Blue-light red-phase pigment and preparation method thereof

Abstract

The present invention relates to perylene compounds having the general formula (I) wherein the symbols and indices are as defined in the description, to a method for preparing same, and to the use thereof. The compound is a perylene compound which is not reported, can be used as a pigment in the fields of coatings and plastics, and has the characteristics of excellent solvent resistance, excellent acid and alkali resistance, excellent heat resistance and easiness in dispersion in the coatings and the plastics. # imgabs0 #

Description

Technical Field

[0001] The present invention relates to the technical field of organic pigments, and in particular to a perylene compound, a preparation method thereof and application thereof. Background Art

[0002] Red to brown perylene pigments are a class of high-performance organic pigments with extremely high resistance to organic solvents and thermal stability, excellent light fastness and weather fastness. They are widely used in high-end industrial coatings, such as automotive original topcoats and repair paints, and coloring applications of high-end plastics such as vinyl polymers or fibers.

[0003] However, there are only 9 perylene pigments listed in the Dye Index, which are:

[0004] CI Pigment Red 123

[0005]

[0006] CI Pigment Red 149

[0007]

[0008] CI Pigment Red 178

[0009]

[0010] CI Pigment Red 179

[0011]

[0012] CI Pigment Red 190

[0013]

[0014] CI Pigment Red 224

[0015]

[0016] CI Pigment Violet 29

[0017]

[0018] CI Pigment Black 31

[0019]

[0020] CI Pigment Black 32

[0021]

[0022] The synthesis of CI Pigment Red 179 was reported in "Study on the Synthesis and Pigmentation Process of Pigment Red 179" (Dyes and Coloring, 2003, 40(5): CI Pigment Red 179 was obtained by reacting a certain amount of 3,4,9,10-perylenetetracarboxylic dianhydride with an excess of methylamine aqueous solution in a pressure autoclave at 140°C for 5 hours. At the same time, the document also introduced that Pigment Red 179 could be obtained by reacting 3,4,9,10-perylenetetracarboxylic acid diimide with methyl p-toluenesulfonate in an alkaline aqueous solution.

[0023] In patent CN 100341947C, BASF reported the synthesis of CI Pigment Violet 29 and CI Pigment Red 224. CI Pigment Violet 29 is obtained by dimerization of 1,8-naphthaleneimide in an inorganic base and an aprotic solvent. CI Pigment Red 224 is obtained by high temperature reaction of CI Pigment Violet 29 in aqueous inorganic acid.

[0024] In patent FR 2343012, BASF Europe reported the synthesis of CI Pigment Black 31. The pigment is obtained by reacting CI Pigment Red 224 with phenylethylamine in water at high temperature.

[0025] Among these perylene pigments, only CI Pigment Red 179 has a certain market share, while the other perylene pigments are less used. This is mainly because perylene pigments have few color systems, narrow color spectrum range and the hue of some perylene pigments is not suitable for commercial application.

[0026] For example, when CI Pigment Red 123 is used in industrial paints, its recoating resistance is poor. At high temperatures (240-300°C) in plastics, the pigment will turn blue and darken. In polyolefins, CI Pigment Red 123 will affect the distortion of injection molded products. Although CI Pigment Red 149 has a bright red color and excellent heat resistance and light fastness, the intermediate 3,5-dimethylaniline required for its synthesis has not yet been mass-produced in my country. CI Pigment Violet 29 is dark brown, close to black. Because its color is not bright, it is not widely used directly. After being diluted with titanium dioxide, the weather resistance of CI Pigment Red 178 decreases rapidly, which also limits its application.

[0027] CI Pigment Red 224 is bright red with a bluish tint, but because it is an acid anhydride and is extremely sensitive to alkali, its application range is not large. It is mainly used as an intermediate in the synthesis of other perylene pigments.

[0028] CI Pigment Red 190 is another perylene pigment with a bluish red color. After dilution, it shows too strong a blue light and is not bright. It is the least used variety among perylene pigments.

[0029] Therefore, although there are many red pigments in the perylene series, there is still a lack of commercially available blue-light red-shade pigments with good solvent resistance and acid and alkali resistance, which limits the further application of perylene pigments. Summary of the invention

[0030] To solve the above problems, the present invention provides a perylene compound and a preparation method thereof; the compound is a class of perylene compounds that have not been reported, which has a blue-red phase and can be used as a pigment. It has good solvent resistance, good acid and alkali resistance, good heat resistance, and is easy to disperse in coatings and plastics, providing a class of perylene pigments for the coating and plastic fields.

[0031] In a first aspect, the present invention provides a perylene compound having the general formula (I):

[0032]

[0033] in:

[0034] Ar groups are independently C6-C 18 Aryl, the C6-C 18 The aryl group may be optionally substituted by a substituent selected from the group consisting of halogen, C1-C 20 Alkyl, C1-C 20 Alkoxy, C1-C 20 Alkylthio, -NO2,

[0035] -CN, C3-C 10 Cycloalkyl, C4-C 20 Cycloalkylalkyl, C4-C 20 Cycloalkylalkoxy, C4-C 20 Cycloalkylalkylthio, C4-C 20 Alkylcycloalkyl or sulfonic acid group; wherein C1-C 20 Alkyl, C1-C 20 Alkoxy, C1-C 20 Alkylthio, C3-C 10 Cycloalkyl, C4-C 20 Cycloalkylalkyl, C4-C 20 Cycloalkylalkoxy, C4-C 20 Cycloalkylalkylthio or C4-C 20 The alkylcycloalkyl group may be optionally substituted with one or more groups independently selected from the group consisting of halogen, -NO2, -CN, hydroxyl, thiol, sulfonic acid, carboxyl or amino;

