CN108690372A

CN108690372A - Isoindoline pigment and its manufacturing method

Info

Publication number: CN108690372A
Application number: CN201810254112.8A
Authority: CN
Inventors: 滨木裕史; 栂井学; 中本秀; 中本秀一
Original assignee: Sumitomo Chemical Co Ltd
Current assignee: Sumitomo Chemical Co Ltd
Priority date: 2017-03-29
Filing date: 2018-03-26
Publication date: 2018-10-23
Anticipated expiration: 2038-03-26
Also published as: CN112442284B; KR102561748B1; CN112521774B; CN108690372B; KR20180110618A; TW201842077A; TWI754733B; CN112521774A; CN112442284A

Abstract

The present invention relates to isoindoline pigment and its manufacturing methods.The present invention provides the manufacturing method of isoindoline pigment, and the method includes following processes:The process for making isoindoline pigment (A) contact and then be separated by solid-liquid separation with sour (Z) in the presence of for 100 mass parts isoindoline pigments (A) being 100 water below mass part, and the process for making the solid of the isoindoline pigment (A) as obtained from aforementioned separation of solid and liquid contact and then be separated by solid-liquid separation with water.

Description

Isoindoline pigment and its manufacturing method

Technical field

The present invention relates to isoindoline (isoindoline) pigment and its manufacturing methods.

Background technology

As yellow or orange pigment, for example, it is known that C.I. pigment yellow 13s 9 etc., which have the compound of isoindoline skeleton, 's.The compound has been used for printing in the fields such as ink, coating.One kind is disclosed in Japanese Unexamined Patent Application 62-10169 bulletins The purification process of isoindoline pigment in the method, makes C.I. pigment yellow 13s 9 suspend in water, then adds benzoic acid, add Heat boiling, after filtering, is washed with water etc..

In Japanese Unexamined Patent Publication 2007-39481 bulletins, disclose by washing C.I. with non-polar organic solvents such as n-hexanes Pigment yellow 13 9, to form the technology for the envelope comprising mill base (color paste) that mist degree is small and pin hole is few.Japanese Unexamined Patent Publication In 2010-174143 bulletins, disclose by the way that C.I. pigment yellows 185 are dissolved in good solvent (DMSO) and keep the pigment molten Liquid is contacted with poor solvent (hydrochloric acid), to make the method for 185 miniaturization of C.I. pigment yellows.

Invention content

The purport of the manufacturing method of isoindoline pigment of the present invention is following aspect.

[1]The manufacturing method of isoindoline pigment, the method includes following processes:

Make different Yin in the presence of for 100 mass parts isoindoline pigments (A) being 100 water below mass part The process that diindyl quinoline pigment (A) is contacted and then is separated by solid-liquid separation with sour (Z), and

Make the work that isoindoline pigment is contacted and then is separated by solid-liquid separation with water as obtained from aforementioned separation of solid and liquid Sequence.

[2]Ru [1]The manufacturing method of the isoindoline pigment, wherein sour (Z) is organic acid.

[3]Ru [1]Huo [2]The manufacturing method of the isoindoline pigment, wherein sour (Z) is carboxylic acid compound.

[4]Ru [1]~[3]Any one of described in isoindoline pigment manufacturing method, wherein sour (Z) is carbon atom The aliphatic saturated carboxylic acid of number 1~5.

[5]The manufacturing method of isoindoline pigment, the method includes following processes:

Process (1) makes isoindoline pigment (A) be contacted with solvent (Z);And

Process (2) recycles the isoindoline pigment (A) contacted with solvent (Z) by being separated by solid-liquid separation,

In the method, the Hansen Solubility Parameter and solvent of isoindoline pigment calculated based on formula (E.1), aforementioned (Z) the distance Ra of Hansen Solubility Parameter is 0MPa^0.5The above 10MPa^0.5Hereinafter, also, solvent (Z) in process (1) Amount is below mass part for more than 0.1 mass parts 10.0 for 1 mass parts isoindoline pigment (A).

[In formula,

δ_D1:Dispersive component (the MPa of the Hansen Solubility Parameter of isoindoline pigment (A)^0.5),

δ_D2:Dispersive component (the MPa of the Hansen Solubility Parameter of solvent (Z)^0.5),

δ_P1:Polar component (the MPa of the Hansen Solubility Parameter of isoindoline pigment (A)^0.5),

δ_P2:Polar component (the MPa of the Hansen Solubility Parameter of solvent (Z)^0.5),

δ_H1:Hydrogen bond ingredient (the MPa of the Hansen Solubility Parameter of isoindoline pigment (A)^0.5),

δ_H2:Hydrogen bond ingredient (the MPa of the Hansen Solubility Parameter of solvent (Z)^0.5)]

[6]Ru [5]The manufacturing method, wherein the dispersion of the solvent (Z) in the Hansen Solubility Parameter of solvent (Z) Ingredient δ_D2For 16.0MPa^0.5The above 19.0MPa^0.5Hereinafter, the polar component δ of solvent (Z)_P2For 9.0MPa^0.5More than 17.0MPa^0.5Hereinafter, the hydrogen bond ingredient δ of solvent (Z)_H2For 6.5MPa^0.5The above 11.0MPa^0.5Below.

[7]Ru [5]Huo [6]The manufacturing method, wherein solvent (Z) includes selected from by ester solvent, ketone solvent, amide At least one of the group of solvent, sulfoxide solvent and sulfoxide solvent composition.

[8]Ru [5]~[7]Any one of described in manufacturing method, wherein the amount of solvent (Z) is relative to the different Yin of 1 mass parts It is below mass part for more than 0.5 mass parts 8.0 for diindyl quinoline pigment.

[9]Ru [1]~[8]Any one of described in manufacturing method, wherein isoindoline pigment include formula (1) indicate Compound.

[In formula (1),

R¹Indicate can be with the carbon atom number 1~40 of substituent group alkyl, can be with substituent group heterocycle or hydrogen The atom ,-CH for including in the alkyl₂And the heterocycle includes the-CH for not constituting ring₂When should-CH₂Can be substituted for- O-,-CO-,-S(O)₂-,-NR^x1-.But do not include passing through replacement-CH₂And formation-COOH and-S (O)₂The case where OH.Separately Outside, the alkyl and the heterocycle can have selected from by-CO₂ ^-With-S (O)₂O^-At least one of group of composition.

R²~R⁹Independently of each other indicate can be with the carbon atom number 1~40 of substituent group alkyl, can be with substituent group Heterocycle, hydrogen atom, halogen atom, cyano, nitro ,-CO₂ ^-Or-S (O)₂O^-,-the CH that includes in the alkyl₂And the heterocycle Base includes the-CH for not constituting ring₂When should-CH₂- O- ,-CO- ,-S (O) can be substituted for₂-,-NR^x1-.But do not include logical Cross replacement-CH₂And formation-COOH and-S (O)₂The case where OH.In addition, the alkyl and the heterocycle can have selected from by- CO₂ ^-With-S (O)₂O^-At least one of group of composition.

R²And R³,R³And R⁴,R⁴And R⁵,R⁶And R⁷And R⁸And R⁹Can together be formed with the carbon atom being respectively bonded can have The ring of substituent group, the ring include the-CH for not constituting ring₂When should-CH₂- O- ,-CO- ,-S (O) can be substituted for₂-,-NR^x1-。 But do not include passing through replacement-CH₂And formation-COOH and-S (O)₂The case where OH.In addition, the ring can have selected from by- CO₂ ^-With-S (O)₂O^-At least one of group of composition.

R^x1Indicate can be with the carbon atom number 1~40 of substituent group alkyl, can be with substituent group heterocycle or hydrogen Atom, the alkyl and the heterocycle can have selected from by-CO₂ ^-With-S (O)₂O^-At least one of group of composition.R^x1In the presence of When multiple, they can be the same or different.

A is the possessed-CO of compound that formula (1) indicates₂ ^-With-S (O)₂O^-Sum, indicate 0~10 in it is arbitrary whole Number.

M^b+Indicate the metal ion of hydrogen cation (hydron) or b valences.M^b+There are it is multiple when, they identical also can may be used With difference.M^b+For hydrogen cation when, the hydrogen cation and aforementioned-CO₂ ^-Or-S (O)₂O^-It is integrally formed and with-CO₂H and-S (O)₂The form of OH exists.

B indicates 1~6 integer.

When a is 0, when m 0, a are 1 or more, m indicates M^b+Number.

When a and m is 0, when n 1, a and m are not 0, n is the number for the relationship for meeting n=b × m/a.]

[10]Ru [9]The manufacturing method, wherein aforementioned isoindoline pigment is the compound that formula (1a) indicates,

The method further includes the manufacturing process for the compound that the formula (1a) in process A or process B indicates.

Process A:After the compound that formula (pt1) indicates is reacted with the compound that formula (pt2) indicates, further in acid In the presence of with formula (pt3) indicate compound and formula (pt4) indicate compound react, to manufacture formula (1a) indicate chemical combination The process of object;

Process B:The compound that the compound and formula (pt4) for the compound, formula (pt3) expression that formula (pt5) indicates indicate Reaction, the process to manufacture the compound that formula (1a) indicates,

[In formula (pt1)~formula (pt5) and formula (1a), R²~R⁹It indicates and identical meaning described previously.R⁴¹Indicate that hydrogen is former The alkyl of son or carbon atom number 1~20.M¹Indicate alkali metal atom.]

[11]Ru [9]Huo [10]The manufacturing method, wherein aforementioned isoindoline pigment is the chemical combination that formula (1b) indicates Object,

The method further includes following processes:

The synthesis procedure of formula (1a) in process A or process B;With

Shown in process C, formula (1b) indicate compound manufacturing process.

Process B:The compound that the compound and formula (pt4) for the compound, formula (pt3) expression that formula (pt5) indicates indicate Reaction, the process to manufacture the compound that formula (1a) indicates;

Process C:The compound that formula (1a) indicates reacts to manufacture formula (1b) expression with the compound that formula (pt6) indicates Compound process,

[In formula (pt1)~formula (pt6) and formula (1b), R¹~R⁹It indicates and identical meaning described previously.R⁴¹Indicate that hydrogen is former The alkyl of son or carbon atom number 1~20.M¹Indicate alkali metal atom.LG¹Indicate halogen atom, mesyloxy, chloromethyl sulphonyl Oxygroup, tosyloxy or trifluoro-methanesulfonyl oxy.Wherein, R¹It is not hydrogen atom.]

[12]Isoindoline pigment, in the powder x-ray diffraction intensity curve of the isoindoline pigment, the angle of diffraction (2 θ) it is for the summation A (10~15 °) of the peak area value in 10.0 ° or more 15.0 ° or less of range, with the aforementioned angle of diffraction (2 θ) The ratio between summation A (25~30 °) of peak area value in 25.0 ° or more 30.0 ° or less of range i.e. A (25~30 °)/A (10~ 15 °) it is 0.4 or more 5 or less.

[13]Ru [12]The isoindoline pigment, wherein (10~15 °) of ratio A (25~30 °)/A is 0.8 or more 5 Below.

[14]Ru [12]Huo [13]The isoindoline pigment, wherein in the angle of diffraction (2 θ) be with 1 or more Peak with summit (peak top) in 20.0 ° or more 30.0 ° or less of range, by maximum intensity in 1 or more the peak When the intensity at peak is as 100%, become 15% or more peak with 2 or more relative intensities.

[15]Ru [12]~[14]Any one of described in isoindoline pigment, wherein the angle of diffraction (2 θ) be 20.0 ° with Maximum peak intensity MS between upper 30.0 ° or less in the peak with summit_20-30, with the angle of diffraction (2 θ) be 8.0 ° less than Maximum peak intensity MS between 20.0 ° in the peak with summit_8-20Show MS_20-30≥0.8×MS_8-20Relationship.

[16]Ru [12]~[15]Any one of described in isoindoline pigment, by formula (1) indicate.

[In formula (1),

M^b+Indicate the metal ion of hydrogen cation or b valences.M^b+There are it is multiple when, they can be the same or different.M^b+ For hydrogen cation when, the hydrogen cation and aforementioned-CO₂ ^-Or-S (O)₂O^-It is integrally formed and with-CO₂H and-S (O)₂The form of OH is deposited .

B indicates 1~6 integer.

When a is 0, when m 0, a are 1 or more, m indicates M^b+Number.

[17]Colored curable resin composition, Qi Baohan [12]~[16]Any one of described in isoindoline pigment, Resin, polymerizable compound, polymerization initiator and solvent.

[18]Colour filter, Qi Baohan [12]~[16]Any one of described in isoindoline pigment.

[19]Display device, Qi Baohan [18]The colour filter.

Description of the drawings

Fig. 1:Fig. 1 is the X-ray diffraction intensity curve of the isoindoline pigment 1 obtained in embodiment 45.

Fig. 2:Fig. 2 is the X-ray diffraction intensity curve of the isoindoline pigment 2 obtained in embodiment 46.

Fig. 3:Fig. 3 is the X-ray diffraction intensity curve of the isoindoline pigment 3 obtained in embodiment 47.

Fig. 4:Fig. 4 is the X-ray diffraction intensity curve of the isoindoline pigment 4 obtained in embodiment 48.

Fig. 5:Fig. 5 is the X-ray diffraction intensity curve of the isoindoline pigment 5 obtained in embodiment 49.

Fig. 6:Fig. 6 is the X-ray diffraction intensity curve of the isoindoline pigment 6 obtained in embodiment 50.

Fig. 7:Fig. 7 is the X-ray diffraction intensity curve of the isoindoline pigment 7 obtained in embodiment 51.

Fig. 8:Fig. 8 is the X-ray diffraction intensity curve of the isoindoline pigment 8 obtained in embodiment 52.

Fig. 9:Fig. 9 is the X-ray diffraction intensity curve of the isoindoline pigment 9A obtained in embodiment 53.

Figure 10:Figure 10 is the X-ray diffraction intensity curve of the isoindoline pigment 9B obtained in embodiment 54.

Figure 11:Figure 11 is the X-ray diffraction intensity curve of the isoindoline pigment 9C obtained in embodiment 55.

Figure 12:Figure 12 is the X-ray diffraction intensity curve of the isoindoline pigment 9D obtained in embodiment 56.

Figure 13:Figure 13 is the X-ray diffraction intensity curve of the isoindoline pigment 9E obtained in embodiment 57.

Figure 14:Figure 14 is the X-ray diffraction intensity curve of the Y185 obtained in comparative example 19.

Figure 15:Figure 15 is the X-ray diffraction intensity curve of the Y139 obtained in comparative example 20.

Specific implementation mode

< manufacturing methods (1) >

As the manufacturing method of the present invention, can enumerate the isoindoline pigment including following processes manufacturing method (hereinafter, Sometimes the manufacturing method is known as " manufacturing method (1) "):

The solid of the isoindoline pigment as obtained from aforementioned separation of solid and liquid is set to contact and then be separated by solid-liquid separation with water Process.

In this specification, above-mentioned isoindoline pigment (A), which refers to crude object of isoindoline pigment etc., has isoindoline The mixture of the compound and impurity (other compounds, salt etc.) of skeleton.Above-mentioned isoindoline pigment (A) is normally solid.

That is, for manufacturing method (1), typically relate to include the isoindoline pigment of following processes manufacturer Method:

(i) make the crude object of isoindoline pigment for the crude object of the isoindoline pigment of 100 mass parts For the process for the separation of solid and liquid such as contacting and then being filtered with acid (Z) in the presence of 100 water below mass part, and

(ii) the isoindoline pigment as obtained from aforementioned separation of solid and liquid is made the solid-liquids such as to contact and then be filtered with water The process of separation.

By manufacturing method (1), purified isoindoline pigment can be obtained.

< acid (Z) >

As sour (Z), organic acid or inorganic acid.As organic acid, carboxylic acid compound can be enumerated and (wrapped in the molecule Containing-COOH bases), sulfoacid compound (in the molecule include-SO₃H yls) etc..

As carboxylic acid compound, formic acid, acetic acid, propionic acid, butyric acid, isobutyric acid, valeric acid, isovaleric acid, pivalic acid, the moon can be enumerated The aliphatic saturated carboxylic acid such as cinnamic acid, myristic acid, palmitic acid, stearic acid, oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid; The aromatic carboxylic acids such as benzoic acid, phthalic acid, M-phthalic acid, terephthalic acid (TPA);Etc..

As sulfoacid compound, the aliphatic sulfonics such as methanesulfonic acid can be enumerated;The aromatic sulphonic acids such as benzene sulfonic acid;Etc..

As inorganic acid, hydrochloric acid, nitric acid, phosphoric acid, sulfuric acid, hydrofluoric acid etc. can be enumerated.

For sour (Z), can also it be used in combination of two or more.As sour (Z), preferably organic acid, more preferably carboxylic acid chemical combination Object, further preferably aliphatic saturated carboxylic acid, more preferably the aliphatic saturated carboxylic acid of carbon atom number 1~5, particularly preferably Acetic acid.

As the method for making isoindoline pigment (A) be contacted with sour (Z), by isoindoline pigment (A) preferably in container Solid, acid (Z) and water mixing method.It, can be to the solid comprising isoindoline pigment (A), water and acid (Z) in mixing Mixed liquor be stirred, mixing time is preferably 1 minute~10 hours, more preferably 10 minutes~5 hours.Based on ultrasonic wave The stirring of vibration is also preferred.

When making isoindoline pigment (A) be contacted with sour (Z), the amount of water is relative to 100 mass parts isoindoline pigments (A) For be 100 below mass part, preferably 80 is below mass part, and more preferably 50 is below mass part, further preferably 30 matter Part is measured hereinafter, being still more preferably 10 below mass part, particularly preferably 1 is below mass part.

It is adjusted by the amount of the water to coexisting, the contrast for the isoindoline pigment (A) that can improve.

Sour (Z) can be diluted with the alcohol series solvents such as water, methanol, hydrogen chloride methanol solution etc., in the water that calculating coexists Amount when, also include these retarder thinners in amount of moisture.For being conducted to the solid of the isoindoline pigment (A) in this process For, the dried object of isoindoline pigment (A) not only can be used, it also may be preferable for obtained by reaction mixture using through separation of solid and liquid That arrives includes the residue of isoindoline pigment (A).In the latter case, include to be used in reaction also in the residue Solvent the case where, calculate coexist water amount when, also include these solvents in amount of moisture.

From the aspect of yield, for 1 mass parts isoindoline pigment (A), the usage amount of sour (Z) is preferably 5 More than mass parts, more than more preferably 7 mass parts, more than further preferably 9 mass parts, preferably 100 is below mass part, more Preferably 50 is below mass part, and further preferably 25 is below mass part.

Make isoindoline pigment (A) with preferably -20 DEG C or more of temperature when sour (Z) contact and in boiling point hereinafter, more excellent 20 DEG C or more 110 DEG C are selected as hereinafter, further preferably 60 DEG C or more 100 DEG C or less.It should be noted that above-mentioned boiling point is Refer to:Any lower temperature in the boiling point of sour (Z) or the boiling point of aforementioned retarder thinner.

In addition, time of contact when isoindoline pigment (A) being made to be contacted with sour (Z) is preferably 10 seconds or more, more preferably 10 minutes or more, further preferably 1 hour or more, preferably 24 hours hereinafter, more preferably 12 hours hereinafter, further it is excellent It is selected as 5 hours or less.

By being separated by solid-liquid separation after so that isoindoline pigment (A) is contacted with sour (Z), thus by isoindoline pigment (A) separation from sour (Z).That is, by being separated by solid-liquid separation, washed isoindoline pigment is obtained.

Be separated by solid-liquid separation preferably by natural filtration, be filtered under diminished pressure, pressure filtration, centrifugal filtration, the implementations such as centrifugation.It can Further to implement the processing such as washing, dry to the isoindoline pigment (A) for eliminating sour (Z).

After removing sour (Z), so that the isoindoline pigment as obtained from separation of solid and liquid is contacted with water, then carry out solid-liquid Separation, is thus further purified isoindoline pigment (A).That is, purified isoindoline pigment can be carried by being separated by solid-liquid separation It takes out.Be separated by solid-liquid separation preferably by natural filtration, be filtered under diminished pressure, pressure filtration, centrifugal filtration, the implementations such as centrifugation.

For the amount of the water when isoindoline pigment as obtained from separation of solid and liquid being made to be contacted with water, from yield side Face considers, for the 1 mass parts isoindoline pigments more than preferably 5 mass parts, it is more than more preferably 7 mass parts, More than further preferably 10 mass parts, preferably 300 is below mass part, and more preferably 150 is below mass part, further preferably It is below mass part for 75.

It, should preferably in container as the method that isoindoline pigment is contacted with water as obtained from separation of solid and liquid is made The method that isoindoline pigment is mixed with water.In mixing, the mixed liquor comprising the isoindoline pigment and water can be carried out Stirring, mixing time is preferably 1 minute~10 hours, more preferably 10 minutes~5 hours.Stirring based on ultrasonic activation It is preferred.

Temperature when the isoindoline pigment as obtained from separation of solid and liquid and water being made to contact be preferably 20 DEG C or more and Boiling point hereinafter, more preferably 40 DEG C or more 90 DEG C hereinafter, further preferably 60 DEG C or more 85 DEG C or less.

Time of contact when the isoindoline pigment as obtained from separation of solid and liquid being made to be contacted with water is preferably 10 seconds or more, More preferably 10 minutes or more, further preferably 1 hour or more, preferably 24 hours hereinafter, more preferably 12 hours hereinafter, Further preferably 5 hours or less.

Can to by above-mentioned (ii) process obtained from isoindoline pigment further implement washing, recrystallization, The processing such as dry.

As the solvent preferably for washing, the amides such as the alcohol series solvents such as methanol, n,N-Dimethylformamide can be enumerated Aromatic hydrocarbon solvents such as the sulfoxide solvents such as series solvent, dimethyl sulfoxide (DMSO), dimethylbenzene etc..In recrystallization, isoindoline pigment can be made It is precipitated from the in the mixed solvent comprising the acid amides series solvents such as the alcohol series solvents such as methanol and N,N-dimethylformamide.

< manufacturing methods (2) >

As the manufacturing method of the present invention, the manufacturing method of following isoindoline pigments can be also enumerated (hereinafter, sometimes will The manufacturing method is known as " manufacturing method (2) "), the method includes following processes:

Process (1) makes isoindoline pigment (A) be contacted with solvent (Z);And

In the method, Hansen Solubility Parameter calculated based on formula (E.1), aforementioned isoindoline pigment (A) with it is molten The distance Ra of the Hansen Solubility Parameter of agent (Z) is 0MPa^0.5The above 10MPa^0.5Hereinafter, also, the solvent (Z) in process (1) Amount it is below mass part for more than 0.1 mass parts 10.0 for 1 mass parts isoindoline pigment (A).

That is, manufacturing method (2) is related to the manufacturing method of following purified isoindoline pigments, the method includes under State process:

Process (1) makes isoindoline pigment (A) be contacted with solvent (Z);And

Process (2) is separated by solid-liquid separation by filtering etc. and obtains purified isoindoline pigment.

Solvent (Z) is the hansen solubility of the Hansen Solubility Parameter and aforementioned solvents (Z) of aforementioned isoindoline pigment (A) The distance Ra of parameter becomes 0MPa^0.5The above 10MPa^0.5Solvent below, also, the amount of solvent (Z) is relative to the different Yin of 1 mass parts It is below mass part for more than 0.1 mass parts 10.0 for diindyl quinoline pigment (A).

< solvents (Z) >

Hansen (Hansen) solubility parameter is the solubility parameter that will be introduced by Hildebrand (Hildebrand) It is divided into dispersion term δ_D, polarity item δ_PAnd hydrogen bond item δ_HThis 3 kinds of ingredients and the parameter indicated in three dimensions.Dispersion term δ_DTable Show the effect based on dispersion force, polarity item δ_PIndicate the effect based on dipolar forces, and, hydrogen bond item δ_HIt indicates based on hydrogen bond force Effect.

The definition and calculating of Hansen Solubility Parameter are written by Charles M.Hansen"Hansen Solubility Parameter:User Handbook"(Hansen Solubility Parameters:A Users Handbook) there is note in (CRC publishing houses, 2007) It carries.By using computer software Hansen Solubility Parameters in Practice (HSPiP), even if to For the solvent that literature value etc. is unknown, also can Hansen Solubility Parameter easily be calculated by its chemical constitution.

In the present invention, using HSPiP the 3rd edition, for the solvent registered in the database, using its value, for not existing Thus the solvent registered in database selects solvent using its estimated value.It should be noted that in the present invention, it will be with different Yin The solvent for meeting the relationship of formula (E.1) between diindyl quinoline pigment (A) is known as solvent (Z).

Solvent (Z) can be the separate solvent formed by a kind of solvent, can also be that the solvent comprising two or more solvent is mixed Close object.When solvent (Z) is solvent mixture, for the Hansen Solubility Parameter of the solvent (Z) in formula (E.1), base is used Average Hansen Solubility Parameter obtained from the mixing ratio (volume ratio) for each solvent for including in solvent mixture.

