Pigment compositions, colored compositions, and molded articles

Abstract

The present invention provides a pigment composition that can improve absorbance across the entire visible light spectrum without increasing absorbance in the ultraviolet region. Furthermore, it provides a colored composition and molded article that achieve high light-shielding properties without interfering with active energy ray curing. [Solution] The pigment composition of the present invention comprises one or more compounds (A) represented by the following general formula (i), and a pigment (B). The pigment composition comprises one or more pigments selected from the group consisting of carbon black, benzodifuranone pigments, and perylene pigments. [C1] TIFF2026095407000040.tif17170

Description

[Technical Field]

[0001] The present invention relates to a pigment composition, a colored composition, and a molded article. This application claims priority based on Japanese Patent Application No. 2024-103976, filed in Japan on June 27, 2024, and the contents of that application are incorporated herein by reference. [Background technology]

[0002] Because carbon black absorbs light across a wide range of wavelengths from ultraviolet to infrared, it has been used as a colorant for the black matrix of color filters in liquid crystal displays, and as a partition material (also called "bank layer material" or "pixel defining layer (PDL) material") to separate light-emitting elements in organic EL displays. However, when carbon black is used as a colorant for photosensitive compositions (photoresists) such as those used in photolithography, its high absorbance in the ultraviolet region inhibits the photopolymerization of the photoresist, making it difficult to form components of the desired shape. Furthermore, because carbon black has relatively low absorbance in the 600-700 nm range, its light-shielding properties across the entire visible region are not sufficient (Patent Document 1). On the other hand, Patent Document 2 discloses a photosensitive coloring composition containing organic black pigments such as benzodifuranone pigments and perylene pigments, and attempts to solve the above problem. [Prior art documents] [Patent Documents]

[0003] [Patent Document 1] Japanese Patent Publication No. 2022-108724 [Patent Document 2] Japanese Patent Publication No. 2016-167030 [Overview of the project] [Problems that the invention aims to solve]

[0004] However, when using black pigments other than carbon black, such as benzodifuranone-based pigments and perylene-based pigments, there is a problem that the light-shielding property in the entire visible region is not sufficient because the absorbance at 600 - 700 nm is relatively low in the visible light region. The present invention can provide a pigment composition capable of improving the absorbance in the entire visible light range without increasing the absorbance in the ultraviolet region by using a compound (A) represented by the following general formula (i) in combination with a pigment (B) such as carbon black, benzodifuranone-based pigment, and perylene-based pigment.

Means for Solving the Problem

[0005] The present invention includes the following aspects. [1] One or more compounds (A) represented by the following general formula (i), and a pigment (B), a pigment composition comprising: The pigment (B) is a pigment composition comprising one or more pigments selected from the group consisting of carbon black, benzodifuranone-based pigments, and perylene-based pigments.

Chemical formula

Chemical formula

[0006] According to the present invention, by using a compound (A) represented by the above general formula (i) in combination with a pigment (B) such as carbon black, benzodifuranone pigment, or perylene pigment, it is possible to provide a pigment composition that can improve the absorbance across the entire visible light region without increasing the absorbance in the ultraviolet region. Furthermore, the colored composition and molded article containing the pigment composition according to the present invention can achieve high light-shielding properties without interfering with active energy ray curing when used as a photoresist. [Modes for carrying out the invention]

[0007] (Pigment composition) A pigment composition according to one embodiment of the present invention comprises one or more compounds (A) represented by the following general formula (i), and a pigment (B).

[0008] [Compound represented by general formula (i) (A)] The aforementioned compound (A) is represented by the following general formula (i).

[0009] [ka]

[0010] In general formula (i), L i1 The following general formula (L i1 This represents the base represented by -1).

[0011] [ka]

[0012] General formula (L i1 -1) Medium, R Li11 , R Li12 and R Li13 Each of these independently represents a hydrogen atom, a halogen atom, a cyano group, a nitro group, an aliphatic hydrocarbon group having 1 to 8 carbon atoms which may have substituents, or an aromatic hydrocarbon group having 6 to 12 carbon atoms which may have substituents. Furthermore, when l represents 2 or 3, RLi12 and R Li13 These are each other R Li12 and R Li13 It may be the same as, or it may be different from, the other. R Li11 , R Li12 and R Li13 Two selected elements may join together to form a ring. R Li11 , R Li12 and R Li13 Preferred elements include hydrogen atoms, chlorine atoms, bromine atoms, and methyl groups. General formula (L i1 -1) In this case, l represents an integer between 1 and 3, with 1 or 2 being preferred. General formula (L i1 -1) Among them, * is A i1 This represents a bonding to A i2 This represents a binding operation.

[0013] L i1 A concrete example is the following equation (L i1 -1-1)~(L i1 Examples of groups represented by -1-10) include the groups represented by -1-10).

[0014] [ka]

[0015] Formula (L i1 -1-1)~(L i1 -1-10) Among them, * is A i1 This represents a bonding to A i2 This represents a binding operation.

[0016] In general formula (i), A i1 The following general formula (A i1 -1) and (A i1 This represents the base represented by (-2).

[0017] [ka]

[0018] General formula (A i1 -1) and (A i1 -2) Medium, R Ai11 Each of these independently represents a hydrogen atom, a monovalent aliphatic hydrocarbon group having 1 to 20 carbon atoms which may have substituents, an aromatic hydrocarbon group having 6 to 12 carbon atoms which may be substituted, or an aralkyl group having 7 to 10 carbon atoms which may be substituted. R Ai11 Preferably, the alkyl group is a linear group having 1 to 6 carbon atoms, and a methyl group is preferred. General formula (A i1 -1) and (A i1 -2) In the middle, * is L i1 This represents a binding operation. In general formula (i), A i2 The formula is as follows (A i2 -1) and (A i2 This represents the base represented by (-2).

[0019] [ka]

[0020] General formula (A i2 -1) and (A i2 -2) Medium, R Ai21 Each of these independently represents a hydrogen atom, a monovalent aliphatic hydrocarbon group having 1 to 20 carbon atoms which may have substituents, an aromatic hydrocarbon group having 6 to 12 carbon atoms which may be substituted, or an aralkyl group having 7 to 10 carbon atoms which may be substituted. R Ai21 Preferably, the alkyl group is a linear group having 1 to 6 carbon atoms, and a methyl group is preferred. General formula (A i2 -1) and (A i2 -2) Among them, ** is L i1 This represents a binding operation. A i1 and A i2 One or more hydrogen atoms in the molecule are independently substituents S i1 It may be replaced by this. substituent S i1represents a halogen atom, a cyano group, a nitro group, an amino group or an ammonium group which may be N-alkylated, a hydroxy group, an allyloxy group, an alkoxy group, a sulfo group, a sulfamoyl group which may be N-alkylated, a carboxyl group, an ester group, an amide group which may be N-alkylated, a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, an aromatic hydrocarbon group having 6 to 12 carbon atoms which may have a substituent, a heterocyclic group having 3 to 12 carbon atoms which may have a substituent or an aralkyl group having 7 to 10 carbon atoms which may have a substituent. Also, substituent S i1 When there are a plurality of them, they may be the same or different. S i1 is preferably a linear alkyl group having 1 to 6 carbon atoms, and preferably a methyl group. Also, a fluorine atom, a chlorine atom, a bromine atom, a trifluoromethyl group are preferable.

[0021] Specific examples of general formula (A i1 -1) include groups represented by the following formulas (A i1 -1-1) to (A i1 -1-4).

[0022]

Chemical formula

[0023] In formulas (A i1 -1-1) to (A i1 -1-4), * represents a bond to L i1 .

[0024] Specific examples of general formula (A i2 -1) include groups represented by the following formulas (A i2 -1-1) to (A i2 -1-4).