[0036] The R1 groups are independently halogen, C1-C 20 Alkyl, C1-C 20 Alkoxy, C1-C 20Alkylthio, -NO2, -CN, C3-C 10 Cycloalkyl, C4-C 20 Cycloalkylalkyl, C4-C 20 Cycloalkylalkoxy, C4-C 20 Cycloalkylalkylthio, C4-C 20 Alkylcycloalkyl or sulfonic acid group; wherein C1-C 20 Alkyl, C1-C 20 Alkoxy, C1-C 20 Alkylthio, C3-C 10 Cycloalkyl, C4-C 20 Cycloalkylalkyl, C4-C 20 Cycloalkylalkoxy, C4-C 20 Cycloalkylalkylthio or C4-C 20 The alkylcycloalkyl group may be optionally substituted with one or more groups independently selected from the group consisting of halogen, -NO2, -CN, hydroxyl, thiol, sulfonic acid, carboxyl or amino;

[0037] The R2 radicals are independently halogen, C1-C 20 Alkyl, C1-C 20 Alkoxy, C1-C 20 Alkylthio, -NO2, -CN, C3-C 10 Cycloalkyl, C4-C 20 Cycloalkylalkyl, C4-C 20 Cycloalkylalkoxy, C4-C 20 Cycloalkylalkylthio, C4-C 20 Alkylcycloalkyl or sulfonic acid group; wherein C1-C 20 Alkyl, C1-C 20 Alkoxy, C1-C 20 Alkylthio, C3-C 10 Cycloalkyl, C4-C 20 Cycloalkylalkyl, C4-C 20 Cycloalkylalkoxy, C4-C 20 Cycloalkylalkylthio or C4-C 20 The alkylcycloalkyl group may be optionally substituted with one or more groups independently selected from the group consisting of halogen, -NO2, -CN, hydroxyl, thiol, sulfonic acid, carboxyl or amino;

[0038] n is 0, 1, 2, 3 or 4;

[0039] m is 0, 1, 2, 3, 4, 5, 6, 7 or 8; and

[0040] q is 0 or 1. BRIEF DESCRIPTION OF THE DRAWINGS

[0041] Figure 1The X-ray diffraction pattern of the perylene-based compound according to Example 1 of the present invention is shown.

[0042] Figure 2 The X-ray diffraction pattern of the perylene-based compound according to Example 2 of the present invention is shown. DETAILED DESCRIPTION

[0043] The term "C6-C 18 "Aryl" refers to a monocyclic, bicyclic or tricyclic aromatic hydrocarbon group containing 6 to 18 carbon atoms, preferably 6 to 10 carbon atoms. 18 As examples of the aryl group, there may be mentioned phenyl, azulenyl, cycloheptatrienyl, biphenyl, dicyclopentaphenyl, fluorenyl, phenanthrenyl, terphenyl, pyrenyl, naphthacene, Preferably it is phenyl or naphthyl; and most preferably it is phenyl.

[0044] “Halogen” refers to F, Cl, Br, I or a combination thereof, preferably F, Cl or a combination thereof.

[0045] The term "C1-C 20 "Alkyl" means a saturated hydrocarbon group having 1 to 20, preferably 1 to 12, more preferably 1 to 8, particularly preferably 1 to 6, and especially preferably 1 to 4 carbon atoms, which may be branched or unbranched. Examples include methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl and isomers thereof, in particular methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, isohexyl and the like. C1-C4 alkyl may be methyl, ethyl, propyl, butyl and isomers thereof, in particular methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl and the like.

[0046] The term "C1-C 20 "Alkoxy" refers to a C1-C 20 The open-chain C1-C 20 Any carbon atom of an alkane is bonded with an oxygen atom as a linker. 20 Alkyl, preferably C1-C 12Alkoxy, more preferably C1-C8 alkoxy, particularly preferably C1-C6 alkoxy. Examples include methoxy, ethoxy, propoxy, butoxy, pentoxy, hexoxy and isomers thereof, in particular methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, tert-butoxy, n-pentoxy, isopentoxy, tert-pentoxy, n-hexoxy, isohexoxy, n-heptoxy, isoheptoxy, n-octoxy or isooctoxy. C1-C4 alkoxy can be methoxy, ethoxy, propoxy, butoxy and isomers thereof, in particular methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, tert-butoxy, etc.

[0047] The term "C1-C 20 "Alkylthio" refers to a C1-C 20 The open-chain C1-C 20 Any carbon atom of an alkane is bonded with a sulfur atom as a linking group. 20 Alkyl, preferably C1-C 12 Alkylthio, more preferably C1-C8 alkylthio, particularly preferably C1-C6 alkylthio. Examples include methylthio, ethylthio, propylthio, butylthio, pentylthio, hexylthio and isomers thereof, in particular methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, sec-butylthio, isobutylthio, tert-butylthio, n-pentylthio, isopentylthio, tert-pentylthio, n-hexylthio, isohexylthio, n-heptylthio, isoheptylthio, n-octylthio or isooctylthio. C1-C4 alkylthio can be methylthio, ethylthio, propylthio, butylthio and isomers thereof, in particular methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, sec-butylthio, isobutylthio, tert-butylthio etc.

[0048] The term "C3-C 10 "Cycloalkyl" refers to a saturated alicyclic monocyclic group having 3 to 10, preferably 3 to 8, more preferably 5 to 6 ring carbon atoms, for example cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl and cyclodecyl.

[0049] The term "C4-C 20 "Cycloalkylalkyl" means an alkyl group substituted by a cycloalkyl group and containing a total of 4 to 20 carbon atoms, preferably 4 to 12, more preferably 4 to 10, and most preferably 4 to 8 carbon atoms, wherein the definitions of alkyl and cycloalkyl apply as herein applied. Examples include cyclopropylmethyl, cyclopropylethyl, cyclopropylpropyl, cyclopropylbutyl, cyclobutylmethyl, cyclobutylethyl, cyclobutylpropyl, cyclobutylbutyl, cyclopentylmethyl, cyclopentylethyl, cyclopentylpropyl, cyclopentylbutyl, cyclohexylmethyl, cyclohexylethyl, cyclohexylpropyl, cyclohexylbutyl, and the like.