In general, the Hansen Solubility Parameter of pigment can be determined by carrying out following experiments, that is, the sample of the pigment is molten Solution measures solubility in the fixed a variety of different solvents of Hansen Solubility Parameter.It herein, for example, will be not in above-mentioned color The Hansen Solubility Parameter of certain other solvent used in the measurement of the Hansen Solubility Parameter of element is denoted as (δ_D2, δ_P2And δ_H2) When, if the point represented by the coordinate is comprised in the inside of the hansen solubility ball of above-mentioned pigment, then it is assumed that solvent energy will be upper State pigmentolysis.On the other hand, if the coordinate points are located at the outside of the hansen solubility ball of above-mentioned pigment, then it is assumed that the solvent is not It can be by above-mentioned pigmentolysis.

In the present invention, following such balls (hansen solubility ball) are found out and using the centre coordinate of the ball as the pigment Hansen Solubility Parameter will be in the solvent that used in above-mentioned solubility test for the ball (hansen solubility ball) The point in the three-dimensional of the solvent of the pigmentolysis can be integrally incorporated in the inside of ball, and the solvent of the pigment cannot be dissolved Point is positioned at the outside of ball.It should be noted that for the specific method of solubility test, it is described in detail in embodiment column.

Isoindoline pigment (A) can be the independent pigment formed by a kind of isoindoline pigment, can also be comprising 2 kinds The mixture of the above isoindoline pigment.Isoindoline pigment (A) is by isoindoline pigment (AI) and isoindoline pigment (AII) when the mixture that this 2 kinds of pigments are formed, the hansen solubility ginseng that formula (E.2) calculates isoindoline pigment (A) can be based on Number.Also volume fraction can be approximatively changed to weight fraction.When the mixture that isoindoline pigment (A) is 3 kinds or more, also may be used The Hansen Solubility Parameter of isoindoline pigment (A) is calculated using same calculating.

(δ_D1, δ_P1, δ_H1)=(x_Iδ_D1 ^Ix_IIδ_D1 ^II, x_Iδ_P1 ^I+x_IIδ_P1 ^II, x_Iδ_H1 ^I+x_IIδ_H1 ^II) (E.2)

[In formula, δ_D1,δ_P1And δ_H1It is identical with formula (E.1).

x_IFor the volume fraction of the isoindoline pigment (AI) in isoindoline pigment (A),

x_IIFor the volume fraction of the isoindoline pigment (AII) in isoindoline pigment (A),

(δ_D1 ^I, δ_P1 ^I, δ_H1 ^I) be isoindoline pigment (AI) Hansen Solubility Parameter,

(δ_D1 ^II, δ_P1 ^II, δ_H1 ^II) be isoindoline pigment (AII) Hansen Solubility Parameter.]

The Hansen Solubility Parameter distance Ra of the Hansen Solubility Parameter of isoindoline pigment (A) and solvent (Z) is by formula (E.1) it defines.The Hansen Solubility Parameter of isoindoline pigment (A) and the Hansen Solubility Parameter distance Ra of solvent (Z) are 0MPa^0.5Above, 10MPa^0.5Hereinafter, preferably 9.0MPa^0.5Hereinafter, more preferably 7.0MPa^0.5Hereinafter, further preferably 5.0MPa^0.5Below.When Ra is more than 10MPa, isoindoline pigment is likely to become low contrast.

[In formula,

In the Hansen Solubility Parameter of solvent (Z), the dispersive component δ of solvent (Z)_D2Preferably 16.0MPa^0.5More than, it is more excellent It is selected as 16.3MPa^0.5More than, further preferably 16.5MPa^0.5More than, preferably 19.0MPa^0.5Hereinafter, more preferably 18.7MPa^0.5Hereinafter, further preferably 18.5MPa^0.5Below.

The polar component δ of solvent (Z)_P2Preferably 9.0MPa^0.5More than, more preferably 9.5MPa^0.5More than, further preferably For 10.0MPa^0.5More than, preferably 17.0MPa^0.5Hereinafter, more preferably 16.7MPa^0.5Hereinafter, further preferably 16.4MPa^0.5Below.

The hydrogen bond ingredient δ of solvent (Z)_H2Preferably 6.5MPa^0.5More than, more preferably 6.8MPa^0.5More than, further preferably For 7.1MPa^0.5More than, preferably 11.0MPa^0.5Hereinafter, more preferably 10.7MPa^0.5Hereinafter, further preferably 10.4MPa^0.5Below.

In the Hansen Solubility Parameter of isoindoline pigment (A), the dispersive component δ of the pigment (A)_D1Preferably 15.5MPa^0.5More than, more preferably 16.0MPa^0.5More than, further preferably 16.5MPa^0.5More than, preferably 18.5MPa^0.5 Hereinafter, more preferably 18.2MPa^0.5Hereinafter, further preferably 18.0MPa^0.5Below.

The polar component δ of the pigment (A)_P1Preferably 9.0MPa^0.5More than, more preferably 10.0MPa^0.5More than, further Preferably 11.0MPa^0.5More than, preferably 17.0MPa^0.5Hereinafter, more preferably 16.0MPa^0.5Hereinafter, further preferably 15.0MPa^0.5Below.

The hydrogen bond ingredient δ of the isoindoline pigment (A)_H1Preferably 6.0MPa^0.5More than, more preferably 7.5MPa^0.5More than, Further preferably 9.0MPa^0.5More than, preferably 14.0MPa^0.5Hereinafter, more preferably 12.5MPa^0.5Hereinafter, further preferably For 11.0MPa^0.5Below.

As solvent (Z), solvent usually used in this field can be used, can enumerate for example that ester solvent is (in the molecule Including-COO- but not comprising-O- solvent), ether solvents (in the molecule include-O- but not comprising-COO- solvent), ether-ether Solvent (solvent for including-COO- and-O- in the molecule), ketone solvent (include-CO- in the molecule but do not include the molten of-COO- Agent), alcoholic solvent (including OH but the solvent not comprising-O- ,-CO- and-COO- in the molecule), aromatic hydrocarbon solvents, amide it is molten Agent, sulfoxide solvent, sulfoxide solvent.

As ester solvent, methyl lactate, ethyl lactate, butyl lactate, 2- hydroxy-methyl isobutyl acids, acetic acid second can be enumerated Ester, n-butyl acetate, isobutyl acetate, amyl formate, isoamyl acetate, butyl propionate, isopropyl isobutyrate, ethyl butyrate, fourth Acid butyl ester, methyl pyruvate, ethyl pyruvate, Propyl pyruvate, methyl acetoacetate, ethyl acetoacetate, Hexacyclonic Acid Ester and gamma-butyrolacton etc..

As ether solvents, ethylene glycol single methyl ether, ethylene glycol monomethyl ether, ethylene glycol monopropyl ether, ethylene glycol can be enumerated Single-butyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, propylene glycol monomethyl ether, third Glycol list ethylether, propylene glycol monopropyl ether, glycol monobutyl ether, 3- methoxyl groups-n-butyl alcohol, 3- methoxyl group -3- methyl fourths Alcohol, tetrahydrofuran, oxinane, 1,4- dioxanes, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethyl Glycol methyl ethyl ether, diethylene glycol dipropyl ether, diethylene glycol dibutyl ether, methyl phenyl ethers anisole, phenetole and methylanisole etc..

As ether-ether solvent, methoxy menthyl acetate, ethyl methoxyacetate, methoxyacetic acid butyl ester, ethoxy can be enumerated Acetic acid methyl ester, ethoxy ethyl acetate, 3- methoxy methyl propionates, 3- methoxypropionates, 3- ethoxypropanoates, 3- ethoxyl ethyl propionates, 2- methoxy methyl propionates, 2- methoxypropionates, 2- methoxy propyls propyl propionate, 2- ethyoxyls Methyl propionate, 2- ethoxyl ethyl propionates, 2- methoxyl groups -2 Methylpropionic acid methyl esters, 2- ethyoxyls -2 Methylpropionic acid ethyl ester, second Sour 3- methoxybutyls, acetic acid 3- methyl -3- methoxybutyls, propylene glycol monomethyl ether, propylene glycol monoethyl second Acid esters, propylene glycol monopropyl ether acetic acid esters, ethylene glycol single methyl ether acetic acid esters, ethylene glycol monomethyl ether acetate, diethylene glycol Single monoethyl ether acetate and diethylene glycol monobutyl ether acetic acid esters etc..

As ketone solvent, 4- hydroxy-4-methyl-2-pentanones, acetone, 2- butanone, 2-HEPTANONE, 3- heptanone, 4- heptan can be enumerated Ketone, 4-methyl-2 pentanone, cyclopentanone, cyclohexanone and isophorone etc..

As alcoholic solvent, methanol, ethyl alcohol, propyl alcohol, butanol, hexanol, cyclohexanol, ethylene glycol, propylene glycol and glycerine can be enumerated Deng.

As aromatic hydrocarbon solvents, benzene,toluene,xylene and mesitylene etc. can be enumerated.

As amide solvent, formamide, n,N-Dimethylformamide, acetamide, n,N-dimethylacetamide, N can be enumerated, N- dimethyl isobutyls amide, N, N- diethylformamides, N, N- diethyl acetamides, N, N- dimethylacetoacetamides, N-Methyl pyrrolidone, N- methyl-E-caprolactams, 1,3- dimethyl-2-imidazolinones and 1,3- dimethyl -3,4,5,6- four Hydrogen -2 (1H)-pyrimidone etc..As amide solvent, preferably n,N-Dimethylformamide, n,N-dimethylacetamide, N- methyl Pyrrolidones, N, N- dimethylacetoacetamides, 1,3-Dimethyl-2-imidazolidinone, more preferably N, N- dimethylacetamides Amine, N-Methyl pyrrolidone, N, N- dimethylacetoacetamides, 1,3- dimethyl-2-imidazolinones.

As sulfoxide solvent, dimethyl sulfoxide (DMSO), diethyl sulfoxide, dipropyl sulfoxide and tetramethylene sulfoxide etc. can be enumerated. As sulfoxide solvent, preferably dimethyl sulfoxide (DMSO), diethyl sulfoxide, more preferably dimethyl sulfoxide (DMSO).

As sulfoxide solvent, dimethyl sulfone, diethyl sulfone, dipropyl sulfone, isopropyl methyl sulfone and sulfolane etc. can be enumerated.Make For sulfoxide solvent, preferably dimethyl sulfone, diethyl sulfone, sulfolane, more preferably sulfolane.

Solvent (Z) is preferably comprised selected from the group being made of ester solvent, ketone solvent, amide solvent, sulfoxide solvent and sulfoxide solvent At least one of, more preferably include at least one of the group for being selected from and being made of amide solvent, sulfoxide solvent and sulfoxide solvent, into One step is preferably comprised selected from least one of the group being made of amide solvent and sulfoxide solvent.

In solvent (Z) 100%, amide solvent, sulfoxide solvent and sulfoxide solvent are preferably 40% or more with volume basis, more Preferably 50% or more, further preferably 60% or more.

As the method for making isoindoline pigment (A) be contacted with solvent (Z), by isoindoline pigment preferably in container (A) and solvent (Z) mixing method.Mixing when, can to the mixed liquor comprising isoindoline pigment (A) and solvent (Z) into Row stirring, mixing time is preferably 1 minute~10 hours, more preferably 10 minutes~5 hours.Stirring based on ultrasonic activation It is also preferred.

Temperature when isoindoline pigment (A) and solvent (Z) being made to contact be preferably the boiling point of -78 DEG C~solvent (Z) hereinafter, The boiling point of more preferably -20 DEG C~solvent (Z) is hereinafter, further preferably 10~50 DEG C.

Time of contact when isoindoline pigment (A) being made to be contacted with solvent (Z) is preferably 10 seconds or more, more preferably 10 points It is more than clock, further preferably 1 hour or more, preferably 24 hours hereinafter, more preferably 12 hours hereinafter, further preferably 5 hours or less.

About the amount of the solvent (Z) in process (1), from the aspect of yield, relative to 1 mass parts isoindoline pigment (A) it is 0.1 mass parts or more for, more than more preferably 0.5 mass parts, more than further preferably 2 mass parts, is 10.0 Below mass part, more preferably 8.0 is below mass part, and further preferably 6.0 is below mass part.

The isoindoline pigment (A) that is conducted in this process indicate to contact with solvent (Z) before isoindoline pigment (A), the dried object of isoindoline pigment (A) not only can be used, it also may be preferable for obtained by reaction mixture using through separation of solid and liquid That arrives includes the residue of isoindoline pigment (A).In the latter case, include to be used in reaction also in the residue Solvent, use in subsequent washing solvent the case where, also include this in the amount of the solvent (Z) in calculating Contact operation The amount for the solvent (Z) for including in a little solvents.

For the isoindoline pigment (A) contacted with solvent (Z), it can be divided from solvent (Z) by being separated by solid-liquid separation From extracting in solid form.That is, by manufacturing method (2), purified isoindoline pigment can be extracted.Gu Liquid separation preferably by natural filtration, be filtered under diminished pressure, pressure filtration, centrifugal filtration, the implementations such as centrifugation.It can be to eliminating The isoindoline pigment (A) of solvent (Z) further implements the processing such as washing, recrystallization, dry.

< isoindoline pigments >

As the present invention, the isoindoline pigment with crystal structure below can be enumerated.

Crystal structure can be identified by powder x-ray diffraction, specifically, in powder x-ray diffraction intensity curve, The summation A (10~15 °) for the peak area value in range that the angle of diffraction (2 θ) is 10.0 ° or more 15.0 ° or less and the aforementioned angle of diffraction The ratio between summation A (25~30 °) of peak area value in range that (2 θ) is 25.0 ° or more 30.0 ° or less i.e. A (25~30 °)/A (10~15 °) are 0.4 or more 5.0 or less 0.4 or more 5 or less, i.e..Present such crystal structure isoindoline pigment (with Under, sometimes referred to as isoindoline pigment A) contrast, phase difference it is excellent.Aforementioned ratio A (25~30 °)/A (10~15 °) is excellent 0.8 or more, more preferably 1.0 or more, preferably 4.7 are selected as hereinafter, more preferably 4.4 or less.

In X-ray diffraction analysis in the present invention, using from the CuK alpha rays to emission of cathodeAs X Radiographic source.As the assay method of specific X-ray diffraction analysis, the method described in embodiment can be used.

The isoindoline pigment of the present invention is preferably 20.0 ° with 1 or more the angle of diffraction (2 θ) in its X-ray diffraction Peak with summit in above 30.0 ° or less of range, using the intensity at the peak of maximum intensity in 1 or more the peak as When 100%, preferably become 15% or more peak with 2 or more relative intensities.Relative intensity becomes 15% or more peak Number be, for example, 20 hereinafter, preferably 10 hereinafter, more preferably 5 or less.

For the isoindoline pigment of the present invention, it is preferred that be in the angle of diffraction (2 θ) of its X-ray diffraction Maximum peak intensity MS between 20.0 ° or more 30.0 ° or less in the peak with summit_20-30, with the angle of diffraction (2 θ) be 8.0 ° with Above and it is less than the maximum peak intensity MS between 20.0 ° in the peak with summit_8-20Show MS_20-30≥0.8×MS_8-20Pass System.MS_20-30Preferably 10 × MS_8-20Hereinafter, more preferably 5 × MS_8-20Below.

As the isoindoline pigment of the present invention, can enumerate in powder x-ray diffraction spectrum, in 2 θ of the angle of diffraction below Isoindoline pigment with peak at (± 0.2).

Example (i):7.3 °, 9.2 °, 16.5 °, 18.9 °, 19.2 °, 21.6 °, 22.4 °, 24.4 °, 25.5 °, 30.6 °, 31.8 °, 32.0 °, 33.7 °

Example (ii):11.4 °, 13.6 °, 14.7 °, 18.3 °, 18.7 °, 19.5 °, 21.5 °, 22.7 °, 24.5 °, 25.0 °, 29.0°

Example (iii):6.7 °, 7.2 °, 10.1 °, 10.6 °, 11.9 °, 12.7 °, 15.1 °, 16.2 °, 18.5 °, 23.3 °, 24.3 °, 26.2 °, 29.2 °

Example (iv):5.9 °, 9.6 °, 11.2 °, 14.1 °, 15.6 °, 18.4 °, 23.9 °, 24.9 °, 25.1 °, 27.0 °

Example (v):9.1 °, 14.3 °, 14.8 °, 15.6 °, 16.7 °, 17.1 °, 19.3 °, 20.7 °, 24.6 °, 25.7 °, 26.1 °, 26.7 °, 27.4 °

Example (vi):8.9 °, 9.3 °, 9.9 °, 11.4 °, 12.0 °, 13.3 °, 14.4 °, 15.6 °, 17.1 °, 17.6 °, 22.7 °, 24.9 °, 25.8 °, 26.3 °

Example (vii):10.0 °, 11.1 °, 14.8 °, 15.1 °, 16.0 °, 17.3 °, 24.8 °, 25.8 °, 26.6 °, 28.0 °, 28.4 °, 29.5 °

Example (viii):13.5 °, 14.4 °, 14.5 °, 22.4 °, 26.0 °, 28.8 °

Example (ix):11.5 °, 11.7 °, 12.4 °, 13.5 °, 14.8 °, 15.6 °, 16.3 °, 16.7 °, 17.7 °, 18.2 °, 23.1 °, 23.6 °, 24.1 °, 25.9 °, 26.3 °, 26.6 °, 26.8 °, 27.2 °, 27.5 °, 28.0 °

Example (x):7.8 °, 8.4 °, 8.6 °, 9.0 °, 13.1 °, 13.5 °, 15.2 °, 20.3 °, 21.3 °, 24.9 °, 26.4 °, 27.0°

Example (xi):13.8 °, 14.3 °, 15.0 °, 17.9 °, 20.4 °, 21.8 °, 26.1 °, 26.4 °, 27.1 °

Example (xii):8.1 °, 10.1 °, 12.9 °, 13.4 °, 15.2 °, 15.8 °, 16.4 °, 17.5 °, 17.9 °, 19.2 °, 19.9 °, 20.4 °, 21.0 °, 22.9 °, 24.3 °, 24.8 °, 26.1 °, 26.3 °, 26.7 °, 27.0 °, 28.7 °, 30.0 °

Example (xiii):8.5 °, 9.7 °, 13.0 °, 13.5 °, 14.9 °, 16.7 °, 20.1 °, 24.9 °, 25.6 °, 26.0 °

The concrete example > of < isoindoline pigments

As isoindoline pigment obtained from each manufacturing method through the invention and the present invention isoindoline pigment, The compound that preferred formula (1) indicates (hereinafter, sometimes referred to as isoindoline pigment (1)).

[In formula (1),

B indicates 1~6 integer.

When a is 0, when m 0, a are 1 or more, m indicates M^b+Number.

It should be noted that about the-CH for including in alkyl₂It is replaced by-O- ,-CO- ,-S (O)₂-,-NR^x1And shape At group carbon atom number, with-O- ,-CO- ,-S (O)₂-,-NR^x1The carbon atom number before being replaced is waited to be counted Number.

In this specification, " substituent group " does not include-COOH and-S (O)₂OH.In addition, " substituent group " does not include by general- CH₂It is substituted for-O- ,-CO- ,-S (O)₂-,-NR^x1Or-NR^x3And the group formed.Hereinafter, sometimes will be by by-CH₂It replaces Change-O- ,-CO- ,-S (O) into₂-,-NR^x1And the group formed is known as " group (Z1) ".Hereinafter, sometimes will be by by-CH₂It replaces Change-O- ,-CO- ,-S (O) into₂-,-NR^x3And the group formed is known as " group (Z2) ".

The compound that formula (1) indicates can be the compound of formula (2) expression (hereinafter, sometimes referred to as isoindoline pigment (2))。

[In formula (2),

R¹¹Indicate can be with the carbon atom number 1~40 of substituent group alkyl, can be with substituent group heterocycle or hydrogen The atom ,-CH for including in the alkyl₂And the heterocycle includes the-CH for not constituting ring₂When should-CH₂Can be substituted for- O-,-CO-,-S(O)₂-,-NR^x3-.But do not include passing through replacement-CH₂And formation-COOH and-S (O)₂The case where OH.

R¹²~R¹⁵Independently of each other indicate can be with the carbon atom number 1~40 of substituent group alkyl, can with replace Heterocycle, hydrogen atom, halogen atom, cyano or the nitro of the base ,-CH for including in the alkyl₂And the heterocycle includes not constitute - the CH of ring₂When should-CH₂- O- ,-CO- ,-S (O) can be substituted for₂-,-NR^x3-.But do not include passing through replacement-CH₂- And formation-COOH and-S (O)₂The case where OH.

R¹²And R¹³,R¹³And R¹⁴And R¹⁴And R¹⁵Ring can be formed together with the carbon atom being respectively bonded, which includes not structure - the CH of cyclization₂When should-CH₂- O- ,-CO- ,-S (O) can be substituted for₂-,-NR^x3-.But do not include by replacement- CH₂And formation-COOH and-S (O)₂The case where OH.In addition, the ring can have substituent group.

R¹⁶Expression-CO-ORⁿ³⁰,-CO-NH₂,-CO-NH(Rⁿ³⁰),-CO-N(Rⁿ³¹)₂,-CO-H,-CO-Rⁿ³⁰Or-S (O)₂- Rⁿ³⁰.Wherein, R¹⁶Expression-CO-NH (Rⁿ³⁰) when, meet at least one party in (a), (b).

(a)R¹²~R¹⁵At least one of indicate can with substituent group carbon atom number 1~40 alkyl, can have Heterocycle, halogen atom, cyano or the nitro of substituted the base ,-CH for including in the alkyl₂And the heterocycle includes not constitute - the CH of ring₂When should-CH₂- O- ,-CO- ,-S (O) can be substituted for₂-,-NR^x3-.But do not include passing through replacement-CH₂- And formation-COOH and-S (O)₂The case where OH.

(b)R¹²And R¹³,R¹³And R¹⁴And R¹⁴And R¹⁵In at least one set of bonding and form ring, which includes not constitute - the CH of ring₂When should-CH₂- O- ,-CO- ,-S (O) can be substituted for₂-,-NR^x3-.But do not include passing through replacement-CH₂- And formation-COOH and-S (O)₂The case where OH.In addition, the ring can have substituent group.R¹²~R¹⁵In the R for not forming ring¹²~ R¹⁵Independently of each other indicate can be with the carbon atom number 1~40 of substituent group alkyl, can be with substituent group heterocycle, hydrogen Atom, halogen atom, cyano or the nitro ,-CH for including in the alkyl₂And the heterocycle includes the-CH for not constituting ring₂When It should-CH₂- O- ,-CO- ,-S (O) can be substituted for₂-,-NR^x3-.But do not include passing through replacement-CH₂And formation-COOH and- S(O)₂The case where OH.

Rⁿ³⁰The usually group of 1 valence indicates to have the alkyl of the carbon atom number 1~35 of substituent group or can have The heterocycle of the substituent group ,-CH for including in the alkyl₂And the heterocycle includes the-CH for not constituting ring₂When should-CH₂It can be with It is substituted for-O- ,-CO- ,-S (O)₂-,-NR^x3-.But do not include passing through replacement-CH₂And formation-COOH and-S (O)₂The feelings of OH Condition.Rⁿ³⁰There are it is multiple when, they can be the same or different.

Rⁿ³¹Indicate can be with the carbon atom number 1~15 of substituent group alkyl or can with the heterocycle of substituent group, - the CH for including in the alkyl₂And the heterocycle includes the-CH for not constituting ring₂When should-CH₂Can be substituted for-O- ,- CO-,-S(O)₂-,-NR^x3-.But do not include passing through replacement-CH₂And formation-COOH and-S (O)₂The case where OH.Rⁿ³¹In the presence of When multiple, they can be the same or different.

X¹The group that expression (1ax) indicates.

[In formula (1ax), R²¹And R²²Independently of each other indicate can with substituent group carbon atom number 1~40 alkyl, Can have heterocycle, hydrogen atom, halogen atom, cyano or the nitro of the substituent group ,-CH for including in the alkyl₂And the heterocycle Base includes the-CH for not constituting ring₂When should-CH₂- O- ,-CO- ,-S (O) can be substituted for₂-,-NR^x3-.But do not include logical Cross replacement-CH₂And formation-COOH and-S (O)₂The case where OH.

R²¹And R²²Can together be formed with the carbon atom being respectively bonded can include not constitute with the ring of substituent group, the ring - the CH of ring₂When should-CH₂- O- ,-CO- ,-S (O) can be substituted for₂-,-NR^x3-.But do not include passing through replacement-CH₂- And formation-COOH and-S (O)₂The case where OH.

* 1 indicates the connecting key with isoindoline ring.

R^x3Indicate can be with the carbon atom number 1~40 of substituent group alkyl, can be with substituent group heterocycle or hydrogen Atom.R^x3There are it is multiple when, they can be the same or different.]]

It should be noted that about the-CH for including in alkyl₂It is replaced by-O- ,-CO- ,-S (O)₂-,-NR^x3And shape At group carbon atom number, with-O- ,-CO- ,-S (O)₂-,-NR^x3The carbon atom number before being replaced is waited to be counted Number.

Isoindoline pigment (2)Without-CO₂ ^-And-S (O)₂O^-.Hereinafter, sometimes by-CO₂ ^-And-S (O)₂O^-Referred to as " hydrogen is just Ion-binding group ".

It include formula (2ax) in previously described formula (1ax).

