in formula (Y1) Y1 ~R Y3 The number of carbon atoms in the alkyl group represented by R is preferably 1 to 12, more preferably 1 to 6, and even more preferably 1 to 4. The alkyl group may be linear, branched, or cyclic, but is preferably linear or branched. Y1 ~R Y3 may be bonded to form a ring. Y1 ~R Y3Examples of the ring formed by combining the above two groups include monocyclic cycloalkyl groups such as a cyclopentyl group or a cyclohexyl group, and polycyclic cycloalkyl groups such as a norbornyl group, a tetracyclodecanyl group, a tetracyclododecanyl group, and an adamantyl group, and a monocyclic cycloalkyl group having 5 to 6 carbon atoms is preferable. In the above cycloalkyl groups, one of the methylene groups constituting the ring may be replaced with a heteroatom such as an oxygen atom, or a group having a heteroatom such as a carbonyl group.
[0203] R in formula (Y2) Y4 ~R Y6 The number of carbon atoms in the alkyl group represented by R is preferably 1 to 12, more preferably 1 to 6, and further preferably 1 to 4. The alkyl group may be linear, branched, or cyclic, but is preferably linear or branched. Y4 ~R Y6 At least two of R are preferably methyl groups. Y4 ~R Y6 may be bonded to form a ring. Examples of the ring that may be formed include the rings explained in formula (Y1).
[0204] In formula (Y3), R Y7 and R Y8 each independently represents a hydrogen atom, an alkyl group, or an aryl group; R Y7 and R Y8 At least one of R is an alkyl group or an aryl group, Y9 represents an alkyl group or an aryl group, R Y7 or R Y8 And, R Y9 may be bonded to form a ring. The alkyl group may be linear, branched, or cyclic. The number of carbon atoms in the alkyl group is preferably 1 to 12, more preferably 1 to 6, and even more preferably 1 to 4. The number of carbon atoms in the aryl group is preferably 6 to 20, and more preferably 6 to 12. R Y7 or R Y8 And, R Y9Examples of the ring formed by bonding with R include a tetrahydrofuranyl group and a tetrahydropyranyl group. Y7 or R Y8 And, R Y9 It is preferable that R is bonded to form a ring. Y7 and R Y8 It is preferable that one of the groups is a hydrogen atom.
[0205] In formula (Y4), Ar Y1 represents an aryl group, R Y10 represents an alkyl group or an aryl group, Ar Y1 and R Y10 and may be bonded to each other to form a ring. The alkyl group preferably has 1 to 12 carbon atoms, more preferably 1 to 6, and even more preferably 1 to 4. The aryl group preferably has 6 to 20 carbon atoms, and more preferably 6 to 12. In formula (Y4), R Y10 is preferably an alkyl group.
[0206] In formula (Y5), R Y11 represents an alkyl group or an aryl group, and is preferably an alkyl group. The number of carbon atoms in the alkyl group is preferably 1 to 12, more preferably 1 to 6, and further preferably 1 to 4. The number of carbon atoms in the aryl group is preferably 6 to 20, and more preferably 6 to 12.
[0207] The molecular weight of the protecting group is preferably 40 to 200, more preferably 40 to 150, and further preferably 40 to 120. When the molecular weight of the protecting group is within the above range, a coloring composition having excellent storage stability and excellent curing property at low temperature can be obtained.
[0208] Specific examples of the protecting group include a 1-methoxyethyl group, a 1-ethoxyethyl group, a 1-n-propoxyethyl group, a 1-n-butoxyethyl group, a 1-t-butoxyethyl group, a 1-cyclopentyloxyethyl group, a 1-cyclohexyloxyethyl group, a cyclohexyl(methoxy)methyl group, an α-methoxybenzyl group, an α-ethoxybenzyl group, an α-n-propoxybenzyl group, a 2-phenyl-1-methoxyethyl group, a 2-phenyl-1-ethoxyethyl group, a 2-phenyl-1-i-propoxyethyl group, a 2-tetrahydrofuranyl group, and a 2-tetrahydropyranyl group. Of these, a 1-ethoxyethyl group, a 1-cyclohexyloxyethyl group, a 2-tetrahydrofuranyl group, and a 2-tetrahydropyranyl group are preferred, and a 1-ethoxyethyl group and a 1-cyclohexyloxyethyl group are more preferred.
[0209] Examples of the polymerizable group contained in the repeating unit B-3 include ethylenically unsaturated bond-containing groups such as a vinyl group, a (meth)allyl group, and a (meth)acryloyl group.
[0210] An example of the repeating unit B-1 is a repeating unit represented by the following formula (B1): An example of the repeating unit B-2 is a repeating unit represented by the following formula (B2): An example of the repeating unit B-3 is a repeating unit represented by the following formula (B3): [ka]
[0211] In formula (B1), X b1 represents a trivalent linking group, L b1 represents a single bond or a divalent linking group; Z b1 represents an acid group. In formula (B2), X b2 represents a trivalent linking group, L b2 represents a single bond or a divalent linking group; Z b2 represents a group in which the acid group is protected with a protecting group. In formula (B3), X b3 represents a trivalent linking group, L b3represents a single bond or a divalent linking group; Z b3 represents a polymerizable group.
[0212] X in formula (B1) b1 a trivalent linking group represented by the formula (B2) b2 and X in formula (B3) b3 The trivalent linking group represented by is not particularly limited. For example, poly(meth)acrylic linking groups, polyalkyleneimine linking groups, polyester linking groups, polyurethane linking groups, polyurea linking groups, polyamide linking groups, polyether linking groups, polystyrene linking groups, bisphenol linking groups, novolac linking groups, etc. are included, with poly(meth)acrylic linking groups, polyether linking groups, polyester linking groups, bisphenol linking groups, and novolac linking groups being preferred, and poly(meth)acrylic linking groups being more preferred.
[0213] L in formula (B1) b1 L in formula (B2) b2 and L of formula (B3). b3 Examples of the divalent linking group represented by include an alkylene group (preferably an alkylene group having 1 to 12 carbon atoms), an arylene group (preferably an arylene group having 6 to 20 carbon atoms), -NH-, -SO-, -SO2-, -CO-, -O-, -COO-, -OCO-, -S-, and a group formed by combining two or more of these. The alkylene group may be linear, branched, or cyclic, and is preferably linear or branched. The alkylene group may have a substituent or may be unsubstituted. Examples of the substituent include a hydroxy group and an alkoxy group.
[0214] Z in formula (B1) b1 Examples of the acid group represented by include a phenolic hydroxy group, a carboxy group, a sulfo group, and a phosphate group. A phenolic hydroxy group or a carboxy group is preferable, and a carboxy group is more preferable.
[0215] Z in formula (B2) b2The group in which the acid group is protected with a protecting group represented by formula (Y1) to formula (Y5) is exemplified, and the acid group is preferably protected with a group represented by formula (Y3) or formula (Y5). The acid group includes a phenolic hydroxy group, a carboxy group, a sulfo group, and a phosphate group, and is preferably a phenolic hydroxy group or a carboxy group, and more preferably a carboxy group.
[0216] Z in formula (B3) b3 Examples of the polymerizable group represented by the formula (I) include ethylenically unsaturated bond-containing groups such as a vinyl group, a (meth)allyl group, and a (meth)acryloyl group.
[0217] When the compound having a cyclic ether group contains a repeating unit B-1, the content of the unit B-1 in the compound having a cyclic ether group is preferably 5 to 85 mol % of all repeating units of the compound having a cyclic ether group. The upper limit is more preferably 60 mol % or less, and even more preferably 40 mol % or less. The lower limit is more preferably 8 mol % or more, and even more preferably 10 mol % or more.
[0218] When the compound having a cyclic ether group contains the repeating unit B-2, the content of the unit B-2 in the compound having a cyclic ether group is preferably 1 to 65 mol% of the total repeating units of the compound having a cyclic ether group. The upper limit is more preferably 45 mol% or less, and even more preferably 30 mol% or less. The lower limit is more preferably 2 mol% or more, and even more preferably 3 mol% or more.
[0219] When the compound having a cyclic ether group contains both the repeating unit B-1 and the repeating unit B-2, the compound having a cyclic ether group preferably contains 0.4 to 3.2 moles of the repeating unit B-2 per mole of the repeating unit B-1, more preferably 0.8 to 2.8 moles, and even more preferably 1.2 to 2.4 moles. According to this embodiment, the storage stability and developability of the colored composition, and the suppression of color mixing in the obtained cured film can be simultaneously achieved at a higher level.
[0220] When the compound having a cyclic ether group contains the repeating unit B-3, the content of the unit B-3 in the compound having a cyclic ether group is preferably 1 to 65 mol% of the total repeating units of the compound having a cyclic ether group. The upper limit is more preferably 45 mol% or less, and even more preferably 30 mol% or less. The lower limit is more preferably 2 mol% or more, and even more preferably 3 mol% or more.
[0221] Specific examples of the compound having a cyclic ether group include compounds having the structures shown below. [ka] [ka]
[0222] Examples of commercially available compounds having a cyclic ether group include naphthalene-modified epoxy resins such as EPICLON HP5000 and EPICLON HP4032D (manufactured by DIC Corporation). Examples of alkyldiphenol-type epoxy resins include EPICLON 820 (manufactured by DIC Corporation). Examples of bisphenol A-type epoxy resins include jER825, jER827, jER828, jER834, jER1001, jER1002, jER1003, jER1055, jER1007, jER1009, and jER1010 (manufactured by Mitsubishi Chemical Corporation), EPICLON860, EPICLON1050, EPICLON1051, and EPICLON1055 (manufactured by DIC Corporation). Examples of bisphenol F type epoxy resins include jER806, jER807, jER4004, jER4005, jER4007, and jER4010 (all manufactured by Mitsubishi Chemical Corporation), EPICLON830 and EPICLON835 (all manufactured by DIC Corporation), LCE-21, and RE-602S (all manufactured by Nippon Kayaku Co., Ltd.), etc. Examples of phenol novolac type epoxy resins include jER152, jER154, jER157S70, and jER157S65 (all manufactured by Mitsubishi Chemical Corporation), EPICLON N-740, EPICLON N-770, and EPICLON N-775 (all manufactured by DIC Corporation), etc. Examples of cresol novolac type epoxy resins include EPICLON N-660, EPICLON N-665, EPICLON N-670, EPICLON N-673, EPICLON N-680, EPICLON N-690, and EPICLON N-695 (all manufactured by DIC Corporation), and EOCN-1020 (manufactured by Nippon Kayaku Co., Ltd.).Examples of aliphatic epoxy resins include ADEKA RESIN EP-4080S, EP-4085S, and EP-4088S (all manufactured by ADEKA Corporation), CELLOXIDE 2021P, CELLOXIDE 2081, CELLOXIDE 2083, CELLOXIDE 2085, EHPE3150, EPOLEAD PB 3600, and EPOLEAD PB 4700 (all manufactured by Daicel Corporation), and Denacol EX-212L, EX-214L, EX-216L, EX-321L, and EX-850L (all manufactured by Nagase ChemteX Corporation). Examples of compounds having an oxetanyl group include OXT-101, OXT-121, OXT-212, and OXT-221 (manufactured by Toagosei Co., Ltd.), OXE-10, and OXE-30 (manufactured by Osaka Organic Chemical Industry Co., Ltd.). Examples of compounds having a cyclic ether group include the compounds described in paragraphs 0034 to 0036 of JP 2013-011869 A, the compounds described in paragraphs 0147 to 0156 of JP 2014-043556 A, the compounds described in paragraphs 0085 to 0092 of JP 2014-089408 A, the compounds described in JP 2017-179172 A, and the compounds described in paragraphs 0117 to 0120 of JP-T-2020-515680 A can also be used.
[0223] The content of the compound having a cyclic ether group in the total solid content of the coloring composition is preferably 1% by mass or more, more preferably 2% by mass or more, and even more preferably 3% by mass or more. The upper limit is preferably 15% by mass or less, and more preferably 10% by mass or less. The content of the compound having a cyclic ether group is preferably 1 to 300 parts by mass relative to 100 parts by mass of CI Pigment Green 7. From the viewpoint of storage stability of the colored composition, the upper limit is more preferably 150 parts by mass or less, even more preferably 100 parts by mass or less, and even more preferably 50 parts by mass or less. From the viewpoint of suppressing color mixing in the obtained cured film, the lower limit is more preferably 2.5 parts by mass or more, even more preferably 5 parts by mass or more, and even more preferably 10 parts by mass or more. The coloring composition of the present invention may contain only one type of compound having a cyclic ether group, or may contain two or more types. When two or more types of compounds having a cyclic ether group are contained, the total amount thereof is preferably within the above range.
[0224] <<Furyl group-containing compounds>> The coloring composition of the present invention preferably contains a compound containing a furyl group (hereinafter also referred to as a furyl group-containing compound). According to this embodiment, the composition has excellent low-temperature curing properties. For example, when a compound containing an ethylenically unsaturated bond-containing group is used as a polymerizable compound, the furyl group of the furyl group-containing compound and the ethylenically unsaturated bond-containing group of the polymerizable compound form a bond at a low temperature of 150°C or less by Diels-Alder reaction, so that the composition has excellent low-temperature curing properties.
[0225] The structure of the furyl group-containing compound is not particularly limited as long as it contains a furyl group (a group obtained by removing one hydrogen atom from furan). As the furyl group-containing compound, the compounds described in paragraphs 0049 to 0089 of JP2017-194662A can be used. In addition, as the furyl group-containing compound, compounds described in JP-A-2000-233581, JP-A-1994-271558, JP-A-1994-293830, JP-A-1996-239421, JP-A-1998-508655, JP-A-2000-001529, JP-A-2003-183348, JP-A-2006-193628, JP-A-2007-186684, JP-A-2010-265377, JP-A-2011-170069, and the like can also be used.
[0226] The furyl group-containing compound may be a monomer or a polymer. It is preferable that the compound is a polymer because it is easy to improve the durability of the film obtained. In the case of a polymer, the weight average molecular weight is preferably 2000 to 70000. The upper limit is more preferably 60000 or less, and even more preferably 50000 or less. The lower limit is more preferably 3000 or more, more preferably 4000 or more, and even more preferably 5000 or more. In the case of a monomer, the molecular weight is preferably less than 2000, more preferably 1800 or less, and even more preferably 1500 or less. The lower limit is preferably 100 or more, more preferably 150 or more, and even more preferably 175 or more. The polymer type furyl group-containing compound is also a component that corresponds to the resin in the coloring composition of the present invention. In addition, the furyl group-containing compound having a polymerizable group is also a component that corresponds to the polymerizable compound in the coloring composition of the present invention.
[0227] An example of a monomer-type furyl group-containing compound (hereinafter also referred to as a furyl group-containing monomer) is a compound represented by the following formula (fur-1). [ka] In the formula, Rf 1 represents a hydrogen atom or a methyl group, and Rf 2 represents a divalent linking group.