[0050] The term "C4-C20 "Cycloalkylalkoxy" refers to an alkoxy group substituted by a cycloalkyl group and containing a total of 4 to 20, preferably 4 to 12, more preferably 4 to 10 carbon atoms, wherein the definitions of cycloalkyl and alkoxy apply as herein. Examples include cyclopropylmethoxy, cyclopropylethoxy, cyclopropylpropoxy, cyclopropylbutoxy, cyclobutylmethoxy, cyclobutylethoxy, cyclobutylpropoxy, cyclobutylbutoxy, cyclopentylmethoxy, cyclopentylethoxy, cyclopentylpropoxy, cyclopentylbutoxy, cyclohexylmethoxy, cyclohexylethoxy, cyclohexylpropoxy, cyclohexylbutoxy and the like.

[0051] The term "C4-C 20 "Cycloalkylalkylthio" refers to an alkylthio group substituted by a cycloalkyl group and containing a total of 4 to 20, preferably 4 to 12, more preferably 4 to 10 carbon atoms, wherein the definitions of cycloalkyl and alkylthio apply as herein applied. Examples include cyclopropylmethylthio, cyclopropylethylthio, cyclopropylpropylthio, cyclopropylbutylthio, cyclobutylmethylthio, cyclobutylethylthio, cyclobutylpropylthio, cyclobutylbutylthio, cyclopentylmethylthio, cyclopentylethylthio, cyclopentylpropylthio, cyclopentylbutylthio, cyclohexylmethylthio, cyclohexylethylthio, cyclohexylpropylthio, cyclohexylbutylthio and the like.

[0052] The term "C4-C 20 "Alkylcycloalkyl" means a cycloalkyl group substituted by an alkyl group and containing a total of 4 to 20 carbon atoms, preferably 4 to 12, more preferably 4 to 10, and most preferably 4 to 8 carbon atoms. The definitions of alkyl and cycloalkyl apply as herein. Examples include methylcyclopropyl, ethylcyclopropyl, propylcyclopropyl, butylcyclopropyl, methylcyclobutyl, ethylcyclobutyl, propylcyclobutyl, butylcyclobutyl, methylcyclopentyl, ethylcyclopentyl, propylcyclopentyl, butylcyclopentyl, methylcyclohexyl, ethylcyclohexyl, propylcyclohexyl, butylcyclohexyl and the like.

[0053] Herein, "R1" refers to a substituent on the perylene ring of the perylene compound of formula (I), which may be located at all possible substituent positions on the perylene ring.

[0054] Herein, "R2" refers to a substituent on the benzene ring of the perylene compound of formula (I), which may be on all possible substituent positions on the benzene ring.

[0055] In a preferred embodiment of the present invention, the Ar groups are independently C6-C 18 Aryl, the C6-C 18 The aryl group may be optionally substituted by a substituent selected from the group consisting of halogen, C1-C 20 Alkyl, C1-C 20 Alkoxy, C1-C 20 Alkylthio, C3-C 10Cycloalkyl, C4-C 20 Cycloalkylalkyl, C4-C 20 Cycloalkylalkoxy, C4-C 20 Cycloalkylalkylthio, C4-C 20 Alkylcycloalkyl or sulfonic acid group; wherein C1-C 20 Alkyl, C1-C 20 Alkoxy, C1-C 20 Alkylthio, C3-C 10 Cycloalkyl, C4-C 20 Cycloalkylalkyl, C4-C 20 Cycloalkylalkoxy, C4-C 20 Cycloalkylalkylthio or C4-C 20 The alkylcycloalkyl group may be optionally substituted with one or more groups independently selected from the group consisting of halogen, -NO2, -CN, hydroxyl, thiol, sulfonic acid, carboxyl or amino;

[0056] More preferably, the Ar groups are independently C6-C 18 Aryl, the C6-C 18 The aryl group may be optionally substituted by a substituent selected from the group consisting of halogen, C1-C 20 Alkyl, C1-C 20 Alkoxy, C1-C 20 Alkylthio, C3-C 10 Cycloalkyl or sulfonic acid group; wherein C1-C 20 Alkyl, C1-C 20 Alkoxy, C1-C 20 Alkylthio or C3-C 10 Cycloalkyl may be optionally substituted with one or more groups independently selected from halogen;

[0057] More preferably, the Ar groups are independently phenyl, which may be optionally substituted by a substituent selected from the group consisting of halogen, C1-C 20 Alkyl, C1-C 20 Alkoxy, C1-C 20 Alkylthio, C3-C 10 Cycloalkyl, C4-C 20 Cycloalkylalkyl, C4-C 20 Cycloalkylalkoxy, C4-C 20 Cycloalkylalkylthio, C4-C 20 Alkylcycloalkyl or sulfonic acid group; wherein C1-C 20 Alkyl, C1-C 20 Alkoxy, C1-C 20 Alkylthio, C3-C 10 Cycloalkyl, C4-C 20 Cycloalkylalkyl, C4-C 20Cycloalkylalkoxy, C4-C 20 Cycloalkylalkylthio or C4-C 20 The alkylcycloalkyl group may be optionally substituted with one or more groups independently selected from the group consisting of halogen, -NO2, -CN, hydroxyl, thiol, sulfonic acid, carboxyl or amino;

[0058] More preferably, the Ar groups are independently phenyl, which may be optionally substituted by a substituent selected from the group consisting of halogen, C1-C 20 Alkyl, C1-C 20 Alkoxy, C1-C 20 Alkylthio, C3-C 10 Cycloalkyl or sulfonic acid group; wherein C1-C 20 Alkyl, C1-C 20 Alkoxy, C1-C 20 Alkylthio or C3-C 10 The cycloalkyl group may be optionally substituted with one or more groups independently selected from halogen.