[In formula (2ax), R²³,R²⁴Independently of each other indicate can with substituent group carbon atom number 1~35 alkyl, can With heterocycle or hydrogen atom with substituent group ,-the CH that includes in the alkyl₂And the heterocycle includes the-CH for not constituting ring₂- When should-CH₂- O- ,-CO- ,-S (O) can be substituted for₂-,-NR^x3-.But do not include passing through replacement-CH₂And formed- COOH and-S (O)₂The case where OH.

* 2 indicate the connecting key with isoindoline ring.

R^x3Indicate can be with the carbon atom number 1~40 of substituent group alkyl, can be with substituent group heterocycle or hydrogen Atom.R^x3There are it is multiple when, they can be the same or different.]

R¹~R⁹,R¹¹~R¹⁵,R²¹~R²²,R^x1And R^x3Alkyl, the R of the carbon atom number 1~40 of expression²³~R²⁴And Rⁿ³⁰Table The alkyl or R for the carbon atom number 1~35 shownⁿ³¹The alkyl of the carbon atom number 1~15 of expression can be aliphatic alkyl and fragrance Race's alkyl, the aliphatic alkyl can be saturation or unsaturated, can be chain or alicyclic ring.

As R¹~R⁹,R¹¹~R¹⁵,R²¹~R²⁴,R^x1,R^x3,Rⁿ³⁰And Rⁿ³¹The saturation or unsaturated chain hydrocarbon group of expression, It is straight that methyl, ethyl, propyl, butyl, amyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl etc. can be enumerated Chain-like alkyl etc.;Isopropyl, (2- methyl) propyl, isobutyl group, sec-butyl, tertiary butyl, (2- ethyls) butyl, isopentyl, new penta Base, tertiary pentyl, (1- methyl) amyl, (2- methyl) amyl, (1- ethyls) amyl, (3- ethyls) amyl, isohesyl, (5- methyl) Branched-chain alkyls such as hexyl, (2- ethyls) hexyl and (3- ethyls) heptyl etc.;Vinyl, 1- acrylic, 2- acrylic (allyls Base), isopropenyl, (1- methyl) vinyl, 2- cyclobutenyls, 3- cyclobutenyls, 1,3- butadienyls, (1- (2- acrylic)) ethylene Base, (1,2- dimethyl) alkenyls such as acrylic and 2- pentenyls;Etc..In addition, as R¹~R⁹,R¹¹~R¹⁵,R²¹~R²⁴, R^x1,R^x3,Rⁿ³⁰Example, further include heptadecyl, octadecyl and eicosyl.For saturation or unsaturated chain hydrocarbon group For carbon atom number, in R¹~R⁹,R¹¹~R¹⁵,R²¹~R²⁴,R^x1,R^x3,Rⁿ³⁰In the case of, preferably 1~30, more preferably 1 ~20, further preferably 1~15 are even more preferably 1~10, and then are still more preferably 1~8, particularly preferably 1 ~5;In Rⁿ³¹In the case of, preferably 1~15, more preferably 1~10 are even more preferably 1~8.

As R¹~R⁹,R¹¹~R¹⁵,R²¹~R²⁴,R^x1,R^x3,Rⁿ³⁰And Rⁿ³¹The saturation of expression or unsaturated ester ring type hydrocarbon Base can enumerate cyclopropyl, 1- methylcyclopropyl groups, cyclobutyl, cyclopenta, cyclohexyl, suberyl, 1- methylcyclohexyls, 2- methyl Cyclohexyl, 3- methylcyclohexyls, 4- methylcyclohexyls, 1,2- Dimethylcyclohexyls, 1,3- Dimethylcyclohexyls, 1,4- dimethyl Cyclohexyl, 2,3- Dimethylcyclohexyls, 2,4- Dimethylcyclohexyls, 2,5- Dimethylcyclohexyls, 2,6- Dimethylcyclohexyls, 3, 4- Dimethylcyclohexyls, 3,5- Dimethylcyclohexyls, 2,2- Dimethylcyclohexyls, 3,3- Dimethylcyclohexyls, 4,4- dimethyl Cyclohexyl, cyclooctyl, 2,4,6- trimethylcyclohexyls, 2,2,6,6- tetramethyl-rings hexyl and 3,3,5,5- tetramethyl-rings hexyl, The naphthenic base such as 4- pentylcyclohexyls, 4- octyls cyclohexyl, 4- cyclohexylcyclohexyls;Cyclohexenyl group (such as hexamethylene -2- alkene, hexamethylene - 3- alkene), cycloheptenyl, the cycloalkenyl groups such as cyclo-octene base;It is norborneol alkyl, adamantyl, bicyclic;2.2.2]Octyl etc..For For the carbon atom number of alicyclic type hydrocarbon, in R¹~R⁹,R¹¹~R¹⁵,R²¹~R²⁴,R^x1,R^x3,Rⁿ³⁰In the case of, preferably 3~ 30, more preferably 3~20, further preferably 4~20 are even more preferably 4~15, are still more preferably 5~15, special It You Xuanwei 5~10, wherein particularly preferably cyclopenta, cyclohexyl, suberyl, cyclooctyl;In Rⁿ³¹In the case of, preferably 4~15, more preferably 5~15 are even more preferably 5~10, wherein particularly preferably cyclopenta, cyclohexyl, suberyl, Cyclooctyl.

R¹~R⁹,R¹¹~R¹⁵,R²¹~R²⁴,R^x1,R^x3And Rⁿ³⁰And Rⁿ³¹The saturation or unsaturated alkyl of expression can be by Group obtained from chain alkyl listed above and alicyclic type hydrocarbon combination, can enumerate such as Cvclopropvlmethvl, cyclopropyl second Base, cyclobutylmethyl, cyclobutylethyl, cyclopentyl-methyl, cyclopentyl ethyl, cyclohexyl methyl, cyclohexyl-ethyl etc. are bonded with 1 The alkyl of a above alicyclic type hydrocarbon.For its carbon atom number, in R¹~R⁹,R¹¹~R¹⁵,R²¹~R²⁴,R^x1,R^x3And Rⁿ³⁰ In the case of, preferably 4~30, more preferably 4~20, further preferably 4~15;In Rⁿ³¹In the case of, preferably 4~ 15。

About R¹~R⁹,R¹¹~R¹⁵,R²¹~R²⁴,R^x1,R^x3And Rⁿ³⁰And Rⁿ³¹The aromatic hydrocarbyl of expression can enumerate benzene Base, o-tolyl, tolyl, p-methylphenyl, 2,3- 3,5-dimethylphenyls, 2,4- 3,5-dimethylphenyls, 2,5- 3,5-dimethylphenyls, 2, 6- 3,5-dimethylphenyls, 3,4- 3,5-dimethylphenyls, 3,5- 3,5-dimethylphenyls, o-isopropyl phenyl, isopropyl phenyl, p-isopropyl Phenyl, o-tert-butyl phenyl, tert-butyl-phenyl, (2- propyl) phenyl bis- to tert-butyl-phenyl, mesitylene base, 2,6-, 2, 4,6- trimethylphenyls, 1- naphthalenes, 2- naphthalenes, 5,6,7,8- tetrahydrochysene -1- naphthalenes, 5,6,7,8- tetrahydrochysene -2- naphthalenes, fluorenyl, phenanthrene The aromatic hydrocarbyls such as base and anthryl;Etc..For the carbon atom number of aromatic hydrocarbyl, in R¹~R⁹,R¹¹~R¹⁵,R²¹~ R²⁴,R^x1,R^x3And Rⁿ³⁰In the case of, preferably 6~30, more preferably 6~20, further preferably 6~15;In Rⁿ³¹Feelings Under condition, preferably 6~15.

R¹~R⁹,R¹¹~R¹⁵,R²¹~R²⁴,R^x1,R^x3,Rⁿ³⁰And Rⁿ³¹The aromatic hydrocarbyl of expression is not particularly limited, as long as It is the alkyl with aromatic series hydrocarbon ring, can is chain alkyl, alicyclic type hydrocarbon and the aromatic hydrocarbyl that will be listed above At least one of combined with aromatic hydrocarbyl listed above obtained from group, benzyl, 2- methylbenzyls, 3- first can be enumerated The aralkyl such as base benzyl, 4- methylbenzyls, phenylethyl, phenyl propyl, 1- methyl-1s-phenylethyl;Phenyl vinyl (benzene second Alkenyl (phenylvinyl group)) etc. aromatic yl alkenyls;The aromatic yl polysulfide yls such as phenylene-ethynylene;The keys such as xenyl, terphenyl Closing has the phenyl of 1 or more phenyl;Cyclohexyl methyl phenyl, benzyl phenyl, (dimethyl (phenyl) methyl) phenyl;Etc., it is right For its carbon atom number, in R¹~R⁹,R¹¹~R¹⁵,R²¹~R²⁴,R^x1,R^x3And Rⁿ³⁰In the case of, preferably 7~30, it is more excellent It is selected as 7~20, further preferably 7~15;In Rⁿ³¹In the case of, preferably 7~15.

R¹~R⁹,R¹¹~R¹⁵,R²¹~R²⁴,R^x1,R^x3,Rⁿ³⁰And Rⁿ³¹The alkyl of expression can with 1 valence substituent group or The substituent group of divalent.For the substituent group of divalent, preferably 2 connecting keys are bonded to same carbon atom and form double bond.

As the substituent group of 1 valence, can enumerate:

The alkyl sulfenyl of the carbon atom numbers 1~10 such as methylsulfany, ethylsulfanyl, propyl sulfenyl and butyl sulfenyl (alkylsulfanyl group);

The halogen atoms such as fluorine atom, chlorine atom, bromine atom and iodine atom;

Nitro;Cyano;

Trifluoromethyl, perfluoro-ethyl, perfluoro propyl, perfluoroisopropyl, perfluoro butyl, perfluoropentyl, perfluoro hexyl, perfluor The fluorine atoms such as heptyl, perfluoro capryl, perfluor nonyl, perfluoro decyl, perfluorocyclohexyl, perfluorophenyl instead of whole hydrogen atoms and The alkyl of obtained carbon atom number 1~20, preferably carbon atom number 1~10;

*-CO-SH;

*-CO-S-CH₃,*-CO-S-CH₂CH₃,*-CO-S-CH₂-CH₂-CH₃,*-CO-S-CH₂-CH₂-CH₂-CH₃Deng with it is same The carbonyl of the sulfur atom linkage of alkyl (carbon atom number of the alkyl is 1~10) bonding;

*-CO-S-C₆H₅Deng the carbonyl for the sulfur atom linkage being bonded with same aryl (carbon atom number of the aryl is 6~20); Etc..

As the substituent group of divalent, can enumerate thio group, imino group, through carbon atom number 1~20 (preferably carbon atom number 1~ 10) imino group etc. that alkyl-substituted imino group, the aryl through carbon atom number 6~20 replace.As through alkyl-substituted Asia Amino can enumerate CH₃- N=, CH₃-CH₂- N=, CH₃-(CH₂)₂- N=, CH₃-(CH₂)₃- N=etc..As what is replaced through aryl Imino group can enumerate C₆H₅- N=etc..

As substituent group, preferably halogen atom;Nitro;Cyano;Fluorine atom is former instead of carbon obtained from whole hydrogen atoms The alkyl of subnumber 1~20;Thiocarbonyl (thiocarbonyl);Etc.,

More preferable fluorine atom, chlorine atom, bromine atom;Nitro;Cyano;Fluorine atom is instead of carbon obtained from whole hydrogen atoms The alkyl of atomicity 1~10;Thiocarbonyl etc..

R¹~R⁹The alkyl of expression, which can have, to be passed through-CH₂It is substituted for-O- ,-CO- ,-S (O)₂-,-NR^x1And it is formed Group (i.e. group (Z1)).

R¹¹~R¹⁵,R²¹~R²⁴,Rⁿ³⁰And Rⁿ³¹The alkyl of expression, which can have, to be passed through-CH₂Be substituted for-O- ,-CO- ,- S(O)₂Or-NR^x3And the group (i.e. group (Z2)) formed.

As group (Z1), group (Z2), can enumerate:

Methoxyl group, ethyoxyl, propoxyl group, isopropoxy, butoxy, isobutoxy, sec-butoxy, tert-butoxy, amyl Oxygroup, hexyl oxygroup, (2- ethyls) hexyl oxygroup, heptyl oxygroup, octyl oxygroup, nonyl oxygroup, phenyl oxygroup and o-tolyl Oxygroup etc. is bonded with the oxygroup for the alkyl that carbon atom number is 1~20, more preferable carbon atom number 1~10 in unilateral side;

Epoxy group;

Formoxyl;

It is acetyl group, propiono, bytyry, tertiary bytyry, valeryl, caproyl, (2- ethyls) caproyl, heptanoyl group, pungent The acyl group (preferably alkanoyl) that the carbon atom numbers such as acyl group, pelargonyl group, benzoyl are 2~22, preferably carbon atom number is 2~12;

Methoxycarbonyl, ethoxy carbonyl, propoxycarbonyl, butoxy carbonyl, tert-butoxycarbonyl, amyl oxygroup carbonyl Base, hexyl Epoxide carbonyl, (2- ethyls) hexyl Epoxide carbonyl, heptyl Epoxide carbonyl and octyl Epoxide carbonyl, nonyl Epoxide carbonyl, Phenyloxycarbonyl, o-tolyl Epoxide carbonyl etc. are bonded with carbon atom number 1~20, the preferably alkyl of carbon atom number 1~10 Epoxide carbonyl;

Amino;

N- methylaminos, N, N- dimethylaminos, N- ethylaminos, N, N- diethylaminos, N- propylcarbamics, N, N- bis- Propylcarbamic, N- isopropylaminos, N, N- diisopropylaminoethyls, N- butylaminos, N, N- dibutylaminos, N- isobutyl group ammonia Base, N, N- diisobutylaminos, N- s-butylaminos, N, N- di-sec-butyls amino, N- tert-butylaminos, N, N- di-t-butyl ammonia Base, N- pentyl aminos, N, N- dipentylaminos, N- (1- ethyl propyls) amino, N, N- bis- (1- ethyl propyls) amino, N- hexyls Amino, N, N- dihexyls amino, N- (2- ethyls) hexylamino, N, N- bis- (2- ethyls) hexylamino, N- heptyl amino, N, N- Diheptyl amino, N- octyl aminos, N, N- dioctylaminos, N- nonylaminos, N, N- dinonyl amino, N- phenyl aminos, N, N- diphenyl aminos, N, N- ethylmethylaminos, N, N- propyl-methylaminos, N, N- isopropylmethylaminos, N, N- butyl first Base amino, N, N- tertbutyl methyls amino and N, N- phenylmethyl amino etc. are former by 1 or 2 carbon atom numbers 1~10, preferably carbon The amino of the alkyl substitution of subnumber 1~20;

Sulfamoyl;

N- Methylsulfamoyls, N, N- DimethylsuIfamoyls, N- ethylsulfamovls, N, N- diethyl aminos sulfonyl, N- propylsulfamovs, N, N- dipropyl sulfamoyl, N- isopropylsulfamoyls base, N, N- diisopropyls sulfamoyl, N- fourths Base sulfamoyl, N, N- dibutylamines sulfonyl, N- isobutyl groups sulfamoyl, N, N- diisobutyls sulfamoyl, N- sec-butyls Sulfamoyl, N, N- di-sec-butyls sulfamoyl, N- tertiary butyls sulfamoyl, N, N- di-t-butyls sulfamoyl, N- amyl ammonia Sulfonyl, N, N- diamyl sulfamoyl, N- (1- ethyl propyls) sulfamoyl, N, N- bis- (1- ethyl propyls) sulfamoyl, N- hexyls sulfamoyl, N, N- dihexyls sulfamoyl, N- (2- ethyls) hexyl sulfamoyl, N, N- bis- (2- ethyls) hexyl ammonia Sulfonyl, N- heptyl sulfamoyl, N, N- diheptyls sulfamoyl, N- octyls sulfamoyl, N, N- dioctyls sulfamoyl, N, N- octyl methyls sulfamoyl, N- nonyls sulfamoyl, N, N- dinonyl sulfamoyl, N- phenyl sulfamoyls base, N, N- hexichol Base sulfamoyl, N, N- ethyl-methyls sulfamoyl, N, N- hydroxypropyl methyls sulfamoyl, N, N- isopropyl methyls sulfamoyl, N, N- butyl methyl sulfamoyl, N, N- tertbutyl methyls sulfamoyl and N, N- phenyl methyl sulfamoyl etc. are by 1 or 2 The sulfamoyl of the alkyl substitution of carbon atom number 1~20, preferably carbon atom number 1~10;

Formylamino;Acetyl-amino, propanoylamino, bytyry amino, 2,2- dimethylpropionylaminos, valeryl Base amino, caproyl amino, (2- ethyls) caproyl amino, heptanoyl group amino, octanoylamino, pelargonyl group amino, capryl The carbon atom numbers 1 such as amino, hendecyl amino, dodecane acyl amino, heneicosane acyl amino, benzoyl-amido~ 22, the preferred alkanoylamino of carbon atom number 1~12;

Hydroxyl;

Formoxyl oxygroup, acetoxyl group, propiono oxygroup, bytyry oxygroup, 2,2- dimethylpropionyloxies, valeryl Oxygroup, caproyl oxygroup, (2- ethyls) caproyl oxygroup, heptanoyl group oxygroup, caprylyl oxygroup, pelargonyl group oxygroup and benzoyl The alkanoyl oxygroup of the carbon atom numbers such as oxygroup 1~20, preferably carbon atom number 1~10;

Methyl sulphonyl, ethylsulfonyl, sulfonyl propyl base, butyl sulfonyl, pentylsulfonyl, hexyl sulfonyl, (2- Ethyl) hexyl sulfonyl, heptyl sulfonyl, octyl sulfonyl, nonyl sulfonyl, decyl sulfonyl, phenyl sulfonyl and to first The sulfonyl through carbon atom number 1~20, the preferably alkyl substitution of carbon atom number 1~10 such as phenyl sulfonyl;

Carbamoyl;

N- methylcarbamoyls, N, N- formyl-dimethylaminos, N- ethylaminocarbonyls, N, N- diethylaminos Formoxyl, N- propvlcarbamovls, N, N- dipropylaminos formoxyl, N- isopropylcarbamoyls, N, N- diisopropyls Carbamoyl, N- Butylcarbamoyls, N, N- dibutylaminos formoxyl, N- butylcarbamoyls, N, N- bis- are different Butylcarbamoyl, N- s-butylaminos formoxyl, N, N- di-sec-butyls carbamoyl, N- t-Butylcarbamoyls, N, N- di-t-butyl carbamoyl, N- pentylcarbamoys, N, N- dipentylaminos formoxyl, N- (1- ethyl propyls) ammonia Base formoxyl, N, N- bis- (1- ethyl propyls) carbamoyl, N- hexylaminos formoxyl, N, N- dihexyls carbamoyl, N- (2- ethyls) hexylamino formoxyl, N, N- bis- (2- ethyls) hexylamino formoxyl, N- heptyl carbamoyl, N, N- bis- Heptyl carbamoyl, N- octyl aminos formoxyl, N, N- dioctylaminos formoxyl, N- nonylcarbamoyls, N, N- bis- Nonylcarbamoyl, N- phenylcarbamoyls, N, N- diphenylcarbamoyls, N, N- ethylmethylaminos formoxyl, N, N- propyl-methylamino formoxyl, N, N- isopropylmethylaminos formoxyl, N, N- butyl methyls carbamoyl, N, uncle N- Butyl methyl carbamoyl and N, N- phenylmethyl amino formoxyls etc. are former by 1 or 2 carbon atom numbers 1~20, preferably carbon The carbamoyl of the alkyl substitution of subnumber 1~10;

*-COCOR^n2a;

*-OCON(R^n2a)₂;

*-N(R^n2a)COOR^n2b;

*-OP(O)(OR^n2a)₂;

*-Si(R^n2a)(R^n2b)(R^n2c);Etc..

In previously described formula, R^n2a,R^n2b,R^n2cIt can be the same or different, indicating respectively can be with the carbon atom of substituent group The alkyl of number 1~35 or the-CH that can include with the heterocycle of substituent group, in the alkyl₂And the heterocycle includes not structure - the CH of cyclization₂When should-CH₂- O- ,-CO- ,-S (O) can be substituted for₂-,-NR^x1-.But do not include by replacement- CH₂And formation-COOH and-S (O)₂The case where OH.In addition, the alkyl or heterocycle can have selected from by-CO₂ ^-With-S (O)₂O^-At least one of group of composition.R^x1It is same as above.For R^n2a,R^n2b,R^n2cConcrete example and preferred range For, other than the example for being 36 or more not comprising carbon atom number, with R¹It is identical.

R¹~R⁹,R¹¹~R¹⁵,R²¹~R²⁴,R^x1,R^x3,Rⁿ³⁰And Rⁿ³¹The heterocycle of expression can be monocycle, or It is polycyclic, preferably include heterocycle of the hetero atom as the inscape of ring.As hetero atom, can enumerate nitrogen-atoms, oxygen atom and Sulphur atom etc..

R¹~R⁹,R¹¹~R¹⁵,R²¹~R²⁴,R^x1,R^x3And Rⁿ³⁰The carbon atom number of the heterocycle of expression is preferably 2~30, more Preferably 3~22, further preferably 3~20 are even more preferably 3~18, are still more preferably 3~15, especially excellent It is selected as 3~14.Rⁿ³¹The carbon atom number of the heterocycle of expression is preferably 2~15, more preferably 3~15, even more preferably for 3~ 14。

As only including nitrogen-atoms as heteroatomic heterocycle, can enumerate aziridine, azetidine, pyrrolidines, The monocycles such as piperidines, piperazine system saturated heterocyclic;Pyrazoles, the miaows such as the pyrroles such as 2,5- dimethyl pyrroles, 2- methylpyrazoles, 3- methylpyrazoles 5 yuan of ring system unsaturated heterocycles such as azoles, 1,2,3- triazoles, 1,2,4- triazoles;The pyrimidines such as pyridine, pyridazine, 6- methylpyrimidines, pyrazine, 6 yuan of ring system unsaturated heterocycles such as 1,3,5- triazines;Indazole, indoline, isoindoline, indoles, indolizine, benzimidazole, quinoline, The quinoxalines such as isoquinolin, 5,6,7,8- tetrahydrochysenes (3- methyl) quinoxaline, 3- methyl-quinoxalines, quinazoline, cinnolines, phthalazines, naphthyridines, The fused bicyclics system such as purine, pteridine, benzopyrazoles, benzo piperidines heterocycle;The fused tricyclics such as carbazole, acridine, azophenlyene system heterocycle;Under State the ring etc. of formula expression.

(in formula, * indicates connecting key)

As only comprising oxygen atom as heteroatomic heterocycle, oxirane, oxetanes, tetrahydrochysene furan can be enumerated Mutter, the monocycles system such as oxinane, 1,3- dioxanes, 1,4- dioxanes, 1- cyclopenta dioxolane it is full And heterocycle;1,4- Er Yangzaluos [4.5]Decane, 1,4- Er Yangzaluos [4.5]The second cycle lines saturated heterocyclic such as nonane;α-second lactone, The lactones such as beta-propiolactone, gamma-butyrolacton, δ-valerolactone system heterocycle;Furans such as 2,3- dimethyl furans, 2,5- dimethyl furans etc. 5 yuan of ring system unsaturated heterocycles;6 yuan of ring system unsaturated heterocycles such as 2H- pyrans, 4H- pyrans;1- benzofurans, 4- methyl benzo pyrroles It mutters equal chromenes, Ben Bing bis- Evil luxuriant (benzodioxole), chroman, the heterochromatic fused bicyclics system heterocycle such as full;Xanthene, dibenzo The fused tricyclics such as furans system heterocycle;Etc..

As only comprising sulphur atom as heteroatomic heterocycle, 5 yuan of ring system saturated heterocyclics such as dithiolane can be enumerated; Thia hexamethylene (thiane), 1,3- dithiane, 2- methyl-1s, 6 yuan of ring system saturated heterocyclics such as 3- dithiane;3 methyl thiophene, 5 yuan of ring system unsaturated heterocycles such as benzothiopyran derivatives such as the thiophene such as 2- carboxy thiophenes, 4H- thiapyrans, benzo tetrahydric thiapyran;Benzothiophene etc. Fused bicyclic system heterocycle etc.;The fused tricyclics such as thianthrene, dibenzothiophenes system heterocycle;Etc..

, as heteroatomic heterocycle, morpholine, 2-Pyrrolidone, 2- methyl-can be enumerated as comprising nitrogen-atoms and oxygen atom The monocycles system saturated heterocyclics such as 2-Pyrrolidone, 2- piperidones, 2- methyl -2- piperidones;4- Jia Ji oxazole Deng oxazoles, 2- methyl are different The monocycles system unsaturated heterocycles such as oxazole, 3- methyl-isoxazole Deng isoxazoles;Benzoxazole, benzoisoxazole, benzoxazine, benzo The fused bicyclics such as dioxane, benzimidazoline system heterocycle;The fused tricyclics such as phenoxazine system heterocycle;Etc..