[0228] Rf 2 Examples of the divalent linking group represented by include an alkylene group, an arylene group, -O-, -CO-, -COO-, -OCO-, -NH-, -S-, and a group obtained by combining two or more of these. The number of carbon atoms in the alkylene group is preferably 1 to 30, more preferably 1 to 20, and even more preferably 1 to 15. The alkylene group may be linear, branched, or cyclic. The number of carbon atoms in the arylene group is preferably 6 to 30, more preferably 6 to 20, and even more preferably 6 to 10. The alkylene group and the arylene group may have a substituent. Examples of the substituent include a hydroxyl group.
[0229] The furyl group-containing monomer is preferably a compound represented by the following formula (fur-1-1). [ka] In the formula, Rf 1 represents a hydrogen atom or a methyl group, and Rf 11 represents -O- or -NH-; Rf 12 Rf represents a single bond or a divalent linking group. 12 Examples of the divalent linking group represented by include an alkylene group, an arylene group, -O-, -CO-, -COO-, -OCO-, -NH-, -S-, and a group obtained by combining two or more of these. The number of carbon atoms in the alkylene group is preferably 1 to 30, more preferably 1 to 20, and even more preferably 1 to 15. The alkylene group may be linear, branched, or cyclic. The number of carbon atoms in the arylene group is preferably 6 to 30, more preferably 6 to 20, and even more preferably 6 to 10. The alkylene group and the arylene group may have a substituent. Examples of the substituent include a hydroxyl group.
[0230] Specific examples of furyl group-containing monomers include compounds having the following structures: 1 represents a hydrogen atom or a methyl group. [ka]
[0231] The polymer type furyl group-containing compound (hereinafter also referred to as furyl group-containing polymer) is preferably a resin containing a repeating unit containing a furyl group, and more preferably a resin containing a repeating unit derived from the compound represented by the above formula (fur-1). In the furyl group-containing polymer, the ratio of the repeating unit containing a furyl group to the total repeating units is preferably 30 to 70 mass%. The lower limit is more preferably 35 mass% or more, and even more preferably 40 mass% or more. The upper limit is more preferably 65 mass% or less, and even more preferably 60 mass% or less. The concentration of the furyl group in the furyl group-containing polymer is preferably 0.5 to 6.0 mmol, and more preferably 1.0 to 4.0 mmol per 1 g of the furyl group-containing polymer. When the concentration of the furyl group is 0.5 mmol or more, preferably 1.0 mmol or more, a cured film having excellent solvent resistance and the like is easily formed. When the concentration of the furyl group is 6.0 mmol or less, preferably 4.0 mmol or less, the coloring composition has good stability over time.
[0232] The furyl group-containing polymer may contain a repeating unit having an acid group and / or a repeating unit having a polymerizable group in addition to the repeating unit having a furyl group. Examples of the acid group include a carboxy group, a phosphoric acid group, a sulfo group, and a phenolic hydroxy group. Examples of the polymerizable group include an ethylenically unsaturated bond-containing group such as a vinyl group, a (meth)allyl group, or a (meth)acryloyl group. When the furyl group-containing polymer contains a repeating unit having an acid group, the acid value of the furyl group-containing polymer is preferably 10 to 200 mgKOH / g, more preferably 40 to 130 mgKOH / g. The proportion of the repeating unit having an acid group is preferably 2 to 25 mass% of the total repeating units of the furyl group-containing polymer. The lower limit is more preferably 4 mass% or more, and even more preferably 5 mass% or more. The upper limit is more preferably 20 mass% or less, and even more preferably 15 mass% or less. When the furyl group-containing polymer contains a repeating unit having a polymerizable group, the proportion of the repeating unit having a polymerizable group is preferably 20 to 60 mass% of the total repeating units of the furyl group-containing polymer. The lower limit is more preferably 25 mass% or more, and even more preferably 30 mass% or more. The upper limit is more preferably 55 mass% or less, and even more preferably 50 mass% or less. When the furyl group-containing polymer contains a repeating unit having a polymerizable group, it is easy to form a cured film having excellent solvent resistance.
[0233] The furyl group-containing polymer can be produced by the method described in paragraphs 0052 to 0101 of JP2017-194662A.
[0234] The content of the furyl group-containing compound is preferably 0.1 to 70% by mass based on the total solid content of the coloring composition. The lower limit is more preferably 2.5% by mass or more, even more preferably 5.0% by mass or more, and even more preferably 7.5% by mass or more. The upper limit is more preferably 65% by mass or less, even more preferably 60% by mass or less, and even more preferably 50% by mass or less. In addition, when a furyl group-containing polymer is used as the furyl group-containing compound, the content of the furyl group-containing polymer in the resin contained in the coloring composition is preferably 0.1 to 100% by mass. The lower limit is more preferably 10% by mass or more, and even more preferably 15% by mass or more. The upper limit is more preferably 90% by mass or less, and even more preferably 80% by mass or less. In addition, when the resin used in the coloring composition of the present invention includes the above-mentioned resin b1, and a furyl group-containing polymer is used as the furyl group-containing compound, the content of the furyl group-containing polymer is preferably 10 to 200 parts by mass relative to 100 parts by mass of the resin b1. The upper limit is more preferably 175 parts by mass or less, and even more preferably 150 parts by mass or less. The lower limit is more preferably 25 parts by mass or more, more preferably 50 parts by mass or more, and even more preferably 150 parts by mass or more. By using the resin b1 and the furyl group-containing polymer in combination, it is easy to form a cured film that is excellent in curability at low temperature and has excellent spectral characteristics. Furthermore, when the ratio of the two is within the above range, the effect of further improving the durability of the obtained film can be expected.
[0235] <<Solvent>> The coloring composition of the present invention preferably contains a solvent. Examples of the solvent include organic solvents. Basically, the solvent is not particularly limited as long as it satisfies the solubility of each component and the coatability of the coloring composition. Examples of the organic solvent include ester-based solvents, ketone-based solvents, alcohol-based solvents, amide-based solvents, ether-based solvents, and hydrocarbon-based solvents. For details of these, reference can be made to paragraph 0223 of International Publication No. 2015 / 166779, the contents of which are incorporated herein by reference. In addition, ester-based solvents substituted with a cyclic alkyl group and ketone-based solvents substituted with a cyclic alkyl group can also be preferably used. Specific examples of organic solvents include polyethylene glycol monomethyl ether, dichloromethane, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, ethyl cellosolve acetate, ethyl lactate, diethylene glycol dimethyl ether, butyl acetate, methyl 3-methoxypropionate, 2-heptanone, 3-pentanone, 4-heptanone, cyclohexanone, 2-methylcyclohexanone, 3-methylcyclohexanone, 4-methylcyclohexanone, cycloheptanone, cyclooctanone, cyclohexyl acetate, cyclopentanone, ethyl carbitol acetate, and butyl ether. Examples of suitable organic solvents include ethyl carbitol acetate, propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, 3-methoxy-N,N-dimethylpropanamide, 3-butoxy-N,N-dimethylpropanamide, propylene glycol diacetate, 3-methoxybutanol, methyl ethyl ketone, gamma butyrolactone, sulfolane, anisole, 1,4-diacetoxybutane, diethylene glycol monoethyl ether acetate, butane-1,3-diyl diacetate, dipropylene glycol methyl ether acetate, and diacetone alcohol. However, aromatic hydrocarbons (benzene, toluene, xylene, ethylbenzene, etc.) as organic solvents may be reduced for environmental reasons (for example, the amount of the organic solvent may be reduced to 50 ppm (parts per million) or less, 10 ppm or less, or 1 ppm or less).
[0236] In the present invention, it is preferable to use a solvent with a low metal content, and the metal content of the solvent is preferably 10 mass ppb (parts per billion) or less. If necessary, a solvent with a mass ppt (parts per trillion) level may be used, and such a high purity solvent is provided, for example, by Toyo Gosei Co., Ltd. (The Chemical Daily, November 13, 2015).
[0237] Methods for removing impurities such as metals from a solvent include, for example, distillation (molecular distillation, thin-film distillation, etc.) and filtration using a filter. The filter used for filtration has a filter pore size of preferably 10 μm or less, more preferably 5 μm or less, and even more preferably 3 μm or less. The filter material is preferably polytetrafluoroethylene, polyethylene, or nylon.
[0238] The solvent may contain isomers (compounds having the same number of atoms but different structures). In addition, the solvent may contain only one type of isomer or multiple types of isomers.
[0239] In the present invention, the content of peroxide in the organic solvent is preferably 0.8 mmol / L or less, and more preferably contains substantially no peroxide.
[0240] The content of the solvent in the coloring composition is preferably 60 to 95% by mass. The upper limit is more preferably 90% by mass or less, even more preferably 87.5% by mass or less, and even more preferably 85% by mass or less. The lower limit is more preferably 65% by mass or more, even more preferably 70% by mass or more, and even more preferably 75% by mass or more. The solvent may be used alone or in combination of two or more. When two or more types are used in combination, the total amount thereof is preferably within the above range.
[0241] In addition, the coloring composition of the present invention preferably does not substantially contain environmentally regulated substances from the viewpoint of environmental regulations. In the present invention, substantially not containing environmentally regulated substances means that the content of the environmentally regulated substances in the coloring composition is 50 mass ppm or less, preferably 30 mass ppm or less, more preferably 10 mass ppm or less, and particularly preferably 1 mass ppm or less. Examples of environmentally regulated substances include benzene; alkylbenzenes such as toluene and xylene; and halogenated benzenes such as chlorobenzene. These are registered as environmentally regulated substances under the REACH (Registration Evaluation Authorization and Restriction of CHemicals) regulations, the PRTR (Pollutant Release and Transfer Register) Act, and the VOC (Volatile Organic Compounds) regulations, and the amount of use and the handling method are strictly regulated. These compounds may be used as solvents when producing each component used in the coloring composition of the present invention, and may be mixed into the coloring composition as a residual solvent. From the viewpoint of human safety and environmental consideration, it is preferable to reduce these substances as much as possible. A method for reducing the environmentally regulated substances includes a method of heating or reducing the pressure in the system to a temperature equal to or higher than the boiling point of the environmentally regulated substances, and distilling off the environmentally regulated substances from the system. In addition, when a small amount of the environmentally regulated substances is distilled off, it is also useful to perform azeotropy with a solvent having a boiling point equivalent to that of the corresponding solvent in order to increase efficiency. In addition, when a compound having radical polymerizability is contained, a polymerization inhibitor or the like may be added and distilled off under reduced pressure in order to suppress crosslinking between molecules caused by the progress of radical polymerization reaction during distillation under reduced pressure. These distillation methods are possible at any stage, that is, at the stage of the raw materials, at the stage of the product of the reaction of the raw materials (for example, a resin solution or a polyfunctional monomer solution after polymerization), or at the stage of the colored composition prepared by mixing these compounds.
[0242] <<Pigment derivatives>> The coloring composition of the present invention may contain a pigment derivative. Examples of the pigment derivative include compounds having a structure in which a portion of a chromophore is substituted with an acid group, a basic group, or a phthalimidomethyl group. Examples of the chromophore constituting the pigment derivative include a quinoline skeleton, a benzimidazolone skeleton, a diketopyrrolopyrrole skeleton, an azo skeleton, a phthalocyanine skeleton, an anthraquinone skeleton, a quinacridone skeleton, a dioxazine skeleton, a perinone skeleton, a perylene skeleton, a thioindigo skeleton, an isoindoline skeleton, an isoindolinone skeleton, a quinophthalone skeleton, a threne skeleton, and a metal complex skeleton. The quinoline skeleton, the benzimidazolone skeleton, the diketopyrrolopyrrole skeleton, the azo skeleton, the quinophthalone skeleton, the isoindoline skeleton, and the phthalocyanine skeleton are preferred, and the azo skeleton and the benzimidazolone skeleton are more preferred. As the acid group possessed by the pigment derivative, a sulfo group or a carboxy group is preferred, and a sulfo group is more preferred. As the basic group possessed by the pigment derivative, an amino group is preferred, and a tertiary amino group is more preferred. Specific examples of pigment derivatives are disclosed in JP-A-56-118462, JP-A-63-264674, JP-A-01-217077, JP-A-03-009961, JP-A-03-026767, JP-A-03-153780, JP-A-03-045662, JP-A-04-2 85669, JP-A-06-145546, JP-A-06-212088, JP-A-06-240158, JP-A-10-030063, JP-A-10-195326, paragraphs 0086 to 0098 of International Publication No. 2011 / 024896, International Publication No. 2012 / 102 399, paragraph numbers 0063 to 0094, International Publication No. 2017 / 038252, paragraph number 0082, JP 2015-151530 A, paragraph number 0171, JP 2011-252065 A, paragraph numbers 0162 to 0183, JP 2003-081972 A, Patent No. 5299151 A, Examples of the compounds include those described in JP-A-2015-172732, JP-A-2014-199308, JP-A-2014-085562, JP-A-2014-035351, JP-A-2008-081565, JP-A-2019-109512, and JP-A-2019-133154.
[0243] The content of the pigment derivative is preferably 0.1 to 30 parts by mass relative to 100 parts by mass of the pigment. The lower limit of this range is more preferably 0.25 parts by mass or more, even more preferably 0.5 parts by mass or more, particularly preferably 0.75 parts by mass or more, and even more preferably 1 part by mass or more. The upper limit of this range is more preferably 25 parts by mass or less, even more preferably 20 parts by mass or less, and particularly preferably 15 parts by mass or less. By having the content of the pigment derivative within the above range, the storage stability of the coloring composition can be further improved. Only one type of pigment derivative may be used, or two or more types may be used in combination. When two or more types are used in combination, the total amount thereof is preferably within the above range.
[0244] <<Polyalkyleneimine>> The coloring composition of the present invention may also contain a polyalkyleneimine. The polyalkyleneimine is used, for example, as a dispersing aid. The dispersing aid is a material for enhancing the dispersibility of a pigment in a coloring composition. The polyalkyleneimine is a polymer obtained by ring-opening polymerization of an alkyleneimine, and has a branched structure containing a primary amino group, a secondary amino group, and a tertiary amino group. The number of carbon atoms in the alkyleneimine is preferably 2 to 6, more preferably 2 to 4, further preferably 2 or 3, and particularly preferably 2.
[0245] The molecular weight of the polyalkyleneimine is preferably 200 or more, more preferably 250 or more. The upper limit is preferably 100,000 or less, more preferably 50,000 or less, even more preferably 10,000 or less, and particularly preferably 2,000 or less. In addition, when the value of the molecular weight of the polyalkyleneimine can be calculated from the structural formula, the molecular weight of the polyalkyleneimine is the value calculated from the structural formula. On the other hand, when the molecular weight of the specific amine compound cannot be calculated from the structural formula or is difficult to calculate, the value of the number average molecular weight measured by the boiling point elevation method is used. In addition, when the molecular weight cannot be measured by the boiling point elevation method or is difficult to measure, the value of the number average molecular weight measured by the viscosity method is used. In addition, when the molecular weight cannot be measured by the viscosity method or is difficult to measure by the viscosity method, the value of the number average molecular weight in terms of polystyrene measured by the GPC (gel permeation chromatography) method is used.
[0246] The amine value of the polyalkyleneimine is preferably 5 mmol / g or more, more preferably 10 mmol / g or more, and even more preferably 15 mmol / g or more.