[0059] In a preferred embodiment of the present invention, the R1 radicals are independently halogen, C1-C 20 Alkyl, C1-C 20 Alkoxy, -NO2, -CN, C3-C 10 Cycloalkyl or sulfonic acid group; wherein C1-C 20 Alkyl, C1-C 20 Alkoxy or C3-C 10 The cycloalkyl group may be optionally substituted with one or more groups independently selected from the group consisting of halogen, -NO2 or -CN;

[0060] Preferably, the R1 groups are independently halogen, C1-C 20 Alkyl, C1-C 20 Alkoxy or sulfonic acid; wherein C1-C 20 Alkyl or C1-C 20 The alkoxy group may be optionally substituted with one or more groups independently selected from the group consisting of halogen, -NO2 or -CN;

[0061] Most preferably, the R1 groups are independently halogen, C1-C 20 Alkyl or C1-C 20 Alkoxy; wherein C1-C 20 Alkyl or C1-C 20 The alkoxy group may be optionally substituted with one or more groups independently selected from halogen.

[0062] In a preferred embodiment of the present invention, the R2 radicals are independently halogen, C1-C20 Alkyl, C1-C 20 Alkoxy, -NO2, -CN, C3-C 10 Cycloalkyl or sulfonic acid group; wherein C1-C 20 Alkyl, C1-C 20 Alkoxy or C3-C 10 The cycloalkyl group may be optionally substituted with one or more groups independently selected from the group consisting of halogen, -NO2 or -CN;

[0063] Preferably, the R2 groups are independently halogen, C1-C 20 Alkyl, C1-C 20 Alkoxy, C3-C 10 Cycloalkyl or sulfonic acid group; wherein C1-C 20 Alkyl, C1-C 20 Alkoxy or C3-C 10 The cycloalkyl group may be optionally substituted with one or more groups independently selected from the group consisting of halogen, -NO2 or -CN;

[0064] Most preferably, the R2 groups are independently halogen, C1-C 20 Alkyl, C1-C 20 Alkoxy or sulfonic acid; wherein C1-C 20 Alkyl or C1-C 20 The alkoxy group may be optionally substituted with one or more groups independently selected from halogen.

[0065] In a preferred embodiment of the present invention, n is an integer of 0-4, preferably 0-2, more preferably 0 or 1.

[0066] In a preferred embodiment of the present invention, m is an integer of 0-6, preferably 0-2, more preferably 0 or 1.

[0067] In a preferred embodiment of the present invention, q is zero.

[0068] In a preferred embodiment of the present invention, q is 1.

[0069] In a preferred embodiment of the present invention,

[0070] Ar groups are independently C6-C 18 Aryl, the C6-C 18 The aryl group may be optionally substituted by a substituent selected from the group consisting of halogen, C1-C 20 Alkyl, C1-C 20 Alkoxy, C1-C 20 Alkylthio, C3-C 10 Cycloalkyl, C4-C 20Cycloalkylalkyl, C4-C 20 Cycloalkylalkoxy, C4-C 20 Cycloalkylalkylthio, C4-C 20 Alkylcycloalkyl or sulfonic acid group; wherein C1-C 20 Alkyl, C1-C 20 Alkoxy, C1-C 20 Alkylthio, C3-C 10 Cycloalkyl, C4-C 20 Cycloalkylalkyl, C4-C 20 Cycloalkylalkoxy, C4-C 20 Cycloalkylalkylthio or C4-C 20 The alkylcycloalkyl group may be optionally substituted with one or more groups independently selected from the group consisting of halogen, -NO2, -CN, hydroxyl, thiol, sulfonic acid, carboxyl or amino;

[0071] The R1 groups are independently halogen, C1-C 20 Alkyl, C1-C 20 Alkoxy, -NO2,

[0072] -CN, C3-C 10 Cycloalkyl or sulfonic acid group; wherein C1-C 20 Alkyl, C1-C 20 Alkoxy or C3-C 10 The cycloalkyl group may be optionally substituted by one or more groups independently selected from the group consisting of halogen,

[0073] -NO2 or -CN;

[0074] The R2 radicals are independently halogen, C1-C 20 Alkyl, C1-C 20 Alkoxy, -NO2,

[0075] -CN, C3-C 10 Cycloalkyl or sulfonic acid group; wherein C1-C 20 Alkyl, C1-C 20 Alkoxy or C3-C 10 The cycloalkyl group may be optionally substituted by one or more groups independently selected from the group consisting of halogen,

[0076] -NO2 or -CN;

[0077] n is an integer of 0-4, preferably 0-2, more preferably 0 or 1;

[0078] m is an integer of 0-6, preferably 0-2, and more preferably 0 or 1.

[0079] In a preferred embodiment of the present invention,

[0080] Ar groups are independently C6-C 18 Aryl, the C6-C 18 The aryl group may be optionally substituted by a substituent selected from the group consisting of halogen, C1-C 20 Alkyl, C1-C 20 Alkoxy, C1-C 20 Alkylthio, C3-C 10 Cycloalkyl or sulfonic acid group; wherein C1-C 20 Alkyl, C1-C 20 Alkoxy, C1-C 20 Alkylthio or C3-C 10 Cycloalkyl may be optionally substituted with one or more groups independently selected from halogen;

[0081] The R1 groups are independently halogen, C1-C 20 Alkyl, C1-C 20 Alkoxy or sulfonic acid; wherein C1-C 20 Alkyl or C1-C 20 The alkoxy group may be optionally substituted with one or more groups independently selected from the group consisting of halogen, -NO2 or -CN;

[0082] The R2 radicals are independently halogen, C1-C 20 Alkyl, C1-C 20 Alkoxy, C3-C 10 Cycloalkyl or sulfonic acid group; wherein C1-C 20 Alkyl, C1-C 20 Alkoxy or C3-C 10 The cycloalkyl group may be optionally substituted by one or more groups independently selected from the following groups: halogen, -NO2 or -CN; n is an integer of 0-4, preferably 0-2, more preferably 0 or 1;

[0083] m is an integer of 0-6, preferably 0-2, and more preferably 0 or 1.