, as heteroatomic heterocycle, 3- methylthiazols, 2,4- dimethyl thiophenes can be enumerated as comprising nitrogen-atoms and sulphur atom The monocyclic heterocycles such as the thiazoles such as azoles;The fused bicyclics such as benzothiazole system heterocycle;The fused tricyclics such as phenthazine system heterocycle;Etc..

Above-mentioned heterocycle can be group made of combination alkyl listed above, can enumerate such as tetrahydrofuran base first Base, methyltetrahydrofuran base etc..

It should be noted that the bonding position of above-mentioned heterocycle is the part that the arbitrary hydrogen atom for including is detached from each ring.

R¹~R⁹The heterocycle of expression includes the-CH for not constituting ring₂When, it should-CH₂It can be by-O- ,-CO- ,-S (O)₂-,- NR^x1It replaces.-CH₂When being replaced, R¹~R⁹The heterocycle of expression includes above-mentioned group (Z1).

R¹¹~R¹⁵,R²¹~R²⁴,Rⁿ³⁰And Rⁿ³¹The heterocycle of expression includes the-CH for not constituting ring₂When, it should-CH₂It can be with By-O- ,-CO- ,-S (O)₂-,-NR^x3It replaces.-CH₂When being replaced, R¹¹~R¹⁵,R²¹~R²⁴,Rⁿ³⁰And Rⁿ³¹The heterocycle of expression Base includes above-mentioned group (Z2).

Aforementioned heterocycle include nitrogen-atoms as its constitution element when, above-mentioned R¹The nitrogen-atoms can be bonded to.

R²And R³,R³And R⁴,R⁴And R⁵,R⁶And R⁷,R⁸And R⁹,R¹²And R¹³,R¹³And R¹⁴,R¹⁴And R¹⁵Or R²¹And R²²Bonding and When forming ring, which can be hydrocarbon ring, or heterocycle.As hydrocarbon ring, aliphatic hydrocarbon ring, aromatic series hydrocarbon ring etc. can be enumerated.

As aliphatic hydrocarbon ring, cyclopropane ring, methyl cyclopropane ring, cyclobutane ring, pentamethylene ring, hexamethylene can be enumerated Ring, cycloheptane ring, hexahydrotoluene ring, 1,1- dimethyl cyclohexanes ring, 1,2- dimethyl cyclohexanes ring, 1,3- dimethyleyelohexanes Alkane ring, 1,4- dimethyl cyclohexanes ring, cyclooctane ring, 1,3,5- trimethyl-cyclohexanes ring, 1,1,3,3- tetramethyls cyclohexane ring, The cycloalkanes hydrocarbon rings such as pentylcyclohexane ring, octylcyclohexane ring, cyclohexyl cyclohexane ring;Cyclohexene ring, cycloheptene ring, cyclo-octene ring Equal cyclenes hydrocarbon ring;Norbornane, adamantane, Shuan Huan [2.2.2]Octane etc..The carbon atom number of aliphatic hydrocarbon ring is, for example, 3~30, Preferably 3~20, more preferably 4~20 are even more preferably 4~15, are still more preferably 5~15, particularly preferably 5 ~10.

As aromatic series hydrocarbon ring, benzene, toluene, ortho-xylene, meta-xylene, paraxylene, cumene, tertiary fourth can be enumerated Bis- (2- propyl) benzene of base benzene, mesitylene, 1,5-, naphthalene, 1,2,3,4- naphthanes, fluorenes, phenanthrene, anthracene;Etc..The carbon of aromatic hydrocarbyl Atomicity is, for example, 6~30, preferably 6~20, more preferably 6~15.

R²And R³,R³And R⁴,R⁴And R⁵,R⁶And R⁷,R⁸And R⁹,R¹²And R¹³,R¹³And R¹⁴,R¹⁴And R¹⁵Or R²¹And R²²Bonding and The ring of formation can have substituent group.As the substituent, it can enumerate and R¹~R⁹,R¹¹~R¹⁵,R²¹~R²⁴,R^x1,R^x3,Rⁿ³⁰With Rⁿ³¹The identical group of substituent group that the alkyl of expression can have.

R²And R³,R³And R⁴,R⁴And R⁵,R⁶And R⁷,R⁸And R⁹The ring for being bonded and being formed includes-the CH for not constituting ring₂When, should- CH₂It can be by-O- ,-CO- ,-S (O)₂-,-NR^x1It replaces.-CH₂When being replaced, R²And R³,R³And R⁴,R⁴And R⁵,R⁶And R⁷,R⁸ And R⁹The ring for being bonded and being formed includes above-mentioned group (Z1).

R¹²And R¹³,R¹³And R¹⁴,R¹⁴And R¹⁵Or R²¹And R²²The ring for being bonded and being formed includes-the CH for not constituting ring₂When, It should-CH₂It can be by-O- ,-CO- ,-S (O)₂-,-NR^x3It replaces.-CH₂When being replaced, R¹²And R¹³,R¹³And R¹⁴,R¹⁴And R¹⁵, Or R²¹And R²²The ring for being bonded and being formed includes above-mentioned group (Z2).

R²And R³,R³And R⁴,R⁴And R⁵,R⁶And R⁷,R⁸And R⁹,R¹²And R¹³,R¹³And R¹⁴,R¹⁴And R¹⁵Or R²¹And R²²Bonding and When forming heterocycle, which can form and above-mentioned R¹~R⁹,R¹¹~R¹⁵,R²¹~R²⁴,R^x1,R^x3,Rⁿ³⁰And Rⁿ³¹The heterocycle of expression The same heterocycle of base.R²And R³,R³And R⁴,R⁴And R⁵,R¹²And R¹³,R¹³And R¹⁴Or R¹⁴And R¹⁵When being bonded and forming heterocycle, this is miscellaneous Ring group and R²~R⁵Or R¹²~R¹⁵The phenyl ring being bonded together, has the ring structure of 2 rings or more.As this have 2 rings with On ring structure heterocycle, for example, the heterocycle of the structure with following formula can be enumerated.

(phenyl ring in formula is equivalent to isoindoline structure possessed by isoindoline pigment (1) or isoindoline pigment (2) In phenyl ring)

R²And R³,R³And R⁴,R⁴And R⁵,R⁶And R⁷,R⁸And R⁹,R¹²And R¹³,R¹³And R¹⁴,R¹⁴And R¹⁵Or R²¹And R²²Bonding and When forming heterocycle, which can have substituent group.As the substituent, it can enumerate and R¹~R⁹,R¹¹~R¹⁵,R²¹~R²⁴, R^x1,R^x3,Rⁿ³⁰And Rⁿ³¹The identical group of substituent group that the alkyl of expression can have.

R²And R³,R³And R⁴,R⁴And R⁵,R⁶And R⁷,R⁸And R⁹The heterocycle for being bonded and being formed includes-the CH for not constituting ring₂When, It should-CH₂It can be by-O- ,-CO- ,-S (O)₂-,-NR^x1It replaces.-CH₂When being replaced, R²And R³,R³And R⁴,R⁴And R⁵,R⁶With R⁷,R⁸And R⁹The ring for being bonded and being formed includes above-mentioned group (Z1).

R¹²And R¹³,R¹³And R¹⁴,R¹⁴And R¹⁵Or R²¹And R²²The heterocycle for being bonded and being formed includes-the CH for not constituting ring₂When, It should-CH₂It can be by-O- ,-CO- ,-S (O)₂-,-NR^x3It replaces.-CH₂When being replaced, R¹²And R¹³,R¹³And R¹⁴,R¹⁴And R¹⁵, Or R²¹And R²²The ring for being bonded and being formed includes above-mentioned group (Z2).

Preferably, R¹~R⁹At least one of, preferably R⁶~R⁹In at least one, more preferable R⁶And R⁷In a side And R⁸And R⁹In a side be alkyl, the and-CH for including in the alkyl₂It is replaced by-O- ,-CO- ,-S (O)₂-,-NR^x1-.But It does not include passing through replacement-CH to be₂And formation-COOH and-S (O)₂The case where OH.In addition, R⁶And R⁷In a side and R⁸And R⁹In A side be the-CH for including in alkyl and the alkyl₂When being replaced, R⁶And R⁷In another party and R⁸And R⁹In another party it is excellent It is selected as selected from by CN, COO^-,S(O)₂O^-1 kind in the group of composition, more preferably CN.

As-CH₂Group obtained from being replaced can enumerate such as-CO-ORⁿ¹⁰(group is-CH₂-CH₂-Rⁿ¹⁰In 2-CH₂Respectively by-CO- ,-O- replace obtained from group) ,-CO-NH₂(group is-CH₂-CH₂2 in-H- CH₂Group obtained from being replaced respectively by-CO- and-NH-) ,-CO-NH (Rⁿ¹⁰) (group is-CH₂-CH₂-Rⁿ¹⁰In 2- CH₂Group obtained from being replaced respectively by-CO- and-NH-) ,-CO-N (Rⁿ¹¹)₂(group is-CH₂-CH₂-Rⁿ¹¹In 2- CH₂Respectively by-CO- and-NRⁿ¹¹Group obtained from replacement) ,-CO-H (group be-CH₂- CH in-H₂It is replaced by-CO- Group obtained from changing) ,-CO-Rⁿ¹⁰(group is-CH₂-Rⁿ¹⁰In-CH₂Group obtained from being replaced by-CO-) or-S (O)₂-Rⁿ¹⁰(group is-CH₂-Rⁿ¹⁰In-CH₂By-S (O)₂Group obtained from replacement) etc..

In formula, Rⁿ¹⁰Indicate can be with the carbon atom number 1~35 of substituent group alkyl or can be with the miscellaneous of substituent group The ring group ,-CH for including in the alkyl₂And the heterocycle includes the-CH for not constituting ring₂When should-CH₂Can be substituted for- O-,-CO-,-S(O)₂-,-NR^x1-.But do not include passing through replacement-CH₂And formation-COOH and-S (O)₂The case where OH.Separately Outside, the alkyl or heterocycle can have selected from by-CO₂ ^-With-S (O)₂O^-At least one of group of composition.R^x1With institute above It states identical.For Rⁿ¹⁰Concrete example and preferred range for, in addition to not comprising carbon atom number be 36 or more example other than, With R¹It is identical.

Rⁿ¹⁰There can be group (Z1).As Rⁿ¹⁰The preferred group (Z1) that can have, the preferably halogens such as chlorine atom Atom;Sulfamoyl;Hydroxyl;Methoxyl group etc. is bonded with the oxygroup of the alkyl of carbon atom number 1~10 in unilateral side;Methoxycarbonyl etc. It is bonded with the Epoxide carbonyl of the alkyl of carbon atom number 1~10;-SO₂NH₂Deng.In addition, Rⁿ¹⁰There can be-CO₂ ^-,-S(O)₂O^-Deng.

In formula, Rⁿ¹¹Indicate can be with the carbon atom number 1~15 of substituent group alkyl or can be with the miscellaneous of substituent group The ring group ,-CH for including in the alkyl₂And the heterocycle includes the-CH for not constituting ring₂When should-CH₂Can be substituted for- O-,-CO-,-S(O)₂-,-NR^x1-.But do not include passing through replacement-CH₂And formation-COOH and-S (O)₂The case where OH.Separately Outside, the alkyl or heterocycle can have selected from by-CO₂ ^-With-S (O)₂O^-At least one of group of composition.R^x1With institute above It states identical.For Rⁿ¹¹Concrete example and preferred range for, in addition to not comprising carbon atom number as 16 or more example with Outside, with R¹It is identical.

Rⁿ¹¹There can be group (Z1).As Rⁿ¹¹The preferred group (Z1) that can have, the preferably halogens such as chlorine atom Atom;Sulfamoyl;Hydroxyl;Methoxyl group etc. is bonded with the oxygroup of the alkyl of carbon atom number 1~10 in unilateral side;Methoxycarbonyl etc. It is bonded with the Epoxide carbonyl of the alkyl of carbon atom number 1~10;-SO₂NH₂Deng.In addition, Rⁿ¹¹There can be-CO₂ ^-,-S(O)₂O^-Deng.

R¹¹~R¹⁵Or R²¹~R²⁴For alkyl when ,-the CH that includes in the alkyl₂- O- ,-CO- ,-S can be substituted for (O)₂-,-NR^x3-.But do not include passing through replacement-CH₂And formation-COOH and-S (O)₂The case where OH.As-CH₂By for Group obtained from changing can enumerate such as-CO-ORⁿ³⁵,-CO-NH₂,-CO-NH(Rⁿ³⁵),-CO-N(Rⁿ³⁶)₂,-CO-H,-CO- Rⁿ³⁵Or-S (O)₂-Rⁿ³⁵Deng (in formula, Rⁿ³⁵For with Rⁿ³⁰Identical meaning, Rⁿ³⁶For with Rⁿ³¹Identical meaning).Especially, as R¹⁶, preferably-CO-ORⁿ³⁰,-CO-NH₂,-CO-NH(Rⁿ³⁰),-CO-N(Rⁿ³¹)₂,-CO-H,-CO-Rⁿ³⁰Or-S (O)₂-Rⁿ³⁰Deng (in formula, Rⁿ³⁰,Rⁿ³¹As hereinbefore).

As-CO-ORⁿ¹⁰,-CO-ORⁿ³⁰,-CO-ORⁿ³⁵, preferably methoxycarbonyl, ethoxy carbonyl, propoxycarbonyl, Tert-butoxycarbonyl, butoxy carbonyl, amyl Epoxide carbonyl, hexyl Epoxide carbonyl, (2- ethyls) hexyl Epoxide carbonyl, heptyl oxygen Base carbonyl, octyl Epoxide carbonyl, nonyl Epoxide carbonyl, decyloxycarbonyl, undecyl Epoxide carbonyl, dodecyl oxygroup carbonyl Base, phenyloxycarbonyl and eicosyl Epoxide carbonyl etc. are bonded with the Epoxide carbonyl etc. of the alkyl of carbon atom number 1~35, more excellent Choosing can enumerate the Epoxide carbonyl etc. for the alkyl for being bonded with carbon atom number 1~10.

As-CO-NH (Rⁿ¹⁰),-CO-N(Rⁿ¹¹)₂,-CO-NH(Rⁿ³⁰),-CO-N(Rⁿ³¹)₂,-CO-NH(Rⁿ³⁵),-CO-N (Rⁿ³⁶)₂, preferably N- methylcarbamoyls, N- ethylaminocarbonyls, N- propvlcarbamovls, N- isopropylamino first Acyl group, N- Butylcarbamoyls, N- butylcarbamoyls, N- s-butylaminos formoxyl, N- tert-butylamino formyls Base, N- pentylcarbamoys, N- (1- ethyl propyls) carbamoyl, N- hexylaminos formoxyl, N- (2- ethyls) hexyl Carbamoyl, N- heptyl carbamoyl, N- octyl aminos formoxyl, N- nonylcarbamoyls, N- Decylamino formyls Base, N- undecyls carbamoyl, N- dodecylaminos formoxyl, N- eicosyls carbamoyl and N- phenyl aminos The carbamoyl etc. that formoxyl etc. is replaced by the alkyl of 1 carbon atom number 1~35;

N, N- formyl-dimethylamino, N, N- ethylmethylaminos formoxyl, N, N- diethylaminos formoxyl, N, N- Propyl-methylamino formoxyl, N, N- dipropylaminos formoxyl, N, N- isopropylmethylaminos formoxyl, N, N- diisopropyls Carbamoyl, N, N- tertbutyl methyls carbamoyl, N, N- diisobutylaminos formoxyl, N, N- di-sec-butyl amino first Acyl group, N, N- di-t-butyls carbamoyl, N, N- butyl methyls carbamoyl, N, N- dibutylaminos formoxyl, N, N- Butyl octyl carbamoyl, N, N- dipentylaminos formoxyl, N, N- bis- (1- ethyl propyls) carbamoyl, N, N- bis- oneself Base carbamoyl, N, N- bis- (2- ethyls) hexylamino formoxyl, N, N- diheptyls carbamoyl, N, N- octyl methyl ammonia Base formoxyl, N, N- dioctylaminos formoxyl, N, N- dinonyl carbamoyl, N, N- decyls methylcarbamoyl, N, N- undecyls methylcarbamoyl, N, N- dodecyl methyls carbamoyl, N, N- phenylmethyl aminos formoxyl and The carbamoyl etc. that N, N- diphenylcarbamoyl etc. is replaced by the alkyl of 2 carbon atom numbers 1~15, can more preferably enumerate The carbamoyl etc. replaced by the alkyl of 1 or 2 carbon atom number 1~10.-CO-NH(Rⁿ¹⁰),-CO-N(Rⁿ¹¹)₂In, it is right For the aforementioned carbamoyl replaced by 1 or 2 alkyl, which can have-COO^-。

As-CO-Rⁿ¹⁰,-CO-Rⁿ³⁰,-CO-Rⁿ³⁵, preferably acetyl group, propiono, bytyry, 2,2- dimethyl propionyl Base, valeryl, caproyl, (2- ethyls) caproyl, heptanoyl group, caprylyl, pelargonyl group, capryl, hendecyl, dodecane Acyl group, heneicosane acyl group, benzoyl, phenyl methyl carbonyl, phenylethyl carbonyl, phenylpropyloxycarbonyl etc. are bonded with carbon original The carbonyl for the alkyl that subnumber is 1~35 can preferably enumerate the carbonyl etc. for being bonded with the alkyl that carbon atom number is 1~10.-CO- Rⁿ¹⁰,-CO-Rⁿ³⁰,-CO-Rⁿ³⁵In, for the carbonyl for being bonded with alkyl, which can have the halogens such as chlorine atom former Son;Sulfamoyl;Hydroxyl;Methoxyl group etc. is bonded with the oxygroup of the alkyl of carbon atom number 1~10 in unilateral side;The keys such as methoxycarbonyl Close the Epoxide carbonyl for the alkyl for having carbon atom number 1~10;Etc..-CO-Rⁿ¹⁰In, it, should for the carbonyl for being bonded with alkyl Alkyl can have-COO^-,S(O)₂O^-Deng.In addition, conduct-CO-Rⁿ¹⁰,-CO-Rⁿ³⁰,-CO-Rⁿ³⁵, further preferably formoxyl.

As-S (O)₂-Rⁿ¹⁰,-S(O)₂-Rⁿ³⁰,-S(O)₂-Rⁿ³⁵, preferably methyl sulphonyl, ethylsulfonyl, propyl sulphur Acyl group, butyl sulfonyl, pentylsulfonyl, hexyl sulfonyl, (2- ethyls) hexyl sulfonyl, heptyl sulfonyl, octyl sulphonyl Base, nonyl sulfonyl, decyl sulfonyl, undecyl sulfonyl, dodecyl sulfonyl, eicosyl sulfonyl, phenyl sulphur Acyl group, p-methylphenyl sulfonyl etc. are bonded with the sulfonyl etc. of the alkyl of carbon atom number 1~35, can more preferably enumerate and be bonded with carbon The sulfonyl etc. of the alkyl of atomicity 1~10.

R²And R³,R³And R⁴,R⁴And R⁵,R¹²And R¹³,R¹³And R¹⁴And R¹⁴And R¹⁵The ring of formation and formula (1) or formula (2) it is different The benzene of indoline skeleton is condensed.As R²And R³,R³And R⁴,R⁴And R⁵,R¹²And R¹³,R¹³And R¹⁴And R¹⁴And R¹⁵The ring of formation with The condensed cyclic structure of aforementioned phenyl ring, can enumerate indenes, naphthalene, biphenylene (biphenylene), indacene (indacene), acenaphthylene, fluorenes, That non-alkene (phenalene), phenanthrene, anthracene, fluoranthene, vinegar phenanthrene alkene (acephenanthrylene), aceanthrylene (aceanthrylene), Ben Bing [9,10]Luxuriant and rich with fragrance (triphenylene), pyrene,N-Methyl-o-phthalimide, N- (1- phenylethyls) O-phthalic The hydrocarbon systems condensed cyclic structure such as acid imide and naphthacene (tetracene) and its partial reduction body are (for example, 9,10- dihydroanthracenes, 1,2,3,4- Naphthane etc.);Indoles, iso-indoles, indazole, quinoline, isoquinolin, phthalazines, quinoxaline, quinazoline, cinnolines, carbazole, carboline, phenanthrene Pyridine, acridine,The nitrogenous annelated heterocycles such as pyridine, phenanthroline, azophenlyene and its partial reduction body;3- hydrogen benzofuran-2-ones etc. are oxygen-containing Annelated heterocycles and its partial reduction body.

R⁶And R⁷The ring or R of formation⁸And R⁹The outer methylene of ring of the ring of formation and the isoindoline skeleton of formula (1) (exomethylene) (C=CH₂) bonding, if to include methylene (C=CH outside the ring₂) including the form of structure enumerate R⁶And R⁷The ring or R of formation⁸And R⁹The ring of formation, can enumerate the outer methylene of carbonyl, ring as such as following groups of A and carbonyl according to The structure of secondary arrangement.* indicates the connecting key with isoindoline skeleton.

[Group A]

[In formula, R²⁵And R²⁶The alkyl that there can be the carbon atom number 1~35 of substituent group is indicated independently of each other, can be had The heterocycle or hydrogen atom of substituted the base ,-CH for including in the alkyl₂- O- ,-CO- ,-S (O) can be substituted for₂-,- NR^x1-.But do not include passing through replacement-CH₂And formation-COOH and-S (O)₂The case where OH.In addition, the alkyl and the heterocycle Base can have selected from by-CO₂ ^-With-S (O)₂O^-At least one of group of composition is used as substituent group.As concrete example and preferably Example, can enumerate aforementioned R¹In in addition to carbon atom number be 36 or more example other than Li Zi ]

R²¹And R²²Outer methylene (the C=CH of ring of the ring of formation and the isoindoline skeleton of formula (2)₂) bonding, if with comprising Outer methylene (the C=CH of the ring₂) including the form of structure enumerate R²¹And R²²The ring of formation, can enumerate such as following groups of B that The structure that the outer methylene of carbonyl, ring and carbonyl of sample are arranged in order.* indicates the connecting key with isoindoline skeleton.

[Group B]

[In formula, R²⁷And R²⁸The alkyl that there can be the carbon atom number 1~35 of substituent group is indicated independently of each other, can be had The heterocycle or hydrogen atom of substituted the base ,-CH for including in the alkyl₂- O- ,-CO- ,-S (O) can be substituted for₂-,- NR^x3-.But do not include passing through replacement-CH₂And formation-COOH and-S (O)₂The case where OH.As concrete example and preference, It can enumerate and aforementioned R²³Same Li Zi ]

R²And R³,R³And R⁴,R⁴And R⁵,R⁶And R⁷,R⁸And R⁹,R¹²And R¹³,R¹³And R¹⁴,R¹⁴And R¹⁵And R²¹And R²²It is formed Ring can have substituent group.As the substituent, it can enumerate and R¹~R⁹,R¹¹~R¹⁵,R²¹~R²⁴,R^x1,R^x3,Rⁿ³⁰And Rⁿ³¹Table The identical group of substituent group that the alkyl shown can have.

As R²~R⁹,R¹²~R¹⁵And R²¹~R²²The halogen of expression can enumerate fluorine atom, chlorine atom, bromine atom and iodine Atom, preferably chlorine atom, bromine atom.

As the isoindoline pigment that formula (1) or formula (2) indicate, R¹~R⁹,R¹¹~R¹⁶,R²¹~R²⁴Change as described below It is preferred to close object.

As R¹And R¹¹, preferred hydrogen atom.

As R²~R⁵, preferred carbon atom numbers 1~10 such as alkyl, methoxyl group of the carbon atom numbers such as hydrogen atom, butyl 1~10 Halogen atoms, the nitro ,-CO such as perfluoroalkyl, the bromine atom of carbon atom numbers 1~10 such as alkoxy, trifluoromethyl₂ ^-,-S(O)₂O^-Deng.

As R¹²~R¹⁵, preferably the carbon atom numbers 1 such as alkyl, methoxyl group of the carbon atom numbers such as hydrogen atom, butyl 1~10~ The halogen atoms such as perfluoroalkyl, the bromine atom of the carbon atom numbers such as 10 alkoxy, trifluoromethyl 1~10, nitro etc..

R⁶And R⁷In a side group (hereinafter referred to as R^6a) or R⁸And R⁹In a side group (hereinafter referred to as R^8a) excellent It is selected as cyano, R⁶And R⁷In R^6aGroup in addition or R⁸And R⁹In R^8aGroup in addition is preferably-COO^-,-CO-ORⁿ¹⁵,- CO-Rⁿ¹⁵,-CO-NH₂,-CO-NH(Rⁿ¹⁵),-CO-N(Rⁿ¹⁶)₂,-CO-H or-S (O)₂-Rⁿ¹⁵(Rⁿ¹⁵With aforementioned Rⁿ¹⁰It is identical, Rⁿ¹⁶ With aforementioned Rⁿ¹¹It is identical).

As-CO-ORⁿ¹⁵, preferably the carbon atom number of the alkyl such as methoxycarbonyl, ethoxy carbonyl be 1~10 alkoxy Carbonyl.