[0247] Specific examples of alkyleneimine include ethyleneimine, propyleneimine, 1,2-butyleneimine, and 2,3-butyleneimine, and are preferably ethyleneimine or propyleneimine, and more preferably ethyleneimine. The polyalkyleneimine is particularly preferably polyethyleneimine. Moreover, the polyethyleneimine preferably contains 10 mol% or more of primary amino groups, more preferably 20 mol% or more, and even more preferably 30 mol% or more of primary amino groups, based on the total of primary amino groups, secondary amino groups, and tertiary amino groups. Commercially available polyethyleneimine products include Epomin SP-003, SP-006, SP-012, SP-018, SP-200, and P-1000 (all manufactured by Nippon Shokubai Co., Ltd.).
[0248] The content of the polyalkyleneimine in the total solid content of the coloring composition is preferably 0.1 to 5 mass%. The lower limit is more preferably 0.2 mass% or more, even more preferably 0.5 mass% or more, and even more preferably 1 mass% or more. The upper limit is more preferably 4.5 mass% or less, even more preferably 4 mass% or less, and even more preferably 3 mass% or less. The content of the polyalkyleneimine is preferably 0.5 to 20 mass parts relative to 100 mass parts of the pigment. The lower limit is more preferably 0.6 mass parts or more, even more preferably 1 mass part or more, and even more preferably 2 mass parts or more. The upper limit is more preferably 10 mass parts or less, and even more preferably 8 mass parts or less. Only one type of polyalkyleneimine may be used, or two or more types may be used. When two or more types are used, the total amount thereof is preferably within the above range.
[0249] <<Curing accelerator>> A curing accelerator may be added to the coloring composition of the present invention for the purpose of promoting the reaction of the polymerizable compound or lowering the curing temperature. Examples of the curing accelerator include a polyfunctional thiol compound having two or more mercapto groups in the molecule. The polyfunctional thiol compound may be added for the purpose of improving stability, odor, resolution, developability, adhesion, etc. The polyfunctional thiol compound is preferably a secondary alkanethiol, and more preferably a compound represented by formula (T1). Formula (T1) [ka] (In formula (T1), n represents an integer of 2 to 4, and L represents a divalent to tetravalent linking group.)
[0250] In formula (T1), the linking group L is preferably an aliphatic group having 2 to 12 carbon atoms, and it is particularly preferable that n is 2 and L is an alkylene group having 2 to 12 carbon atoms.
[0251] Examples of the curing accelerator include methylol compounds (for example, compounds exemplified as crosslinking agents in paragraph 0246 of JP-A-2015-034963), amines, phosphonium salts, amidine salts, and amide compounds (for example, curing agents described in paragraph 0186 of JP-A-2013-041165), base generators (for example, ionic compounds described in JP-A-2014-055114), and cyanate compounds (for example, For example, a compound described in paragraph 0071 of JP-A-2012-150180), an alkoxysilane compound (for example, an alkoxysilane compound having an epoxy group described in JP-A-2011-253054), an onium salt compound (for example, a compound exemplified as an acid generator in paragraph 0216 of JP-A-2015-034963, or a compound described in JP-A-2009-180949) can also be used.
[0252] When the colored composition of the present invention contains a curing accelerator, the content of the curing accelerator is preferably from 0.3 to 8.9 mass %, more preferably from 0.8 to 6.4 mass %, of the total solid content of the colored composition.
[0253] <<Silane coupling agents>> The coloring composition of the present invention can contain a silane coupling agent. As the silane coupling agent, a silane compound having at least two functional groups with different reactivity in one molecule is preferable. As the silane coupling agent, a silane compound having at least one group selected from a vinyl group, an epoxy group, a styrene group, a methacryl group, an amino group, an isocyanurate group, a ureido group, a mercapto group, a sulfide group, and an isocyanate group, and an alkoxy group is preferable. Specific examples of the silane coupling agent include N-2-(aminoethyl)-3-aminopropylmethyldimethoxysilane (Shin-Etsu Chemical Co., Ltd., KBM-602), N-2-(aminoethyl)-3-aminopropyltrimethoxysilane (Shin-Etsu Chemical Co., Ltd., KBM-603), 3-aminopropyltrimethoxysilane (Shin-Etsu Chemical Co., Ltd., KBM-903), 3-aminopropyltriethoxysilane (Shin-Etsu Chemical Co., Ltd., KBE-903), 3-methacryloxypropyltrimethoxysilane (Shin-Etsu Chemical Co., Ltd., KBM-503), and 3-glycidoxypropyltrimethoxysilane (Shin-Etsu Chemical Co., Ltd., KBM-403). For details of the silane coupling agent, refer to the description in paragraphs 0155 to 0158 of JP 2013-254047 A, the contents of which are incorporated herein by reference. When the coloring composition of the present invention contains a silane coupling agent, the content of the silane coupling agent is preferably 0.001 to 20 mass%, more preferably 0.01 to 10 mass%, and particularly preferably 0.1 mass% to 5 mass% of the total solid content of the coloring composition. The coloring composition of the present invention may contain only one type of silane coupling agent, or may contain two or more types. When two or more types are contained, the total amount thereof is preferably within the above range.
[0254] <<Polymerization inhibitor>> The coloring composition of the present invention may contain a polymerization inhibitor. Examples of the polymerization inhibitor include hydroquinone, p-methoxyphenol, di-t-butyl-p-cresol, pyrogallol, t-butylcatechol, benzoquinone, 4,4'-thiobis(3-methyl-6-t-butylphenol), 2,2'-methylenebis(4-methyl-6-t-butylphenol), and N-nitrosophenylhydroxyamine salts (ammonium salts, cerous salts, etc.). When the coloring composition of the present invention contains a polymerization inhibitor, the content of the polymerization inhibitor is preferably 0.0001 to 5 mass% of the total solid content of the coloring composition. The coloring composition of the present invention may contain only one type of polymerization inhibitor, or may contain two or more types. When two or more types are contained, the total amount thereof is preferably within the above range.
[0255] <<Ultraviolet absorber>> The coloring composition of the present invention may contain an ultraviolet absorber. As the ultraviolet absorber, a conjugated diene compound, an aminodiene compound, a salicylate compound, a benzophenone compound, a benzotriazole compound, an acrylonitrile compound, a hydroxyphenyltriazine compound, an indole compound, a triazine compound, or the like may be used. For details, the descriptions in paragraphs 0052 to 0072 of JP-A-2012-208374, paragraphs 0317 to 0334 of JP-A-2013-068814, and paragraphs 0061 to 0080 of JP-A-2016-162946 may be referred to, and the contents of these may be incorporated herein. Examples of commercially available ultraviolet absorbers include UV-503 (manufactured by Daito Chemical Co., Ltd.). In addition, examples of benzotriazole compounds include the MYUA series (The Chemical Daily, February 1, 2016) manufactured by Miyoshi Oil and Fat. In addition, the compounds described in paragraphs 0049 to 0059 of Japanese Patent No. 6268967 can also be used as ultraviolet absorbents. When the coloring composition of the present invention contains an ultraviolet absorbent, the content of the ultraviolet absorbent is preferably 0.1 to 10 mass%, more preferably 0.1 to 5 mass%, and particularly preferably 0.1 to 3 mass% of the total solid content of the coloring composition. In addition, the ultraviolet absorbent may be used alone or in combination with two or more types. When two or more types are used, the total amount is preferably within the above range.
[0256] <<Surfactants>> The coloring composition of the present invention may contain a surfactant. As the surfactant, various surfactants such as fluorine-based surfactants, nonionic surfactants, cationic surfactants, anionic surfactants, and silicone surfactants may be used. As the surfactant, the surfactants described in paragraphs 0238 to 0245 of WO 2015 / 166779 may be mentioned, the contents of which are incorporated herein by reference.
[0257] In the present invention, the surfactant is preferably a fluorosurfactant. By including a fluorosurfactant in the coloring composition, the liquid properties (particularly, fluidity) can be further improved, and the liquid saving can be further improved. In addition, a film with less unevenness in thickness can be formed.
[0258] From the viewpoint of environmental friendliness, it is also preferable to use a silicone-based surfactant as the surfactant.
[0259] The fluorine content in the fluorine-based surfactant is preferably 3 to 40% by mass, more preferably 5 to 30% by mass, and particularly preferably 7 to 25% by mass. A fluorine-based surfactant having a fluorine content within this range is effective in terms of uniformity of the thickness of the coating film and liquid saving properties, and also has good solubility in a coloring composition.
[0260] Examples of fluorine-based surfactants include those described in paragraphs 0060 to 0064 of JP 2014-041318 A (corresponding paragraphs 0060 to 0064 of WO 2014 / 017669 A), those described in paragraphs 0117 to 0132 of JP 2011-132503 A, and those described in JP 2020-008634 A, the contents of which are incorporated herein by reference. Commercially available fluorine-based surfactants include, for example, Megafac F-171, F-172, F-173, F-176, F-177, F-141, F-142, F-143, F-144, F-437, F-475, F-477, F-479, F-482, F-554, F-555-A, F-556, F-557, F-558, F-559, F-560, F-561, F-565, F-563, F-568, F-575, F-780, EXP, MFS-330, and R-01. , R-40, R-40-LM, R-41, R-41-LM, RS-43, TF-1956, RS-90, R-94, RS-72-K, DS-21 (all manufactured by DIC Corporation), Fluorard FC430, FC431, FC171 (all manufactured by Sumitomo 3M Limited), Surflon S-382, SC-101, SC-103, SC-104, SC-105, SC-1068, SC-381, SC-383, S-393, KH-40 (all manufactured by AGC Corporation), PolyFox Examples of such agents include PF636, PF656, PF6320, PF6520, PF7002 (all manufactured by OMNOVA), Ftergent 208G, 215M, 245F, 601AD, 601ADH2, 602A, 610FM, 710FL, 710FM, 710FS, FTX-218 (all manufactured by NEOS Co., Ltd.).
[0261] In addition, the fluorosurfactant may be an acrylic compound that has a molecular structure with a functional group containing a fluorine atom, and when heat is applied, the functional group containing the fluorine atom is broken and the fluorine atom volatilizes. Examples of such fluorosurfactants include the Megafac DS series manufactured by DIC Corporation (The Chemical Daily (February 22, 2016), Nikkei Business Daily (February 23, 2016)), such as Megafac DS-21.
[0262] In addition, it is also preferable to use a polymer of a fluorine atom-containing vinyl ether compound having a fluorinated alkyl group or a fluorinated alkylene ether group and a hydrophilic vinyl ether compound as the fluorine-based surfactant. Examples of such a fluorine-based surfactant include the fluorine-based surfactants described in JP 2016-216602 A, the contents of which are incorporated herein by reference.
[0263] The fluorosurfactant may be a block polymer. The fluorosurfactant may be a fluorine-containing polymer compound that contains a repeating unit derived from a (meth)acrylate compound having a fluorine atom and a repeating unit derived from a (meth)acrylate compound having two or more (preferably five or more) alkyleneoxy groups (preferably ethyleneoxy groups, propyleneoxy groups). In addition, the fluorine-containing surfactants described in paragraphs 0016 to 0037 of JP-A-2010-032698 and the following compounds are also exemplified as the fluorosurfactant used in the present invention. [ka] The weight average molecular weight of the above compound is preferably 3,000 to 50,000, for example, 14,000. In the above compound, % indicating the proportion of repeating units is mol %.
[0264] In addition, the fluorine-based surfactant may be a fluorine-containing polymer having an ethylenically unsaturated bond-containing group in a side chain.Specific examples include the compounds described in paragraphs 0050 to 0090 and 0289 to 0295 of JP 2010-164965 A, and Megafac RS-101, RS-102, RS-718K, and RS-72-K manufactured by DIC Corporation.In addition, the fluorine-based surfactant may be the compounds described in paragraphs 0015 to 0158 of JP 2015-117327 A.
[0265] In addition, it is also preferable from the viewpoint of environmental regulations to use the surfactants described in WO 2020 / 084854 as a substitute for surfactants having a perfluoroalkyl group having 6 or more carbon atoms.
[0266] It is also preferable to use a fluorine-containing imide salt compound represented by formula (fi-1) as a surfactant. [ka] In formula (fi-1), m represents 1 or 2, n represents an integer of 1 to 4, α represents 1 or 2, and X α+ is an α-valent metal ion, primary ammonium ion, secondary ammonium ion, tertiary ammonium ion, quaternary ammonium ion, or NH4 + Represents.
[0267] Examples of nonionic surfactants include glycerol, trimethylolpropane, trimethylolethane, and their ethoxylates and propoxylates (e.g., glycerol propoxylate, glycerol ethoxylate, etc.), polyoxyethylene lauryl ether, polyoxyethylene stearyl ether, polyoxyethylene oleyl ether, polyoxyethylene octylphenyl ether, polyoxyethylene nonylphenyl ether, polyethylene glycol dilaurate, polyethylene glycol distearate, and sorbitan fat. Examples of the fatty acid ester include Pluronic L10, L31, L61, L62, 10R5, 17R2, and 25R2 (manufactured by BASF), Tetronic 304, 701, 704, 901, 904, and 150R1 (manufactured by BASF), Solsperse 20000 (manufactured by Lubrizol Japan Co., Ltd.), NCW-101, NCW-1001, and NCW-1002 (manufactured by Wako Pure Chemical Industries, Ltd.), Paionin D-6112, D-6112-W, and D-6315 (manufactured by Takemoto Oil Co., Ltd.), Olfin E1010, and Surfynol 104, 400, and 440 (manufactured by Nissin Chemical Industry Co., Ltd.).
[0268] Examples of silicone surfactants include Toray Silicone DC3PA, Toray Silicone SH7PA, Toray Silicone DC11PA, Toray Silicone SH21PA, Toray Silicone SH28PA, Toray Silicone SH29PA, Toray Silicone SH30PA, Toray Silicone SH8400, FZ-2122 (all manufactured by Toray Dow Corning Co., Ltd.), TSF-4440, TSF-4300, TSF-4445, TSF-4460, TSF-4452 (all manufactured by Momentive Performance Materials Co., Ltd.), KP-341, KF-6001, KF-6002 (all manufactured by Shin-Etsu Chemical Co., Ltd.), BYK-307, BYK-322, BYK-323, BYK-330, BYK-3760, BYK-UV3510 (all manufactured by BYK-Chemie).
[0269] The content of the surfactant in the total solid content of the coloring composition is preferably 0.001% by mass to 5.0% by mass, more preferably 0.005% by mass to 3.0% by mass. The surfactant may be one type or two or more types. In the case of two or more types, the total amount is preferably within the above range.