[0084] In a preferred embodiment of the present invention,

[0085] The Ar groups are independently phenyl groups, which may be optionally substituted with substituents selected from the following group:

[0086] Halogen, C1-C 20 Alkyl, C1-C 20 Alkoxy, C1-C 20 Alkylthio, C3-C 10 Cycloalkyl, C4-C 20 Cycloalkylalkyl, C4-C 20Cycloalkylalkoxy, C4-C 20 Cycloalkylalkylthio, C4-C 20 Alkylcycloalkyl or sulfonic acid group; wherein C1-C 20 Alkyl, C1-C 20 Alkoxy, C1-C 20 Alkylthio, C3-C 10 Cycloalkyl, C4-C 20 Cycloalkylalkyl, C4-C 20 Cycloalkylalkoxy, C4-C 20 Cycloalkylalkylthio or C4-C 20 The alkylcycloalkyl group may be optionally substituted with one or more groups independently selected from the group consisting of halogen, -NO2, -CN, hydroxyl, thiol, sulfonic acid, carboxyl or amino;

[0087] The R1 groups are independently halogen, C1-C 20 Alkyl, C1-C 20 Alkoxy or sulfonic acid; wherein C1-C 20 Alkyl or C1-C 20 The alkoxy group may be optionally substituted with one or more groups independently selected from halogen;

[0088] The R2 radicals are independently halogen, C1-C 20 Alkyl, C1-C 20 Alkoxy or sulfonic acid; wherein C1-C 20 Alkyl or C1-C 20 The alkoxy group may be optionally substituted with one or more groups independently selected from halogen;

[0089] n is an integer of 0-4, preferably 0-2, more preferably 0 or 1;

[0090] m is an integer of 0-6, preferably 0-2, and more preferably 0 or 1.

[0091] In a preferred embodiment of the present invention,

[0092] The Ar groups are independently phenyl groups, which may be optionally substituted with substituents selected from the following group:

[0093] Halogen, C1-C 20 Alkyl, C1-C 20 Alkoxy, C1-C 20 Alkylthio, C3-C 10 Cycloalkyl or sulfonic acid group; wherein C1-C 20 Alkyl, C1-C 20 Alkoxy, C1-C 20 Alkylthio or C3-C 10Cycloalkyl may be optionally substituted with one or more groups independently selected from halogen;

[0094] The R1 groups are independently halogen, C1-C 20 Alkyl, C1-C 20 Alkoxy or sulfonic acid; wherein C1-C 20 Alkyl or C1-C 20 The alkoxy group may be optionally substituted with one or more groups independently selected from halogen;

[0095] The R2 radicals are independently halogen, C1-C 20 Alkyl, C1-C 20 Alkoxy or sulfonic acid; wherein C1-C 20 Alkyl or C1-C 20 The alkoxy group may be optionally substituted with one or more groups independently selected from halogen;

[0096] n is an integer of 0-4, preferably 0-2, more preferably 0 or 1;

[0097] m is an integer of 0-6, preferably 0-2, and more preferably 0 or 1.

[0098] In a preferred embodiment of the present invention, the Ar groups are independently of one another phenyl, n is 0, and m is 0.

[0099] In a preferred embodiment of the present invention, the Ar groups are independently phenyl, and the R2 groups are independently halogen or C1-C 20 Alkyl, preferably C1-C5 alkyl, such as methyl, ethyl, propyl or butyl, n is 1, and m is 0.

[0100] In a preferred embodiment of the present invention, the Ar groups are independently phenyl, the R2 groups are independently chlorine or methyl, n is 1, and m is 0.

[0101] In a preferred embodiment of the present invention, the perylene compound has the formula (II), (III), (IV) or (V):

[0102]

[0103]

[0104] In a second aspect, the present invention provides a method for preparing a perylene compound of general formula (I), comprising making a compound of formula (VI):

[0105]

[0106] Reaction with a compound of formula (VII):

[0107]

[0108] wherein Ar, R1, R2, m, n and q are as defined above.

[0109] In the reaction, the compound of formula (VII) can be used in the form of its salt, such as hydrochloride, sulfate, nitrate and the like.

[0110] The molar ratio of the compound of formula (VI) to the compound of formula (VII) may be 1:2 to 1:10, preferably 1:2.5 to 1:5, and more preferably 1:3 to 1:5.

[0111] The reaction is carried out in the presence of a catalyst. Suitable catalysts may be soluble zinc salts, such as zinc acetate, zinc chloride, zinc sulfate, zinc benzoate, zinc stearate, etc., which may be in the form of hydrates or non-hydrates. The amount of the catalyst may be 0.5-15% by weight, preferably 5-10% by weight, based on the total weight of the reactants used.

[0112] The reaction can be carried out in a solvent. Suitable solvents can be polar solvents, particularly preferably high boiling point polar solvents. The high boiling point polar solvent can have a boiling point of 100-250° C., preferably 120-220° C. Suitable solvents are, for example, water, ethylene glycol, N,N-dimethylformamide, N,N-dimethylacetamide, imidazole, pyridine, quinoline, N-methylpyrrolidone, N-ethylpyrrolidone, dimethyl sulfoxide, γ-butyrolactone, glycerol or a mixture of two or more thereof. The amount of solvent used can be 40-95% by weight of the total amount of the reaction system, preferably 60-90% by weight, and more preferably 75-85% by weight.

[0113] A pH adjuster may be added to the reaction system to adjust the pH of the reaction system to pH 6 to 9. Suitable pH adjusters are, for example, soluble organic or inorganic bases, such as triethylamine, diethylamine, pyridine, quinoline, potassium hydroxide, sodium hydroxide, potassium carbonate, sodium carbonate or cesium carbonate.