[0025]

Chemical formula

[0026] In formulas (A i2 -1-1) to (A i2 -1-4), ** represents a bond to L i1 .

[0027] In general formula (i), B m- represents a polyoxometalate anion. m represents an integer from 1 to 20, preferably 1 to 5.

[0028] As the polyoxometalate anion of B m- , known polyoxometalate anions can be used.

[0029] Here, the polyoxometalate anion may be an isopolyoxometalate anion represented by (M p O q ) m- , or a heteropolyoxometalate anion represented by (Z p M q O r ) m- (in the above formula, Z is a heteroatom, M is a polyatom, O is an oxygen atom, and p, q, and r represent the composition ratios of the respective atoms). Examples of the polyatom M include elements such as Mo, W, Ti, V, Nb, and Ta. Examples of the heteroatom Z include elements such as P, Si, B, As, Ge, S, Co, Zn, Al, and H.

[0030] Specifically, (PW 12 O 40 )[[ID=四十九]] 3- , (SiW 12 O 40 )[[ID=五十五]] 4- , (BW 12 O 40 )[[ID=六十一]] 5- , (SW 12 O 40 )[[ID=六十七]] 2- , (PMo 12 O[[ID=七十一]] 40 )[[ID=七十三]] 3- , (SiMo 12 O 40 )[[ID=七十九]] 4- , (BMo 12 O40 ) 5- , (SMo 12 O 40 ) 2- Keggin-type heteropolyoxometalate anions such as (P2W 18 O 62 ) 6- (Si2W 18 O 62 ) 8- (S2W 18 O 62 ) 4- (P2Mo 18 O 62 ) 6- , (Si2Mo 18 O 62 ) 8- , (S2Mo 18 O 62 ) 4- Dawson-type heteropolyoxometalate anions such as (PW9O 34 ) 9- , (PW 10 O 36 ) 7- , (PW 11 O 39 ) 7- (PMo9O 34 ) 9- , (PMo 10 O 36 ) 7- , (PMo 11 O 39 ) 7- (SiW9O 34 ) 10- (SiW 10 O 36 ) 8- (SiW 11 O 39 ) 8- (SiMo9O 34 ) 10- , (SiMo 10 O 36 ) 8- , (SiMo 11 O 39 ) 8- (P2W 17 O 61 ) 10- (P2W 15 O 56 )12- (H2P2W 12 O 48 ) 12- (NaP5W 30 O 110 ) 14- (P2Mo 17 O 61 ) 10- (P2Mo 15 O 56 ) 12- (H2Mo2W 12 O 48 ) 12- , (NaP5Mo 30 O 110 ) 14- such as the deficient heteropolyoxometalate anion (WO4); 2- (W6O 19 ) 2- , (W7O 24 ) 6- , (W 10 O 32 ) 4- (MoO4) 2- , (Mo6O 19 ) 2- (Mo7O 24 ) 6- , (Mo 10 O 32 ) 4- Examples include isopolyoxometalate anions such as those mentioned above; and various other polyoxometalate anions such as Strandberg type, Anderson type, Allman-Waugh type, Weakley-Yamase type, Dexter-Silverton type, and Preyssler type.

[0031] The same can be used with the polyoxometalate anion structure described above, in which all or part of tungsten or molybdenum is replaced with at least one element selected from molybdenum, tungsten, titanium, vanadium, niobium, tantalum, iron, manganese, cobalt, nickel, and zinc; in which all or part of phosphorus or silicon is replaced with at least one element selected from boron, arsenic, and germanium; or in which all or part of tungsten or molybdenum is replaced with at least one element selected from molybdenum, tungsten, titanium, vanadium, niobium, tantalum, iron, manganese, cobalt, nickel, and zinc, and all or part of phosphorus or silicon is replaced with at least one element selected from boron, arsenic, and germanium. The polyoxometalate anions described above can be used individually or in combination. Furthermore, the isomers of these polyoxometalate anions, identified by α-, β-, γ-, etc., can also be used individually or in combination.

[0032] Among the above, polyoxometalate anions are preferably used because they themselves have a good hue, appropriate size and valency, can obtain a stable solid state when bonded to the dye structure of the cationic part, and the hue of the compound does not easily change.

[0033] Such as B m- The polyoxometalate anion is a polyoxometalate anion containing at least tungsten (PW 12 O 40 ) 3- (SiW 12 O 40 ) 4- (BW 12 O 40 ) 5- , (SW 12 O 40 ) 2- , (PMo t W 12-t O 40 ) 3- , (SiMot W 12-t O 40 ) 4- , (BMo t W 12-t O 40 ) 5- , (SMo t W 12-t O 40 ) 2- Keggin-type heteropolyoxometalate anions such as (P2W 18 O 62 ) 6- (Si2W 18 O 62 ) 8- (S2W 18 O 62 ) 4- (P2Mo t W 18-t O 62 ) 6- , (Si2Mo t W 18-t O 62 ) 8- , (S2Mo t W 18-t O 62 ) 4- Dawson-type heteropolyoxometalate anions such as (PW9O 34 ) 9- , (PW 10 O 36 ) 7- , (PW 11 O 39 ) 7- , (PMo t W 9-t O 34 ) 9- , (PMo t W 10-t O 36 ) 7- , (PMo t W 11-t O 39 ) 7- (SiW9O 34 ) 10- (SiW 10 O 36 ) 8- (SiW 11 O 39 ) 8- , (SiMo t W9-t O 34 ) 10- , (SiMo t W 10-t O 36 ) 8- , (SiMo t W 11-t O 39 ) 8- (P2W 17 O 61 ) 10- (P2W 15 O 56 ) 12- (H2P2W 12 O 48 ) 12- (NaP5W 30 O 110 ) 14- (P2Mo t W 17-t O 61 ) 10- (P2Mo t W 15-t O 56 ) 12- (H2Mo t W 14-t O 48 ) 12- , (NaP5Mo t W 30-t O 110 ) 14- such as the deficient heteropolyoxometalate anion (WO4); 2- (W6O 19 ) 2- , (W7O 24 ) 6- , (W 10 O 32 ) 4- Examples include isopolyoxometalate anions such as (where t is 0 or a positive integer).

[0034] A particularly preferred form is (PMo y W 12-y O 40 ) 3- A heteropolyoxometalate anion represented by where y is an integer 0, 1, 2, or 3, or (SiMo z W 12-z O 40 ) 4-Examples include heteropolyoxometalate anions, where z is an integer of 0, 1, 2, or 3.

[0035] B m- Specifically, as a polyoxometalate anion, (PW 12 O 40 ) 3- (PMoW 11 O 40 ) 3- (SiW 12 O 40 ) 4- , or (SiMoW 11 O 40 ) 4- It is preferable that this is the case. Compounds containing such polyoxometalate anions include 12-tungst(VI) phosphate, 12-tungst(VI) phosphate n hydrate, 12-tungst(VI) sodium phosphate n hydrate, 12-tungst(VI) potassium phosphate n hydrate, 12-tungst(VI) ammonium phosphate n hydrate, phosphotungstmolybdic acid, phosphotungstmolybdic acid n hydrate, phosphotungstmolybdate sodium n hydrate, phosphotungstmolybdate potassium n hydrate, and phosphotungstmolybdate ammonium Examples include nium n hydrate, 12-tungst(VI) silicate, 12-tungst(VI) silicate n hydrate, 12-tungst(VI) sodium silicate n hydrate, 12-tungst(VI) potassium silicate n hydrate, 12-tungst(VI) ammonium silicate n hydrate, silatungstmolybdic acid, silatungstmolybdic acid n hydrate, silatungstmolybdate sodium n hydrate, silatungstmolybdate potassium n hydrate, and silatungstmolybdate ammonium n hydrate.

[0036] n represents an integer between 1 and 20, preferably between 1 and 5, and is determined such that the total charge of equation (i) is zero.