As-CO-Rⁿ¹⁵, preferably phenylcarbonyl group etc. is bonded with the carbonyl of the aromatic ring of carbon atom number 6~10;Ethyl carbonyl Base, butyl carbonyl etc. are bonded with the carbonyl of the alkyl of carbon atom number 1~10;It is bonded with phenyl methyl, phenylethyl etc. and carbon original The carbonyl of the alkyl of the carbon atom number 1~10 of the aromatic ring bonding of subnumber 6~10.In addition, being bonded with aromatic ring at this On the carbon atom of carbonyl, the carbonyl for being bonded with alkyl, the carbonyl for being bonded with the alkyl being bonded with aromatic ring etc., it can be bonded with The halogen atoms such as chlorine atom;-CO₂ ^-;-S(O)₂O^-;Sulfamoyl;Hydroxyl;Methoxyl group etc. unilateral side be bonded with carbon atom number 1~ The oxygroup of 10 alkyl;Methoxycarbonyl etc. is bonded with the Epoxide carbonyl of the alkyl of carbon atom number 1~10;Etc..

As-CO-NH (Rⁿ¹⁵), preferably methylaminocarbonyl etc. is bonded with the amino carbonyl of the alkyl of carbon atom number 1~10 Base, phenyl amino carbonyl etc. are bonded with the amino carbonyl of the aromatic series hydrocarbon ring of carbon atom number 6~10.In addition, being bonded with alkane at this On the carbon atom of the amino carbonyl of base, the amino carbonyl for being bonded with aromatic series hydrocarbon ring etc. ,-CO can be bonded with₂ ^-。

As-CO-N (Rⁿ¹⁶)₂, preferably Dimethylaminocarbonyl etc. is bonded with the ammonia of the alkyl of 2 carbon atom numbers 1~10 Base carbonyl.

Aforementioned R⁸And R⁹The case where structure for forming above-mentioned group of A is also preferred.

R²¹And R²²In a side group (hereinafter referred to as R^21a) it is preferably cyano, R²¹And R²²In R^21aGroup in addition Preferably and R¹⁶Same group.

As R¹⁶, preferably-CO-ORⁿ³⁰,-CO-Rⁿ³⁰,-CO-NH₂,-CO-NH(Rⁿ³⁰),-CO-N(Rⁿ³¹)₂,-CO-H,-S (O)₂-Rⁿ³⁰Deng.

As-CO-ORⁿ³⁰, preferably the carbon atom number of the alkyl such as methoxycarbonyl, ethoxy carbonyl be 1~10 alkoxy Carbonyl.

As-CO-Rⁿ³⁰, preferably phenylcarbonyl group etc. is bonded with the carbonyl of the aromatic ring of carbon atom number 6~10, butyl carbonyl Base etc. is bonded with the carbonyl of the alkyl of carbon atom number 1~10;It is bonded with phenyl methyl, phenylethyl etc. and carbon atom number 6~10 Aromatic ring bonding carbon atom number 1~10 alkyl carbonyl.In addition, in the carbonyl, the bonding that are bonded with aromatic ring On the carbon atom for having the carbonyl of alkyl, the carbonyl for being bonded with the alkyl being bonded with aromatic ring, the halogen such as chlorine atom can be bonded with Plain atom;Sulfamoyl;Hydroxyl;Methoxyl group etc. is bonded with the oxygroup of the alkyl of carbon atom number 1~10 in unilateral side;Methoxycarbonyl Etc. the Epoxide carbonyl for the alkyl for being bonded with carbon atom number 1~10;Etc..

As-CO-NH (Rⁿ³⁰), preferably methylaminocarbonyl etc. is bonded with the amino carbonyl of the alkyl of carbon atom number 1~10 Base, phenyl amino carbonyl etc. are bonded with the amino carbonyl of the aromatic series hydrocarbon ring of carbon atom number 6~10.

As-CO-N (Rⁿ³¹)₂, preferably Dimethylaminocarbonyl etc. is bonded with the ammonia of the alkyl of 2 carbon atom numbers 1~10 Base carbonyl.

Aforementioned R²¹And R²²The case where structure for forming above-mentioned group of B is also preferred.

As R²³And R²⁴, preferred hydrogen atom.

M^b+Preferably hydrogen cation or Li⁺,Na⁺,K⁺Deng the metal cation more than metal ion of 1 valence, divalent, more preferably For metal cation more than hydrogen cation or divalent, most preferably hydrogen cation.As metal cation more than divalent, can lift The cation for going out the metal of race of the 2nd race of the periodic table of elements~the 15th, can preferably enumerate Mg²⁺,Ca²⁺,Sr²⁺,Ba²⁺,Cd²⁺,Ni² ⁺,Zn²⁺,Cu²⁺,Hg²⁺,Fe²⁺,Co²⁺,Sn²⁺,Pb²⁺And Mn²⁺The metal cation of equal divalents;Al³⁺,Fe³⁺And Cr³⁺Etc. trivalents gold Belong to cation;Sn⁴⁺,Mn⁴⁺,Ce⁴⁺Deng the metal cation of 4 valences, Mg can be more preferably enumerated²⁺,Ca²⁺,Sr²⁺,Ba²⁺,Ni²⁺,Zn²⁺, Cu²⁺,Fe²⁺,Co²⁺,Sn²⁺,Mn²⁺,Al³⁺,Fe³⁺,Cr³⁺,Sn⁴⁺And Mn⁴⁺, can further preferably enumerate Mg²⁺,Ca²⁺,Sr²⁺,Ba² ⁺,Zn²⁺,Cu²⁺,Fe²⁺,Mn²⁺,Al³⁺,Fe³⁺,Cr³⁺And Mn⁴⁺.It should be noted that M^b+For hydrogen cation when, the hydrogen cation With-CO₂ ^-Or-S (O)₂O^-Bonding and with-COOH or-S (O)₂The form of OH exists.

A is preferably 1~10, more preferably 1~5, most preferably 2~4.

As the concrete example for the compound that formula (1) or formula (2) indicate, can enumerate in the compound that for example formula (Ia) indicates R³¹,L¹,L²,R³²,B¹B², n, m and M^b+The compound for being combined as any one of 1~table of table 4 and formula (Ib) indicate change Close R in object³³,L³,B¹B², n, m and M^b+The compound for being combined as any one of 5~table of table 6.It should be noted that R³¹, R³²,R³³The arbitrary part-structure that expression (HH1)~formula (HH18) indicates.B¹B²What expression (BB1)~formula (BB9) indicated Arbitrary part-structure.

(in formula, wave is indicated comprising E bodies and Z bodies this two sides) table 1

Table 2

Table 3

Table 4

Table 5

Table 6

In compound shown in table, preferred compound number is 28~31,37~40,46~49,73~76,82~ 85,91~94,136~139,154~157,190~193,199~202,208~211,244~247,298~301 change Close object.

For the isoindoline pigment (isoindoline pigment (1)) that formula (1) indicates, in R¹(to be when hydrogen atom When the isoindoline pigment that formula (1a) indicates), it can be manufactured by following manner:Formula (pt1) indicate compound (hereinafter, Sometimes referred to as phthalonitrile compound) it is reacted (hereinafter, sometimes referred to as alkoxide cpd) with the compound of formula (pt2) expression, Then, the compound (hereinafter, sometimes referred to as compound (pt3)) and formula further indicated in the presence of acid with formula (pt3) (pt4) compound indicated is reacted (hereinafter, sometimes referred to as compound (pt4)).In addition, for isoindoline pigment (1) For, in R¹For hydrogen atom when (be formula (1a) indicate isoindoline pigment when), can be manufactured by following manner:Formula (pt5) compound (hereinafter, sometimes referred to as 1,3- diiminoisoindoles compound), compound (pt3) and the chemical combination indicated Object (pt4) reacts.In addition, R¹When not being hydrogen atom (when being the isoindoline pigment that formula (1b) indicates), what formula (1b) indicated Compound that isoindoline pigment and the formula (pt6) that isoindoline pigment can be indicated by further formula (1a) indicate (hereinafter, Sometimes referred to as compound (pt6)) it reacts to manufacture.In formula (1), M^b+For metal ion when (be formula (1c) indicate iso-indoles When quinoline pigment), the isoindoline pigment that formula (1c) indicates can pass through the isoindoline pigment and formula of further formula (1b) expression (pt7) compound that compound (hereinafter, sometimes referred to as compound (pt7)), the formula (pt8) indicated indicates is (hereinafter, sometimes referred to as Compound (pt8)) it reacts to manufacture.

[In formula (pt1)~formula (pt8) and formula (1a)~formula (1c), R¹~R⁹,M^b+, a, m and n indicate and phase described previously Same meaning.R⁴¹,R⁴²Hydrogen atom and/or the alkyl of carbon atom number 1~20 are indicated independently of each other.M¹,M²Mutual indepedent earth's surface Show alkali metal atom.LG¹,LG²Indicate halogen atom, mesyloxy, chloromethyl sulfonyloxy, tosyloxy or trifluoro Mesyloxy.]

As R⁴¹,R⁴²The alkyl of the carbon atom number 1~20 of expression, can enumerate methyl, ethyl, propyl, isopropyl, butyl, Isobutyl group, sec-butyl and tertiary butyl etc. can preferably enumerate the alkyl of carbon atom number 1~6.

R⁴¹Preferably alkyl.R⁴²Preferably hydrogen atom.

As M¹,M²The alkali metal atom of expression can enumerate lithium atom, sodium atom and potassium atom.

About the usage amount for the alkoxide cpd that formula (pt2) indicates, for 1 mole of phthalonitrile compound, Usually 0.1~10 mole, preferably 0.2~5 mole, more preferably 0.3~3 mole, further preferably 0.4~2 mole.

About total usage amount of compound (pt3) and compound (pt4), relative to phthalonitrile compound or 1,3- bis- For 1 mole of iminoisoindoline compound, usually 2~20 moles, preferably 2~10 moles, more preferably 2~6 rub You, further preferably 2~4 moles.It should be noted that compound (pt3) can be identical with compound (pt4).

As acid, the inorganic acids such as hydrogen chloride, hydrogen bromide, hydrogen iodide, sulfuric acid, nitric acid, fluosulfonic acid, phosphoric acid can be enumerated;Methylsulphur The sulfonic acid such as acid, trifluoromethanesulfonic acid and p-methyl benzenesulfonic acid;The carboxylics such as acetic acid, citric acid, formic acid, gluconic acid, lactic acid, oxalic acid and tartaric acid Acid can preferably enumerate hydrogen chloride, hydrogen bromide, sulfuric acid, methanesulfonic acid, trifluoromethanesulfonic acid, p-methyl benzenesulfonic acid and carboxylic acid, can more preferably lift Go out acetic acid.

About the usage amount of acid, for 1 mole of phthalonitrile compound, usually 1~500 mole, preferably It is 5~200 moles, more preferably 20~100 moles.

Phthalonitrile compound, alkoxide cpd, compound (pt3) and compound (pt4) reaction usually can be molten Implement in the presence of agent.As solvent, water can be enumerated;The nitrile solvents such as acetonitrile;Methanol, ethyl alcohol, 2- propyl alcohol, n-butyl alcohol, 1- amylalcohols And the alcoholic solvents such as 1- octanols;The ether solvents such as tetrahydrofuran;The ketone solvents such as acetone;The ester solvents such as ethyl acetate;The aliphatic such as hexane Hydrocarbon solvent;The aromatic hydrocarbon solvents such as toluene;The halogenated hydrocarbon solvents such as dichloromethane and chloroform;N,N-dimethylformamide and N- methyl The amide solvents such as pyrrolidones;The sulfoxide solvents such as dimethyl sulfoxide (DMSO) can preferably enumerate water, nitrile solvent, alcoholic solvent, ether solvents, ketone Solvent, ester solvent, aromatic hydrocarbon solvents, halogenated hydrocarbon solvent, amide solvent and sulfoxide solvent can more preferably enumerate water, acetonitrile, first Alcohol, ethyl alcohol, 2- propyl alcohol, n-butyl alcohol, 1- amylalcohols, 1- octanols, tetrahydrofuran, acetone, ethyl acetate, toluene, dichloromethane, chlorine Imitative, N,N-dimethylformamide, DMAC N,N' dimethyl acetamide, N-Methyl pyrrolidone, 1,3- dimethyl-2-imidazolinones and 1, 3- dimethyl -3,4, -2 (1H)-pyrimidone of 5,6- tetrahydrochysene and dimethyl sulfoxide (DMSO), can further preferably enumerate water, acetonitrile, methanol, Ethyl alcohol, 2- propyl alcohol, n-butyl alcohol, 1- amylalcohols, 1- octanols, acetone, dichloromethane, chloroform, N,N-dimethylformamide, N, N- diformazans - 2 (1H)-pyrimidone of yl acetamide, 1,3- dimethyl-2-imidazolinones and 1,3- dimethyl -3,4,5,6- tetrahydrochysenes, N- methyl pyrroles Pyrrolidone and dimethyl sulfoxide (DMSO) can particularly preferably enumerate water, acetonitrile, methanol, ethyl alcohol, 2- propyl alcohol, N-Methyl pyrrolidone and two Methyl sulfoxide.About the usage amount of solvent, for 1 mass parts phthalonitrile compound, usually 1~1000 mass Part.

Phthalonitrile compound, alkoxide cpd, compound (pt3) and compound (pt4) reaction temperature be usually 0 ~200 DEG C, preferably 0~100 DEG C, more preferably 0~50 DEG C.Reaction time is usually 0.5~300 hour.

The reaction of 1,3- diiminoisoindoles compound, compound (pt3) and compound (pt4) usually can be in solvent In the presence of implement.As solvent, water can be enumerated;The nitrile solvents such as acetonitrile;Methanol, ethyl alcohol, 2- propyl alcohol, n-butyl alcohol, 1- amylalcohols and The alcoholic solvents such as 1- octanols;The ether solvents such as tetrahydrofuran;The ketone solvents such as acetone;The ester solvents such as ethyl acetate;The aliphatic hydrocarbons such as hexane Solvent;The aromatic hydrocarbon solvents such as toluene;The halogenated hydrocarbon solvents such as dichloromethane and chloroform;N,N-dimethylformamide and N- methyl pyrroles The amide solvents such as pyrrolidone;The sulfoxide solvents such as dimethyl sulfoxide (DMSO), can preferably enumerate nitrile solvent, alcoholic solvent, ether solvents, ketone solvent, Ester solvent, aromatic hydrocarbon solvents, halogenated hydrocarbon solvent, amide solvent and sulfoxide solvent, can more preferably enumerate acetonitrile, methanol, ethyl alcohol, 2- propyl alcohol, n-butyl alcohol, 1- amylalcohols, 1- octanols, tetrahydrofuran, acetone, ethyl acetate, toluene, dichloromethane, chloroform, N, N- bis- Methylformamide, DMAC N,N' dimethyl acetamide, N-Methyl pyrrolidone, 1,3- dimethyl-2-imidazolinones and 1,3- dimethyl- - 2 (1H)-pyrimidone of 3,4,5,6- tetrahydrochysene and dimethyl sulfoxide (DMSO), can further preferably enumerate acetonitrile, methanol, ethyl alcohol, 2- propyl alcohol, N-butyl alcohol, 1- amylalcohols, 1- octanols, acetone, dichloromethane, chloroform, N,N-dimethylformamide, DMAC N,N' dimethyl acetamide, N- Methyl pyrrolidone, 1,3- dimethyl-2-imidazolinones and -2 (1H)-pyrimidone of 1,3- dimethyl -3,4,5,6- tetrahydrochysenes and two Methyl sulfoxide can particularly preferably enumerate n,N-Dimethylformamide, n,N-dimethylacetamide, n-butyl alcohol, N- crassitudes Ketone, 1,3- dimethyl-2-imidazolinones and -2 (1H)-pyrimidone of 1,3- dimethyl -3,4,5,6- tetrahydrochysenes and dimethyl sulfoxide (DMSO).It closes In the usage amount of solvent, for 1, the 3- diiminoisoindole compounds of 1 mass parts, usually 1~1000 matter Measure part.

The reaction temperature of 1,3- diiminoisoindoles compound, compound (pt3) and compound (pt4) is usually 0 ~200 DEG C, preferably 0~100 DEG C, more preferably 0~80 DEG C.Reaction time is usually 0.5~300 hour.

About the usage amount of compound (pt6), for 1 mole of the isoindoline pigment that formula (1a) indicates, usually It is 1~10 mole, preferably 1~5 mole, more preferably 1~3 mole, further preferably 1~2 mole.

In addition, when making compound (pt6) be reacted, alkali has preferably coexisted.As alkali, triethylamine, 4- can be enumerated The metals such as organic bases, sodium methoxide, sodium ethoxide, sodium tert-butoxide, the potassium tert-butoxides such as (N, N- dimethylamino) pyridine, pyridine, piperidines The organo-metallic compounds such as alkoxide, butyl lithium, tert-butyl lithium and phenyl lithium;The nothings such as lithium hydroxide, sodium hydroxide and potassium hydroxide Machine alkali.

It usually 1~10 rubs for 1 mole of the isoindoline pigment that formula (1a) indicates about the usage amount of alkali You, preferably 1~5 mole, more preferably 1~3 mole, further preferably 1~2 mole.

In addition, the reaction of compound (pt6) can usually be implemented in the presence of the solvent.Solvent can from in O-phthalic Nitrile compound, alkoxide cpd, compound (pt3) and compound (pt4) reaction in select in the same range of solvent that uses It selects.

About the usage amount of solvent, for 1 mass parts of isoindoline pigment that formula (1b) indicates, usually 1~ 1000 mass parts.Usually -90~200 DEG C of the reaction temperature of compound (pt6), preferably -80~100 DEG C, more preferably 0~ 50℃.Reaction time is usually 0.5~300 hour.

When the isoindoline pigment that formula (1b) indicates does not have sulfo group, the isoindoline pigment of formula (1b) expression can be passed through It reacts to import sulfo group with sulfonating agents such as oleum or chlorosulfonic acids.

About the SO in oleum₃Usage amount, relative to formula (1b) indicate 1 mole of isoindoline pigment for, Usually 1~50 mole, preferably 5~40 moles, more preferably 5~30 moles, further preferably 5~25 moles.About The usage amount of sulfuric acid in oleum, for 1 mole of the isoindoline pigment that formula (1b) indicates, usually 1~200 Mole, preferably 10~100 moles, more preferably 10~75 moles, further preferably 10~50 moles.

About the usage amount of chlorosulfonic acid, for 1 mole of the isoindoline pigment that formula (1b) indicates, usually 1~ 500 moles, preferably 10~300 moles, more preferably 10~200 moles, further preferably 10~150 moles.

The reaction temperature of sulfonation is usually -20~200 DEG C, preferably -10~100 DEG C, more preferably 0~50 DEG C.Reaction Time is usually 0.5~300 hour.

When the isoindoline pigment that formula (1b) indicates has carboxyl or sulfo group, compound (pt7) and compound (pt8) can be made Reaction, to which manufacture includes M^b+Formula (1c) indicate isoindoline pigment.

About compound (pt7), the metal alkoxides such as sodium methoxide, sodium ethoxide, sodium tert-butoxide, potassium tert-butoxide, butyl can be enumerated The organo-metallic compounds such as lithium, tert-butyl lithium and phenyl lithium;The inorganic bases such as lithium hydroxide, sodium hydroxide and potassium hydroxide.It is preferred that For lithium hydroxide, sodium hydroxide, potassium hydroxide.

About the usage amount of compound (pt7), for 1 mole of the isoindoline pigment that formula (1b) indicates, usually It is 0.1~10 mole, preferably 0.2~10 mole, more preferably 1~5 mole.

About the usage amount of compound (pt8), for 1 mole of the isoindoline pigment that formula (1b) indicates, usually It is 0.1~10 mole, preferably 0.2~10 mole, more preferably 1~5 mole.

Formula (1b) indicate isoindoline pigment, compound (pt7), compound (pt8) reaction usually can be in solvent In the presence of implement.As solvent, water can be enumerated;The nitrile solvents such as acetonitrile;Methanol, ethyl alcohol, 2- propyl alcohol, n-butyl alcohol, 1- amylalcohols and 1- The alcoholic solvents such as octanol;The ether solvents such as tetrahydrofuran;The ketone solvents such as acetone;The ester solvents such as ethyl acetate;The aliphatic hydrocarbons such as hexane are molten Agent;The aromatic hydrocarbon solvents such as toluene;The halogenated hydrocarbon solvents such as dichloromethane and chloroform;N,N-dimethylformamide and N- methylpyrroles The amide solvents such as alkanone;And the sulfoxide solvents such as dimethyl sulfoxide (DMSO), it can preferably enumerate water, nitrile solvent, alcoholic solvent, ether solvents, ketone Solvent, ester solvent, aromatic hydrocarbon solvents, halogenated hydrocarbon solvent, amide solvent and sulfoxide solvent, can more preferably enumerate water, acetonitrile, Methanol, ethyl alcohol, 2- propyl alcohol, n-butyl alcohol, 1- amylalcohols, 1- octanols, tetrahydrofuran, acetone, ethyl acetate, toluene, dichloromethane, chlorine Imitative, n,N-Dimethylformamide, N-Methyl pyrrolidone and dimethyl sulfoxide (DMSO), can further preferably enumerate water, acetonitrile, methanol, Ethyl alcohol, 2- propyl alcohol, n-butyl alcohol, 1- amylalcohols, 1- octanols, acetone, dichloromethane, chloroform, N,N-dimethylformamide, N- methyl pyrroles Pyrrolidone and dimethyl sulfoxide (DMSO) can particularly preferably enumerate water, acetonitrile, methanol, ethyl alcohol and 2- propyl alcohol.

About the usage amount of solvent, for 1 mass parts of isoindoline pigment that formula (1b) indicates, usually 1~ 1000 mass parts.

Isoindoline pigment that formula (1b) indicates, compound (pt7), the reaction temperature of compound (pt8) be usually 0~ 200 DEG C, preferably 0~100 DEG C, more preferably 0~50 DEG C.Reaction time is usually 0.5~300 hour.

The method that isoindoline pigment (1) is extracted from reaction mixture is not particularly limited, using known each Kind method extracts.For example, can be filtered to extract isoindoline to reaction mixture by after the completion of reaction Pigment (1).In addition, after being filtered, obtained residue can be washed with solvent.In addition, after being filtered, it can Implement column chromatography, recrystallization or sublimation purification.

Isoindoline pigment in the present invention can be contained in composition below.

(I) include the composition (the 1st composition) of isoindoline pigment and solvent (E).

(II) composition (the 2nd composition) comprising isoindoline pigment, resin (B) and solvent (E) will be (hereinafter, sometimes will 1st composition and the 2nd composition are known as coloured composition).

(III) (the 3rd group of the composition comprising isoindoline pigment, resin (B), polymerizable compound (C) and solvent (E) Close object).

(IV) include isoindoline pigment, resin (B), polymerizable compound (C), polymerization initiator (D) and solvent (E) Composition (the 4th composition).(hereinafter, the 3rd composition and the 4th composition are known as colored curable resin composition sometimes).

For (I) includes the coloured composition of isoindoline pigment and solvent (E), isoindoline pigment preferably disperses In solvent (E).In addition, by the coloured composition comprising isoindoline pigment (A) and solvent (E) or can also include resin (B) coloured composition is further mixed with polymerizable compound (C), polymerization initiator (D) etc., to prepare colored curable Resin combination.

< colorants (A1) >

Aforementioned 1st~the 4th composition also may include the colorant other than isoindoline pigment (hereinafter, sometimes referred to as colouring Agent (A1)), it may include one kind or two or more colorant (A1).

Colorant (A1) can be dyestuff, can also be pigment.As dyestuff, Colour Index (The Society can be enumerated Of Dyers and Colourists are published) and Dyeing Note (Se Ran companies) described in known dye.In addition, according to Chemical constitution can enumerate azo dyes, anthraquinone dye, triphenhlmethane dye, xanthene dye and phthalocyanine dye etc..Colorant (A1) it can be isoindoline pigment.Also two or more in these dyestuffs can be used in combination.

Specifically, the dyestuff of following such Colour Index (C.I.) number can be enumerated.

C.I. solvent yellow 14,15,23,24,25,38,62,63,68,79,81,82,83,89,94,98,99,162;

C.I. Indian yellow 1,3,7,9,11,17,23,25,29,34,36,38,40,42,54,65,72,73,76,79,98, 99,111,112,113,114,116,119,123,128,134,135,138,139,140,144,150,155,157,160, 161,163,168,169,172,177,178,179,184,190,193,196,197,199,202,203,204,205,207, 212,214,220,221,228,230,232,235,238,240,242,243,251;

C.I. active yellow 2,76,116;

C.I. directly Huang 2,4,28,33,34,35,38,39,43,44,47,50,54,58,68,69,70,71,86,93, 94,95,98,102,108,109,129,132,136,138,141;

C.I. disperse yellow 51,54,76;

C.I. solvent orange 2,7,11,15,26,41,54,56,99;

C.I. acid orange 6,7,8,10,12,26,50,51,52,56,62,63,64,74,75,94,95,107,108, 149,162,169,173;

C.I. reactive orange 16;

C.I. direct orange 26,34,39,41,46,50,52,56,57,61,64,65,68,70,96,97,106,107;

C.I. solvent red 24,49,90,91,111,118,119,122,124,125,127,130,132,143,145, 146,150,151,155,160,168,169,172,175,181,207,218,222,227,230,245,247;

C.I. acid red 73,80,91,92,97,138,151,211,274,289;

C.I. acid violet 34,102;

C.I. disperse violet 26,27;

C.I. solvent violet 11,13,14,26,31,36,37,38,45,47,48,51,59,60;

C.I. solvent blue 19 4,18,35,36,45,58,59,59:1,63,68,69,78,79,83,94,97,98,100, 101,102,104,105,111,112,122,128,132,136,139;

C.I. acid blue 25,27,40,45,78,80,112;

C.I. direct indigo plant 40;

C.I. disperse blue 1,14,56,60;

C.I. solvent green 1,3,5,28,29,32,33;

C.I. acid green 3,5,9,25,27,28,41;

C.I. Viride Nitens 1;

C.I. vat green 1 etc..