[0114] The reaction may be carried out at a temperature of 100-250°C, preferably 120-220°C.

[0115] The reaction can be carried out under an inert atmosphere. Suitable inert atmospheres include nitrogen or other inert gases such as helium, preferably nitrogen.

[0116] The reaction time may be 1-24 hours, preferably 2-12 hours, more preferably 4-8 hours.

[0117] After the reaction, the reaction mixture can be filtered, and the filter cake can be washed one or more times with an alcohol (e.g., methanol, ethanol, n-propanol or n-butanol, etc., preferably methanol), and then washed one or more times with an alkali (e.g., potassium hydroxide, sodium hydroxide, sodium carbonate or potassium carbonate) solution, and finally washed one or more times with water. Then, the obtained reaction product can be dried, for example, in a blast oven at 50-120° C., preferably 60-100° C., and the drying time can be 1-10 hours, preferably 2-8 hours.

[0118] The perylene compounds of the present invention are a class of perylene compounds that have not been reported before, can be used as pigments, have good solvent resistance, good acid and alkali resistance, good heat resistance, and are easy to disperse in coatings and plastics, and provide a class of perylene pigments for the coating and plastic fields.

[0119] Therefore, the present invention provides use of the perylene compound as a pigment.

[0120] The perylene compounds of the present invention can be used as pigments in coatings and plastics.

[0121] Suitable coatings may be water-based coatings, solvent-based coatings or powder coatings, etc.

[0122] Suitable plastics may be polyolefins such as polyethylene, polypropylene, polybutene, polyisobutylene and poly-4-methyl-1-pentene, polyolefin copolymers, cycloolefin copolymers, polytetrafluoroethylene (PTFE), ethylene / tetrafluoroethylene copolymers, polyvinylidene fluoride, polyvinyl chloride, polyvinylidene chloride, polyvinyl alcohol, polyvinyl esters such as polyvinyl acetate, vinyl ester copolymers such as ethylene / vinyl acetate copolymers, polyvinyl acetals such as polyvinyl acetal and polyvinyl butyral, polyvinyl ketals, polyamides such as nylon 6, nylon 12, nylon 6,6, polyimides, polycarbonates, polycarbonate copolymers and physical blends of polycarbonates with acrylic acid-butadiene-styrene copolymers, acrylonitrile-styrene-acrylate copolymers, polymethyl methacrylate, polybutyl acrylate, polybutyl methacrylate, polybutylene terephthalate and polyethylene terephthalate, Polyesters such as polyethylene terephthalate, polybutylene terephthalate and polyethylene naphthalate, copolymers, transesterification products and physical mixtures (blends) of the above polyalkylene terephthalates, poly(meth)acrylates, polyacrylamides, polyacrylonitrile, poly(meth)acrylate / polyvinylidene fluoride blends, polyurethanes, polystyrenes, styrene copolymers such as styrene / butadiene copolymers, styrene / acrylonitrile copolymers (SAN), styrene / ethyl methacrylate copolymers, styrene / butadiene / ethyl acrylate copolymers, styrene / acrylonitrile / methacrylate copolymers, acrylonitrile / butadiene / styrene copolymers (ABS) and methacrylate / butadiene / styrene copolymers, polyethers such as polyphenylene ethers, polyether ketones, polysulfones, polyether sulfones, polyoxymethylenes, polysiloxanes, ionomers, thermoplastic and thermosetting polyurethanes and mixtures thereof.

[0123] The specific embodiments described below will help those skilled in the art to understand the present invention, but are not intended to limit the scope of the present invention.

[0124] Embodiment 1. A perylene compound having the general formula (I):

[0125]

[0126] in:

[0127] Ar groups are independently C6-C 18 Aryl, the C6-C 18 The aryl group may be optionally substituted by a substituent selected from the group consisting of halogen, C1-C 20 Alkyl, C1-C 20 Alkoxy, C1-C 20 Alkylthio, -NO2,

[0128] -CN, C3-C 10 Cycloalkyl, C4-C 20Cycloalkylalkyl, C4-C 20 Cycloalkylalkoxy, C4-C 20 Cycloalkylalkylthio, C4-C 20 Alkylcycloalkyl or sulfonic acid group; wherein C1-C 20 Alkyl, C1-C 20 Alkoxy, C1-C 20 Alkylthio, C3-C 10 Cycloalkyl, C4-C 20 Cycloalkylalkyl, C4-C 20 Cycloalkylalkoxy, C4-C 20 Cycloalkylalkylthio or C4-C 20 The alkylcycloalkyl group may be optionally substituted with one or more groups independently selected from the group consisting of halogen, -NO2, -CN, hydroxyl, thiol, sulfonic acid, carboxyl or amino;

[0129] The R1 groups are independently halogen, C1-C 20 Alkyl, C1-C 20 Alkoxy, C1-C 20 Alkylthio, -NO2, -CN, C3-C 10 Cycloalkyl, C4-C 20 Cycloalkylalkyl, C4-C 20 Cycloalkylalkoxy, C4-C 20 Cycloalkylalkylthio, C4-C 20 Alkylcycloalkyl or sulfonic acid group; wherein C1-C 20 Alkyl, C1-C 20 Alkoxy, C1-C 20 Alkylthio, C3-C 10 Cycloalkyl, C4-C 20 Cycloalkylalkyl, C4-C 20 Cycloalkylalkoxy, C4-C 20 Cycloalkylalkylthio or C4-C 20 The alkylcycloalkyl group may be optionally substituted with one or more groups independently selected from the group consisting of halogen, -NO2, -CN, hydroxyl, thiol, sulfonic acid, carboxyl or amino;