[0270] <<Other additives>> The coloring composition of the present invention may contain various additives, such as fillers, adhesion promoters, antioxidants, and aggregation inhibitors, as necessary. Examples of these additives include those described in paragraphs 0155-0156 of JP-A-2004-295116, the contents of which are incorporated herein by reference. In addition, examples of the antioxidant include phenolic compounds, phosphorus compounds (e.g., compounds described in paragraph 0042 of JP-A-2011-090147), and thioether compounds. Examples of commercially available products include the Adeka STAB series (AO-20, AO-30, AO-40, AO-50, AO-50F, AO-60, AO-60G, AO-80, AO-330, etc.) manufactured by ADEKA CORPORATION. In addition, as the antioxidant, a polyfunctional hindered amine antioxidant described in WO 2017 / 006600, an antioxidant described in WO 2017 / 164024, or an antioxidant described in paragraphs 0023 to 0048 of Japanese Patent No. 6268967 can also be used. Only one type of antioxidant may be used, or two or more types may be used. In addition, the coloring composition of the present invention may contain a latent antioxidant as necessary. Examples of the latent antioxidant include compounds in which a site functioning as an antioxidant is protected by a protecting group, and the protecting group is removed by heating at 100 to 250°C or heating at 80 to 200°C in the presence of an acid / base catalyst to function as an antioxidant. Specific examples of the latent antioxidant include compounds described in WO 2014 / 021023, WO 2017 / 030005, and JP 2017-008219. Examples of commercially available products include Adeka Arcles GPA-5001 (manufactured by ADEKA Corporation). The coloring composition of the present invention may contain a sensitizer or light stabilizer described in paragraph 0078 of JP-A-2004-295116, a thermal polymerization inhibitor described in paragraph 0081 of the same publication, or a storage stabilizer described in paragraph 0242 of JP-A-2018-091940.
[0271] From the viewpoint of environmental regulations, the use of perfluoroalkylsulfonic acid and its salt, and perfluoroalkylcarboxylic acid and its salt may be restricted. In the coloring composition of the present invention, when the content of the above-mentioned compounds is reduced, the content of perfluoroalkylsulfonic acid (particularly perfluoroalkylsulfonic acid having 6 to 8 carbon atoms in the perfluoroalkyl group) and its salt, and perfluoroalkylcarboxylic acid (particularly perfluoroalkylcarboxylic acid having 6 to 8 carbon atoms in the perfluoroalkyl group) and its salt is preferably in the range of 0.01 ppb to 1,000 ppb, more preferably in the range of 0.05 ppb to 500 ppb, and even more preferably in the range of 0.1 ppb to 300 ppb, based on the total solid content of the coloring composition. The coloring composition of the present invention may be substantially free of perfluoroalkylsulfonic acid and its salt, and perfluoroalkylcarboxylic acid and its salt. For example, a coloring composition that is substantially free of perfluoroalkylsulfonic acid and its salt, and perfluoroalkylcarboxylic acid and its salt may be selected by using a compound that can be a substitute for perfluoroalkylsulfonic acid and its salt, and a compound that can be a substitute for perfluoroalkylcarboxylic acid and its salt. Examples of compounds that can be a substitute for regulated compounds include compounds that are excluded from the scope of regulation due to the difference in the number of carbon atoms in the perfluoroalkyl group. However, the above content does not prevent the use of perfluoroalkylsulfonic acid and its salt, and perfluoroalkylcarboxylic acid and its salt. The coloring composition of the present invention may contain perfluoroalkylsulfonic acid and its salt, and perfluoroalkylcarboxylic acid and its salt within the maximum allowable range.
[0272] <Containment Container> The container for storing the coloring composition of the present invention is not particularly limited, and a known container can be used. In addition, it is also preferable to use a multi-layer bottle whose inner wall is made of six types of six-layer resin or a bottle with a seven-layer structure made of six types of resin as the container, in order to suppress the incorporation of impurities into the raw materials or the coloring composition. Examples of such containers include the containers described in JP-A-2015-123351. In addition, it is also preferable to make the inner wall of the container out of glass or stainless steel in order to prevent metal elution from the inner wall of the container, increase the storage stability of the composition, and suppress the deterioration of the components.
[0273] <Method of producing colored composition> The coloring composition of the present invention can be produced by mixing the above-mentioned components. When producing the coloring composition, all components may be simultaneously dissolved and / or dispersed in a solvent to produce the coloring composition, or, if necessary, each component may be appropriately prepared as two or more solutions or dispersions, which are mixed at the time of use (at the time of application) to produce the coloring composition.
[0274] In addition, the production of the coloring composition may include a process for dispersing particles such as pigments. In the process for dispersing the pigment, mechanical forces used for dispersing the pigment include compression, squeezing, impact, shear, and cavitation. Specific examples of these processes include a bead mill, a sand mill, a roll mill, a ball mill, a paint shaker, a microfluidizer, a high-speed impeller, a sand grinder, a flow jet mixer, high-pressure wet atomization, and ultrasonic dispersion. In addition, in the grinding of the pigment in a sand mill (bead mill), it is preferable to use beads with a small diameter, increase the filling rate of the beads, and perform the treatment under conditions that increase the grinding efficiency. In addition, it is preferable to remove coarse particles by filtration, centrifugation, or the like after the grinding treatment. In addition, the process and dispersing machine for dispersing the pigment may be suitably used as described in "Dispersion Technology Encyclopedia, published by Joho Kika Co., Ltd., July 15, 2005" or "Dispersion Technology and Industrial Application Practices Focusing on Suspension (Solid / Liquid Dispersion System) Comprehensive Data Collection, published by Management Development Center Publishing Department, October 10, 1978" and in paragraph number 0022 of JP2015-157893A. In addition, in the process for dispersing the pigment, a salt milling process may be performed to refine the particles. For the materials, equipment, processing conditions, etc. used in the salt milling process, the descriptions in, for example, JP2015-194521A and JP2012-046629A may be referred to.
[0275] In producing a coloring composition, it is preferable to filter the coloring composition with a filter for the purpose of removing foreign matter and reducing defects. As the filter, any filter that has been used for filtering purposes can be used without any particular limitation. For example, filters using materials such as fluororesins such as polytetrafluoroethylene (PTFE) and polyvinylidene fluoride (PVDF), polyamide resins such as nylon (e.g., nylon-6, nylon-6,6), and polyolefin resins (including high-density and ultra-high-molecular-weight polyolefin resins) such as polyethylene and polypropylene (PP) are exemplified. Among these materials, polypropylene (including high-density polypropylene) and nylon are preferred.
[0276] The pore size of the filter is preferably 0.01 to 7.0 μm, more preferably 0.01 to 3.0 μm, and even more preferably 0.05 to 0.5 μm. If the pore size of the filter is within the above range, fine foreign matter can be removed more reliably. The nominal value of the filter manufacturer can be referred to for the pore size value of the filter. Various filters provided by Nippon Pall Corporation (DFA4201NIEY, DFA4201NAEY, DFA4201J006P, etc.), Advantech Toyo Co., Ltd., Nippon Integris Co., Ltd. (formerly Nippon Microlith Co., Ltd.), Kitz Microfilter Co., Ltd., etc. can be used.
[0277] It is also preferable to use a fibrous filter medium as the filter. Examples of fibrous filter medium include polypropylene fiber, nylon fiber, and glass fiber. Commercially available products include SBP type series (SBP008, etc.), TPR type series (TPR002, TPR005, etc.), and SHPX type series (SHPX003, etc.) manufactured by ROKI TECHNO CORPORATION. When using a filter, different filters (for example, a first filter and a second filter, etc.) may be combined. In this case, filtration with each filter may be performed only once, or may be performed two or more times. Filters with different pore sizes within the above-mentioned range may be combined. Filtration with the first filter may be performed only on the dispersion liquid, and filtration with the second filter may be performed after mixing with other components.
[0278] <Cured film> The cured film of the present invention is a film obtained by curing the above-mentioned colored composition of the present invention. The cured film of the present invention can be used for color filters and the like. Specifically, it can be preferably used as a colored layer (pixel) of a color filter, and more preferably used as a green pixel. The thickness of the cured film of the present invention can be appropriately adjusted depending on the purpose, but is preferably 0.5 to 3.0 μm. The lower limit is more preferably 0.8 μm or more, even more preferably 1.0 μm or more, and even more preferably 1.1 μm or more. The upper limit is more preferably 2.5 μm or less, even more preferably 2.0 μm or less, and even more preferably 1.8 μm or less.
[0279] The cured film of the present invention preferably has a maximum transmittance of 65% or more for light having a wavelength of 495 nm or more and less than 550 nm, more preferably 70% or more, and even more preferably 75% or more. Furthermore, the average transmittance for light having a wavelength of 495 nm or more and less than 550 nm is preferably 60% or more, more preferably 65% or more, and even more preferably 70% or more. In addition, the transmittance for light with a wavelength of 450 nm is preferably 10% or less, more preferably 5% or less, and even more preferably 2% or less. Moreover, the average transmittance for light having a wavelength of 400 nm or more and 450 nm or less is preferably 10% or less, more preferably 5% or less, and even more preferably 1% or less. Moreover, the average transmittance for light having a wavelength of 540 nm or more and 610 nm or less is preferably 60% or less, more preferably 50% or less, and even more preferably 40% or less.
[0280] <Color filters> Next, the color filter of the present invention will be described. The color filter of the present invention has the above-mentioned cured film of the present invention. Preferably, the cured film of the present invention is used as a colored pixel of the color filter, more preferably as a green pixel. The color filter of the present invention can be used in a solid-state imaging device or a display device.
[0281] The color filter of the present invention preferably has color pixels of other hues in addition to the pixels of the cured film of the present invention. Examples of color pixels of other hues include blue pixels, red pixels, yellow pixels, magenta pixels, and cyan pixels. A preferred embodiment of the color filter of the present invention includes an embodiment having a green pixel, a red pixel, and a blue pixel composed of the cured film of the present invention. The color filter may have a structure in which each color pixel is embedded in a space partitioned, for example, in a lattice shape, by partition walls. In this case, the partition wall preferably has a lower refractive index than each color pixel. In addition, the partition wall may be formed in the configuration described in U.S. Patent Application Publication No. 2018 / 0040656.
[0282] The red pixel, which is preferably used in combination with the pixel of the cured film of the present invention, preferably contains a red colorant. The content of the red colorant in the colorant contained in the red pixel is preferably 30% by mass or more, more preferably 40% by mass or more. The upper limit of the content of the red colorant in the colorant contained in the red pixel may be 100% by mass, 99% by mass or less, 95% by mass or less, or 90% by mass or less. In addition, the red pixel preferably contains 40% by mass or more of the red colorant, more preferably 50% by mass or more, and even more preferably 60% by mass or more. In addition, the upper limit of the content of the red colorant is preferably 80% by mass or less, more preferably 70% by mass or less, and even more preferably 60% by mass or less. Red colorants include CI Pigment Red 1, 2, 3, 4, 5, 6, 7, 9, 10, 14, 17, 22, 23, 31, 38, 41, 48:1, 48:2, 48:3, 48:4, 49, 49:1, 49:2, 52:1, 52:2, 53:1, 57:1, 60:1, 63:1, 66, 67, 81:1, 81:2, 81:3, 83, 88, 90, 105, 112, 119, 122, 123, 144, 146, 149, 150, 155, 166, 168, 16 9,170,171,172,175,176,177,178,179,184,185,187,188,190,200,202,206,207,208,209,210,216,220,224,226,242,246,254,255,264,269,270,272,279,291,294,295,296,297 and the like, and CI Pigment Red 177,179,254,264,269,272 is preferred.
[0283] The red pixel preferably further contains a yellow colorant in addition to the red colorant. The content of the yellow colorant is preferably 3 to 60 parts by mass, more preferably 5 to 50 parts by mass, and further preferably 10 to 40 parts by mass, per 100 parts by mass of the red colorant. Yellow colorants include CI Pigment Yellow 1, 2, 3, 4, 5, 6, 10, 11, 12, 13, 14, 15, 16, 17, 18, 20, 24, 31, 32, 34, 35, 35:1, 36, 36:1, 37, 37:1, 40, 42, 43, 53, 55, 60, 61, 62, 63, 65, 73, 74, 77, 81, 83, 86, 93, 94, 95, 97, 98, 100, 101, 104, 106, 108, 109, 110, 113, 114, 115, 116, 117, 118, 119, 120, 123, 125, 126, 127, 128, 129, 137, 138, 139, 147, 148, 150, 151, 152, 153, 154, 155, 156, 161, 162, 164, 166, 167, 168, 169, 170, 171, 172, 173, 174, 175, 176, 177, 179, 180, 181, 182, 185, 187, 188, 193, 194, 199, 213, 214, 215, 228, 231, 232, 233, 234, 235, 236, and the like, and CI Pigment Yellow 138, 139, 150, 185 is preferred.
[0284] The red pixel has a maximum transmittance of 5% or less for light having a wavelength of 400 to 550 nm, more preferably 3% or less, and even more preferably 1% or less. The average transmittance of 400 to 550 nm for light having a wavelength of 400 to 550 nm is preferably 3% or less, more preferably 1% or less, and even more preferably 0.5% or less. The minimum transmittance of 600 to 700 nm for light having a wavelength of 10% or more, more preferably 25% or more, and even more preferably 40% or more. The average transmittance of 600 to 700 nm for light having a wavelength of 80% or more, more preferably 90% or more, and even more preferably 95% or more.
[0285] The blue pixel, which is preferably used in combination with the pixel of the cured film of the present invention, preferably contains a blue colorant. The content of the blue colorant in the colorant contained in the blue pixel is preferably 40% by mass or more, more preferably 60% by mass or more. In addition, the blue pixel preferably contains 20% by mass or more of the blue colorant, more preferably 25% by mass or more, and even more preferably 30% by mass or more. The upper limit of the content of the blue colorant is preferably 80% by mass or less, more preferably 70% by mass or less, and even more preferably 60% by mass or less. Examples of the blue colorant include blue pigments such as CI Pigment Blue 1, 2, 15, 15:1, 15:2, 15:3, 15:4, 15:6, 16, 22, 29, 60, 64, 66, 79, 80, 87, and 88, and CI Pigment Blue 15:6 is preferred.
[0286] The blue pixel more preferably contains at least one selected from a purple colorant and a red colorant in addition to the blue colorant. The content of the purple colorant is preferably 10 to 90 parts by mass, more preferably 20 to 75 parts by mass, and even more preferably 30 to 60 parts by mass, relative to 100 parts by mass of the blue colorant. Examples of the purple colorant and the red colorant include purple pigments such as CI Pigment Violet 1, 19, 23, 27, 32, 37, 42, 60, and 61, and xanthene compounds. Examples of the xanthene compound include salt-forming compounds obtained by reacting a resin having a cationic group on the side chain with a xanthene acid dye, as described in paragraphs 0025 to 0077 of JP-A-2016-180834.
[0287] The blue pixel has a maximum transmittance of 50% or more for light having a wavelength of 400 to 500 nm, more preferably 60% or more, and even more preferably 70% or more. The average transmittance of 400 to 500 nm for light having a wavelength of 400 to 500 nm is preferably 40% or more, more preferably 50% or more, and even more preferably 60% or more. The minimum transmittance of 550 to 700 nm for light having a wavelength of 30% or less, more preferably 20% or less, and even more preferably 10% or less. The average transmittance of 550 to 700 nm for light having a wavelength of 25% or less, more preferably 10% or less, and even more preferably 5% or less.