[0037] Specific examples of compound (A) represented by general formula (i) include the compounds represented by the following structural formulas (i-1) to (i-5).

[0038] [ka]

[0039] Compound (A) represented by general formula (i) may be one or more compounds used in combination. The content of compound (A) represented by general formula (i) in 100% by mass of the pigment composition is preferably 0.1 to 80.0% by mass, preferably 1.0 to 75.0% by mass, and preferably 5.0 to 70.0% by mass, from the viewpoint of UV transmittance and light shielding properties.

[0040] (Method for synthesizing compound (A) represented by general formula (i)) Compound (A) represented by general formula (i) can be obtained from known dyes, for example, B m- It can be synthesized by lake fermentation with a polybasic acid or polybasic salt having a polyoxometalate anion represented by . The synthesis method will be explained below using an example where compound (A) represented by general formula (i) is the same as general formula (I) below.

[0041] [ka] (In formula (I), X represents a methyl group or halogen atom. R 1 ~R 14 Each independently represents a hydrogen atom, a halogen atom, a cyano group, a nitro group, an optionally N-alkylated amino group or ammonium group, a hydroxyl group, an allyloxy group, an alkoxy group, a sulfo group, an optionally N-alkylated sulfamoyl group, a carboxyl group, an ester group, an optionally N-alkylated amide group, an optionally substituted hydrocarbon group having 1 to 12 carbon atoms, an optionally substituted aromatic hydrocarbon group having 6 to 12 carbon atoms, or an optionally substituted heterocyclic group having 3 to 12 carbon atoms, and R 1 ~R 4 Two adjacent elements are selected from R. 5 ~R 8 Two adjacent elements are selected from R. 11 and R12 , or R 13 and R 14 These may be joined together to form a ring. B m- This represents a polyoxometalate anion, m represents an integer between 1 and 20. n represents an integer between 1 and 20. However, n is determined such that the total charge of equation (I) is zero. The dye represented by the following formula (II) is B m- It can be synthesized by lake formation with a polybasic acid or polybasic salt having a polyoxometalate anion represented by the formula (II). The water-soluble dye represented by the following formula (II) becomes a pigment of the water-insoluble compound represented by the general formula (I).

[0042] [ka]

[0043] (In formula (II), X represents a methyl group or halogen atom. R 1 ~R 14 Each independently represents a hydrogen atom, a halogen atom, a cyano group, a nitro group, an optionally N-alkylated amino group or ammonium group, a hydroxyl group, an allyloxy group, an alkoxy group, a sulfo group, an optionally N-alkylated sulfamoyl group, a carboxyl group, an ester group, an optionally N-alkylated amide group, an optionally substituted hydrocarbon group having 1 to 12 carbon atoms, an optionally substituted aromatic hydrocarbon group having 6 to 12 carbon atoms, or an optionally substituted heterocyclic group having 3 to 12 carbon atoms, and R 1 ~R 4 Two adjacent elements are selected from R. 5 ~R 8 Two adjacent elements are selected from R. 11 and R 12 , or R 13 and R 14 These may be joined together to form a ring. Y -This represents an anion, m represents an integer between 1 and 20. n represents an integer between 1 and 20. However, n is determined such that the total charge of equation (I) is zero.

[0044] Y - The above dye uses an anion of chloride ions, and B m- When a polybasic acid having a polyoxometalate anion represented by is used, the compound represented by general formula (I) can be produced by dehydrochlorination and salt exchange. - The above dye uses an anion of chloride ions and B m- When using polybasic salts having a polyoxometalate anion represented by , for example, a polyoxometalate alkali metal salt, the compound represented by general formula (I) can be produced by salt exchange via an alkali metal chloride removal reaction.

[0045] Compared to the hydrogen chloride dechlorination reaction using the polybasic acid described above, it is preferable to first convert the polybasic acid into a polyoxometalate alkali metal salt before carrying out the alkali metal chloride dechlorination reaction. This is because it ensures reliable salt exchange, resulting in higher yields of the compound, as well as producing fewer by-products and a higher purity compound. Of course, the polyoxometalate alkali metal salt can also be purified by recrystallization or other methods before use.

[0046] The amount of heteropoly acid or polyoxometalate alkali metal salt used as the anion source for the compound of the present invention is preferably such that the negative and positive charges are equimolar, depending on the valence of the anions and the valence of the dye cations, when carrying out the above reaction. Alternatively, the reaction can be carried out by adjusting the number of moles to something other than equimolars, if necessary.

[0047] The dye represented by formula (II) can be synthesized by known methods, such as those described in "Functional Dyes" (Shin Okawara et al., Kodansha Ltd., published March 10, 1992, pp. 98 to 117) and "Photosensitive Dyes" (supervised by Masaaki Hayami, Sangyo Tosho Co., Ltd., published October 17, 1997, pp. 11 to 31), or commercially available dyes can be used.

[0048] For example, NK-10374 manufactured by Nagase Vita Corporation is R 1 ~R 8 is a hydrogen atom, and R 9 ~R 14 X is a methyl group, X is a methyl group, Y - This is the p-toluenesulfonate anion, where m=n=1, and it is represented by the following formula.

[0049] [ka]

[0050] NK-10739 manufactured by Nagase Vita Co., Ltd. is R 1 ~R 8 is a hydrogen atom, and R 9 ~R 14 X is a methyl group, X is a chlorine atom, and Y - This is the p-toluenesulfonate anion, where m=n=1, and it is represented by the following formula.

[0051] [ka]

[0052] NK-10759 manufactured by Nagase Vita Corporation is R 1 ~R 8 is a hydrogen atom, and R 9 ~R 14 X is a methyl group, X is a bromine atom, and Y - This is the p-toluenesulfonate anion, where m=n=1, and it is represented by the following formula.

[0053] [ka]

[0054] [Pigment (B)] The pigment (B) comprises one or more pigments selected from the group consisting of carbon black, benzodifuranone pigments, and perylene pigments. In 100% by mass of the pigment composition of this embodiment, the content of pigment (B) is preferably 20.0 to 99.9% by mass, preferably 25.0 to 99.0% by mass, and preferably 30.0 to 95.0% by mass, from the viewpoint of light shielding properties.

[0055] As the carbon black, carbon black used as a pigment, manufactured by known methods such as the contact method, furnace method, or thermal method, can be used. Examples of commercially available carbon black include carbon black from Mitsubishi Chemical Corporation, Orion Engineered Carbons, Asahi Carbon, Tokai Carbon, Degussa, Cabot, and Biller.

[0056] The aforementioned carbon blacks manufactured by Mitsubishi Chemical Corporation include MA7, MA77, MA8, MA11, MA100, MA100R, MA220, MA230, MA600, #5, #10, #20, #25, #30, #32, #33, #40, #44, #45, #47, #50, #52, #55, #650, #750, #850, and #950. Examples include #960, #970, #980, #990, #1000, #2200, #2300, #2350, #2400, #2600, #3050, #3150, #3250, #3600, #3750, #3950, #4000, #4010, OIL7B, OIL9B, OIL11B, OIL30B, OIL31B, etc.

[0057] Examples of carbon black manufactured by Orion Engineered Carbons include the COLOR-BLACK series, SPECIAL-BLACK series, PRINTEX series, HIBLACK series, NEROX series, and NIPex series.

[0058] Examples of carbon black manufactured by Asahi Carbon include the SUNBLACK series, #70 series, and #80 series. Examples of carbon black manufactured by Tokai Carbon Co., Ltd. include the Toka Black #7000 series and the #8000 series.