As pigment, known pigment can be used, can enumerate for example in Colour Index (The Society of Dyers And Colourists are published) in be classified as the pigment of " pigment (Pigment) ".Two or more can be combined.

Specifically, can enumerate C.I. pigment yellows 1,3,12,13,14,15,16,17,20,24,31,53,83,86,93, 94,109,110,117,125,128,129,137,138,139,147,148,150,153,154,166,173,185,194, 214 equal yellow uitramarines;

C.I. the orange pigments such as pigment orange 13,31,36,38,40,42,43,51,55,59,61,64,65,71,73;

C.I. Pigment Red 9,97,105,122,123,144,149,166,168,176,177,180,192,209,215, 216, the red pigments such as 224,242,254,255,264,265,266,268,269,273;

C.I. pigment blue 15,15:3,15:4,15:6, the blue pigments such as 60;

C.I. the violet pigments such as pigment violet 1,19,23,29,32,36,38;

C.I. the viridine greens such as pigment Green 7,36,58,59.

As colorant (A1), preferably weld and yellow uitramarine by them (hereinafter, be referred to as " yellow coloring sometimes Agent "), green dye and viridine green (hereinafter, being sometimes referred to as them " green colourant "), more preferable yellow uitramarine and green Color pigment, further preferred viridine green.

As weld, can enumerate in above-mentioned dyestuff, form and aspect be classified as yellow dyestuff can as yellow uitramarine It enumerates in above-mentioned pigment, form and aspect and is classified as yellow pigment.

As green dye, in above-mentioned dyestuff, form and aspect can be enumerated and be classified as green dyestuff, it, can as viridine green It enumerates in above-mentioned pigment, form and aspect and is classified as green pigment.

In viridine green, preferred phthalocyanine color is more preferably selected from by halogenated copper phthalocyanine pigment and zinc halide phthalocyanine color At least one of group of composition, further preferably in the group being made of C.I. pigment Green 7s, 36,58 and 59 at least It is a kind of.

For 100 mass parts isoindoline pigments, the amount of colorant (A1) is 0 mass parts or more, 900 mass parts Hereinafter, preferably 300 is below mass part, more preferably 100 is below mass part.

< dispersants >

For isoindoline pigment or colorant (A1) (hereinafter, as refer to isoindoline pigment and colorant (A1) this The concept of two sides, sometimes referred to as colorant AX.As colorant AX, preferably isoindoline pigment) for, it as needed, can be with Implement following processing:Rosin processing;Utilize the surface of the progress such as the colorant derivative for having imported acidic-group or basic group Processing;The grafting that the surfaces colorant AX carry out is handled using high-molecular compound etc.;Particle based on sulfuric acid particles method etc. Change is handled;The carrying out washing treatment using the progress such as organic solvent, water for removing impurity;It will be ionic using ion-exchange etc. The processing etc. that impurity removes.The grain size of colorant AX is preferably generally uniform.It is carried out by so that colorant AX is contained dispersant Decentralized processing can form colorant AX states evenly dispersed in dispersion liquid as a result,.

As dispersant, surfactant etc. can be enumerated, can be cationic system, anionic system, nonionic system and both sexes In arbitrary surfactant.Specifically, the surfactant etc. of Polyester, polyamine system and acrylic acid series etc. can be enumerated. These dispersants can be used alone or combine two or more and use.As dispersant, if being indicated with trade name, KP can be enumerated (SHIN-ETSU HANTOTAI's chemical industry (strain) system), FLOWLEN (common prosperity society chemistry (strain) system), SOLSPERSE (registered trademark) (Zeneca (strain) System), EFKA (registered trademark) (BASF AG's system), AJISPER (registered trademark) (Ajinomoto Fine-Techno Co., Inc. make) and Disperbyk (registered trademark) (BYK-Chemie corporations), BYK (registered trademark) (BYK-Chemie companies System) etc..

Using dispersant, about the usage amount of dispersant, for 100 mass parts colorant AX, Preferably 200 is below mass part, and more than more preferably 5 mass parts 150 is below mass part.The usage amount of dispersant is in model above-mentioned When enclosing interior, there is the tendency that the solution containing colorant AX of dispersity evenly can be obtained.

For the content of the colorant AX in coloured composition, in the total amount of solid state component, usually 1 mass % The above 90 mass % hereinafter, preferably 1 mass % or more, 80 mass % hereinafter, more preferably 5 mass % or more, 75 mass % with Under.For the content of the isoindoline pigment in coloured composition, in the total amount of solid state component, usually 1 mass % The above 90 mass % hereinafter, preferably 1 mass % or more, 80 mass % hereinafter, more preferably 5 mass % or more, 75 mass % with Under.

For the content of the colorant AX in colored curable resin composition, in the total amount of solid state component, lead to Often for 1 mass % or more, 90 mass % hereinafter, preferably 1 mass % or more, 80 mass % are hereinafter, more preferably 5 mass % or more 75 mass % or less.For the content of the isoindoline pigment in colored curable resin composition, in solid state component In total amount, usually 1 mass % or more, 90 mass % hereinafter, preferably 1 mass % or more, 80 mass % hereinafter, more preferably 5 Quality % or more 75 mass % or less.

" total amount of solid state component " so-called in this specification refers to the coloured composition from the present invention or colored curable tree The total amount of remaining ingredient after solvent (E) is removed in oil/fat composition.The total amount of solid state component and total amount relative to solid state component For the content of each ingredient analysis method known to liquid chromatography or gas chromatography etc. can be utilized to measure.

< solvents (E) >

Solvent (E) is not particularly limited, and solvent usually used in this field can be used.Such as ester solvent can be enumerated (including-COO- but the solvent not comprising-O- in the molecule), ether solvents (include-O- in the molecule but do not include-COO-'s Solvent), ether-ether solvent (solvent for including-COO- and-O- in the molecule), ketone solvent (include-CO- but not wrap in the molecule Solvent containing-COO-), alcoholic solvent (including OH but the solvent not comprising-O- ,-CO- and-COO- in the molecule), aromatic hydrocarbon Solvent, amide solvent, dimethyl sulfoxide (DMSO) etc..

As solvent (E), can enumerate:Ethyl lactate, butyl lactate, 2- hydroxy-methyl isobutyl acids, n-butyl acetate, butyric acid The ester solvents such as ethyl ester, butyl butyrate, ethyl pyruvate, methyl acetoacetate, adnoral acetate and gamma-butyrolacton are (in molecule The interior solvent comprising-COO- but not comprising-O-);

Ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, propylene glycol monomethyl ether, 3- methoxyl groups-n-butyl alcohol, diethyl two The ether solvents such as alcohol dimethyl ether, diethylene glycol methyl ethyl ether (including-O- but the solvent not comprising-COO- in the molecule);

3- methoxy methyl propionates, 3- ethoxyl ethyl propionates, acetic acid 3- methoxybutyls, propylene glycol monomethyl ether The ether-ethers solvents such as ester, ethylene glycol monomethyl ether acetate, diethylene glycol monoethyl ether acetic acid esters (in the molecule include-COO- and- The solvent of O-);

The ketone solvents such as 4- hydroxy-4-methyl-2-pentanones, heptanone, 4-methyl-2 pentanone, cyclohexanone (include in the molecule- CO- but the solvent for not including-COO-);

The alcoholic solvents such as butanol, cyclohexanol, propylene glycol (include OH in the molecule but molten not comprising-O- ,-CO- and-COO- Agent);

The amide solvents such as N,N-dimethylformamide, DMAC N,N' dimethyl acetamide and N-Methyl pyrrolidone.

As solvent (E), more preferable propylene glycol monomethyl ether, propylene glycol monomethyl ether, ethyl lactate, N- methyl Pyrrolidones and 3- ethoxyl ethyl propionates.

Including when solvent (E), about the containing ratio of solvent (E), relative to colored curable resin composition total amount and Speech, preferably 70~95 mass %, more preferably 75~92 mass %.In other words, the solid-state of colored curable resin composition The total amount of ingredient is preferably 5~30 mass %, more preferably 8~25 mass %.The content of solvent (E) is in aforementioned range When, flatness when coating becomes good, and additionally, there are following tendencies:When forming colour filter, colour saturation will not be insufficient, because This display characteristic becomes good.

< resins (B) >

Resin (B) is not particularly limited, preferably alkali soluble resins, more preferably has from selected from by unsaturated carboxylic acid With the resin of the structural unit of at least one kind of (a) (hereinafter, sometimes referred to as " monomer (a) ") in the group of unsaturated carboxylic acid anhydrides composition. Resin (B) is preferably also with selected from by the monomer from cyclic annular ether structure and ethylenic bond unsaturated bond with carbon atom number 2~4 (b) structural unit of (hereinafter, sometimes referred to as " monomer (b) "), from can be copolymerized with monomer (a) monomer (c) (still, with Monomer (a) and monomer (b) are different.) (hereinafter, sometimes referred to as " monomer (c) ") structural unit and there is ethylene linkage on side chain At least one of the group of structural unit composition of formula unsaturated bond structural unit.

As monomer (a), specifically, such as acrylic acid, methacrylic acid, maleic anhydride, itaconic anhydride, 3 can be enumerated, 4,5,6- tetrabydrophthalic anhydrides, mono succinate (2- (methyl) acryloyl group oxygroup ethyl) ester etc., preferably acrylic acid, first Base acrylic acid, maleic anhydride.

Monomer (b) is preferably the cyclic annular ether structure with carbon atom number 2~4 (for example, selected from by oxirane ring, oxygen Azetidine ring and tetrahydrofuran ring composition group in it is at least one kind of) and (methyl) acryloyl group oxygroup monomer.

It should be noted that " (methyl) acrylic acid " so-called in this specification, indicates selected from by acrylic acid and metering system It is at least one kind of in the group of acid composition.The records such as " (methyl) acryloyl group " and " (methyl) acrylate ", which also have, similarly to be contained Justice.

As monomer (b), can enumerate for example (methyl) glycidyl acrylate, vinylbenzyl glycidyl base ether, (methyl) acrylic acid 3,4- epoxy San Huans [5.2.1.0^2,6]Last of the ten Heavenly stems ester, 3- ethyls -3- (methyl) acryloyl group oxygroup methyl oxa- ring Butane, (methyl) tetrahydrofurfuryl acrylate etc., preferably (methyl) glycidyl acrylate, (methyl) acrylic acid 3,4- rings Oxygen San Huan [5.2.1.0^2,6]Last of the ten Heavenly stems ester, 3- ethyls -3- (methyl) acryloyl group oxygroup methy oxetane.

As monomer (c), such as (methyl) methyl acrylate, (methyl) butyl acrylate, (methyl) acrylic acid can be enumerated Cyclohexyl, (methyl) acrylic acid 2- methyl cyclohexyls, (methyl) acrylic acid San Huan [5.2.1.0^2,6]Decane -8- base esters, (methyl) Benzyl acrylate, (methyl) acrylic acid 2- hydroxy methacrylates, N-phenylmaleimide, N- N-cyclohexylmaleimides, N- benzyls Maleimide, styrene, vinyltoluene etc., preferably styrene, vinyltoluene, N-phenylmaleimide, N- rings Hexyl maleimide, N- benzyl maleimides etc..

Resin with the structural unit with ethylenic bond unsaturated bond on side chain can by by monomer (b) addition in list The copolymer of body (a) and monomer (c) or monomer (a) addition is manufactured in the copolymer of monomer (b) and monomer (c).The tree Fat can also be that monomer (a) addition is made to be obtained in monomer (b) and the copolymer of monomer (c) and then reacted with carboxylic acid anhydrides Resin.

The weight average molecular weight according to polystyrene conversion of resin (B) is preferably 3,000~100,000, more preferably 5, 000~50,000, further preferably 5,000~30,000.

The Fen Ziliangfenbu &#91 of resin (B);Weight average molecular weight (Mw)/number-average molecular weight (Mn)s ]Preferably 1.1~6, more preferably It is 1.2~4.

The acid value of resin (B) is preferably 50~170mg-KOH/g, more preferably 60~150mg- in terms of solid state component conversion KOH/g, further preferably 70~135mg-KOH/g.Herein, acid value is as neutralization 1g resins (B) required hydroxide The amount (mg) of potassium and the value measured, for example, can be titrated by using potassium hydroxide aqueous solution so as to find out.

About the containing ratio of resin (B), for the total amount of solid state component, preferably 7~65 mass %, more preferably For 13~60 mass %, further preferably 17~55 mass %.

< polymerizable compounds (C) >

Polymerizable compound (C) is gathered using the living radical and/or acid that are generated by polymerization initiator (D) The compound of conjunction can be enumerated such as the compound of the ethylenic bond unsaturated bond with polymerism, preferably (methyl) acrylic acid Ester compounds.

Wherein, polymerizable compound (C) is preferably the polymerizable compound with 3 or more ethylenic bond unsaturated bonds.Make For such polymerizable compound, such as trimethylolpropane tris (methyl) acrylate, pentaerythrite three (methyl) can be enumerated Acrylate, pentaerythrite four (methyl) acrylate, dipentaerythritol five (methyl) acrylate, six (first of dipentaerythritol Base) acrylate etc..

The weight average molecular weight of polymerizable compound (C) is preferably 150 or more 2,900 hereinafter, more preferably 250 or more 1, 500 or less.

Including when polymerizable compound (C), about the containing ratio of polymerizable compound (C), relative to the total of solid state component For amount, preferably 7~65 mass %, more preferably 13~60 mass %, further preferably 17~55 mass %.

< polymerization initiators (D) >

For polymerization initiator (D), as long as can be generated by the effect of light, heat living radical, acid etc. to The compound for causing polymerization, can use known polymerization initiator without particular limitation.It is free as activity is generated The polymerization initiator of base can enumerate such as N- benzoyls Oxy-1-(4- phenylsulfartyls phenyl) butane-1- ketone-2- imines, N- Benzoyl Oxy-1-(4- phenylsulfartyls phenyl) octane-1- ketone-2- imines, N- benzoyls Oxy-1-(4- phenylsulfartyls Phenyl) -3- cyclopenta propane -1- ketone -2- imines, 2- methyl -2- morpholinoes (morpholino) -1- (4- methylsulfanylphenyls) Propane -1- ketone, 2- dimethylaminos -1- (4- morphlinophenyls) -2- benzyl butane -1- ketone, 1- hydroxycyclohexylphenylketones, 2, It is bis- (the trichloromethyl) -6- piperonyl -1,3,5- triazines of 4-, 2,4,6- trimethyl benzoyl diphenyl base phosphine oxides, 2,2 '-bis- (2- chlorphenyls) -4,4 ', 5,5 '-tetraphenyl bisglyoxaline (biimidazole) etc..

Including when polymerization initiator (D), about the content of polymerization initiator (D), relative to resin (B) and polymerism chemical combination For 100 mass parts of total amount of object (C), preferably 0.1~100 mass parts, more preferably 20~70 mass parts.Polymerization initiator (D) when content is in aforementioned range, there are susceptibilitys to improve, can shorten the tendency of time for exposure, therefore, the life of colour filter Yield improves.

< polymerization trigger auxiliary agents (D1) >

Polymerization trigger auxiliary agent (D1) be in order to promote using polymerization initiator come cause polymerization polymerizable compound it is poly- The compound or sensitizer closed and used.Comprising polymerization trigger auxiliary agent (D1), in general, can be with polymerization initiator (D) it is applied in combination.

As polymerization trigger auxiliary agent (D1), 4,4 '-bis- (dimethylamino) benzophenone (common name Michler's ketons can be enumerated (Michler ' s ketone)), 4,4 '-bis- (diethylamino) benzophenone, 9,10- dimethoxys anthracene, 2,4- diethyl thiophenes Ton ketone, N-phenylglycine etc..

Using polymerization trigger auxiliary agent (D1), about its content, relative to resin (B) and polymerizable compound (C) for 100 mass parts of total amount, preferably 0.1~30 mass parts, more preferably 1~20 mass parts.Polymerization trigger auxiliary agent (D1) amount within the above range when, exist can with higher susceptibility formed colored pattern, so that the productivity of colour filter is improved Tendency.

< levelling agents (F) >

As levelling agent (leveling agent) (F), silicone based surfactants, fluorine system surfactant can be enumerated And the silicone based surfactants etc. with fluorine atom.They can have polymerizable group on side chain.

As silicone based surfactants, the surfactant etc. with siloxanes key in the molecule can be enumerated.Specifically For, can enumerate Toray Silicone DC3PA, Toray Silicone SH7PA, Toray Silicone DC11PA, Toray Silicone SH21PA,Toray Silicone SH28PA,Toray Silicone SH29PA,Toray Silicone SH30PA, Toray Silicone SH8400 (trade names:Dow Corning Toray Co., Ltd. system), KP321, KP322, KP323, KP324, KP326, KP340, KP341 (SHIN-ETSU HANTOTAI's chemical industry (strain) system), TSF400, TSF401, TSF410, TSF4300, TSF4440, TSF4445, TSF4446, TSF4452 and TSF4460 (Momentive Performance Materials Japan contracts commercial firm system) etc..

As fluorine system surfactant, the surfactant etc. with fluorocarbon chain in the molecule can be enumerated.Specifically, can Enumerate Fluorad (registered trademark) FC430, Fluorad FC431 (Sumitomo 3M Ltd. systems), MEGAFACE (registrars Mark) F142D, MEGAFACE F171, MEGAFACE F172, MEGAFACE F173, MEGAFACE F177, MEGAFACE F183, MEGAFACE F554, MEGAFACE R30, MEGAFACE RS-718-K (DIC (strain) systems), EFTOP (registered trademark) EF301,EFTOP EF303,EFTOP EF351,EFTOP EF352(Mitsubishi Materials Electronic Chemicals Co., Ltd. system), Surflon (registered trademark) S381, Surflon S382, Surflon SC101, Surflon SC105 (Asahi Glass (strain) system) and E5844 (Daikin Fine Chemical Kenkyusho, K.K. system) etc..

As the silicone based surfactants with fluorine atom, can enumerate has siloxanes key and fluorocarbon chain in the molecule Surfactant etc..Specifically, MEGAFACE (registered trademark) R08, MEGAFACE BL20, MEGAFACE can be enumerated F475, MEGAFACE F477 and MEGAFACE F443 (DIC (strain) systems) etc..

When containing levelling agent (F), for its content, relative to coloured composition or colored curable resin composition Total amount for, usually 0.0005 mass % or more, 1 mass % hereinafter, preferably 0.001 mass % or more, 0.5 mass % with Under, more preferably 0.001 mass % or more, 0.2 mass % are hereinafter, further preferably 0.002 mass % or more, 0.1 mass % Hereinafter, particularly preferably 0.005 mass % or more, 0.1 mass % or less.When the content of levelling agent (F) is in aforementioned range, The flatness of colour filter can be made good.

The above-mentioned resins of < (B), polymerizable compound (C), polymerization initiator (D), polymerization trigger auxiliary agent (D1), levelling agent (F) ingredient (hereinafter, sometimes referred to as " other compositions ") > other than

As needed, coloured composition of the invention may include high-molecular compound other than filler, resin (B), close Close the known ingredient in this technical field such as accelerating agent, antioxidant, light stabilizer, chain-transferring agent.

< colour filters >

Can colour filter be formed by the colored curable resin composition of the present invention.It, can as the method for forming colored pattern Enumerate photoetching process, ink-jet method, print process etc..Wherein, preferred photoetching process.

Aforementioned colour filter is as display device (liquid crystal display device, organic el device, Electronic Paper etc.) and solid-state image pick-up device The colour filter used in part is useful.

Embodiment

Hereinafter, enumerating embodiment further specifically describes the present invention, but the present invention is not limited certainly by following embodiments System, naturally it is also possible to suitably be changed in the range of can meet aforementioned/aftermentioned purport, they are comprised in this hair In bright technical scope.It should be noted that hereinafter, unless otherwise instructed, " part " refers to " mass parts ", " % " refers to " matter Measure % ".

Below in an example, mass spectrum (LC is utilized:1200 type of Agilent systems, MASS:Agilent LC/MSD6130 Type) it confirmed the structure of compound.

Resin utilizes GPC method according to the weight average molecular weight (Mw) of polystyrene conversion and the measurement of number-average molecular weight (Mn) It carries out under the following conditions.

Device:HLC-8120GPC (Tosoh (strain) systems)

Column:TSK-GELG2000HXL

Column temperature:40℃

Solvent:Tetrahydrofuran

Flow velocity:1.0mL/ minute

Analyze the solid component concentration of sample:0.001~0.01 mass %

Sample size:50μL

Detector:RI

Correction standard substance:TSK STANDARD POLYSTYRENE F-40,F-4,F-288,A-2500,A-500 (Tosoh (strain) systems)

By the ratio between the weight average molecular weight to convert according to polystyrene obtained through the above way and number-average molecular weight (Mw/ Mn) it is used as dispersion degree.

It finds out following such balls (hansen solubility ball) and finds out the Chinese of isoindoline pigment by the centre coordinate of the ball Gloomy solubility parameter, for the ball (hansen solubility ball), by will try in the solvent used in solubility test The point tested in the three-dimensional of the solvent of the isoindoline pigmentolysis used is integrally incorporated in the inside of ball, and will not test The point of the solvent of the middle isoindoline pigmentolysis used is located at the outside of ball.

Solubility test:At 23 DEG C, for isoindoline pigment, using the following solvents of 200 times of weight, lead to Cross whether visually observation isoindoline pigment is dissolved in each solvent, the solvent is:Isosorbide-5-Nitrae-dioxane, n-butyl alcohol, 2- phenoxetols, acetone, acetonitrile, chloroform, hexamethylene, cyclohexanol, dibasic acid ester, diacetone alcohol, diethylene glycol, N, N- diformazans Base formamide, dimethyl sulfoxide (DMSO), dipropylene glycol, ethyl alcohol, ethyl acetate, gamma-butyrolacton, hexane, 2- butanone, methanol, 4- methyl- 2 pentanone, dichloromethane, butyl acetate, N-Methyl pyrrolidone, 1- methoxy-2-propanols, propylene glycol -1- monomethyl ethers -2- Acetic acid esters (propylene glycol 1-monomethyl ether 2-acetate), carbonic acid 1, the Asias 2- propyl ester, four chloroethenes Alkene, tetrahydrofuran, toluene, 1,3-Dimethyl-2-imidazolidinone, N, N '-dimethyl trimethylene urea, tetramethylurea.

The identification and utilization X-ray powder of the crystal structure of each pigment measures to carry out.X-ray powder for identifying crystal form The condition of measurement is as described below.Area value can be calculated by analysis software (PDXL2, Rigaku corporation).

Device:Rigaku RINT2000

X-ray:Cu-K alpha rays

Device controls:Concentric method

Measure angle:5~50 °

Voltage:40kV

Electric current:40mA

Embodiment 1

By 34 parts of 3.4 parts of 1,3- diiminoisoindoles (Tokyo chemical conversion industry (strain) system) and N,N-dimethylformamide Mixing.Added into obtained mixture 5- cyano -4-oxopentanoic acid (according to Journal of Organic Chemistry, 1992,57 (18), the method synthesis described in 5005-5013) 12 parts, stirring in 10 hours is carried out at 45 DEG C.It is mixed to what is obtained It closes object to be filtered, to 100 parts of the acetic acid containing 0.3 part of water is added in 10 parts of residue, stirring in 2 hours is carried out at 80 DEG C. Obtained mixture is filtered, to 300 parts of water is added in 9.8 parts of residue, stirring in 2 hours is carried out at 80 DEG C.To To mixture be filtered, with the filtered residues of 300 parts of methanol washing, obtain 9.5 parts of residue.To residual after washing 15 parts of n,N-Dimethylformamide is added in 9.5 parts of excess, carries out stirring for 2 hours at 80 DEG C.It is cooled to 0 DEG C, is carried out 2 hours Stirring.Obtained mixture is filtered, is washed with 60 parts of methanol, then obtained residue is subtracted at 60 DEG C Press dry it is dry, obtain 7.6 parts of isoindoline pigments 1 formed by formula (I-1) compound represented (compound number 136) (receive 82%) rate is.Wave indicates to include E bodies, Z bodies or their mixture (in embodiment, similarly hereinafter).

The identification > of < isoindolines pigment 1

(mass spectrum) ionization mode=ESI+:M/z=[M+H]⁺394

Accurate molecular weight (Exact Mass):393

Embodiment 2

3.4 parts of the 1,3- diiminoisoindoles of embodiment 1 are changed to 5- nitro -1,3- diiminoisoindoles 4.5 parts of (according to Journal of Heterocyclic Chemistry, 1994,31 (4), the method synthesis described in 1017), In addition to this, it is synthesized using method similarly to Example 1, obtains 8.7 parts by formula (I-2) compound represented (chemical combination Object number is the isoindoline pigment 2 (yield 80%) 137) formed.