[0288] <Structure> The structure of the present invention has a green pixel, a red pixel, and a blue pixel obtained by using the above-mentioned colored composition of the present invention. The green pixel preferably has the spectral characteristics described in the above-mentioned section on the cured film of the present invention. In addition, the red pixel and the blue pixel preferably have the spectral characteristics described in the above-mentioned section on the color filter.
[0289] <Pixel formation method> A method for forming pixels will now be described. By using the colored composition of the present invention, for example, green pixels can be formed.
[0290] The method for forming pixels preferably includes a step of forming a colored composition layer by applying a colored composition on a support, a step of exposing the colored composition layer in a pattern, and a step of developing the colored composition layer after exposure. In forming pixels, it is preferable to perform all steps at a temperature of 150°C or less. In the present invention, "perform all steps at a temperature of 150°C or less" means that all steps of forming pixels using a colored composition are performed at a temperature of 150°C or less. When a step of heating is further provided after developing the colored composition layer after exposure, this heating step is also performed at a temperature of 150°C or less. Each step will be described in detail below.
[0291] In the step of forming the coloring composition layer, the coloring composition is applied onto a support to form the coloring composition layer. Examples of the support include a glass substrate, a polycarbonate substrate, a polyester substrate, an aromatic polyamide substrate, a polyamideimide substrate, and a polyimide substrate. An organic light-emitting layer may be formed on these substrates. In addition, an undercoat layer may be provided on the substrate to improve adhesion with an upper layer, prevent diffusion of a substance, or flatten the surface. The undercoat layer may be formed, for example, using a composition obtained by removing a colorant from the above-mentioned coloring composition of the present invention. The surface contact angle of the undercoat layer is preferably 20 to 70° when measured with diiodomethane. In addition, it is preferably 30 to 80° when measured with water. If the surface contact angle of the undercoat layer is within the above range, the resin composition has good wettability. The surface contact angle of the undercoat layer can be adjusted, for example, by adding a surfactant.
[0292] The coloring composition can be applied by a known method. For example, a dropping method (drop casting), a slit coating method, a spray method, a roll coating method, a rotary coating method (spin coating), a casting coating method, a slit and spin method, a pre-wetting method (for example, a method described in JP-A-2009-145395), various printing methods such as ejection printing such as inkjet (for example, on-demand method, piezo method, thermal method), nozzle jet, flexographic printing, screen printing, gravure printing, reverse offset printing, and metal mask printing method, a transfer method using a mold, and a nanoimprint method can be mentioned. The application method in inkjet is not particularly limited, and examples thereof include the method shown in "Expanding and Usable Inkjet - Infinite Possibilities Seen in Patents -, published in February 2005, Sumibe Techno Research" (particularly pages 115 to 133), and the methods described in JP 2003-262716 A, JP 2003-185831 A, JP 2003-261827 A, JP 2012-126830 A, JP 2006-169325 A, etc. In addition, for the application method of the coloring composition, the descriptions in WO 2017 / 030174 and WO 2017 / 018419 can be referred to, and the contents of these are incorporated herein.
[0293] The colored composition layer formed on the support may be dried (prebaked). When prebaking is performed, the prebaking temperature is preferably 80° C. or less, more preferably 70° C. or less, even more preferably 60° C. or less, and particularly preferably 50° C. or less. The lower limit may be, for example, 40° C. or more. The prebaking time is preferably 10 to 3600 seconds. Prebaking can be performed using a hot plate, an oven, or the like.
[0294] Next, the coloring composition layer is exposed to light in a pattern (exposure step). For example, the coloring composition layer can be exposed to light in a pattern by using a stepper exposure machine or a scanner exposure machine through a mask having a predetermined mask pattern. This allows the exposed part to be cured.
[0295] Examples of radiation (light) that can be used for exposure include g-line and i-line. Light with a wavelength of 300 nm or less (preferably light with a wavelength of 180 to 300 nm) can also be used. Examples of light with a wavelength of 300 nm or less include KrF line (wavelength 248 nm) and ArF line (wavelength 193 nm), with KrF line (wavelength 248 nm) being preferred. Long-wave light sources with wavelengths of 300 nm or more can also be used.
[0296] In addition, during exposure, light may be continuously irradiated or may be irradiated in pulses (pulse exposure). Pulse exposure is an exposure method in which light irradiation and pauses are repeated in a short cycle (for example, millisecond level or less). In the case of pulse exposure, the pulse width is preferably 100 nanoseconds (ns) or less, more preferably 50 nanoseconds or less, and even more preferably 30 nanoseconds or less. There is no particular limit to the lower limit of the pulse width, but it can be 1 femtosecond (fs) or more, and can also be 10 femtoseconds or more. The frequency is preferably 1 kHz or more, more preferably 2 kHz or more, and even more preferably 4 kHz or more. The upper limit of the frequency is preferably 50 kHz or less, more preferably 20 kHz or less, and even more preferably 10 kHz or less. The maximum instantaneous illuminance is 50,000,000 W / m 2 More preferably, it is 100,000,000 W / m 2 More preferably, it is 200,000,000 W / m or more. 2 It is more preferable that the upper limit of the maximum instantaneous illuminance is 1000000000 W / m 2 Preferably, it is less than 800,000,000 W / m 2 More preferably, it is 500,000,000 W / m or less. 2 It is more preferable that the pulse width is equal to or less than 1000 s. The pulse width refers to the time during which light is irradiated in a pulse period. The frequency refers to the number of pulse periods per second. The maximum instantaneous irradiance refers to the average irradiance during the time during which light is irradiated in a pulse period. The pulse period refers to a period in which light irradiation and pause in pulse exposure constitute one cycle.
[0297] The irradiation amount (exposure amount) is, for example, 0.03 to 2.5 J / cm 2 The lower limit is preferably 0.05 J / cm 2 More preferably, it is 0.2 J / cm or more. 2 More preferably, it is 0.5 J / cm or more. 2 More preferably, it is 0.8 J / cm or more.2 More preferably, it is 1.0 J / cm or more. 2 It is even more preferable that the upper limit is 2.0 J / cm or more. 2 More preferably, it is 1.5 J / cm or less. 2 The exposure illuminance can be appropriately set, for example, to 50 mW / cm or less. 2 ~10W / cm 2 The lower limit of the exposure illuminance is preferably 500 mW / cm 2 More preferably, it is 800 mW / cm or more. 2 More preferably, it is 1000 mW / cm or more. 2 It is even more preferable that the upper limit of the exposure illuminance is 10 W / cm or more. 2 It is preferable that the power consumption is less than 7 W / cm 2 More preferably, it is 5 W / cm or less. 2 It is even more preferable that:
[0298] The oxygen concentration during exposure can be appropriately selected. In addition to exposure in air, exposure can be performed in a low-oxygen atmosphere with an oxygen concentration of 19 volume% or less (e.g., 15 volume%, 5 volume%, or substantially oxygen-free), or in a high-oxygen atmosphere with an oxygen concentration of more than 21 volume% (e.g., 22 volume%, 30 volume%, or 50 volume%). The oxygen concentration and exposure illuminance can be appropriately combined, for example, at an oxygen concentration of 10 volume% and an illuminance of 1 W / cm. 2 , oxygen concentration 35% by volume, illuminance 2W / cm 2 etc.
[0299] In addition, light with a wavelength of more than 350 nm and less than 380 nm (preferably i-line) is irradiated at 1 J / cm 2 It is also preferable to expose the colored composition layer by irradiation with the above-mentioned exposure amount. By exposing the colored composition layer in this manner, it is possible to sufficiently cure the colored composition layer, and it is possible to produce pixels having excellent properties such as solvent resistance.
[0300] Next, the colored composition layer after exposure is developed. That is, the unexposed portion of the colored composition layer is developed and removed to form a pattern (pixel). The unexposed portion of the colored composition layer can be developed and removed using a developer. As a result, the colored composition layer in the unexposed portion in the exposure step is dissolved into the developer, and only the photocured portion remains. The temperature of the developer is preferably, for example, 20 to 30°C. The development time is preferably 20 to 180 seconds. In addition, in order to improve the removability of residues, the process of shaking off the developer every 60 seconds and supplying new developer may be repeated several times.
[0301] Examples of the developer include organic solvents and alkaline developers, and alkaline developers are preferred. As the alkaline developer, an alkaline aqueous solution (alkaline developer) obtained by diluting an alkaline agent with pure water is preferred. Examples of the alkaline agent include organic alkaline compounds such as ammonia, ethylamine, diethylamine, dimethylethanolamine, diglycolamine, diethanolamine, hydroxylamine, ethylenediamine, tetramethylammonium hydroxide, tetraethylammonium hydroxide, tetrapropylammonium hydroxide, tetrabutylammonium hydroxide, ethyltrimethylammonium hydroxide, benzyltrimethylammonium hydroxide, dimethylbis(2-hydroxyethyl)ammonium hydroxide, choline, pyrrole, piperidine, and 1,8-diazabicyclo-[5.4.0]-7-undecene, and inorganic alkaline compounds such as sodium hydroxide, potassium hydroxide, sodium carbonate, sodium hydrogencarbonate, sodium silicate, and sodium metasilicate. As the alkaline agent, compounds with a large molecular weight are preferred in terms of the environment and safety. The concentration of the alkaline agent in the alkaline aqueous solution is preferably 0.001 to 10% by mass, more preferably 0.01 to 1% by mass. The developer may further contain a surfactant. Examples of the surfactant include the surfactants described above, and nonionic surfactants are preferred. The developer may be produced as a concentrated solution from the viewpoint of convenience of transportation and storage, and then diluted to a required concentration when used. The dilution ratio is not particularly limited, but can be set in the range of, for example, 1.5 to 100 times. It is also preferred to wash (rinse) with pure water after development. It is also preferred to rinse by supplying a rinsing liquid to the colored composition layer after development while rotating the support on which the colored composition layer after development has been formed. It is also preferred to perform the rinsing by moving the nozzle for ejecting the rinsing liquid from the center of the support to the periphery of the support. In this case, the nozzle may be moved while gradually decreasing the moving speed when moving the nozzle from the center of the support to the periphery. By performing the rinsing in this manner, the in-plane variation of the rinsing can be suppressed. The same effect can also be obtained by gradually decreasing the rotation speed of the support while moving the nozzle from the center to the periphery of the support.
[0302] After development and drying, it is also preferable to carry out additional exposure treatment or heat treatment (post-baking). Additional exposure treatment and post-baking are hardening treatments after development to complete hardening.
[0303] When post-baking is performed, the heating temperature is preferably 150°C or less. The upper limit of the heating temperature is more preferably 120°C or less, and even more preferably 100°C or less. The lower limit of the heating temperature is not particularly limited as long as it can promote the curing of the composition, but is more preferably 50°C or more, and even more preferably 75°C or more. The heating time is preferably 1 minute or more, more preferably 5 minutes or more, and even more preferably 10 minutes or more. There is no particular limit to the upper limit, but from the viewpoint of productivity, 20 minutes or less is preferable. It is also preferable to perform post-baking under an inert gas atmosphere. According to this embodiment, thermal polymerization can be progressed with very high efficiency without being inhibited by oxygen, and even when pixels are manufactured at a temperature of 120°C or less throughout the entire process, pixels having good flatness and excellent properties such as solvent resistance can be manufactured. Examples of inert gases include nitrogen gas, argon gas, helium gas, etc., and nitrogen gas is preferable. The oxygen concentration during post-baking is preferably 100 ppm or less.
[0304] When performing additional exposure treatment, it is preferable to expose by irradiating light having a wavelength of 254 to 350 nm. In a more preferred embodiment, the step of patternwise exposing the coloring composition layer (exposure before development) is performed by irradiating the coloring composition layer with light having a wavelength of more than 350 nm and not more than 380 nm (preferably light having a wavelength of 355 to 370 nm, more preferably i-line), and the additional exposure treatment (exposure after development) is preferably performed by irradiating the coloring composition layer after development with light having a wavelength of 254 to 350 nm (preferably light having a wavelength of 254 nm). According to this embodiment, the coloring composition layer can be appropriately cured by the first exposure (exposure before development), and the entire coloring composition layer can be almost completely cured by the next exposure (exposure after development). As a result, even under low temperature conditions, the coloring composition layer can be sufficiently cured to form pixels having excellent properties such as solvent resistance, adhesion, and rectangularity. When exposure is performed in two stages like this, the coloring composition is used as a photopolymerization initiator, and the absorption coefficient at a wavelength of 365 nm in methanol is 1.0 × 10 3 Photopolymerization initiator A1 with a concentration of 1.0×10 at 365 nm in methanol and a concentration of 1.0×10 2 mL / gcm or less and an extinction coefficient at a wavelength of 254 nm of 1.0 x 10 3 It is preferable to use a photopolymerization initiator A2 containing the photopolymerization initiator A2 at a concentration of 1 mL / gcm or more.
[0305] Exposure after development can be carried out, for example, using an ultraviolet photoresist curing device, which may irradiate light having a wavelength of, for example, 254 to 350 nm as well as other light (for example, i-line).
[0306] Furthermore, the exposure source spectrum when performing additional exposure treatment is preferably a continuous spectrum, and from the viewpoint of improving solvent resistance and adhesion to the substrate, it is preferable that it has a spectral distribution different from that of the exposure before development, for example, the following radiations can be mentioned. Among them, (b) and (c) are preferred in that they can achieve a higher level of improvement in solvent resistance and adhesion to the substrate. Furthermore, when the (A) colorant contains a dye, the dye generally absorbs ultraviolet light or short-wavelength visible light and may be photodecomposed, so radiation (c) with fewer high-intensity components on the short-wavelength side is preferred. (a) Radiation having a different spectral distribution from that of the exposure light before development, and in which the peak intensity at a wavelength of 313 nm (j-line) is 1 / 6 or more and less than 1 / 3 of the peak intensity at a wavelength of 365 nm (i-line). (b) Radiation having a different spectral distribution from that of the exposure light before development, the peak intensity at a wavelength of 313 nm (j-line) being 1 / 3 or more of the peak intensity at a wavelength of 365 nm (i-line). There is no particular upper limit to the peak intensity at a wavelength of 313 nm, but it is preferably smaller than the peak intensity at a wavelength of 365 nm, and more preferably 3 / 4 or less. (c) Radiation having a different spectral distribution from that of the exposure light before development, including wavelengths of 405 nm (h-line) and 436 nm (g-line), with peak intensities at wavelengths of 313 nm (j-line) and 365 nm (i-line) being 1 / 4 or less, preferably 1 / 10 or less, and more preferably 1 / 20 of the smaller of the peak intensities at wavelengths of 405 nm (h-line) and 436 nm (g-line). Note that there is no particular lower limit for the peak intensities at wavelengths of 313 nm (j-line) and 365 nm (i-line). In this case, the exposure before development is preferably radiation having a wavelength of 365 nm (i-line), 405 nm (h-line), and 436 nm (g-line), and the peak intensity at a wavelength of 313 nm (j-line) is less than 1 / 6 of the peak intensity at a wavelength of 365 nm (i-line).