[0059] Examples of carbon blacks manufactured by Degussa include Printex (registered trademark; hereinafter the same) 3, Printex 3OP, Printex 30, Printex 30OP, Printex 40, Printex 45, Printex 55, Printex 60, Printex 75, Printex 80, Printex 85, Printex 90, Printex A, Printex L, Printex G, Printex P, Printex U, Printex V, Printex G, Special Black 550, Special Black 350, Special Black 250, Special Black 100, Special Black 6, Special Black 5, Special Black 4, Color Black FW1, Color Black FW2, Color Black FW2V, Color Black FW18, Color Black FW18, Color Black FW200, Color Black S160, Color Black S170, and others.

[0060] Examples of carbon blacks manufactured by Cabot include Monarch (registered trademark; hereinafter the same) 120, Monarch 280, Monarch 460, Monarch 800, Monarch 880, Monarch 900, Monarch 1000, Monarch 1100, Monarch 1300, Monarch 1400, Monarch 4630, REGAL (registered trademark; hereinafter the same) 99, REGAL 99R, REGAL 415, REGAL 415R, REGAL 250, REGAL 250R, REGAL 330, REGAL 400R, REGAL 55R0, REGAL 660R, BLACK PEARLS 480, PEARLS 130, VULCAN (registered trademark) XC72R, ELFTEX (registered trademark)-8, and others.

[0061] Examples of Biller carbon blacks include RAVEN11, RAVEN14, RAVEN15, RAVEN16, RAVEN22, RAVEN30, RAVEN35, RAVEN40, RAVEN410, RAVEN420, RAVEN450, RAVEN500, RAVEN780, RAVEN850, RAVEN890H, RAVEN1000, RAVEN1020, RAVEN1040, RAVEN1060U, RAVEN1080U, RAVEN1170, RAVEN1190U, RAVEN1250, RAVEN1500, RAVEN2000, RAVEN2500U, RAVEN3500, RAVEN5000, RAVEN5250, RAVEN5750, and RAVEN7000.

[0062] Carbon black that has been surface-treated is preferred. Surface treatment methods include oxidation treatment, such as the Fenton reaction. The carbon black is preferably carbon black that has been surface-treated with iron elements.

[0063] <Benzodifuranone pigments> Examples of the benzodifuranone pigments mentioned above include compounds represented by the following general formula (1).

[0064] [ka]

[0065] In formula (1), R 1 and R 6 These are, independently of each other, a hydrogen atom, CH3, CF3, a fluorine atom, or a chlorine atom; R 2 , R 3 , R 4 , R 5 , R 7 , R 8 , R 9 and R 10 It is independent of all other hydrogen atoms, halogen atoms, and R 11 COOH, COOR 11 COO - CONH2, CONHR 11 CONR 11 R 12 , CN, OH, OR 11 COCR 11 , OOCNH2, OOCNHR 11 , OOCNR 11 R 12 NO2, NH2, NHR 11 , NR 11 R 12 , NHCOR 12 , NR 11 COR 12 N=CH2, N=CHR 11 N=CR 11 R 12 SH, SR 11 SOR 11 SO2R 11 SO3R 11 SO3H, SO3 - SO2NH2, SO2NHR 11 or SO2NR 11 R 12 is; Furthermore, R 2 and R 3 , R 3 and R 4 , R 4 and R 5 , R 7 and R 8 , R8 and R 9 , and R 9 and R 10 At least one combination selected from the group consisting of the following is directly bonded to each other, or is an oxygen atom, sulfur atom, NH or NR 11 They can also be connected to each other by bridges; R 11 and R 12 These are, independently of each other, an alkyl group having 1 to 12 carbon atoms, a cycloalkyl group having 3 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms, a cycloalkenyl group having 3 to 12 carbon atoms, or an alkynyl group having 2 to 12 carbon atoms.

[0066] The geometric isomers of the compound represented by general formula (1) have the following core structures (with substituents omitted in the structural formulas), and the trans-trans isomer is probably the most stable.

[0067] [ka]

[0068] If the compound represented by general formula (1) is anionic, it is preferable that its charge is compensated by any known suitable cation, such as a metal, organic, inorganic, or metal-organic cation, specifically alkali metals, alkaline earth metals, transition metals, primary ammonium, secondary ammonium, tertiary ammonium such as trialkylammonium, quaternary ammonium such as tetraalkylammonium, or an organometallic complex. Furthermore, if the geometric isomer of the compound represented by general formula (1) is anionic, it is preferable that it be a similar salt.

[0069] In the substituents of general formula (1) and their definitions, the following are preferred because they tend to increase the shielding rate. This is because the following substituents do not absorb and are not thought to affect the hue of the pigment. R 2 , R 4 , R 5 , R 7 , R 9and R 10 These atoms are preferably a hydrogen atom, a fluorine atom, or a chlorine atom, and more preferably a hydrogen atom, independently of each other. R 3 and R 8 These are preferably hydrogen atoms, NO2, OCH3, OC2H5, bromine atoms, chlorine atoms, CH3, C2H5, N(CH3)2, N(CH3)(C2H5), N(C2H5)2, α-naphthyl, β-naphthyl, SO3H, or SO3 - It is, and more preferably, a hydrogen atom or SO3H.

[0070] R 1 and R 6 These are preferably a hydrogen atom, CH3, or CF3, and more preferably a hydrogen atom, independently of each other. Preferably, R 1 and R 6 , R 2 and R 7 , R 3 and R 8 , R 4 and R 9 , and R 5 and R 10 At least one combination selected from the group consisting of is identical, and more preferably, R 1 is R 6 It is identical to R 2 is R 7 It is identical to R 3 is R 8 It is identical to R 4 is R 9 It is identical to and R 5 is R 10 It is identical to [the other one].

[0071] The alkyl group having 1 to 12 carbon atoms is, for example, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, a 2-methylbutyl group, an n-pentyl group, a 2-pentyl group, a 3-pentyl group, a 2,2-dimethylpropyl group, an n-hexyl group, a heptyl group, an n-octyl group, a 1,1,3,3-tetramethylbutyl group, a 2-ethylhexyl group, a nonyl group, a decyl group, an undecyl group or a dodecyl group.

[0072] The cycloalkyl group having 3 to 12 carbon atoms is, for example, a cyclopropyl group, a cyclopropylmethyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cyclohexylmethyl group, a trimethylcyclohexyl group, a tsujyl group, a norbornyl group, a bornyl group, a norcaril group, a caril group, a menthyl group, a norpinyl group, a pinyl group, a 1-adamantyl group or a 2-adamantyl group.

[0073] The alkenyl group having 2 to 12 carbon atoms is, for example, a vinyl group, an allyl group, a 2-propen-2-yl group, a 2-buten-1-yl group, a 3-buten-1-yl group, a 1,3-butadien-2-yl group, a 2-penten-1-yl group, a 3-penten-2-yl group, a 2-methyl-1-butene-3-yl group, a 2-methyl-3-butene-2-yl group, a 3-methyl-2-butene-1-yl group, a 1,4-pentadien-3-yl group, a hexenyl group, an octenyl group, a nonenyl group, a decenyl group or a dodecenyl group.

[0074] The cycloalkenyl group having 3 to 12 carbon atoms is, for example, a 2-cyclobuten-1-yl group, a 2-cyclopenten-1-yl group, a 2-cyclohexen-1-yl group, a 3-cyclohexen-1-yl group, a 2,4-cyclohexadien-1-yl group, a 1-p-menthen-8-yl group, a 4(10)-tsujen-10-yl group, a 2-norbornen-1-yl group, a 2,5-norbornadien-1-yl group, a 7,7-dimethyl-2,4-norcaradien-3-yl group or a camphyl group.