The identification > of < isoindolines pigment 2

(mass spectrum) ionization mode=ESI+:M/z=[M+H]⁺439

Accurate molecular weight (Exact Mass):438

Embodiment 3

4- carboxyl -1- methyl phenylpropionates (being synthesized according to the method described in WO2005/012220) are dissolved in for 30.0 parts In 900 parts of THF.On one side by the temperature of obtained mixture remain -50 DEG C or less, while pass through 120 minutes be added dropwise 1mol/L it is bis- Hexane solution (the Northeast chemistry of (trimethyl silyl) lithium amide (Lithium bis (trimethylsilyl) amide) (strain) makes) 576 parts, stir within 30 minutes.On one side remain -50 DEG C or less, while pass through 90 minutes be added dropwise acetonitrile (Northeast chemistry (strain) makes) 36 parts, 25 DEG C are warming up to, carries out stirring for 6 hours in 25 DEG C.Reaction solution is washed, with anhydrous sodium sulfate to second Acetoacetic ester extract is dried, and distillation removal solvent is passed through using ethyl acetate/n-hexane (volume ratio 2/1) after filtering Reprecipitation purifies residue, obtains 4- carboxyls -1- (4- cyano -3- oxygroups butyl) benzene 26.6 parts (yields 85%).

The 5- cyano of embodiment 1-12 parts of 4-oxopentanoic acid is changed to 4- carboxyls-1- (4- cyano-3- oxygroups butyl) benzene It 12 parts, in addition to this, is synthesized using method similarly to Example 1, obtains 9.6 parts by formula (I-3) compound represented The isoindoline pigment 3 (yield 75%) that (compound number 154) is formed.

The identification > of < isoindolines pigment 3

(mass spectrum) ionization mode=ESI+:M/z=[M+H]⁺546

Accurate molecular weight (Exact Mass):545

Embodiment 4

By 3.4 parts of 1,3- diiminoisoindoles be changed to 5- nitro -1,3- diiminoisoindoles (according to Journal ofHeterocyclic Chemistry,31(4),1017-20;Method synthesis described in 1994) 4.5 parts, it removes It except this, is synthesized using method similarly to Example 3, obtains 10.9 parts by formula (I-4) compound represented (compound Number is the isoindoline pigment 4 (yield 79%) 155) formed.

The identification > of < isoindolines pigment 4

(mass spectrum) ionization mode=ESI+:M/z=[M+H]⁺591

Accurate molecular weight (Exact Mass):590

Embodiment 5

4- methoxycarbonvl-phenyls acetic acid (being synthesized according to the method described in WO2015/100363) is dissolved in for 18 parts In 540 parts of THF.On one side by the temperature of obtained mixture remain -50 DEG C or less, while pass through 120 minutes be added dropwise 1mol/L it is bis- 371 parts of the hexane solution (Northeast chemistry (strain) system) of (trimethyl silyl) lithium amide, stir within 30 minutes.It keeps on one side 23 parts of acetonitrile (Northeast chemistry (strain) system) is added dropwise for -50 DEG C or less, on one side through 90 minutes, is warming up to 25 DEG C, it is small to carry out 6 in 25 DEG C When stir.Reaction solution is washed, acetic acid ethyl ester extract is dried with anhydrous sodium sulfate, distillation removal is molten after filtering Agent purifies residue using ethyl acetate/n-hexane (volume ratio 2/1) by reprecipitation, obtains to Cyanoacetyl benzene Guanidine-acetic acid 13 parts (yields 70%).

The 5- cyano of embodiment 1-12 parts of 4-oxopentanoic acid is changed to 11 parts of Cyanoacetyl phenylacetic acid, except this it Outside, it is synthesized using method similarly to Example 1, obtains 9.5 parts by formula (I-5) compound represented (compound number For the isoindoline pigment 5 (yield 74%) 82) formed.

The identification > of < isoindolines pigment 5

(mass spectrum) ionization mode=ESI+:M/z=[M+H]⁺518

Accurate molecular weight (Exact Mass):517

Embodiment 6

By the 5- cyano of embodiment 2-12 parts of 4-oxopentanoic acid be changed to 4- (2- Cyanoacetyls) benzoic acid (according to Method synthesis described in US2680731) 14 parts, in addition to this, is synthesized, obtained using method similarly to Example 2 9.6 parts of isoindoline pigments 6 (yield 80%) formed by formula (I-6) compound represented (compound number 47).

The identification > of < isoindolines pigment 6

(mass spectrum) ionization mode=ESI+:M/z=[M+H]⁺535

Accurate molecular weight (Exact Mass):534

Embodiment 7

It is different that 3.4 parts of the 1,3- diiminoisoindoles of embodiment 1 are changed to 5- (trifluoromethyl) -1,3- diiminos 5- cyano -12 parts of 4-oxopentanoic acid is changed to 3- (2- Cyanoacetyls) benzene by 5 parts of indoline (Apichemical corporations) Formic acid is (according to Bioorganic&Medicinal Chemistry Letters, 2010,20 (3), the side described in 922-926 Method synthesizes) 14.2 parts, it in addition to this, is synthesized using method similarly to Example 1, obtains 9.1 parts by shown in formula (I-7) Compound (compound number 40) formed isoindoline pigment 7 (yield 70%).

The identification > of < isoindolines pigment 7

(mass spectrum) ionization mode=ESI+:M/z=[M+H]⁺558

Accurate molecular weight (Exact Mass):557

Embodiment 8

Phthalic acid mono-methyl (Aldrich systems) is dissolved in 600 parts of THF for 20 parts.The mixture that will be obtained on one side Temperature remain -50 DEG C or less, on one side through 120 minutes be added dropwise bis- (trimethyl silyl) lithium amides of 1mol/L hexane it is molten 444 parts of liquid (Northeast chemistry (strain) system), stir within 30 minutes.On one side remain -50 DEG C or less, while pass through 90 minutes be added dropwise second 27 parts of nitrile (Northeast chemistry (strain) system), is warming up to 25 DEG C, carries out stirring for 6 hours in 25 DEG C.Reaction solution is washed, use is anhydrous Acetic acid ethyl ester extract is dried in sodium sulphate, and distillation removal solvent, uses ethyl acetate/n-hexane (volume ratio after filtering 2/1), residue to be purified by reprecipitation, 2- (2- Cyanoacetyls) benzoic acid 16 parts (yields 75%) is obtained.

3.4 parts of the 1,3- diiminoisoindoles of embodiment 1 are changed to 5- methoxyl group -1,3- diimino iso-indoles 5- cyano -12 parts of 4-oxopentanoic acid is changed to 14 parts of 2- (2- Cyanoacetyls) benzoic acid, removed by 4.1 parts of quinoline (Aldrich systems) It except this, is synthesized using method similarly to Example 1, obtains 8.8 parts by formula (I-8) compound represented (compound Number is the isoindoline pigment 8 (yield 72%) 30) formed.

The identification > of < isoindolines pigment 8

(mass spectrum) ionization mode=ESI+:M/z=[M+H]⁺520

Accurate molecular weight (Exact Mass):519

Embodiment 9

4.5 parts of the 5- nitro -1,3- diiminoisoindoles of embodiment 6 are changed to 1,3- diiminoisoindoles 3.4 parts of (Tokyo chemical conversion industry (strain) system), in addition to this, is synthesized using method similarly to Example 1, obtain 8 parts by The isoindoline pigment 9 (yield 80%) that formula (I-9) compound represented (compound number 46) is formed.

The identification > of < isoindolines pigment 9

(mass spectrum) ionization mode=ESI+:M/z=[M+H]⁺490

Accurate molecular weight (Exact Mass):489

Comparative example 1

By 34 parts of 3.4 parts of 1,3- diiminoisoindoles (Tokyo chemical conversion industry (strain) system) and N,N-dimethylformamide Mixing.Added into obtained mixture 5- cyano -4-oxopentanoic acid (according to Journal of Organic Chemistry, 1992,57 (18), the method synthesis described in 5005-5013) 12 parts, stirring in 10 hours is carried out at 45 DEG C.It is mixed to what is obtained It closes object to be filtered, to 300 parts of water is added in 9.8 parts of residue, stirring in 2 hours is carried out at 80 DEG C.To obtained mixture It is filtered, with 300 parts of filtered residues of washing of methanol, obtains 9.5 parts of residue.To 9.5 parts of residue after washing Middle 15 parts of addition n,N-Dimethylformamide, carries out stirring for 2 hours at 80 DEG C.55 DEG C are cooled to, 7.5 parts of methanol is added, it is cold But to 0 DEG C, stir within 2 hours.Obtained mixture is filtered, it is dry to carry out decompression to obtained residue at 60 DEG C It is dry, obtain 5.6 parts of isoindoline pigments 1 (yield 60%) formed by formula (I-1) compound represented.

Comparative example 2

The 5- cyano of comparative example 1-12 parts of 4-oxopentanoic acid is changed to 4- carboxyls-1- (4- cyano-3- oxygroups butyl) benzene It 12 parts, in addition to this, is synthesized using method same as comparative example 1, obtains 5.7 parts by formula (I-3) compound represented The isoindoline pigment 3 (yield 47%) of formation.

Comparative example 3

The 5- cyano of comparative example 1-12 parts of 4-oxopentanoic acid is changed to 11 parts of Cyanoacetyl phenylacetic acid, except this it Outside, it is synthesized using method same as comparative example 1, obtains 8.0 parts of iso-indoles formed by formula (I-5) compound represented Quinoline pigment 5 (yield 63%).

Comparative example 4

By 34 parts of 3.4 parts of 1,3- diiminoisoindoles (Tokyo chemical conversion industry (strain) system) and N,N-dimethylformamide Mixing.4- (2- Cyanoacetyls) benzoic acid is added into obtained mixture (to close according to the method described in US2680731 At) 4.9 parts, it carries out stirring for 10 hours at 45 DEG C.Obtained mixture is filtered, is contained to being added in 10 parts of residue 100 parts of the acetic acid of 0.3 part of water, carries out stirring for 2 hours at 80 DEG C.Obtained mixture is filtered, it is right with 300 parts of methanol 9.5 parts of residue is washed.Obtained mixture is filtered, to adding N, N- dimethyl formyls in 9.5 parts of residue 15 parts of amine, carries out stirring for 2 hours at 80 DEG C.55 DEG C are cooled to, 7.5 parts of methanol is added, is cooled to 0 DEG C, stir within 2 hours It mixes.Obtained mixture is filtered, obtained residue is dried under reduced pressure at 60 DEG C, obtains 5.6 parts by formula (I- 9) the isoindoline pigment 9 (yield 60%) that compound represented is formed.

Comparative example 5

By the 5- cyano of comparative example 1-12 parts of 4-oxopentanoic acid be changed to 4- (2- Cyanoacetyls) benzoic acid (according to Method synthesis described in US2680731) 4.9 parts, in addition to this, is synthesized, obtained using method same as comparative example 1 4.6 parts of isoindoline pigments 9 (yield 50%) formed by formula (I-9) compound represented.

Synthesis example 1

Appropriate nitrogen is flowed into the flask with reflux condensing tube, dropping funel and blender, is replaced as nitrogen atmosphere, It is packed into 371 parts of propylene glycol monomethyl ether, 85 DEG C are heated to while stirring.Next, acrylic acid was added dropwise through 5 hours 54 parts, acrylic acid 3,4- epoxy San Huans [5.2.1.0^2,6]Decane -8- base esters and acrylic acid 3,4- epoxy San Huans [5.2.1.0^2,6] The mixture (trade name " E-DCPA ", (strain) Daicel systems) of decane -9- base esters) 225 parts, (isomers mixes vinyltoluene Object) 81 parts, solution made of 160 parts of dissolvings of propylene glycol monomethyl ether.After the completion of dropwise addition of initiator solution, identical At a temperature of kept for 4 hours, it is then cooled to room temperature, obtain the solution for the copolymer (resin B 1) that solid state component is 37.5%. The weight average molecular weight of the resin B 1 arrived is 10,600, dispersion degree 2.0, and solid state component acid value is 115mg-KOH/g.

Embodiment 10

(1) preparation of coloured composition

Following substances are mixed, using ball mill, so that isoindoline pigment 1 is disperseed, obtains coloured composition 1,

Next, following substances are mixed, colored curable resin composition 1 is obtained,

(2) making of film is coloured

Using spin-coating method, the film thickness toast later after becomes 2 μm of mode, in the glass substrate (Eagle of 5cm square XG;Corning corporations) on be coated with colored curable resin composition, then, in 100 DEG C carry out 3 minutes prebake conditions, formed Coloring compositions nitride layer.After placing cooling, exposure machine (TME-150RSK is used;TOPCON CORPORATION systems), in air gas Under atmosphere, with 80mJ/cm²Light exposure (on the basis of 365nm) light irradiation is carried out to the coloring compositions nitride layer that is formed on substrate. After light irradiation, in an oven, is toasted after being carried out 30 minutes in 230 DEG C, obtain coloring film.Use DEKTAK3 (Japanese vacuum Technology (strain) is made), the film thickness of the colored pattern to obtaining is measured." film thickness " one that the film thickness of colored pattern is shown in Table 7 In column.

(3) contrast is evaluated

For obtained coloring film, contrast meter (CT-1 is used:Pot slope motor (strain), color evaluating BM-5A: TOPCON CORPORATION systems, light source:F-10, light polarizing film:Pot slope motor (strain)) measure contrast.It should be noted that surveying The blank value of timing is 30,000.Show the result in table 7.

Embodiment 11~18 and comparative example 6~10

As colorant (A), iso-indoles is replaced using the isoindoline pigment obtained in embodiment comparative example above-mentioned In addition to this quinoline pigment 1 carries out similarly to Example 10.Show the result in table 7.

Table 7

Embodiment 19

4- carboxyl -1- methyl phenylpropionates (being synthesized according to the method described in WO 2005/012220) are dissolved in for 30 parts In 900 parts of THF.On one side by the temperature of obtained mixture remain -50 DEG C or less, while pass through 120 minutes be added dropwise 1mol/L it is bis- 576 parts of the hexane solution (Northeast chemistry (strain) system) of (trimethyl silyl) lithium amide, stir within 30 minutes.It keeps on one side 36 parts of acetonitrile (Northeast chemistry (strain) system) is added dropwise for -50 DEG C or less, on one side through 90 minutes, is warming up to 25 DEG C, it is small to carry out 6 in 25 DEG C When stir.Reaction solution is washed, acetic acid ethyl ester extract is dried with anhydrous sodium sulfate, distillation removal is molten after filtering Agent purifies residue using ethyl acetate/n-hexane (volume ratio 2/1) by reprecipitation, obtains 4- carboxyls -1- (4- cyanogen Base -3- oxygroups butyl) benzene 27 parts (yields 85%).

By the 100 parts of mixing of 1.0 parts of phthalonitrile (phthalonitrile) (Tokyo chemical conversion industry (strain) system) and methanol. On one side by the temperature of obtained mixture remain 5 DEG C or less, while pass through 28% methanol solution of sodium methylate (and light be added dropwise within 30 minutes Pure medicine industrial (strain) system) 0.9 part, it carries out stirring for 6 hours at 5 DEG C.On one side by the temperature of obtained mixture remain 5 DEG C with Under, on one side add 4.7 parts of acetic acid.4- carboxyls -1- (4- cyano -3- oxygroups butyl) 4.1 parts of benzene is added into obtained mixture, It carries out stirring for 26 hours at 45 DEG C.Obtained mixture is filtered, uses 100 parts of water, 100 parts of methanol, N, N- bis- successively 20 parts of 5 parts of methylformamide, methanol debris, are dried under reduced pressure at 60 DEG C, obtain the compound 2.3 of formula (I-3) expression Part.12 parts of mixing of 2.3 parts of compound and n,N-dimethylacetamide that obtained formula (I-1) is indicated, it is small to carry out 3 at 20 DEG C When stir.Obtained mixture is filtered, obtained residue is dried under reduced pressure at 60 DEG C, obtains 2.3 parts of formulas (I-3) the isoindoline pigment 3 (compound number 154) (yield 55%) indicated.

The identification > of < isoindolines pigment 3

(mass spectrum) ionization mode=ESI+:M/z=[M+H]⁺546

Accurate molecular weight (Exact Mass):545

The Hansen Solubility Parameter > of < isoindolines pigment 3

The Hansen Solubility Parameter of isoindoline pigment 3 is (δ_D1, δ_P1, δ_H1)=(17.3,13.5,10.0).

Embodiment 20

1.0 parts of the phthalonitrile of embodiment 19 is changed to 4- nitrophthalonitriles (Tokyo chemical conversion industry (strain) system) It 1.4 parts, in addition to this, is synthesized using method similarly to Example 19.Obtain the iso-indoles of 3.7 parts of formulas (I-4) expression Quinoline pigment 4 (compound number 155) (yield 63%).

The identification > of < isoindolines pigment 4

(mass spectrum) ionization mode=ESI+:M/z=[M+H]⁺591

Accurate molecular weight (Exact Mass):590

The Hansen Solubility Parameter > of < isoindolines pigment 4

The Hansen Solubility Parameter of isoindoline pigment 4 is (δ_D1, δ_P1, δ_H1)=(17.0,13.2,9.9).

Embodiment 21

4- carboxyls -1- (4- cyano -3- oxygroups butyl) 4.1 parts of benzene of embodiment 19 is changed to 3- (2- Cyanoacetyls) Benzoic acid is (according to Bioorganic&Medicinal Chemistry Letters, 2010,20 (3), described in 922-926 Method synthesizes) 4.7 parts, in addition to this, synthesized using method similarly to Example 19.Obtain 2.9 parts of formula (I-10) tables The isoindoline pigment 10 (compound number 37) (yield 76%) shown.

The identification > of < isoindolines pigment 10

(mass spectrum) ionization mode=ESI+:M/z=[M+H]⁺490

Accurate molecular weight (Exact Mass):489

The Hansen Solubility Parameter > of < isoindolines pigment 10

The Hansen Solubility Parameter of isoindoline pigment 10 is (δ_D1, δ_P1, δ_H1)=(17.0,12.5,9.9).

Embodiment 22

4- carboxyls -1- (4- cyano -3- oxygroups butyl) 4.1 parts of benzene of embodiment 19 is changed to 4- (2- Cyanoacetyls) 4.7 parts of benzoic acid (being synthesized according to the method described in US2680731), in addition to this, utilizes method similarly to Example 19 It is synthesized.Obtain the isoindoline pigment 9 (compound number 46) (yield 76%) of 2.9 parts of formulas (I-11) expression.

The identification > of < isoindolines pigment 9

(mass spectrum) ionization mode=ESI+:M/z=[M+H]⁺490

Accurate molecular weight (Exact Mass):489

The Hansen Solubility Parameter > of < isoindolines pigment 9

The Hansen Solubility Parameter of isoindoline pigment 9 is (δ_D1, δ_P1, δ_H1)=(17.0,12.5,9.7).

Embodiment 23

The n,N-dimethylacetamide of embodiment 22 is changed to N, N- dimethylacetoacetamides are in addition to this, sharp It is synthesized with method similarly to Example 22.Obtain 2.6 parts of isoindoline pigments 9 (yield 68%).

Embodiment 24

The n,N-dimethylacetamide of embodiment 22 is changed to dimethyl sulfoxide (DMSO), in addition to this, using with embodiment 22 Same method is synthesized.Obtain 2.4 parts of isoindoline pigments 9 (yield 65%).

Embodiment 25

The n,N-dimethylacetamide of embodiment 22 is changed to 1,3-Dimethyl-2-imidazolidinone, in addition to this, is utilized Method similarly to Example 22 is synthesized.Obtain 2.4 parts of isoindoline pigments 9 (yield 65%).

Embodiment 26

The n,N-dimethylacetamide of embodiment 22 is changed to N-Methyl pyrrolidone, in addition to this, using with implementation 22 same method of example is synthesized.Obtain 2.0 parts of isoindoline pigments 9 (yield 53%).

Embodiment 27

The DMAC N,N' dimethyl acetamide of embodiment 22 is changed to DMAC N,N' dimethyl acetamide/gamma-butyrolacton/N- methyl pyrroles In addition to this mixed solvent (volume ratio 66/16/18) of pyrrolidone is synthesized using method similarly to Example 22. Obtain 2.4 parts of isoindoline pigments 9 (yield 65%).

Embodiment 28

The DMAC N,N' dimethyl acetamide of embodiment 22 is changed to the mixed solvent of DMAC N,N' dimethyl acetamide/sulfolane (volume ratio 49/51) is in addition to this synthesized using method similarly to Example 22.Obtain 2.5 parts of isoindoline colors Plain 9 (yields 66%).

Embodiment 29

The DMAC N,N' dimethyl acetamide of embodiment 22 is changed to the mixed of DMAC N,N' dimethyl acetamide/N-Methyl pyrrolidone Bonding solvent (volume ratio 44/56) is in addition to this synthesized using method similarly to Example 22.Obtain 2.6 parts of different Yin Diindyl quinoline pigment 9 (yield 68%).

Embodiment 30

The mixing that the DMAC N,N' dimethyl acetamide of embodiment 22 is changed to DMAC N,N' dimethyl acetamide/dimethyl sulfoxide (DMSO) is molten Agent (volume ratio 82/18) is in addition to this synthesized using method similarly to Example 22.Obtain 2.3 parts of isoindolines Pigment 9 (yield 60%).

Embodiment 31

It is sub- that the DMAC N,N' dimethyl acetamide of embodiment 22 is changed to DMAC N,N' dimethyl acetamide/2- butanone/carbonic acid 1,2- Propyl ester mixed solvent (volume ratio 66/26/8) is in addition to this synthesized using method similarly to Example 22.It obtains 2.8 parts of isoindoline pigments 9 (yield 73%).

Comparative example 11

The n,N-dimethylacetamide of embodiment 19 is changed to n-hexane, in addition to this, using similarly to Example 19 Method synthesized.Obtain 3 parts of isoindoline pigments 3 (yield 72%).

Comparative example 12

The n,N-dimethylacetamide of embodiment 20 is changed to n-hexane, in addition to this, using similarly to Example 20 Method synthesized.Obtain 4.5 parts of isoindoline pigments 4 (yield 77%).

Comparative example 13

The n,N-dimethylacetamide of embodiment 21 is changed to n-hexane, in addition to this, using similarly to Example 21 Method synthesized.Obtain 3.2 parts of isoindoline pigments 10 (yield 84%).

Comparative example 14

The n,N-dimethylacetamide of embodiment 22 is changed to n-hexane, in addition to this, using similarly to Example 22 Method synthesized.Obtain 3.1 parts of isoindoline pigments 9 (yield 81%).

Embodiment 32

(1) preparation of coloured composition

Following substances are mixed, using ball mill, so that isoindoline pigment 3 is disperseed, obtains coloured composition 2-1,

Next, following substances are mixed, colored curable resin composition 2-1 is obtained,

(2) making of film is coloured

Using spin-coating method, the film thickness toast later after becomes 2 μm of mode, in the glass substrate (Eagle of 5cm square XG;Corning corporations) on be coated with colored curable resin composition 2-1, then, in 100 DEG C carry out 3 minutes prebake conditions, shape At coloring compositions nitride layer.After placing cooling, exposure machine (TME-150RSK is used;TOPCON CORPORATION systems), in air Under atmosphere, with 80mJ/cm²Light exposure (on the basis of 365nm) illumination is carried out to the coloring compositions nitride layer that is formed on substrate It penetrates.After light irradiation, in an oven, is toasted after being carried out 30 minutes in 230 DEG C, obtain coloring film.Use DEKTAK3 (Japan Vacuum technique (strain) is made), the film thickness of the colored pattern to obtaining is measured." the film that the film thickness of colored pattern is shown in Table 8 In a thickness " column.

(3) contrast is evaluated

For obtained coloring film, contrast meter (CT-1 is used:Pot slope motor (strain), color evaluating BM-5A: TOPCON CORPORATION systems, light source:F-10, light polarizing film:Pot slope motor (strain)) measure contrast.It should be noted that surveying The blank value of timing is 30,000.Show the result in table 8.

Embodiment 33~44 and comparative example 15~18

As colorant (A), iso-indoles is replaced using the isoindoline pigment obtained in embodiment comparative example above-mentioned In addition to this quinoline pigment 3 is carried out similarly with embodiment 32.Show the result in table 8.