[0307] Radiation exhibiting such spectral characteristics can be obtained, for example, by using a light source exhibiting the above-mentioned spectral characteristics, or by passing radiation emitted from a high-pressure mercury lamp through an ultraviolet cut filter or a bandpass filter.
[0308] The exposure dose after development is 0.03 to 4.0 J / cm 2 is preferable, and 0.05 to 3.5 J / cm 2 The difference in wavelength between the light used for exposure before development and the light used for exposure after development is preferably 200 nm or less, and more preferably 100 to 150 nm.
[0309] <Display device> The display device of the present invention has the above-mentioned cured film of the present invention. Examples of the display device include liquid crystal display devices and organic electroluminescence display devices. The definition of the display device and details of each display device are described in, for example, "Electronic Display Devices" (written by Sasaki Akio, published by Kogyo Chosakai Co., Ltd. in 1990) and "Display Devices" (written by Ibuki Yoshiaki, published by Sangyo Tosho Co., Ltd. in 1989). Liquid crystal display devices are described in, for example, "Next Generation Liquid Crystal Display Technology" (edited by Uchida Tatsuo, published by Kogyo Chosakai Co., Ltd. in 1994). There are no particular limitations on the liquid crystal display device to which the present invention can be applied, and the present invention can be applied to various types of liquid crystal display devices described in the above "Next Generation Liquid Crystal Display Technology."
[0310] The organic electroluminescence display device may have a light source made of a white organic electroluminescence element. The white organic electroluminescence element is preferably a tandem structure. The tandem structure of the organic electroluminescence element is described in JP 2003-045676 A, edited by Akiyoshi Mikami, "The Frontline of Organic EL Technology Development - High Brightness, High Precision, Long Life, Know-how Collection", Technical Information Association, pp. 326-328, 2008, etc. The spectrum of white light emitted by the organic EL element preferably has strong maximum emission peaks in the blue region (430 nm to 485 nm), green region (530 nm to 580 nm), and yellow region (580 nm to 620 nm). In addition to these emission peaks, it is more preferable that the organic EL element has a maximum emission peak in the red region (650 nm to 700 nm).
[0311] The organic electroluminescence display device may have a lens on the color filter. The lens may have various shapes derived by optical system design, such as a convex shape and a concave shape. For example, a concave shape (concave lens) can easily improve the light collecting property. The lens may be in direct contact with the color filter, or another layer such as an adhesion layer or a planarization layer may be provided between the lens and the color filter. The lens may be arranged and used in the manner described in International Publication No. WO 2018 / 135189.
[0312] <Solid-state imaging element> The colored composition and the cured film of the present invention can also be used for a solid-state imaging device. The configuration of the solid-state imaging device is not particularly limited as long as it has the cured film of the present invention and functions as a solid-state imaging device, and examples thereof include the following configurations.
[0313] The substrate has a plurality of photodiodes constituting a light receiving area of a solid-state imaging device (such as a CCD (charge-coupled device) image sensor or a CMOS (complementary metal oxide semiconductor) image sensor) and a transfer electrode made of polysilicon or the like, a light shielding film having an opening only for the light receiving portion of the photodiode on the photodiode and the transfer electrode, a device protection film made of silicon nitride or the like formed on the light shielding film so as to cover the entire light shielding film and the light receiving portion of the photodiode, and a color filter on the device protection film. Furthermore, the device protection film may have a light collecting means (e.g., a microlens, etc., the same below) on the device protection film and below the color filter (on the side closer to the substrate), or a light collecting means on the color filter. The pixels of the color filter may be embedded in a space partitioned by partitions, for example, in a lattice shape. In this case, the refractive index of the partitions is preferably lower than the refraction of the pixels. Examples of imaging devices having such a structure include those described in JP 2012-227478 A, JP 2014-179577 A, WO 2018 / 043654 A, and U.S. Patent Application Publication No. 2018 / 0040656 A. Imaging devices equipped with a solid-state imaging element can be used for digital cameras, electronic devices having an imaging function (such as mobile phones), as well as vehicle-mounted cameras and surveillance cameras. EXAMPLES
[0314] The present invention will be specifically described below with reference to examples. The materials, amounts, ratios, processing contents, processing procedures, etc. shown in the following examples can be appropriately changed without departing from the spirit of the present invention. Therefore, the scope of the present invention is not limited to the specific examples shown below.
[0315] <Preparation of pigment dispersion> (Pigment dispersion P-G1) 10.40 parts by mass of CI Pigment Green 7 (average primary particle diameter 50 nm), 2.60 parts by mass of Pigment Derivative 1, 6.50 parts by mass of Dispersant 1, and 80.50 parts by mass of propylene glycol monomethyl ether acetate (PGMEA) were mixed, and the mixture was dispersed for 5 hours in an Eiger mill (Eiger Japan, "Mini Model M-250MKII") using zirconia beads with a diameter of 1 mm, and then filtered through a filter with a pore size of 5 μm to prepare pigment dispersion P-G1.
[0316] (Pigment dispersion P-G2) 12.60 parts by mass of CI Pigment Green 36, 1.26 parts by mass of Pigment Derivative 1, 5.04 parts by mass of Dispersant 1, and 81.10 parts by mass of PGMEA were mixed, and then dispersed for 5 hours in an Eiger mill (Eiger Japan, "Mini Model M-250MKII") using zirconia beads having a diameter of 1 mm. The mixture was then filtered through a filter having a pore size of 5 μm to prepare pigment dispersion P-G2.
[0317] (Pigment dispersion P-G3) 12.60 parts by mass of CI Pigment Green 58, 1.26 parts by mass of Pigment Derivative 1, 5.04 parts by mass of Dispersant 1, and 81.10 parts by mass of PGMEA were mixed, and then dispersed for 5 hours in an Eiger mill (Eiger Japan, "Mini Model M-250MKII") using zirconia beads having a diameter of 1 mm. The mixture was then filtered through a filter having a pore size of 5 μm to prepare pigment dispersion P-G3.
[0318] (Pigment dispersion P-G4) 12.60 parts by mass of CI Pigment Green 59, 1.26 parts by mass of Pigment Derivative 1, 5.04 parts by mass of Dispersant 1, and 81.10 parts by mass of PGMEA were mixed, and then dispersed for 5 hours in an Eiger mill (Eiger Japan, "Mini Model M-250MKII") using zirconia beads having a diameter of 1 mm. The mixture was then filtered through a filter having a pore size of 5 μm to prepare pigment dispersion P-G4.
[0319] (Pigment dispersion P-G5) 10.40 parts by mass of CI Pigment Green 7 (average primary particle diameter: 50 nm), 2.60 parts by mass of Pigment Derivative 3, 6.50 parts by mass of Dispersant 3, and 80.50 parts by mass of PGMEA were mixed, and then dispersed for 5 hours in an Eiger mill (Eiger Japan, "Mini Model M-250MKII") using zirconia beads with a diameter of 1 mm. The mixture was then filtered through a filter with a pore size of 5 μm to prepare pigment dispersion P-G5.
[0320] (Pigment dispersion P-G6) 12.60 parts by mass of CI Pigment Green 59, 1.26 parts by mass of Pigment Derivative 3, 5.04 parts by mass of Dispersant 3, and 81.10 parts by mass of PGMEA were mixed, and then dispersed for 5 hours in an Eiger mill (Eiger Japan, "Mini Model M-250MKII") using zirconia beads having a diameter of 1 mm. The mixture was then filtered through a filter having a pore size of 5 μm to prepare pigment dispersion P-G6.
[0321] (Pigment dispersion P-G7) 14 parts by mass of CI Pigment Green 7 (average primary particle diameter 50 nm), 0.49 parts by mass of polyethyleneimine (Epomin SP-003, manufactured by Nippon Shokubai Co., Ltd.), 4.41 parts by mass of Dispersant 4, and 81.1 parts by mass of PGMEA were mixed, and the mixture was dispersed for 5 hours in an Eiger mill ("Mini Model M-250MKII" manufactured by Eiger Japan Co., Ltd.) using zirconia beads having a diameter of 1 mm, and then filtered through a filter with a pore size of 5 μm to prepare pigment dispersion liquid P-G7.
[0322] (Pigment dispersion P-G8) 14 parts by mass of CI Pigment Green 59, 0.49 parts by mass of polyethyleneimine (Epomin SP-003, manufactured by Nippon Shokubai Co., Ltd.), 4.41 parts by mass of dispersant 4, and 81.1 parts by mass of PGMEA were mixed, and the mixture was dispersed for 5 hours in an Eiger mill ("Mini Model M-250MKII" manufactured by Eiger Japan Co., Ltd.) using zirconia beads having a diameter of 1 mm, and then filtered through a filter with a pore size of 5 μm to prepare pigment dispersion liquid P-G8.
[0323] (Pigment dispersion P-G9) 14 parts by mass of CI Pigment Green 7 (average primary particle diameter: 50 nm), 8.2 parts by mass of Dispersant 5, 6.8 parts by mass of Dispersant 6, and 72.5 parts by mass of PGMEA were mixed, and then dispersed for 5 hours in an Eiger mill (Eiger Japan, "Mini Model M-250MKII") using zirconia beads with a diameter of 1 mm. The mixture was then filtered through a filter with a pore size of 5 μm to prepare pigment dispersion P-G9.
[0324] (Pigment dispersion P-G10) 14 parts by mass of CI Pigment Green 59, 8.2 parts by mass of Dispersant 5, 6.8 parts by mass of Dispersant 6, and 72.5 parts by mass of PGMEA were mixed, and then dispersed for 5 hours in an Eiger mill (Eiger Japan, "Mini Model M-250MKII") using zirconia beads with a diameter of 1 mm. The mixture was then filtered through a filter with a pore size of 5 μm to prepare pigment dispersion P-G10.
[0325] (Pigment dispersion P-Y1) 12.0 parts by mass of CI Pigment Yellow 150, 1.2 parts by mass of Pigment Derivative 2, 6.8 parts by mass of Dispersant 2, and 80.0 parts by mass of PGMEA were mixed, and then dispersed for 5 hours in an Eiger mill (Eiger Japan, "Mini Model M-250MKII") using zirconia beads having a diameter of 1 mm. The mixture was then filtered through a filter having a pore size of 5 μm to prepare pigment dispersion P-Y1.
[0326] (Pigment dispersion P-Y2) 12.0 parts by mass of CI Pigment Yellow 129, 1.2 parts by mass of Pigment Derivative 1, 6.8 parts by mass of Dispersant 1, and 80.0 parts by mass of PGMEA were mixed, and then dispersed for 5 hours in an Eiger mill (Eiger Japan, "Mini Model M-250MKII") using zirconia beads having a diameter of 1 mm. The mixture was then filtered through a filter having a pore size of 5 μm to prepare pigment dispersion P-Y2.
[0327] (Pigment dispersion P-Y3) 12.0 parts by mass of CI Pigment Yellow 139, 1.2 parts by mass of Pigment Derivative 1, 6.8 parts by mass of Dispersant 1, and 80.0 parts by mass of PGMEA were mixed, and then dispersed for 5 hours in an Eiger mill (Eiger Japan, "Mini Model M-250MKII") using zirconia beads having a diameter of 1 mm. The mixture was then filtered through a filter having a pore size of 5 μm to prepare pigment dispersion P-Y3.
[0328] (Pigment dispersion P-Y4) 12.0 parts by mass of CI Pigment Yellow 185, 1.2 parts by mass of Pigment Derivative 1, 6.8 parts by mass of Dispersant 1, and 80.0 parts by mass of PGMEA were mixed, and then dispersed for 5 hours in an Eiger mill (Eiger Japan, "Mini Model M-250MKII") using zirconia beads having a diameter of 1 mm. The mixture was then filtered through a filter having a pore size of 5 μm to prepare pigment dispersion P-Y4.
[0329] (Pigment dispersion P-Y5) 12.0 parts by mass of CI Pigment Yellow 185, 1.2 parts by mass of Pigment Derivative 3, 6.8 parts by mass of Dispersant 3, and 80.0 parts by mass of PGMEA were mixed, and then dispersed for 5 hours in an Eiger mill (Eiger Japan, "Mini Model M-250MKII") using zirconia beads having a diameter of 1 mm. The mixture was then filtered through a filter having a pore size of 5 μm to prepare pigment dispersion P-Y5.
[0330] (Pigment dispersion P-Y6) 14 parts by mass of CI Pigment Yellow 185, 0.49 parts by mass of polyethyleneimine (Epomin SP-003, manufactured by Nippon Shokubai Co., Ltd.), 4.41 parts by mass of dispersant 4, and 81.1 parts by mass of PGMEA were mixed, and the mixture was dispersed for 5 hours in an Eiger mill ("Mini Model M-250MKII" manufactured by Eiger Japan Co., Ltd.) using zirconia beads having a diameter of 1 mm, and then filtered through a filter with a pore size of 5 μm to prepare pigment dispersion liquid P-Y6.
[0331] (Pigment dispersion P-Y7) 14 parts by mass of CI Pigment Yellow 129, 0.49 parts by mass of polyethyleneimine (Epomin SP-003, manufactured by Nippon Shokubai Co., Ltd.), 4.41 parts by mass of dispersant 4, and 81.1 parts by mass of PGMEA were mixed, and the mixture was dispersed for 5 hours in an Eiger mill ("Mini Model M-250MKII" manufactured by Eiger Japan Co., Ltd.) using zirconia beads having a diameter of 1 mm, and then filtered through a filter with a pore size of 5 μm to prepare pigment dispersion liquid P-Y7.
[0332] (Pigment dispersion P-Y8) 14 parts by mass of CI Pigment Yellow 139, 0.49 parts by mass of polyethyleneimine (Epomin SP-003, manufactured by Nippon Shokubai Co., Ltd.), 4.41 parts by mass of dispersant 4, and 81.1 parts by mass of PGMEA were mixed, and the mixture was dispersed for 5 hours in an Eiger mill ("Mini Model M-250MKII" manufactured by Eiger Japan Co., Ltd.) using zirconia beads having a diameter of 1 mm, and then filtered through a filter with a pore size of 5 μm to prepare pigment dispersion liquid P-Y8.
[0333] (Pigment dispersion P-Y9) 14 parts by mass of CI Pigment Yellow 150, 0.49 parts by mass of polyethyleneimine (Epomin SP-003, manufactured by Nippon Shokubai Co., Ltd.), 4.41 parts by mass of dispersant 4, and 81.1 parts by mass of PGMEA were mixed, and the mixture was dispersed for 5 hours in an Eiger mill ("Mini Model M-250MKII" manufactured by Eiger Japan Co., Ltd.) using zirconia beads having a diameter of 1 mm, and then filtered through a filter with a pore size of 5 μm to prepare pigment dispersion liquid P-Y9.
[0334] (Pigment dispersion P-Y10) 12.25 parts by mass of CI Pigment Yellow 185, 1.75 parts by mass of Pigment Derivative 4, 10 parts by mass of Dispersant 7, and 76 parts by mass of PGMEA were mixed, and then dispersed for 5 hours in an Eiger mill (Eiger Japan, "Mini Model M-250MKII") using zirconia beads having a diameter of 1 mm. The mixture was then filtered through a filter having a pore size of 5 μm to prepare pigment dispersion P-Y10.