[0075] The alkynyl group having 2 to 12 carbon atoms is, for example, 1-propyn-3-yl group, 1-butyn-4-yl group, 1-pentyn-5-yl group, 2-methyl-3-butyn-2-yl group, 1,4-pentadiyn-3-yl group, 1,3-pentadiyn-5-yl group, 1-hexyn-6-yl group, cis-3-methyl-2-penten-4-yn-1-yl group, trans-3-methyl-2-penten-4-yn-1-yl group, 1,3-hexadiyn-5-yl group, 1-octyn-8-yl group, 1-nonyn-9-yl group, 1-decyn-10-yl group or 1-dodecyn-12-yl group.

[0076] The halogen atom is, for example, a fluorine atom, a chlorine atom, a bromine atom or an iodine atom.

[0077] Specific examples of the compound represented by the general formula (1) include those having the following structural formulas.

[0078]

Chemical formula

[0079] Specific examples of the benzodifuranone-based pigment include, for example, Irgaphor (registered trademark) Black S 0100 CF (manufactured by BASF) manufactured by BASF.

[0080] <Perylene-based pigment> Examples of the perylene-based pigment include one or more of those having the following structural formulas.

[0081]

Chemical formula

[0083] [Dispersant] The aforementioned dispersants include Disperbyk-101, 103, 107, 108, 110, 111, 116, 130, 140, 154, 161, 162, 163, 164, 165, 166, 167, 168, 170, 171, 174, 180, 181, 182, 183, 184, 185, 190, 2000, 2001, 2009, 2010, 2020, 2025, 2050, 2070, 2095, 2150, 2155, 2163, 2164 or LPN6919, BYK-LPN21116, BYK-LPN21324 etc. from BYK Chemie Japan, and SOLSPERSE from Lubrizol Japan. -3000, 9000, 13000, 13240, 13650, 13940, 16000, 17000, 18000, 20000, 21000, 24000, 26000, 27000, 28000, 31845, 32000, 32500, 32550, 33500, 32600, 34750, 35 100, 36600, 38500, 41000, 41090, 53095, 55000, 56000, 76500, etc., BASF EFKA-46, 47, 48, 452, 4008, 4009, 4010, 4015, 4020, 4047, 4050, 4055, 4060, 4080, 4400, Examples include 4401, 4402, 4403, 4406, 4408, 4300, 4310, 4320, 4330, 4340, 450, 451, 453, 4540, 4550, 4560, 4800, 5010, 5065, 5066, 5070, 7500, 7554, 1101, 120, 150, 1501, 1502, 1503, etc., as well as Ajispa-PA111, PB711, PB821, PB822, PB824, etc., manufactured by Ajinomoto Fine Techno Co., Ltd. In addition, leveling agents, coupling agents, and cationic surfactants may also be used. As the aforementioned dispersant, acrylic dispersants such as BYK-LPN21116 and Disperbyk-2000, which have good pigment dispersibility, are preferred.

[0084] [resin] As the aforementioned resin, for example, a photosensitive resin and / or an alkali-soluble resin can be used. Examples of the photosensitive resin include thermoplastic resins such as urethane resins, acrylic resins, polyamic acid resins, polyimide resins, styrene maleic acid resins, and styrene maleic anhydride resins. Examples of alkali-soluble resins include (meth)acrylic copolymers having carboxyl groups and epoxy (meth)acrylate resins having carboxyl groups. When using the aforementioned photosensitive resin, a known and conventional photopolymerization initiator may be used in combination. Examples of alkali-soluble resins include ZCR-1569H (manufactured by Nippon Kayaku Co., Ltd., alkali-soluble epoxy (meth)acrylate) and SPC-3410 (manufactured by Showa Denko Corporation, alkali-soluble (meth)acrylic copolymer).

[0085] [solvent] Examples of solvents include organic solvents and water. Examples of the organic solvents that can be used include aromatic solvents such as toluene, xylene, and methoxybenzene; acetic acid ester solvents such as ethyl acetate, butyl acetate, propylene glycol monomethyl ether acetate, and propylene glycol monoethyl ether acetate; propionate solvents such as ethoxyethyl propionate; alcohol solvents such as methanol, ethanol, and 1-methoxy-2-propanol; ether solvents such as butyl cellosolve, propylene glycol monomethyl ether, diethylene glycol ethyl ether, and diethylene glycol dimethyl ether; ketone solvents such as methyl ethyl ketone, methyl isobutyl ketone, and cyclohexanone; aliphatic hydrocarbon solvents such as hexane; nitrogen compound solvents such as N,N-dimethylformamide, γ-butyrolactam, N-methyl-2-pyrrolidone, aniline, and pyridine; lactone solvents such as γ-butyrolactone; and carbamic acid esters such as a 48:52 mixture of methyl carbamate and ethyl carbamate.

[0086] [Activated energy ray monomer] Examples of the active energy ray monomers include tricyclodecanedimethanol di(meth)acrylate, ethoxylated bisphenol A di(meth)acrylate, hexanediol di(meth)acrylate, EO-modified bisphenol A di(meth)acrylate, hexanediol EO-modified di(meth)acrylate, hydroxypivalate neopentyl glycol di(meth)acrylate, neopentyl glycol PO-modified di(meth)acrylate, tripropylene glycol di(meth)acrylate, and dipropylene glycol di(meth)acrylate. Crylate, polyethylene glycol di(meth)acrylate, glycerin di(meth)acrylate, 2-[2-(vinyloxy)ethoxy]ethyl (meth)acrylate, 1,6-hexanediol di(meth)acrylate, 1,4-butanediol di(meth)acrylate, 1,3-butylene glycol di(meth)acrylate, 1,9-nonanediol di(meth)acrylate, 1,10-decanediol di(meth)acrylate, neopentyl glycol di(meth)acrylate, EO-modified 1,6-hexanediol di(meth)acrylate Lilate, propylene oxide-modified neopentyl glycol di(meth)acrylate, tripropylene glycol di(meth)acrylate, dipropylene glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, bisphenol A PO-modified di(meth)acrylate, bisphenol F EO-modified di(meth)acrylate, tricyclodecane dimethanol di(meth)acrylate, tetraethylene glycol di(meth)acrylate, polyethylene glycol di(meth)acrylate, polypropylene glycol Di(meth)acrylate, PO-modified tri(meth)acrylate of glycerin, 2-hydroxy-3-acryloyloxypropyl(meth)acrylate, EO-modified di(meth)acrylate of bisphenoxyethanol fluorene, polytetramethylene glycol di(meth)acrylate, phenoxyethylene glycol (meth)acrylate, stearyl(meth)acrylate, 2-(meth)acryloyloxyethyl succinate, trifluoroethyl(meth)acrylate, 3-methyl-1,5-pentanediol di(meth)acrylate, 2,3-[(meth)acryloyloxymethyl]norbornane, 2,5-[(meth)acryloyloxymethyl]norbornane, 2,6-[(meth)acryloyloxymethyl]norbornane, 1,3-adamantyl di(meth)acrylate, 1,3-bis[(meth)acryloyloxymethyl]adamantane, tris(hydroxyethyl)isocyanurate di(meth)acrylate, 3,9-bis[1,1-dimethyl-2-(meth)acryloyloxyethyl]-2,4,8,1 Difunctional monomers such as 0-tetraoxospiro[5.5]undecane, trimethylolpropane tri(meth)acrylate, trimethylolpropane EO-modified tri(meth)acrylate, trimethylolpropane PO-modified tri(meth)acrylate, glycerin propoxy tri(meth)acrylate, pentaerythritol tri(meth)acrylate, EO-modified glycerol acrylate, PO-modified glycerol triacrylate, pentaerythritol triacrylate, E Examples of photopolymerizable monomers include trifunctional monomers such as O-modified phosphate triacrylate, trimethylolpropane triacrylate, caprolactone-modified trimethylolpropane triacrylate, HPA-modified trimethylolpropane triacrylate, (EO) or (PO)-modified trimethylolpropane triacrylate, and alkyl-modified dipentaerythritol triacrylate; and polyfunctional monomers such as pentaerythritol tetra(meth)acrylate, pentaerythritol EO-modified tetra(meth)acrylate, ditrimethylolpropane tetra(meth)acrylate, ditrimethylolpropane tetra(meth)acrylate, pentaerythritol ethoxytetra(meth)acrylate, pentaerythritol tetra(meth)acrylate, dipentaerythritol hydroxypenta(meth)acrylate, alkyl-modified dipentaerythritol penta(meth)acrylate, and dipentaerythritol hexa(meth)acrylate.