[0130] The R2 radicals are independently halogen, C1-C 20 Alkyl, C1-C 20 Alkoxy, C1-C 20 Alkylthio, -NO2, -CN, C3-C 10 Cycloalkyl, C4-C 20 Cycloalkylalkyl, C4-C 20 Cycloalkylalkoxy, C4-C 20 Cycloalkylalkylthio, C4-C 20Alkylcycloalkyl or sulfonic acid group; wherein C1-C 20 Alkyl, C1-C 20 Alkoxy, C1-C 20 Alkylthio, C3-C 10 Cycloalkyl, C4-C 20 Cycloalkylalkyl, C4-C 20 Cycloalkylalkoxy, C4-C 20 Cycloalkylalkylthio or C4-C 20 The alkylcycloalkyl group may be optionally substituted with one or more groups independently selected from the group consisting of halogen, -NO2, -CN, hydroxyl, thiol, sulfonic acid, carboxyl or amino;

[0131] n is 0, 1, 2, 3 or 4;

[0132] m is 0, 1, 2, 3, 4, 5, 6, 7 or 8; and

[0133] q is 0 or 1.

[0134] Embodiment 2. The compound according to embodiment 1, wherein the Ar groups are independently phenyl, and the phenyl group may be optionally substituted by a substituent selected from the group consisting of halogen, C1-C 20 Alkyl, C1-C 20 Alkoxy, C1-C 20 Alkylthio, C3-C 10 Cycloalkyl or sulfonic acid group; wherein C1-C 20 Alkyl, C1-C 20 Alkoxy, C1-C 20 Alkylthio or C3-C 10 The cycloalkyl group may be optionally substituted with one or more groups independently selected from halogen.

[0135] Embodiment 3. A compound according to embodiment 2, wherein the Ar groups are independently phenyl, optionally substituted with one or more groups selected from methyl, ethyl, n-propyl, isopropyl, fluorine, chlorine, bromine, iodine, sulfonic acid and methoxy.

[0136] Embodiment 4. The compound according to embodiment 1, wherein the R1 group is independently halogen, C1-C 20 Alkyl, C1-C 20 Alkoxy or sulfonic acid; wherein C1-C 20 Alkyl or C1-C 20 The alkoxy group may be optionally substituted with one or more groups independently selected from halogen;

[0137] Preferably, the R1 radical is, independently of one another, fluorine, chlorine, bromine, iodine or sulfonic acid at each occurrence.

[0138] Embodiment 5. The compound according to embodiment 1, wherein the R2 group is independently halogen, C1-C 20 Alkyl, C1-C 20 Alkoxy or sulfonic acid; wherein C1-C 20 Alkyl or C1-C 20 The alkoxy group may be optionally substituted with one or more groups independently selected from the group consisting of halogen, -NO2 or -CN;

[0139] Preferably, the R2 radicals are, independently of one another, methyl, ethyl, n-propyl, isopropyl, fluorine, chlorine, bromine, iodine, sulfonic acid or methoxy at each occurrence,

[0140] More preferably, the R2 radicals are independently at each occurrence methyl or chlorine,

[0141] The position of the R2 group is located at the ortho or meta position of the bridging oxygen atom.

[0142] Embodiment 6. A compound according to any one of embodiments 1-5, wherein n is 0 and m is 0.

[0143] Embodiment 7. A compound according to any one of embodiments 1-5, wherein n is 1 and m is 0.

[0144] Embodiment 8. A compound according to any one of embodiments 1-5, wherein: the Ar groups are independently phenyl,

[0145] n is 0, and

[0146] m is 0.

[0147] Embodiment 9. A compound according to any one of embodiments 1-5, wherein: the Ar groups are independently phenyl,

[0148] The R2 groups are independently halogen or C1-C5 alkyl,

[0149] n is 1,

[0150] m is 0, and

[0151] q is 0.

[0152] Embodiment 10. The compound according to embodiment 9, wherein:

[0153] The Ar groups are independently phenyl,

[0154] The R2 radicals are independently chlorine or methyl,

[0155] n is 1,

[0156] m is 0, and

[0157] q is 0.

[0158] Embodiment 11. A compound according to any one of Embodiments 1-5, wherein the perylene compound has formula (II), (III), (IV) or (V):

[0159]

[0160]

[0161] Embodiment 12. A method for preparing a perylene compound according to any one of Embodiments 1 to 11, comprising making a compound of formula (VI):

[0162]

[0163] Reaction with a compound of formula (VII):

[0164]

[0165] wherein Ar, R1, R2, m, n and q are as defined in any one of embodiments 1-11.

[0166] Embodiment 13. The method according to embodiment 12, wherein the molar ratio of the compound of formula (VI) to the compound of formula (VII) is 1:2 to 1:10, preferably 1:2.5 to 1:5, and more preferably 1:3 to 1:5.

[0167] Embodiment 14. The method according to embodiment 12 or 13, wherein the reaction is carried out in the presence of a catalyst selected from soluble zinc salts, such as zinc acetate, zinc chloride, zinc sulfate, zinc benzoate, zinc stearate.

[0168] Embodiment 15. Use of the perylene compound according to any one of Embodiments 1 to 11 as a pigment.

[0169] The present invention will be further described below in conjunction with specific embodiments, but they should not be construed as limiting the scope of protection of the present invention.

[0170] Elemental analysis test

[0171] Using Elementar's Vario Micro Cube fully automatic elemental analyzer, elemental analysis tests were performed on the compounds in Examples 1-4 in accordance with JY / T 0580-2020 General Rules for Analysis Methods of Elemental Analyzers.

[0172] Example 1

[0173] 3,4,9,10-perylenetetracarboxylic acid dianhydride (50 g, 0.13 mol), 4-phenoxyaniline (61.1 g, 0.33 mol), zinc acetate dihydrate (1 g, 0.005 mol) were added to 500 g of imidazole. The mixture was stirred at 300 rpm for 30 min at room temperature to make the materials uniformly dispersed. Then, nitrogen was replaced three times to keep the reaction system in a nitrogen atmosphere.