[0335] (Pigment dispersion P-Y11) 12.25 parts by mass of CI Pigment Yellow 129, 1.75 parts by mass of Pigment Derivative 4, 10 parts by mass of Dispersant 7, and 76 parts by mass of PGMEA were mixed, and then dispersed for 5 hours in an Eiger mill (Eiger Japan, "Mini Model M-250MKII") using zirconia beads having a diameter of 1 mm. The mixture was then filtered through a filter having a pore size of 5 μm to prepare pigment dispersion P-Y11.
[0336] (Pigment dispersion P-Y12) 12.25 parts by mass of CI Pigment Yellow 139, 1.75 parts by mass of Pigment Derivative 4, 10 parts by mass of Dispersant 7, and 76 parts by mass of PGMEA were mixed, and then dispersed for 5 hours in an Eiger mill (Eiger Japan, "Mini Model M-250MKII") using zirconia beads having a diameter of 1 mm. The mixture was then filtered through a filter having a pore size of 5 μm to prepare pigment dispersion P-Y12.
[0337] (Pigment dispersion P-Y13) 12.25 parts by mass of CI Pigment Yellow 150, 1.75 parts by mass of Pigment Derivative 4, 10 parts by mass of Dispersant 7, and 76 parts by mass of PGMEA were mixed, and then dispersed for 5 hours in an Eiger mill (Eiger Japan, "Mini Model M-250MKII") using zirconia beads having a diameter of 1 mm. The mixture was then filtered through a filter having a pore size of 5 μm to prepare pigment dispersion P-Y14.
[0338] (Pigment dispersion P-Y14) 12.0 parts by mass of Yellow Pigment 1, 1.2 parts by mass of Pigment Derivative 1, 6.8 parts by mass of Dispersant 8, and 80.0 parts by mass of PGMEA were mixed, and then dispersed for 5 hours in an Eiger mill (Eiger Japan, "Mini Model M-250MKII") using zirconia beads having a diameter of 1 mm. The mixture was then filtered through a filter having a pore size of 5 μm to prepare pigment dispersion P-Y14.
[0339] Yellow pigment 1: Compound having the following structure (isoindoline compound) [ka]
[0340] Pigment derivative 1: A compound having the following structure [ka] Pigment derivative 2: A compound having the following structure [ka] Pigment derivative 3: A compound having the following structure [ka]
[0341] Pigment derivative 4: A compound having the following structure [ka]
[0342] Dispersant 1: Resin having the following structure (weight average molecular weight: 24,000; the number attached to the main chain is the molar ratio, and the number attached to the side chain is the number of repeating units). [ka] Dispersant 2: Resin having the following structure [ka] Dispersant 3: Resin with the following structure (the number attached to the main chain is the molar ratio, and the number attached to the side chain is the number of repeating units. Weight average molecular weight 21,000, acid value 36 mgKOH / g) [ka]
[0343] Dispersant 4: A resin synthesized by the following method. 50 parts by mass of methyl methacrylate, 30 parts by mass of n-butyl methacrylate, 20 parts by mass of t-butyl methacrylate, and 45.4 parts by mass of propylene glycol monomethyl ether acetate (PGMEA) were charged into a reaction vessel, and the atmospheric gas was replaced with nitrogen gas. The inside of the reaction vessel was heated to 70°C, 6 parts by mass of 3-mercapto-1,2-propanediol was added, and 0.12 parts by mass of AIBN (azobisisobutyronitrile) was further added, and the reaction was allowed to proceed for 12 hours. It was confirmed that 95% had reacted by measuring the solid content. Next, 9.7 parts by mass of pyromellitic anhydride, 70.3 parts by mass of PGMEA, and 0.20 parts by mass of DBU (1,8-diazabicyclo-[5.4.0]-7-undecene) as a catalyst were added, and the reaction was allowed to proceed for 7 hours at 120°C. The reaction was terminated after confirming that 98% or more of the acid anhydride had been half-esterified by measuring the acid value, to obtain a resin having the following structure and an acid value of 43 mgKOH / g and a weight average molecular weight of 9,000. [ka]
[0344] Dispersant 5: 40 mass% PGMEA solution of resin synthesized by the following method. A reaction vessel equipped with a gas inlet tube, a condenser, an agitator, and a thermometer was charged with 133 parts by mass of methoxypropyl acetate, and the temperature was raised to 100°C while replacing with nitrogen. 40 parts by mass of N,N-dimethylaminoethyl methacrylate, 160 parts by mass of n-butyl methacrylate, 61 parts by mass of methoxypropyl acetate, and 6 parts by mass of 2,2'-azobis(2,4-dimethylvaleronitrile) were charged into a dropping vessel, stirred until homogenous, and then dropped into the reaction vessel over 2 hours, and then reacted at the same temperature for 3 hours to obtain a resin (vinyl resin having a tertiary amino group) with an amine value of 61 mgKOH / g and a weight average molecular weight of 8700. PGMEA was added to the obtained resin to adjust the solid content concentration to 40% by mass, and dispersant 5 was obtained.
[0345] Dispersant 6: 40 mass% PGMEA solution of resin synthesized by the following method. In a reaction vessel equipped with a gas inlet tube, a temperature controller, a condenser, and a stirrer, 10 parts by mass of methacrylic acid, 20 parts by mass of methyl methacrylate, 90 parts by mass of 2-methoxyethyl methacrylate, 40 parts by mass of tert-butyl methacrylate, 20 parts by mass of n-butyl acrylate, 20 parts by mass of tert-butyl acrylate, and 50 parts by mass of PGMEA were charged and replaced with nitrogen gas. The reaction vessel was heated to 50°C and stirred while 12 parts by mass of 3-mercapto-1,2-propanediol was added. The temperature was raised to 90°C, and a solution obtained by adding 0.1 parts by mass of 2,2'-azobisisobutyronitrile to 90 parts by mass of PGEMA was added and reacted for 7 hours. It was confirmed that 95% of the monomer had reacted by non-volatile content measurement. Next, 35 parts by mass of trimellitic anhydride, 50 parts by mass of PGMEA, and 0.4 parts by mass of 1,8-diazabicyclo-[5.4.0]-7-undecene as a catalyst were added, and the mixture was reacted at 100° C. for 7 hours. The reaction was terminated when it was confirmed by measuring the acid value that 98% or more of the acid anhydride had been half-esterified, and a resin with an acid value of 62 mgKOH / g and a weight average molecular weight of 9000 was obtained. PGMEA was added to the obtained resin to adjust the solid content concentration to 40% by mass, and dispersant 6 was obtained.
[0346] Dispersant 7: 40 mass% PGMEA solution of resin synthesized by the following method. A reaction vessel equipped with a gas inlet tube, a temperature controller, a condenser, and a stirrer was charged with 10 parts by mass of methacrylic acid, 90 parts by mass of methyl methacrylate, 60 parts by mass of ethyl acrylate, 40 parts by mass of tert-butyl acrylate, and 50 parts by mass of PGMEA, and the atmosphere was replaced with nitrogen gas. The reaction vessel was heated to 50°C and 12 parts by mass of 3-mercapto-1,2-propanediol was added while stirring. The temperature was raised to 90°C, and a solution of 0.1 parts by mass of 2,2'-azobisisobutyronitrile added to 90 parts by mass of PGEMA was added and reacted for 7 hours. It was confirmed that 95% of the monomer had reacted by measuring the non-volatile content. Next, 19 parts by mass of pyromellitic anhydride, 50 parts by mass of PGMEA, and 0.4 parts by mass of 1,8-diazabicyclo-[5.4.0]-7-undecene as a catalyst were added, and the mixture was reacted at 100° C. for 7 hours. The reaction was terminated when it was confirmed by measuring the acid value that 98% or more of the acid anhydride had been half-esterified, and a resin with an acid value of 70 mgKOH / g and a weight average molecular weight of 10,000 was obtained. PGMEA was added to the obtained resin to adjust the solid content concentration to 40% by mass, and dispersant 7 was obtained.
[0347] Dispersant 8: BYK-LPN6919 (manufactured by BYK-Chemie)
[0348] <Preparation of Coloring Composition> The raw materials shown in the table below were mixed and stirred, and then filtered using a nylon filter having a pore size of 0.45 μm (manufactured by Nippon Pall Co., Ltd.) to prepare a colored composition.
[0349] [Table 1]
[0350] [Table 2]
[0351] [Table 3]
[0352] [Table 4]
[0353] [Table 5]
[0354] [Table 6]
[0355] [Table 7]
[0356] [Table 8]
[0357] [Table 9]
[0358] The raw materials listed in the above table are abbreviated as follows: (Pigment dispersion) P-G1 to P-G10, P-Y1 to P-Y14: The above-mentioned pigment dispersions P-G1 to P-G10, P-Y1 to P-Y14
[0359] (Photopolymerization initiator) I1: Irgacure OXE02 (BASF, oxime compound) I2: Omnirad 2959 (IGM Resins BV, hydroxyalkylphenone compound) I3: Omnirad 379 (IGM Resins BV, aminoalkylphenone compound) I4: Compound having the following structure (oxime compound) [ka] I5: Irgacure OXE01 (BASF, oxime compound)
[0360] (Compounds Having Cyclic Ether Groups) E1: EHPE3150 (manufactured by Daicel Corporation, epoxy resin with the following structure, cyclic ether group content 5.70 mmol / g, weight average molecular weight 2282, n=15, R=C6H 13 O2) [ka] E2: EPICLON N-695 (DIC Corporation, cresol novolac type epoxy resin having the following structure, cyclic ether group content 4.74 mmol / g, weight average molecular weight 3583, n=18) [ka]
[0361] E3: 40% by mass solution of epoxy resin having the following structure (cyclic ether group content: 5.33 mmol / g, weight average molecular weight: 11,000) in PGMEA [ka]
[0362] E4: 40% by mass solution of epoxy resin having the following structure (cyclic ether group content: 3.95 mmol / g, weight average molecular weight: 10,000) in PGMEA [ka]
[0363] E5: 40% by mass solution of epoxy resin having the following structure (cyclic ether group content: 5.33 mmol / g, weight average molecular weight: 10,000) in PGMEA [ka]
[0364] E6: 40% by mass PGMEA solution of epoxy resin synthesized by the following method 5.1 parts by mass of benzyl methacrylate, 0.8 parts by mass of N-phenylmaleimide, 0.6 parts by mass of styrene, and 13.2 parts by mass of glycidyl methacrylate were placed in a reaction vessel together with 78.9 parts by mass of propylene glycol methyl ether acetate, and then the mixture was heated to 75°C in a nitrogen atmosphere. After the reactants reached 75°C, 1.2 parts by mass of a thermal polymerization initiator (V-65, Fujifilm Wako Pure Chemical Industries, Ltd.) was added, and the mixture was allowed to react for 12 hours. A thermal polymerization inhibitor and a catalyst were added to the resin solution thus obtained, and then 0.1 parts by mass of methacrylic acid was added in an air atmosphere, and the mixture was allowed to react for 16 hours while maintaining the temperature at 120°C to synthesize an epoxy resin. The weight average molecular weight of this epoxy resin was 4500, the content of the repeating unit of the (meth)acrylic structure in which the branched chain end was substituted with an epoxy group was 49 mol%, and the content of the repeating unit of the (meth)acrylic structure in which the branched chain end was substituted with an alkenyl group was 21 mol%.
[0365] E7: 40% by mass PGMEA solution of epoxy resin synthesized by the following method 5.1 parts by mass of benzyl methacrylate, 0.8 parts by mass of N-phenylmaleimide, 0.6 parts by mass of styrene, and 13.2 parts by mass of 3,4-epoxycyclohexylmethyl methacrylate were added to a reaction vessel together with 78.9 parts by mass of propylene glycol methyl ether acetate, and then the mixture was heated to 75°C in a nitrogen atmosphere. After the reactants reached 75°C, 1.2 parts by mass of a thermal polymerization initiator (V-65, Fujifilm Wako Pure Chemical Industries, Ltd.) was added, and the mixture was allowed to react for 12 hours. After adding a thermal polymerization inhibitor and a catalyst to the resin solution thus obtained, 0.1 parts by mass of methacrylic acid was added in an air atmosphere, and the mixture was allowed to react for 16 hours while maintaining the temperature at 120°C to synthesize an epoxy resin. This epoxy resin had a weight average molecular weight of 4700, a content of repeating units having a (meth)acrylic structure whose branched chain terminals were substituted with epoxy groups was 49 mol %, and a content of repeating units having a (meth)acrylic structure whose branched chain terminals were substituted with alkenyl groups was 21 mol %.
[0366] E8: Denacol EX-810 (manufactured by Nagase ChemteX Corporation, ethylene glycol diglycidyl ether, molecular weight 174)
[0367] E9: 40% by mass solution of resin (weight average molecular weight 9200) with the following structure in PGMEA [ka]
[0368] O1: OXT-221 (Toagosei Co., Ltd., 3-ethyl-3{[(3-ethyloxetan-3-yl)methoxy]methyl}oxetane, a compound having an oxetanyl group)
[0369] O2: 40% by mass solution of the resin with the following structure (cyclic ether group content 3.83 mmol / g, weight average molecular weight 9800) in PGMEA [ka]
[0370] (polymerizable compound) M1: Aronix M-402 (manufactured by Toagosei Co., Ltd., a mixture of dipentaerythritol hexaacrylate and dipentaerythritol pentaacrylate) M2: Compound having the following structure [ka] M3: Compound with the following structure (a+b+c=3) [ka] M4: Compound having the following structure [ka] M5: A mixture of compounds having the following structure [ka] M6: Aronix M-350 (manufactured by Toagosei Co., Ltd., trimethylolpropane ethylene oxide modified triacrylate)
[0371] (resin) B1: 40% by mass solution of resin having the following structure (weight average molecular weight 12000, the number added to the main chain is the molar ratio) in PGMEA [ka] B2: 40% by mass solution of resin having the following structure (weight average molecular weight 11,000, the number added to the main chain is the molar ratio) in PGMEA. [ka]
[0372] (Surfactant) G1: BYK-330 (BYK-Chemie, silicone surfactant) G2: Compound with the following structure (weight average molecular weight 14,000, the percentage indicating the proportion of repeating units is mol%, fluorosurfactant) [ka] G3: KF-6001 (Shin-Etsu Chemical Co., Ltd., silicone surfactant) G4: Toray Silicone SH8400 (manufactured by Toray Dow Corning Co., Ltd.)