[0087] [Photopolymerization initiator] Examples of the photopolymerization initiators include 1-hydroxycyclohexylphenyl ketone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, 1-[4-(2-hydroxyethoxy)phenyl]-2-hydroxy-2-methyl-1-propan-1-one, thioxanthone and thioxanthone derivatives, 2,2'-dimethoxy-1,2-diphenylethane-1-one, diphenyl(2,4,6-trimethoxybenzoyl)phosphine oxide, 2,4,6-trimethylbenzoyldiphenylphosphine oxide, and bis(2,4,6-trimethylbenzoyl). Examples include phenylphosphine oxide, 2-methyl-1-(4-methylthiophenyl)-2-morpholinopropan-1-one, 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-1-butanone, ethyl phenyl(2,4,6-trimethylbenzoyl)phosphinate, polymeric TPO-L, 1,2-octanedione,1-[4-(phenylthio)phenyl-,2-(O-benzoyl oxime)], or ethanone,1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazole-3-yl-,1-(O-acetyl oxime)]. Other commercially available photopolymerization initiators include, for example, "Omnirad-1173", "Omnirad-184", "Omnirad-127", "Omnirad-369", "Omnirad-379", "Omnirad-907", "Omnirad-4265", "Omnirad-1000", "Omnirad-651", "Omnirad-TPO", "Omnirad-819", "Omnirad-2022", "Omnirad-2100", "Omnirad-2959", "Omnirad-754", "Omnirad-784", "Omnirad-500", "Omnirad-819", "Omnirad TPO-L", "Omnipol TP", "Omnirad OXE01", "Omnirad OXE02", and "Omnirad Examples include "OXE03" (manufactured by IGM), "KayaCure-DETX", "KayaCure-MBP", "KayaCure-DMBI", "KayaCure-EPA", "KayaCure-OA" (manufactured by Nippon Kayaku Co., Ltd.), "ByCure-10", "ByCure-55" (manufactured by Stauffa Chemical), "Trigonal P1" (manufactured by Akzo), "Sandoz 1000" (manufactured by Sandoz), "Deep" (manufactured by Apjohn), "Quantacure-PDO", "Quantacure-ITX", "Quantacure-EPD" (manufactured by Ward Blenkinsop), "Runtecure-1104" (manufactured by Runtec), and "ADEKA Cruise NCI-831E" (manufactured by ADEKA).

[0088] [Composition of the coloring composition] The amount of dispersant in 100% by mass of the aforementioned coloring composition may be 1 to 90% by mass, or 3 to 50% by mass, as solid content, from the viewpoint of dispersibility. From the viewpoint of film-forming properties, the content of the resin in 100% by mass of the colored composition may be 1 to 90% by mass, or 3 to 50% by mass, as solid content. The solvent content in 100% by mass of the colored composition may be 10 to 95% by mass, or 40 to 90% by mass, from the viewpoint of dispersibility and film-forming properties. In 100% by mass of the coloring composition, the content of the active energy ray monomer may be 1 to 20% by mass, and may also be 3 to 10% by mass from the viewpoint of active energy ray curability. In 100% by mass of the coloring composition, the content of the photoinitiator may be 0.5 to 5% by mass, and may also be 0.5 to 3% by mass from the viewpoint of active energy ray curability.

[0089] (Molded body) The molded body of one embodiment of the present invention is a molded body formed from the coloring composition of the present embodiment. When the coloring composition of the present embodiment contains photosensitive components (the active energy ray monomer, photoinitiator) (in that case, the coloring composition of the present embodiment may be referred to as a "photosensitive coloring composition"), it is preferably a cured product of the coloring composition of the present embodiment. Examples of the molded body include a black matrix layer of a color filter constituting a display element such as a liquid crystal display, a partition material layer (also referred to as a bank layer or a pixel defining layer (PDL)) that separates light emitting elements in a display element such as an organic EL (OLED) display, and a black column spacer layer that performs light shielding between pixels and maintains a cell gap in a display device such as a liquid crystal display.

[0090] As a method for manufacturing the molded body of the present embodiment (for example, a black matrix layer, a bank layer, a black column spacer layer), for example, a typical method is a photolithography method. After performing pattern exposure with ultraviolet rays through a photomask on the above-mentioned coloring composition (photosensitive coloring composition) containing an active energy ray monomer and a photoinitiator, the unexposed portion can be washed with an organic solvent, alkaline water, etc. to form a molded body. Examples of the film forming method of the photosensitive coloring composition include a method of coating on a transparent substrate such as glass by a spin coating method, a slit coating method, a roll coating method, an inkjet method, etc.

[0091] <Black matrix layer> The aforementioned black matrix layer is a layer located on the light extraction side of a display element such as a liquid crystal display, which adjusts the light-emitting region. Preferably, the black matrix layer is located on the light extraction side, separated from the pixel division layer and the pixel portion, and is a layer that adjusts the light-emitting region from the pixel portion. The aforementioned black matrix layer is a cured film obtained by curing a photosensitive colored composition containing the colored composition of this embodiment. The black matrix layer formed using the colored composition of this embodiment does not interfere with active energy ray curing when used as a photoresist before curing with active energy rays. Furthermore, the cured black matrix layer can achieve high light-shielding properties.

[0092] The optical density of the black matrix layer at visible light wavelengths per 1 μm of film thickness is preferably 0.5 to 4.0, and more preferably 1.0 to 4.0.

[0093] [Bank layer] The bank layer is a partition material layer that surrounds each of multiple pixels in a display element such as an organic light-emitting diode (OLED) display, separating the light-emitting elements. The bank layer has multiple openings to ensure insulation from the electrodes of the display element and to partition (separate) each pixel region. The bank layer also functions as a partition to allow the formation of the functional layer that performs the display function of the display element during the manufacturing process described later, without affecting adjacent pixels. The bank layer can be formed using a photosensitive colored composition containing the colored composition of this embodiment. The thickness of the bank layer may be, for example, 0.1 μm to 10.0 μm. The bank layer formed using the colored composition of this embodiment does not interfere with active energy ray curing when used as a photoresist before curing with active energy rays. Furthermore, the cured bank layer can achieve high light shielding properties.

[0094] The optical density of the bank layer at visible light wavelengths per 1 μm of film thickness is preferably 0.5 to 4.0. The absorbance at 365 nm per 1 μm of film thickness of the bank layer is preferably 0.8 or less, more preferably 0.7 or less, and even more preferably 0.6 or less. It may also be 0.8 or more. In particular, when the bank layer thickness is 1 μm or more (it may also be 2 μm or more, or 5 μm or more), the present invention can sufficiently reduce the absorbance at 365 nm while maintaining the optical density at visible light wavelengths within a predetermined range. For example, when manufacturing the bank layer by the photoresist method, pattern exposure is performed by irradiating with ultraviolet light through a photomask, but the present invention enables pattern formation without hindering photocuring.

[0095] [Black column spacer layer] The aforementioned black column spacer is a structure provided in display elements such as liquid crystal displays to maintain the cell gap while ensuring light shielding between pixels. The black column spacer is placed between the pixel portion and the opposing substrate and plays a role in achieving both optical performance and mechanical stability of the display element. The black column spacer can be formed using a photosensitive colored composition containing the colored composition of this embodiment. The black column spacer layer formed using the colored composition of this embodiment does not interfere with active energy ray curing when used as a photoresist before curing with active energy rays. Furthermore, the cured black column spacer layer can achieve high light shielding properties.