Table 8

DMAc=N, N- dimethylacetylamide, DMAA=N, N- dimethylacetoacetamides, DMSO=dimethyl sulfoxide (DMSO)s

DMI=1,3- dimethyl-2-imidazolinone, NMP=N- methyl pyrrolidones, GBL=gamma-butyrolactons

SF=sulfolane, MEK=2- butanone, PC=carbonic acid 1, the Asias 2- propyl ester

Embodiment 45

By the 300 parts of mixing of 3 parts of phthalonitrile (Tokyo chemical conversion industry (strain) system) and methanol.The mixture that will be obtained on one side Temperature remain 5 DEG C or less, through 30 minutes 28% methanol solution of sodium methylate (and Wako Pure Chemical Industries (strain) make) be added dropwise on one side It 2.71 parts, carries out stirring for 6 hours in 5 DEG C.On one side by the temperature of obtained mixture remain 5 DEG C or less, while add acetic acid 34 parts.Added into obtained mixture 5- cyano -4-oxopentanoic acid (according to Journal of Organic Chemistry, 1992,57 (18), the method synthesis described in 5005-5013) 12 parts, it carries out stirring for 26 hours in 45 DEG C.Mixing to obtaining Object is filtered, and uses 15 parts of 300 parts of water, 300 parts of methanol, n,N-Dimethylformamide filtered residues of washing successively.In 60 DEG C are dried under reduced pressure obtained residue, and obtaining 7.4 parts, (compound number is by formula (I-1) compound represented 136) the isoindoline pigment 1 (yield 80%) formed.Wave expression is the mixture (similarly hereinafter) of E bodies and Z bodies.By different Yin The X-ray diffraction intensity curve of diindyl quinoline pigment 1 is shown in Fig. 1.

The identification > of < isoindolines pigment 1

(mass spectrum) ionization mode=ESI+:M/z=[M+H]⁺394

Accurate molecular weight (Exact Mass):393

Embodiment 46

By 3 parts of the phthalonitrile of embodiment 45 be changed to 4- nitrophthalonitriles (Tokyo chemical conversion industry (strain) make, 4.1 parts), it in addition to this, is synthesized using method same as embodiment 45, obtains 7.3 parts of chemical combination shown in formula (I-2) The isoindoline pigment 2 (yield 71%) that object (compound number 137) is formed.By the X-ray diffraction of isoindoline pigment 2 Intensity curve is shown in Fig. 2.

The identification > of < isoindolines pigment 2

(mass spectrum) ionization mode=ESI+:M/z=[M+H]⁺439

Accurate molecular weight (Exact Mass):438

Embodiment 47

4- carboxyl -1- methyl phenylpropionates (being synthesized according to the method described in WO 2005/012220) are dissolved in for 30.0 parts In 900 parts of THF.On one side by the temperature of obtained mixture remain -50 DEG C or less, while pass through 120 minutes be added dropwise 1mol/L it is bis- 576 parts of the hexane solution (Northeast chemistry (strain) system) of (trimethyl silyl) lithium amide, stir within 30 minutes.It keeps on one side 36 parts of acetonitrile (Northeast chemistry (strain) system) is added dropwise for -50 DEG C or less, on one side through 90 minutes, is warming up to 25 DEG C, it is small to carry out 6 in 25 DEG C When stir.Reaction solution is washed, acetic acid ethyl ester extract is dried with anhydrous sodium sulfate, distillation removal is molten after filtering Agent purifies residue using ethyl acetate/n-hexane (volume ratio 2/1) by reprecipitation, obtains 4- carboxyls -1- (4- cyanogen Base -3- oxygroups butyl) benzene 26.6 parts (yields 85%).

The 5- cyano of embodiment 45-12 parts of 4-oxopentanoic acid is changed to 4- carboxyls-1- (4- cyano-3- oxygroups butyl) benzene It 12 parts, in addition to this, is synthesized using method same as embodiment 45, obtains 7.7 parts by formula (I-3) compound represented The isoindoline pigment 3 (yield 60%) that (compound number 154) is formed.The X-ray diffraction of isoindoline pigment 3 is strong Line of writing music is shown in Fig. 3.

The identification > of < isoindolines pigment 3

(mass spectrum) ionization mode=ESI+:M/z=[M+H]⁺546

Accurate molecular weight (Exact Mass):545

Embodiment 48

3 parts of the phthalonitrile of embodiment 45 is changed to 4- nitrophthalonitriles (Tokyo chemical conversion industry (strain) system) 4 Part, 5- cyano -12 parts of 4-oxopentanoic acid is changed to 4- carboxyls -1- (4- cyano -3- oxygroups butyl) 12 parts of benzene, in addition to this, It is synthesized using method same as embodiment 45.Obtaining 8.7 parts, (compound number is by formula (I-4) compound represented 155) the isoindoline pigment 4 (yield 63%) formed.The X-ray diffraction intensity curve of isoindoline pigment 4 is shown in figure 4。

The identification > of < isoindolines pigment 4

(mass spectrum) ionization mode=ESI+:M/z=[M+H]⁺591

Accurate molecular weight (Exact Mass):590

Embodiment 49

4- carboxyl -1- methyl phenylpropionates (being synthesized according to the method described in WO2015/100363) are dissolved in THF for 18 parts In 540 parts.On one side by the temperature of obtained mixture remain -50 DEG C or less, while pass through 120 minutes be added dropwise 1mol/L bis- (three Methyl silicane base) lithium amide 371 parts of hexane solution (Northeast chemistry (strain) system), stir within 30 minutes.Remain on one side- 50 DEG C or less, through 90 minutes 23 parts of acetonitrile (Northeast chemistry (strain) system) was added dropwise on one side, be warming up to 25 DEG C, carried out 6 hours in 25 DEG C Stirring.Reaction solution is washed, acetic acid ethyl ester extract is dried with anhydrous sodium sulfate, distillation removal is molten after filtering Agent purifies residue using ethyl acetate/n-hexane (volume ratio 2/1) by reprecipitation, obtains to Cyanoacetyl benzene Guanidine-acetic acid 13 parts (yields 70%).

The 5- cyano of embodiment 45-12 parts of 4-oxopentanoic acid is changed to, to 11 parts of Cyanoacetyl phenylacetic acid, to remove this Except, it is synthesized using method same as embodiment 45, obtaining 8.7 parts, (compound is compiled by formula (I-5) compound represented Number for 82) formed isoindoline pigment 5 (yield 68%).The X-ray diffraction intensity curve of isoindoline pigment 5 is shown in Fig. 5.

The identification > of < isoindolines pigment 5

(mass spectrum) ionization mode=ESI+:M/z=[M+H]⁺518

Accurate molecular weight (Exact Mass):517

Embodiment 50

By the 5- cyano of embodiment 46-12 parts of 4-oxopentanoic acid be changed to 4- (2- Cyanoacetyls) benzoic acid (according to Method synthesis described in US2680731) 14 parts, in addition to this, is synthesized, obtained using method same as embodiment 46 10 parts of isoindoline pigments 6 (yield 83%) formed by formula (I-6) compound represented (compound number 47).It will be different The X-ray diffraction intensity curve of indoline pigment 6 is shown in Fig. 6.

The identification > of < isoindolines pigment 6

(mass spectrum) ionization mode=ESI+:M/z=[M+H]⁺535

Accurate molecular weight (Exact Mass):534

Embodiment 51

3 parts of the phthalonitrile of embodiment 45 is changed to 4- (trifluoromethyl) phthalonitrile (according to Japanese Unexamined Patent Publication Method synthesis described in 6-41137) 4.6 parts, 5- cyano -12 parts of 4-oxopentanoic acid is changed to 3- (2- Cyanoacetyls) benzene Formic acid is (according to Bioorganic&Medicinal Chemistry Letters, 2010,20 (3), the side described in 922-926 Method synthesizes) 14.2 parts, it in addition to this, is synthesized using method same as embodiment 45, obtains 7.7 parts and (changed by formula (I-7) It is the isoindoline pigment 7 (yield 59%) that 40) compound represented is formed to close object number.The X of isoindoline pigment 7 is penetrated Line diffracted intensity curve is shown in Fig. 7.

The identification > of < isoindolines pigment 7

(mass spectrum) ionization mode=ESI+:M/z=[M+H]⁺558

Accurate molecular weight (Exact Mass):557

Embodiment 52

3 parts of the phthalonitrile of embodiment 45 is changed to 3.7 parts of 4- methoxyl groups phthalonitrile (Aldrich systems), it will 5- cyano -12 parts of 4-oxopentanoic acid is changed to 14 parts of 2- (2- Cyanoacetyls) benzoic acid, in addition to this, using with embodiment 45 Same method is synthesized, and 7.7 parts of iso-indoles formed by formula (I-8) compound represented (compound number 30) are obtained Quinoline pigment 8 (yield 63%).The X-ray diffraction intensity curve of isoindoline pigment 8 is shown in Fig. 8.

The identification > of < isoindolines pigment 8

(mass spectrum) ionization mode=ESI+:M/z=[M+H]⁺520

Accurate molecular weight (Exact Mass):519

Embodiment 53

4.05 parts of the 4- nitrophthalonitriles of embodiment 50 are changed to phthalonitrile (Tokyo chemical conversion industry (strain) System) 3 parts, it in addition to this, is synthesized using method same as embodiment 50, obtains 9.7 parts of chemical combination shown in formula (I-9) The isoindoline pigment 9A (yield 85%) that object (compound number 46) is formed.The X-ray of isoindoline pigment 9A is spread out It penetrates intensity curve and is shown in Fig. 9.

The identification > of < isoindoline pigments 9A

(mass spectrum) ionization mode=ESI+:M/z=[M+H]⁺490

Accurate molecular weight (Exact Mass):489

Embodiment 54

By the 128 parts of mixing of 1.3 parts of phthalonitrile (Tokyo chemical conversion industry (strain) system) and methanol.The mixing that will be obtained on one side The temperature of object remains 5 DEG C or less, on one side through 30 minutes 28% methanol solution of sodium methylate of dropwise addition (and Wako Pure Chemical Industries (strain) are made) It 1.2 parts, carries out stirring for 6 hours at 5 DEG C.On one side by the temperature of obtained mixture remain 5 DEG C or less, while add acetic acid 32 parts.4.9 parts of 4- (2- Cyanoacetyls) benzoic acid is added into obtained mixture, carries out stirring for 26 hours at 45 DEG C. Obtained mixture is filtered, with 150 parts of 150 parts of water, methanol debris.At 80 DEG C, with N, N- dimethyl methyls The residue dissolving that 500 parts of amide makes, is subsequently cooled to 60 DEG C, adds 250 parts of methanol.It is cooled to 0 DEG C, is filtered, Obtained residue is dried under reduced pressure in 60 DEG C, obtains 1.71 parts of iso-indoles formed by formula (I-9) compound represented Quinoline pigment 9B (yield 35%).The X-ray diffraction intensity curve of isoindoline pigment 9B is shown in Figure 10.

Embodiment 55

By the 128 parts of mixing of 1.3 parts of phthalonitrile (Tokyo chemical conversion industry (strain) system) and n-butyl alcohol.It is mixed by what is obtained on one side The temperature for closing object remains 5 DEG C or less, on one side through 30 minutes dropwise addition 28% methanol solution of sodium methylate (and Wako Pure Chemical Industries (strain) System) 1.2 parts, it carries out stirring for 6 hours at 5 DEG C.On one side by the temperature of obtained mixture remain 5 DEG C or less, while add 37 parts of acetic acid.4.9 parts of 4- (2- Cyanoacetyls) benzoic acid is added into obtained mixture, at 45 DEG C stir within 26 hours It mixes.Obtained mixture is filtered, with 150 parts of 150 parts of water, methanol debris.In 80 DEG C, with N, N- dimethyl methyls The residue dissolving that 500 parts of amide makes, is subsequently cooled to 60 DEG C, adds 250 parts of methanol.It is cooled to 0 DEG C, is filtered, Obtained residue is dried under reduced pressure in 60 DEG C, obtains 3.51 parts of iso-indoles formed by formula (I-9) compound represented Quinoline pigment 9C (yield 72%).The X-ray diffraction intensity curve of isoindoline pigment 9C is shown in Figure 11.

Embodiment 56

By the 128 parts of mixing of 1.3 parts of phthalonitrile (Tokyo chemical conversion industry (strain) system) and methanol.The mixing that will be obtained on one side The temperature of object remains 5 DEG C or less, on one side through 30 minutes 28% methanol solution of sodium methylate of dropwise addition (and Wako Pure Chemical Industries (strain) are made) It 1.2 parts, carries out stirring for 6 hours at 5 DEG C.On one side by the temperature of obtained mixture remain 5 DEG C or less, while add acetic acid 38 parts.4.9 parts of 4- (2- Cyanoacetyls) benzoic acid is added into obtained mixture, carries out stirring for 26 hours at 45 DEG C. Obtained mixture is filtered, with 150 parts of 150 parts of water, methanol debris.At 80 DEG C, with N, N- dimethyl second The residue that the mixed solvent 15 parts (volume ratios 1/1) of amide and dimethyl sulfoxide (DMSO) makes suspends, and is subsequently cooled to 60 DEG C, Add 250 parts of methanol.It is cooled to 0 DEG C, is filtered, obtained residue is dried under reduced pressure in 60 DEG C, obtains 3.01 parts The isoindoline pigment 9D (yield 62%) formed by formula (I-9) compound represented.By the X-ray of isoindoline pigment 9D Diffracted intensity curve is shown in Figure 12.

Embodiment 57

Obtained in embodiment 56 2.0 parts of isoindoline pigment 9D is mixed for 50 parts with dimethylbenzene, carries out 8 under reflux Hour stirring.Obtained mixture is filtered, obtained residue is dried under reduced pressure in 60 DEG C, obtain 2.0 parts by The isoindoline pigment 9E (yield 99%) that formula (I-9) compound represented is formed.The X-ray of isoindoline pigment 9E is spread out It penetrates intensity curve and is shown in Figure 13.

Comparative example 19

According to the method synthetic dyestuff Huang 185 described in the embodiment 1 of Japanese Unexamined Patent Application 55-157657 bulletins (Y185).The X-ray diffraction intensity curve of Y185 is shown in Figure 14.

Comparative example 20

According to the method synthetic dyestuff Huang 139 (Y139) described in US2007-0119345 bulletins.By the X-ray of Y139 Diffracted intensity curve is shown in Figure 15.

Embodiment 58

(1) preparation of coloured composition

Following substances are mixed, using ball mill, so that isoindoline pigment 1 is disperseed, obtains coloured composition 3-1,

Next, following substances are mixed, colored curable resin composition 3-1 is obtained,

(2) making of film is coloured

Using spin-coating method, the film thickness toast later after becomes 2 μm of mode, in the glass substrate (Eagle of 5cm square XG;Corning corporations) on be coated with colored curable resin composition 3-1, then, in 100 DEG C carry out 3 minutes prebake conditions, shape At coloring compositions nitride layer.After placing cooling, exposure machine (TME-150RSK is used;TOPCON CORPORATION systems), in air Under atmosphere, with 80mJ/cm²Light exposure (on the basis of 365nm) illumination is carried out to the coloring compositions nitride layer that is formed on substrate It penetrates.After light irradiation, in an oven, is toasted after being carried out 30 minutes in 230 DEG C, obtain coloring film.Use DEKTAK3 (Japan Vacuum technique (strain) is made), the film thickness of the colored pattern to obtaining is measured." the film that the film thickness of colored pattern is shown in Table 9 In a thickness " column.

(3) contrast is evaluated

For obtained coloring film, contrast meter (CT-1 is used:Pot slope motor (strain), color evaluating BM-5A: TOPCON CORPORATION systems, light source:F-10, light polarizing film:Pot slope motor (strain)), measure contrast.It should be noted that Blank value when measurement is 30,000.Show the result in table 9.

(4) phase difference value is evaluated

For obtained coloring film, phase difference value measurement device (ellipsometer (ellipsometer) is used;Japan's light splitting Corporation), it is measured under conditions of measurement wavelength is 550nm, refractive index is 1.5.Show the result in table 9.

Embodiment 59~70 and comparative example 21~22

As colorant (A) following substances are used instead of 10 parts of isoindoline pigment 1:

10 parts of isoindoline pigment 2 (embodiment 59),

10 parts of isoindoline pigment 3 (embodiment 60),

10 parts of isoindoline pigment 4 (embodiment 61),

10 parts of isoindoline pigment 5 (embodiment 62),

10 parts of isoindoline pigment 6 (embodiment 63),

10 parts of isoindoline pigment 7 (embodiment 64),

10 parts of isoindoline pigment 8 (embodiment 65),

10 parts of isoindoline pigment 9A (embodiment 66),

10 parts of isoindoline pigment 9B (embodiment 67),

10 parts of isoindoline pigment 9C (embodiment 68),

10 parts of isoindoline pigment 9D (embodiment 69),

10 parts of isoindoline pigment 9E (embodiment 70),

The pigment yellow 185 (comparative example 21) obtained in 10 parts of comparative example 19, or

The pigment yellow 13 9 (comparative example 22) obtained in 10 parts of comparative example 20,

In addition to this, it is carried out according to mode same as embodiment 58.Show the result in table 9.Table 9

Claims

1. the manufacturing method of isoindoline pigment, the method includes following processes:

Make isoindoline in the presence of for 100 mass parts isoindoline pigments (A) being 100 water below mass part The process that pigment (A) is contacted and then is separated by solid-liquid separation with sour (Z), and

The solid of the isoindoline pigment (A) as obtained from the separation of solid and liquid is set to contact and then be separated by solid-liquid separation with water Process.

2. the manufacturing method of isoindoline pigment as described in claim 1, wherein sour (Z) is organic acid.

3. the manufacturing method of isoindoline pigment as described in claim 1, wherein sour (Z) is carboxylic acid compound.

4. the manufacturing method of isoindoline pigment as described in claim 1, wherein sour (Z) is the fat of carbon atom number 1~5 Race's saturated carboxylic acid.

5. the manufacturing method of isoindoline pigment, the method includes following processes:

Process (1) makes isoindoline pigment (A) be contacted with solvent (Z);And

In the method, Hansen Solubility Parameter and the solvent (Z) of isoindoline pigment calculated based on formula (E.1), described The distance Ra of Hansen Solubility Parameter is 0MPa^0.5The above 10MPa^0.5Hereinafter, also, solvent (Z) in process (1) amount it is opposite It is below mass part for more than 0.1 mass parts 10.0 for 1 mass parts isoindoline pigment (A),

In formula,

δ_H2:Hydrogen bond ingredient (the MPa of the Hansen Solubility Parameter of solvent (Z)^0.5)。

6. manufacturing method as claimed in claim 5, wherein the dispersion of the solvent (Z) in the Hansen Solubility Parameter of solvent (Z) Ingredient δ_D2For 16.0MPa^0.5The above 19.0MPa^0.5Hereinafter, the polar component δ of solvent (Z)_P2For 9.0MPa^0.5More than 17.0MPa^0.5Hereinafter, the hydrogen bond ingredient δ of solvent (Z)_H2For 6.5MPa^0.5The above 11.0MPa^0.5Below.

7. manufacturing method as claimed in claim 5, wherein solvent (Z) include selected from by ester solvent, ketone solvent, amide solvent, At least one of the group of sulfoxide solvent and sulfoxide solvent composition.

8. manufacturing method as claimed in claim 5, wherein the amount of solvent (Z) is for 1 mass parts isoindoline pigment It is below mass part for more than 0.5 mass parts 8.0.

9. the manufacturing method as described in claim 1 or 5, wherein isoindoline pigment includes the compound that formula (1) indicates,

In formula (1),

R¹Indicate can be with the carbon atom number 1~40 of substituent group alkyl, can be with substituent group heterocycle or hydrogen atom, - the CH for including in the alkyl₂And the heterocycle includes the-CH for not constituting ring₂When should-CH₂Can be substituted for-O- ,- CO-,-S(O)₂-,-NR^x1, do not include passing through replacement-CH still₂And formation-COOH and-S (O)₂The case where OH, in addition, should Alkyl and the heterocycle can have selected from by-CO₂ ^-With-S (O)₂O^-At least one of group of composition,

R²~R⁹Independently of each other indicate can be with the carbon atom number 1~40 of substituent group alkyl, can be with the miscellaneous of substituent group Ring group, hydrogen atom, halogen atom, cyano, nitro ,-CO₂ ^-Or-S (O)₂O^-,-the CH that includes in the alkyl₂And the heterocycle packet Containing-the CH for not constituting ring₂When should-CH₂- O- ,-CO- ,-S (O) can be substituted for₂-,-NR^x1, do not include by replacing still Change-CH₂And formation-COOH and-S (O)₂The case where OH, in addition, the alkyl and the heterocycle can have selected from by-CO₂ ^-With- S(O)₂O^-At least one of group of composition,

R²And R³,R³And R⁴,R⁴And R⁵,R⁶And R⁷And R⁸And R⁹Can together be formed with the carbon atom being respectively bonded can have substitution The ring of base, the ring include the-CH for not constituting ring₂When should-CH₂- O- ,-CO- ,-S (O) can be substituted for₂-,-NR^x1, but It does not include passing through replacement-CH to be₂And formation-COOH and-S (O)₂The case where OH, in addition, the ring can have selected from by-CO₂ ^- With-S (O)₂O^-At least one of group of composition,

R^x1Indicate can be with the carbon atom number 1~40 of substituent group alkyl, can be with substituent group heterocycle or hydrogen atom, The alkyl and the heterocycle can have selected from by-CO₂ ^-With-S (O)₂O^-At least one of group of composition, R^x1There are multiple When, they can be the same or different,

A is the possessed-CO of compound that formula (1) indicates₂ ^-With-S (O)₂O^-Sum, indicate 0~10 in arbitrary integer,

M^b+Indicate the metal ion of hydrogen cation or b valences, M^b+There are it is multiple when, they can be the same or different, M^b+For hydrogen When cation, the hydrogen cation and the-CO₂ ^-Or-S (O)₂O^-It is integrally formed and with-CO₂H and-S (O)₂The form of OH exists,

B indicates 1~6 integer,

When a is 0, when m 0, a are 1 or more, m indicates M^b+Number,

When a and m is 0, when n 1, a and m are not 0, n is the number for the relationship for meeting n=b × m/a.

10. manufacturing method as claimed in claim 9, wherein the isoindoline pigment is the compound that formula (1a) indicates,

The method further includes the manufacturing process for the compound that the formula (1a) in process A or process B indicates,

Process A:After the compound that formula (pt1) indicates is reacted with the compound that formula (pt2) indicates, further in the presence of acid The lower compound indicated with formula (pt3) and the compound of formula (pt4) expression are reacted, to manufacture compound that formula (1a) indicates Process;

Process B:The compound of compound, the compound that formula (pt3) indicates and formula (pt4) expression that formula (pt5) indicates is anti- It answers, the process to manufacture the compound that formula (1a) indicates,

In formula (pt1)~formula (pt5) and formula (1a), R²~R⁹Indicate meaning same as above, R⁴¹Indicate hydrogen atom or carbon The alkyl of atomicity 1~20, M¹Indicate alkali metal atom.

11. manufacturing method as claimed in claim 9, wherein the isoindoline pigment is the compound that formula (1b) indicates,

The method further includes following processes:

The synthesis procedure of formula (1a) in process A or process B;With

Shown in process C, formula (1b) indicate compound manufacturing process,

Process B:The compound of compound, the compound that formula (pt3) indicates and formula (pt4) expression that formula (pt5) indicates is anti- It answers, the process to manufacture the compound that formula (1a) indicates;

Process C:The compound that formula (1a) indicates reacts to manufacture the change of formula (1b) expression with the compound that formula (pt6) indicates The process for closing object,

In formula (pt1)~formula (pt6) and formula (1b), R¹~R⁹Indicate meaning same as above, R⁴¹Indicate hydrogen atom or carbon The alkyl of atomicity 1~20, M¹Indicate alkali metal atom, LG¹Indicate halogen atom, mesyloxy, chloromethyl sulfonyloxy, Tosyloxy or trifluoro-methanesulfonyl oxy, wherein R¹It is not hydrogen atom.

12. isoindoline pigment, in the powder x-ray diffraction intensity curve of the isoindoline pigment, the angle of diffraction (2 θ) is The summation A (10~15 °) of peak area value in 10.0 ° or more 15.0 ° or less of range and the angle of diffraction (2 θ) are 25.0 ° The ratio between summation A (25~30 °) of peak area value in above 30.0 ° or less of range is that A (25~30 °)/A (10~15 °) is 0.4 or more 5 or less.

13. isoindoline pigment as claimed in claim 12, wherein (10~15 °) of ratio A (25~30 °)/A is 0.8 or more 5 or less.

14. isoindoline pigment as claimed in claim 12, wherein with 1 or more the angle of diffraction (2 θ) be 20.0 ° with Peak with summit in upper 30.0 ° or less of range, using the intensity at the peak of maximum intensity in 1 or more the peak as 100% When, become 15% or more peak with 2 or more relative intensities.

15. isoindoline pigment as claimed in claim 12, wherein the angle of diffraction (2 θ) be 20.0 ° or more 30.0 ° or less it Between with summit peak in maximum peak intensity MS_20-30And the angle of diffraction (2 θ) be 8.0 ° less than 20.0 ° between have Maximum peak intensity MS in the peak of summit_8-20Show MS_20-30≥0.8×MS_8-20Relationship.

16. isoindoline pigment as claimed in claim 12 is indicated by formula (1),

In formula (1),

B indicates 1~6 integer,

When a is 0, when m 0, a are 1 or more, m indicates M^b+Number,

17. colored curable resin composition, it includes isoindoline pigment, resin, the polymerisms described in claim 12 Close object, polymerization initiator and solvent.

18. colour filter, it includes the isoindoline pigments described in claim 12.

19. display device, it includes the colour filters described in claim 18.