[0373] (solvent) S1:PGMEA S2: Cyclohexanone S3: Anisole S4: Diacetone alcohol
[0374] <Evaluation>
[0375] (Evaluation of spectral characteristics) Each coloring composition was applied onto a glass substrate using a spin coater so that the film thickness after drying would be 1.5 μm, and then dried on a hot plate at 100° C. for 2 minutes. Thereafter, an exposure illuminance of 20 mW / cm 2 was applied using an ultra-high pressure mercury lamp. 2 , exposure dose 100mJ / cm 2 The film was then heated on a hot plate at 100° C. for 20 minutes and allowed to cool to form a cured film. The absorbance of the obtained cured film in the wavelength range of 300 to 800 nm was measured using an ultraviolet-visible-near infrared spectrophotometer (UV3600, manufactured by Shimadzu Corporation) with a glass substrate as a reference, and the following wavelengths 1 and 2 were measured. Wavelength 1: Of the absorbance of light with wavelengths of 400 to 700 nm, the wavelength on the long wavelength side where the absorbance is 0.2 when the absorbance of light with a wavelength of 450 nm is taken as 1. Wavelength 2: Of the absorbance of light with wavelengths of 400 to 700 nm, when the absorbance of light with a wavelength of 450 nm is taken as 1, the wavelength on the short wave side where the absorbance is 0.2
[0376] <Evaluation of color mixing> Using a spin coater, each coloring composition was applied onto a glass substrate so that the film thickness after drying would be 1.5 μm, and then dried on a hot plate at 100° C. for 2 minutes. Then, using an ultra-high pressure mercury lamp, the coating was exposed to light with an exposure illuminance of 20 mW / cm 2 , exposure dose 100mJ / cm 2 The film was exposed under the following conditions. Next, paddle development was performed at 23°C for 60 seconds using a 0.3% by mass aqueous solution of tetramethylammonium hydroxide. After that, the film was rinsed with a spin shower and further washed with pure water. Then, the film was heated on a hot plate at 100°C for 20 minutes and allowed to cool to form a cured film. The transmittance (T1) of light with a wavelength of 450 nm of the obtained cured film was measured using MCPD-3000 (manufactured by Otsuka Electronics Co., Ltd.). Next, a coloring composition for color mixing evaluation was applied onto this cured film using a spin coater so that the film thickness after drying would be 1.5 μm, and the coating film of the coloring composition for color mixing evaluation was formed by drying for 2 minutes on a hot plate at 100 ° C., thereby forming a laminated film. For the coloring composition for color mixing evaluation, the coloring composition 1 for forming blue pixels used in forming blue pixels in Example 1001 described later was used. Next, the glass substrate on which this laminated film was formed was placed on the horizontal rotating table of a spin-shower developer (DW-30 type, manufactured by Chemitronics Co., Ltd.), and paddle development was performed for 60 seconds at 23 ° C. using a 60% diluted solution of CD-2000 (manufactured by Fujifilm Electronic Materials Co., Ltd.), and the coating film of the coloring composition for color mixing evaluation formed on the cured film was developed and removed. Next, the above-mentioned glass substrate was fixed to the horizontal rotating table by a vacuum chuck method, and while rotating the glass substrate at a rotation speed of 50 rpm by a rotating device, pure water was supplied from a spray nozzle in a shower from above the center of rotation to perform a rinsing treatment, and then spray-dried. Using MCPD-3000 (manufactured by Otsuka Electronics Co., Ltd.), the transmittance (T2) of light with a wavelength of 450 nm of the cured film after the coating film of the colored composition for evaluating color mixing was developed and removed was measured. The rate of change in transmittance was calculated from the following formula, and color mixing was evaluated according to the following evaluation criteria. Rate of change in transmittance (%) = {|Transmittance (T1) - Transmittance (T2)| / Transmittance (T1)} x 100 S: The change in transmittance is less than 0.1% A: The rate of change in transmittance is 0.1% or more and less than 0.25%. B: The rate of change in transmittance is 0.25% or more and less than 1%. C: The rate of change in transmittance is 1% or more and less than 2.5%. D: The rate of change in transmittance is 2.5% or more and less than 5%. E: The rate of change in transmittance is 5% or more.
[0377] (Evaluation of storage stability) The viscosity (V1) of the colored composition immediately after production obtained above was measured using "RE-85L" manufactured by Toki Sangyo Co., Ltd. The colored composition was left to stand for 3 days under a temperature condition of 40°C, and then the viscosity (V2) was measured. The viscosity increase rate was calculated from the following formula, and the storage stability was evaluated according to the following evaluation criteria. The viscosity of the colored composition was measured in a state where the temperature was adjusted to 23°C. The evaluation criteria were as follows, and the evaluation results are shown in the table below. Viscosity increase rate (%) = [(viscosity (V2) - viscosity (V1)) / viscosity (V1)] × 100 S: Viscosity increase rate is less than 0.1% A: The viscosity increase rate is 0.1% or more and less than 0.25%. B: Viscosity increase rate is 0.25% or more and less than 1% C: Viscosity increase rate is 1% or more and less than 2.5% D: Viscosity increase rate is 2.5% or more and less than 5% E: Viscosity increase rate is 5% or more
[0378] [Table 10] [Table 11]
[0379] As shown in the above table, the examples were evaluated as having better color mixing than the comparative examples. In addition, the cured films obtained using the colored compositions of the examples had high transmittance for light with a wavelength of about 500 nm, and had excellent sensitivity as green pixels. The same effect was obtained when the surfactant in Example 1 was replaced with a surfactant (KF-6001, manufactured by Shin-Etsu Chemical Co., Ltd.).
[0380] (Example 1001) The coloring composition for forming green pixels was applied onto a silicon wafer by spin coating so that the film thickness after formation was 1.5 μm. Then, the wafer was heated at 100° C. for 2 minutes using a hot plate. Then, an i-line stepper exposure apparatus FPA-3000i5+ (manufactured by Canon Inc.) was used to expose the wafer at 200 mJ / cm 2The substrate was exposed to light through a mask with a dot pattern of 3 μm square. Then, paddle development was performed at 23° C. for 60 seconds using a 0.3% by mass aqueous solution of tetramethylammonium hydroxide. After that, the substrate was rinsed with a spin shower and further washed with pure water. Then, a green colored pattern (green pixel) was formed by heating at 100° C. for 20 minutes using a hot plate. Similarly, the red pixel forming coloring composition 1 and the blue pixel forming coloring composition 1 were sequentially patterned to form a red colored pattern (red pixel) and a blue colored pattern (blue pixel), respectively, to form a structure. The coloring composition of Example 1 was used as the green pixel forming coloring composition. The red pixel forming coloring composition 1 and the blue pixel forming coloring composition 1 will be described later. The obtained structure was incorporated into an organic electroluminescence display device according to a known method. This organic electroluminescence display device had a suitable image recognition ability.
[0381] [Coloring composition for forming red pixels 1] The mixture having the following composition was stirred and mixed uniformly, and then filtered through a 1.0 μm filter to prepare a colored composition 1 for forming red pixels. Pigment dispersion DR-1: 30.2 parts by weight Pigment dispersion DY-1: 8.4 parts by weight Compound having a cyclic ether group 1: 15.2 parts by mass Polymerizable compound (Aronix M-402, manufactured by Toagosei Co., Ltd.) 0.7 part by mass Photopolymerization initiator (Irgacure OXE02, manufactured by BASF) 0.3 parts by mass PGMEA...44.2 parts by mass
[0382] [Coloring composition for forming blue pixels 1] A mixture of the following composition was stirred and mixed uniformly, and then filtered through a 1.0 μm filter to prepare colored composition 1 for forming blue pixels. Pigment dispersion liquid DB-1...10.4 parts by mass Pigment dispersion DV-1: 6.1 parts by weight Compound having a cyclic ether group 1: 24.2 parts by mass Polymerizable compound (Aronix M-402, manufactured by Toagosei Co., Ltd.) 0.7 part by mass Photopolymerization initiator (Irgacure OXE02, manufactured by BASF) 0.3 parts by mass PGMEA...44.2 parts by mass
[0383] The pigment dispersion DR-1 used was prepared by the following method. 11.0 parts by mass of CI Pigment Red 264, 21.5 parts by mass of Dispersant 11, 1 part by mass of Dispersant (EFKA4300, manufactured by BASF), and 66.5 parts by mass of PGMEA were mixed, and the mixture was dispersed for 5 hours in an Eiger mill (Mini Model M-250MKII, manufactured by Eiger Japan) using zirconia beads having a diameter of 1 mm, and then filtered through a filter having a pore size of 5 μm to prepare pigment dispersion liquid DR-1.
[0384] The pigment dispersion DY-1 used was prepared by the following method. 23.5 parts by mass of CI Pigment Yellow 139, 7 parts by mass of Dispersant 11, 3 parts by mass of a dispersant (EFKA4300, manufactured by BASF), and 66.5 parts by mass of PGMEA were mixed, and the mixture was dispersed for 5 hours in an Eiger mill (Mini Model M-250MKII, manufactured by Eiger Japan) using zirconia beads having a diameter of 1 mm, and then filtered through a filter with a pore size of 5 μm to prepare pigment dispersion liquid DY-1.
[0385] The pigment dispersion DB-1 used was prepared by the following method. 11.0 parts by mass of CI Pigment Blue 15:6, 21.5 parts by mass of Dispersant 11, 1 part by mass of Dispersant (EFKA4300, manufactured by BASF), and 66.5 parts by mass of PGMEA were mixed, and the mixture was dispersed for 5 hours in an Eiger mill (Mini Model M-250MKII, manufactured by Eiger Japan) using zirconia beads having a diameter of 1 mm, and then filtered through a filter having a pore size of 5 μm to prepare pigment dispersion liquid DB-1.
[0386] The pigment dispersion DV-1 used was prepared by the following method. 11.0 parts by mass of CI Pigment Violet 23, 21.5 parts by mass of Dispersant 11, 1 part by mass of Dispersant (EFKA4300, manufactured by BASF), and 66.5 parts by mass of PGMEA were mixed, and the mixture was dispersed for 5 hours in an Eiger mill (Mini Model M-250MKII, manufactured by Eiger Japan) using zirconia beads having a diameter of 1 mm, and then filtered through a filter having a pore size of 5 μm to prepare pigment dispersion liquid DV-1.
[0387] Dispersant 11 used was prepared by the following method. A separable 4-neck flask was equipped with a thermometer, a cooling tube, a nitrogen gas inlet tube, a dropping tube and a stirrer. 196 parts by mass of PGMEA was charged into the reaction vessel, which was heated to 80°C and replaced with nitrogen in the reaction vessel. From the dropping tube, a mixture of 37.2 parts by mass of n-butyl methacrylate, 12.9 parts by mass of 2-hydroxyethyl methacrylate, 12.0 parts by mass of methacrylic acid, 20.7 parts by mass of paracumylphenol ethylene oxide modified acrylate (manufactured by Toagosei Co., Ltd., Aronix M110), and 1.1 parts by mass of 2,2'-azobisisobutyronitrile was dropped over 2 hours. After the dropping was completed, the reaction was continued for another 3 hours to obtain a resin (Mw = 30000). After cooling to room temperature, the mixture was diluted with PGMEA to adjust the solid content concentration to 20% by mass, and dispersant 11 was prepared.
[0388] For compound 1 having a cyclic ether group, a 40 mass % PGMEA solution of an epoxy resin having the following structure (cyclic ether group content: 5.33 mmol / g, weight average molecular weight: 11,000) was used. [ka]
Claims
1. A coloring composition comprising a colorant, a resin, a polymerizable compound, a photopolymerization initiator, and a compound having a cyclic ether group, The colorants include Color Index Pigment Green 7 and a yellow colorant; the yellow colorant is at least one selected from Color Index Pigment Yellow 129, Color Index Pigment Yellow 138, Color Index Pigment Yellow 139, Color Index Pigment Yellow 150 and Color Index Pigment Yellow 185; The green colorant contained in the coloring composition is The content of Color Index Pigment Green 7 is 99.5% by mass or more, or the pigment contains Color Index Pigment Green 7 and another green colorant other than Color Index Pigment Green 7, the other green colorant being at least one selected from Color Index Pigment Green 36, Color Index Pigment Green 58 and Color Index Pigment Green 59, and the content of the other green colorant is 25 to 200 parts by mass per 100 parts by mass of Color Index Pigment Green 7; The content of the yellow colorant is 25 to 600 parts by mass per 100 parts by mass of Color Index Pigment Green 7, the total content of Color Index Pigment Green 7 and the yellow colorant in the total amount of the colorants contained in the coloring composition is 90 to 100 mass%, or the total content of Color Index Pigment Green 7, the other green colorant, and the yellow colorant in the total amount of the colorants contained in the coloring composition is 90 to 100 mass%, The compound having a cyclic ether group is A repeating unit having a cyclic ether group; at least one repeating unit selected from a repeating unit having an acid group, a repeating unit having a group in which an acid group is protected by a protecting group, and a repeating unit having a polymerizable group; is a compound having the formula The content of the compound having a cyclic ether group is 1 to 300 parts by mass per 100 parts by mass of Color Index Pigment Green 7, The colored composition was applied onto a glass substrate, dried at 100° C. for 2 minutes, and then irradiated with light having an illuminance of 20 mW / cm using an ultra-high pressure mercury lamp. 2 , exposure dose 100 mJ / cm 2 and then heated on a hot plate at 100° C. for 20 minutes to form a film having a thickness of 1.5 μm. When the absorbance of the film with respect to light having a wavelength of 450 nm is taken as 1, the wavelength at which the absorbance becomes 0.2 is in the wavelength range of 540 nm to 610 nm. Colored composition.
2. The colored composition according to claim 1 , wherein the compound having a cyclic ether group has a weight average molecular weight of 1,500 or more.
3. The colored composition according to claim 1 or 2, wherein the repeating unit having a cyclic ether group is a repeating unit having a polyether structure, a repeating unit having a novolak structure, or a repeating unit having a (meth)acrylic structure.
4. The colored composition according to any one of claims 1 to 3, wherein the repeating unit having a cyclic ether group contains an aliphatic hydrocarbon ring in a main chain structure.
5. The colored composition according to any one of claims 1 to 4, wherein the compound having a cyclic ether group includes a compound having an epoxy group and a compound having an oxetanyl group.
6. The colored composition was applied onto a glass substrate, dried at 100° C. for 2 minutes, and then irradiated with light having an illuminance of 20 mW / cm using an ultra-high pressure mercury lamp. 2 , exposure dose 100 mJ / cm 2 and then heated on a hot plate at 100° C. for 20 minutes to form a film having a thickness of 1.5 μm, the film has an absorbance of 0.2 at wavelengths in the wavelength range of 470 nm or more and 520 nm or less and in the wavelength range of 540 nm or more and 610 nm or less, when the absorbance of the film at wavelength 450 nm is taken as 1.
7. The colored composition according to any one of claims 1 to 6, wherein the content of the colorant in the total solid content of the colored composition is 15 mass% or more.
8. The colored composition according to any one of claims 1 to 7, which is used for forming a cured film at a temperature of 150°C or less throughout all steps.
9. A cured film obtained by using the colored composition according to any one of claims 1 to 8.
10. A structure having a green pixel, a red pixel and a blue pixel, the green pixel being obtained by using the coloring composition according to any one of claims 1 to 8.
11. A color filter comprising the cured film according to claim 9.
12. A display device comprising the cured film according to claim 9.
Citation Information
Patent Citations
Colorant composition, color filter and liquid crystal display device
JP2014041341A
Photosensitive coloring composition and color filter
JP2019113823A
Photosensitive colored composition and color filter
JP2019139230A
Coloring composition, color filter, solid state imaging device, and liquid crystal display
JP2020101575A