[0096] The optical density of the black column spacer at visible light wavelengths per 1 μm of film thickness is preferably 0.5 to 4.0, and more preferably 1.0 to 4.0. [Examples]

[0097] The present invention will be described in more detail below with reference to examples, but the present invention is not limited to these examples.

[0098] The raw materials used in each of the examples described below are shown below. [Compound represented by general formula (i) (A)] The compounds represented by formulas (i-1) to (i-5) listed in Table 1 were used. The synthesis methods for each compound are shown in Synthesis Examples 1 to 5 below.

[0099] [Table 1]

[0100] [Pigment (B)] <Pigment 1> Pigment 1 consists of a compound represented by the following formula (molecular weight: 448.39).

[0101] [ka]

[0102] <Pigment 2> Pigment 2 consists of a compound represented by the following formula (molecular weight: 636.67) (molar ratio 50:50).

[0103] [ka]

[0104] <Pigment 3> MCF88, Mitsubishi Chemical Corporation, Carbon Black

[0105] <Pigment 4> Pigment Violet29

[0106] [ka]

[0107] <Pigment 5> Pigment Blue 15:6

[0108] [ka]

[0109] [Dispersant] Dispersant 1: BYK-LPN21116, BIC Chemi Japan Co., Ltd., acrylic, solids content 40% by mass Dispersant 2: DISPERBYK-2000, Big Chemi Japan Co., Ltd., acrylic-based, solids content 40% by mass

[0110] [resin] Resin 1: ZL-295B, Seiko PMC, alkali-soluble resin, solid content 40% by mass

[0111] [solvent] PGMAC: Propylene glycol monomethyl ether acetate, Kuraray Trading Co., Ltd. PGME: 1-Methoxy-2-propanol, Kanto Chemical Co., Ltd.

[0112] (Synthesis Example 1) "Synthesis of the compound represented by formula (i-1)" In a glass flask equipped with a stirrer, thermometer, condenser, and dropping device, 2.50 g of the compound NK-10739 (manufactured by Nagase Vita Co., Ltd.) and 375 g of a water / methanol=1 / 1 mixed solvent were charged and stirred at 50°C for 30 minutes to dissolve.

[0113] [ka]

[0114] Next, 5.19 g of sodium 12-tungst(VI) phosphate n hydrate (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) was dissolved in 42 g of a water / methanol = 1 / 1 mixed solvent, and this solution was added dropwise over 30 minutes using a dropping apparatus. After the addition was complete, the mixture was stirred at 50°C for a further 90 minutes to insolubilize it. After cooling to room temperature, the mixture was filtered and washed three times with 300 mL of pure water. The filtered solid was gelatinized with 200 mL of pure water, stirred for 30 minutes, and then filtered again. The obtained solid was dried at 90°C for 16 hours to obtain the compound represented by the above formula (i-1) (5.64 g).

[0115] (Synthesis Example 2) "Synthesis of the compound represented by formula (i-2)" In a glass flask equipped with a stirrer, thermometer, condenser, and dropping device, 2.50 g of the compound NK-10759 (manufactured by Nagase Vita Co., Ltd.) and 375 g of a water / methanol=1 / 1 mixed solvent were charged and stirred at 50°C for 30 minutes to dissolve.

[0116] [ka]

[0117] Next, 4.83 g of sodium 12-tungst(VI) phosphate n-hydrate (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) was dissolved in 60 g of a water / methanol = 1 / 1 mixed solvent, and this solution was added dropwise over 30 minutes using a dropping apparatus. After the addition was complete, the mixture was stirred at 50°C for a further 90 minutes to insolubilize it. After cooling to room temperature, the mixture was filtered and washed with 150 mL of pure water. The filtered solid was gelatinized with 200 mL of pure water and stirred for 30 minutes. After stirring, the mixture was filtered again and washed with 150 mL of pure water. The resulting solid was dried at 90°C for 16 hours to obtain the compound represented by the above formula (i-2) (5.59 g).

[0118] (Synthesis Example 3) "Synthesis of the compound represented by formula (i-3)" In a glass flask equipped with a stirrer, thermometer, condenser, and dropping device, 2.00 g of the compound NK-10374 (manufactured by Nagase Vita Co., Ltd.) and 269 g of a water / methanol=1 / 1 mixed solvent were charged and stirred at 50°C for 30 minutes to dissolve.

[0119] [ka]

[0120] Next, 4.31 g of sodium 12-tungst(VI) phosphate n hydrate (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) was dissolved in 31 g of a water / methanol mixed solvent (1 / 1 ratio). This solution was added dropwise over 30 minutes using a dropping apparatus. After the addition was complete, the mixture was stirred at 50°C for a further 90 minutes to insolubilize it. After cooling to room temperature, the mixture was filtered, and the filtered solid was gelatinized with 400 mL of pure water and stirred for 30 minutes. The mixture was filtered again and washed with 200 mL of pure water. The resulting solid was dried at 90°C for 16 hours to obtain the compound represented by formula (i-3) above (4.72 g).

[0121] (Synthesis Example 4) "Synthesis of the compound represented by formula (i-4)" 40 g of compound (i-4-1), 16.5 g of triethyl orthoformate, and 40 ml of pyridine were placed in a reaction vessel and heated under reflux and stirred in an oil bath at 120°C for 60 minutes. After the reaction was complete, 40 ml of ethyl acetate was added, followed by 200 ml of diisopropyl ether to precipitate crystals. After cooling, the mixture was filtered off. This was dried to obtain 29 g of the compound represented by compound (i-4-2).

[0122] [ka]

[0123] [ka]

[0124] Next, 2.50 g of the above compound (i-4-2) and 375 g of a water / methanol=1 / 1 mixed solvent were placed in a glass flask equipped with a stirrer, thermometer, condenser, and dropping device, and the mixture was stirred at 50°C for 30 minutes to dissolve the compound.

[0125] Next, 5.50 g of sodium 12-tungst(VI) phosphate n hydrate (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) was dissolved in 45 g of a water / methanol = 1 / 1 mixed solvent, and this solution was added dropwise over 30 minutes using a dropping apparatus. After the addition was complete, the mixture was stirred at 50°C for a further 90 minutes to insolubilize it. After cooling to room temperature, the mixture was filtered and washed three times with 300 mL of pure water. The filtered solid was gelatinized with 200 mL of pure water, stirred for 30 minutes, and then filtered again. The obtained solid was dried at 90°C for 16 hours to obtain the compound represented by the above formula (i-4) (5.80 g).

[0126] (Synthesis Example 5) "Synthesis of the compound represented by formula (i-5)" In a glass flask equipped with a stirrer, thermometer, condenser, and dropper, 2.00 g of compound NK-10739 (manufactured by Nagase Vita Co., Ltd.) and 300 g of a water / methanol=1 / 1 mixed solvent were charged and stirred at 50°C for 30 minutes to dissolve. Next, a solution of 2.84 g of sodium silicate dodecahydrate (manufactured by Mitsuwa Chemical Co., Ltd.) dissolved in 36 g of a water / methanol=1 / 1 mixed solvent was added dropwise over 30 minutes using the dropper. After the addition was complete, the mixture was stirred at 50°C for a further 90 minutes to insolubilize it. After cooling to room temperature, the mixture was filtered and washed three times with 150 mL of pure water. The filtered solid was gelatinized with 200 mL of pure water and stirred for 30 minutes. The mixture was filtered again, and the resulting solid was dried at 90°C for 16 hours to obtain the compound represented by the above formula (i-5) (3.39 g).

[0127] (Examples 1-30, Comparative Examples 1-3) In Example 1, pigment composition P-1 was obtained in Example P1 described below. The results are shown in Table 2. Then, in Example C1 described below, colored composition A-1 of this example was obtained. The results are shown in Table 3. To evaluate pigment composition P-1 and colored composition A-1 of this example, an evaluation colored composition was prepared and evaluated in Example CE1. The evaluation results are shown in Tables 4 and 5. Examples 2-30 and Comparative Examples 1-3 were prepared in the same manner as in Example 1, with pigment compositions and colored compositions being manufactured respectively. Evaluation colored compositions were also prepared and evaluated. The results are shown in Tables 2-4.

[0128] (Examples P1-P30, Comparative Examples P1-P3) "Manufacturing of pigment compositions" A pigment composition was prepared by mixing compound (A) represented by general formula (i) and pigment (B) to obtain the composition shown in Table 2.

[0129] [Table 2]

[0130] (Examples C1-C30, Comparative Examples C1-C3) [Manufacturing of coloring compositions] A colored composition was prepared by mixing the pigment composition, dispersant, and solvent prepared to match the composition shown in Table 3, and dispersing them for 4 hours using 0.3-0.4 mm zircon beads in a paint shaker (Toyo Seiki Seisakusho Co., Ltd., test disperser). In the table, "non-volatile content" refers to the solid content of the compound (A) represented by general formula (i), the pigment (B), and the dispersant.

[0131] [Table 3]

[0132] (Examples CE1-CE30, Comparative Examples CE1-CE3) [Manufacturing of colored compositions for evaluation] An evaluation coloring composition was produced by mixing a coloring composition, a resin, and a solvent manufactured to have the compositions of Tables 4 and 5. In the table, "non-volatile content" means the compound (A) represented by the general formula (i), the pigment (B), the solid content of the dispersant, and the resin.

[0133]

Table 4

[0134]

Table 5

[0135] [Preparation of Glass Substrate for Evaluation] The evaluation coloring composition was spin-coated on soda glass (manufactured by Nippon Sheet Glass Co., Ltd., glass plate), dried at 90 °C for 3 minutes, and then fired at 230 °C for 1 hour to obtain a glass substrate for evaluation with a film thickness of 1 μm.

[0136] [Measurement of Ultraviolet-Visible Absorption Spectrum and Transmission Spectrum] Using the above glass substrate for evaluation, the absorption spectrum and transmission spectrum from 300 nm to 780 nm were measured at a 1 nm pitch using a U-3900 manufactured by Hitachi High-Technologies Corporation.

[0137] <Evaluation of OD (Light-Shielding Property)> From the transmission spectrum, the luminance Y in the C light source per 1 μm of film thickness from 380 nm to 780 nm was calculated. The luminance Y is obtained by multiplying the spectral distribution of the C light source, the stimulus value (y) of the equal-color function, and the transmittance at each wavelength and integrating over the above wavelength range. Using the luminance Y, the OD per 1 μm of film thickness was calculated based on the following formula: OD = -Log 10 (Y / 100)

[0138] The evaluation criteria are shown below. A: Exceeding 1.0 B: 0.9 or more and 1.0 or less C: Less than 0.9

[0139] <Absorbance at 365nm (evaluation of UV transmittance)> The absorbance at 365 nm was obtained from the absorption spectrum. The measurement results were then evaluated based on the following criteria.

[0140] The evaluation criteria are as follows: A: Less than 0.7 B: 0.7 or more and 0.8 or less C: Exceeding 0.8

[0141] (Consideration) From Example 1 and Comparative Examples 1-3, it can be seen that pigment compositions using a combination of compound (A) represented by general formula (i) and a predetermined pigment (B) exhibit excellent light-shielding and UV-transmitting properties. Furthermore, Comparative Example 3 showed that using copper phthalocyanine instead of the compound represented by general formula (i) resulted in insufficient improvement. Furthermore, from Examples 2 to 30, it was found that similar effects can be obtained even when using various pigments or compounds represented by various general formulas (i), or when the content is changed.

Claims

1. One or more compounds (A) represented by the following general formula (i), A pigment composition comprising pigment (B), A pigment composition in which the pigment (B) comprises one or more pigments selected from the group consisting of carbon black, benzodifuranone pigments, and perylene pigments. 【Chemistry 1】 (In general formula (i), L ｉ１ The following general formula (L ｉ１ -1) 【Chemistry 2】 (General form (L) ｉ１ -1) Middle R Ｌｉ１１ , R Ｌｉ１２ and R Ｌｉ１３ Each of these independently represents a hydrogen atom, a halogen atom, a cyano group, a nitro group, an aliphatic hydrocarbon group having 1 to 8 carbon atoms which may have substituents, or an aromatic hydrocarbon group having 6 to 12 carbon atoms which may have substituents. R Ｌｉ１１ , R Ｌｉ１２ and R Ｌｉ１３ Two selected from them may be combined with each other to form a ring, l represents an integer from 1 to 3. * is A ｉ１ This represents a bonding action to, ** is A ｉ２ (Represents a binding operation to [a specific element].) It represents a base represented by, A ｉ１ The following general formula (A ｉ１ -1) and (A ｉ１ -2) 【Transformation 3】 (General formula (A ｉ１ -1) and (A ｉ１ -2) Medium, R Ａｉ１１ Each of these independently represents a hydrogen atom, a monovalent aliphatic hydrocarbon group having 1 to 20 carbon atoms which may have substituents, an aromatic hydrocarbon group having 6 to 12 carbon atoms which may be substituted, or an aralkyl group having 7 to 10 carbon atoms which may be substituted. * is L ｉ１ (Represents a binding operation to [a specific element].) This represents a group selected from the group consisting of groups represented by , A ｉ２ The formula is as follows (A ｉ２ -1) and (A ｉ２ -2) 【Chemistry 4】 (General formula (A ｉ２ -1) and (A ｉ２ -2) Medium, R Ａｉ２１ Each of these independently represents a hydrogen atom, a monovalent aliphatic hydrocarbon group having 1 to 20 carbon atoms which may have substituents, an aromatic hydrocarbon group having 6 to 12 carbon atoms which may be substituted, or an aralkyl group having 7 to 10 carbon atoms which may be substituted. ** is L ｉ１ (Represents a binding operation to [a specific element].) This represents a group selected from the group consisting of groups represented by , A ｉ１ and A ｉ２ One or more hydrogen atoms in the molecule are independently substituents S ｉ１ It may also be replaced by, Substituent S ｉ１ This represents a halogen atom, a cyano group, a nitro group, an N-alkylated amino group or ammonium group, a hydroxyl group, an allyloxy group, an alkoxy group, a sulfo group, an N-alkylated sulfamoyl group, a carboxyl group, an ester group, an N-alkylated amide group, a hydrocarbon group having 1 to 20 carbon atoms which may be substituted, an aromatic hydrocarbon group having 6 to 12 carbon atoms which may be substituted, a heterocyclic group having 3 to 12 carbon atoms which may be substituted, or an aralkyl group having 7 to 10 carbon atoms which may be substituted. Substituent S ｉ１ If there are multiple items, they may be the same or different. B ｍ－ This represents a polyoxometalate anion, m represents an integer from 1 to 20. n represents an integer between 1 and 20, n is determined such that the total charge in equation (i) is zero.

2. The pigment composition according to claim 1, wherein the content of compound (A) represented by the general formula (i) in 100% by mass of the pigment composition is 0.1 to 80.0% by mass.

3. The pigment composition according to claim 1 or 2, wherein the content of the pigment (B) in 100% by mass of the pigment composition is 20.0 to 99.9% by mass.

4. A coloring composition comprising the pigment composition according to claim 1 or 2.

5. A molded article formed from the colored composition described in claim 4.

6. The molded body according to claim 5, wherein the molded body is a black matrix layer, a bank layer, or a black column spacer layer.

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