[0174] The reaction system was gradually heated to 195°C, kept warm for 6 hours, then cooled to room temperature, and the reaction solution was poured into 1000g of water. The filter cake was filtered and washed twice with 200g of methanol, twice with 200g of 1% potassium hydroxide solution, and once with 100g of water.

[0175] The filter cake was placed in a forced air oven at 80°C and dried for 5 h to obtain a red pigment with a yield of 95%.

[0176] Element analysis test values: Carbon content: 79.11%, Hydrogen content: 3.50%, Nitrogen content: 3.72%

[0177] Theoretical values ​​of elemental analysis of this compound: carbon content 79.33%, hydrogen content: 3.61%, nitrogen content: 3.85%

[0178] The XRD spectrum of the obtained pigment was measured using a BURKERD8 X-ray diffractometer, and the results are shown in Figure 1 middle.

[0179] Example 2

[0180] 3,4,9,10-perylenetetracarboxylic acid dianhydride (50 g, 0.13 mol), 4-benzyloxyaniline (77.7 g, 0.39 mol), zinc acetate dihydrate (1 g, 0.005 mol) were added to 500 g of quinoline. The mixture was stirred at 300 rpm for 30 min at room temperature to uniformly disperse the materials in quinoline. The reaction system was then replaced with nitrogen three times to place it in a nitrogen atmosphere.

[0181] The reaction system was gradually heated to 200°C, kept at this temperature for 4 hours, then cooled to room temperature, and the reaction solution was poured into 1000g of water. The filter cake was filtered and washed twice with 200g of methanol, twice with 200g of 1% potassium hydroxide solution, and once with 100g of water.

[0182] The filter cake was placed in a forced air oven at 80°C and dried for 5 h to obtain a red pigment with a yield of 97%.

[0183] Element analysis test values: Carbon content: 79.24%, Hydrogen content: 3.92%, Nitrogen content: 3.67%

[0184] Theoretical values ​​of elemental analysis of this compound: carbon content 79.56%, hydrogen content: 4.01%, nitrogen content: 3.71%

[0185] The XRD spectrum of the obtained pigment was measured using a BURKERD8 X-ray diffractometer, and the results are shown in Figure 2 middle.

[0186] Example 3

[0187] 3,4,9,10-perylenetetracarboxylic acid dianhydride (50 g, 0.13 mol), 3-chloro-4-phenoxyaniline (85.7 g, 0.39 mol), zinc acetate dihydrate (1 g, 0.005 mol) were added to 500 g of N-methylpyrrolidone. The mixture was stirred at 300 rpm for 30 min at room temperature to uniformly disperse the materials in N-methylpyrrolidone. The reaction system was then replaced with nitrogen three times to place it in a nitrogen atmosphere.

[0188] The reaction system was gradually heated to 200°C, kept at this temperature for 6 hours, then cooled to room temperature, and the reaction solution was poured into 1000g of water. The filter cake was filtered and washed twice with 200g of methanol, twice with 200g of 1% potassium hydroxide solution, and once with 100g of water.

[0189] The filter cake was placed in a forced air oven at 80°C and dried for 5 h to obtain a red pigment with a yield of 95%.

[0190] Element analysis test values: Carbon content: 72.12%, Hydrogen content: 3.06%, Nitrogen content: 3.65%

[0191] Theoretical values ​​of elemental analysis of this compound: carbon content 72.46%, hydrogen content: 3.04%, nitrogen content: 3.52%

[0192] Example 4

[0193] 3,4,9,10-perylenetetracarboxylic acid dianhydride (50 g, 0.13 mol), 2-methyl-4-phenoxyaniline (69.7 g, 0.35 mol), zinc acetate dihydrate (1 g, 0.005 mol) were added to 500 g N,N-dimethylformamide. The mixture was stirred at 300 rpm for 30 min at room temperature to uniformly disperse the materials in N,N-dimethylformamide. The reaction system was then replaced with nitrogen three times to place it in a nitrogen atmosphere.

[0194] The reaction system was gradually heated to 150°C until the reaction system was close to reflux. After 6 hours of heat preservation, the reaction system was cooled to room temperature and the reaction solution was poured into 1000g of water. The filter cake was filtered and washed twice with 200g of methanol, twice with 200g of 1% potassium hydroxide solution, and finally once with 100g of water.

[0195] The filter cake was placed in a forced air oven at 80°C and dried for 5 h to obtain a red pigment with a yield of 97%.

[0196] Element analysis test values: Carbon content: 79.17%, Hydrogen content: 4.43%, Nitrogen content: 3.55%

[0197] Theoretical values ​​of elemental analysis of this compound: carbon content 79.56%, hydrogen content: 4.01%, nitrogen content: 3.71%

[0198] Performance measurement

[0199] Determination of hue value

[0200] The hue values ​​of the pigment of Example 1 in different systems were measured using a spectrophotometer CM-26d obtained from Japan Metalon Corporation. The results are shown in Table 1.

[0201] Table 1. Hue values ​​of the pigments of Example 1 in different systems

[0202]

[0203] * Alkyd resin system (Xinhua Resin 3150) coating system, where the full color test method is to add 5% of the total weight of the coating formula pigment, and the wet film thickness of the scraped coating is 100 microns; AM diluted color test system is the same as AM full color, except that 10% TiO2 (Kronos 2310) based on the weight of the pigment is added;

[0204] **Polyvinyl chloride resin system (Formosa Plastics (Ningbo) Co., Ltd. S-65), the pigment addition in the PVC full color test is 0.2%, and the PVC diluted color system is the same as the PVC full color, except that 10% TiO2 (Kronos 2310) based on the weight of the pigment is added.

[0205] As can be seen from Table 1, the perylene pigment of the present invention is a red pigment which is pink in diluted color.

[0206] Solvent resistance

[0207] Take 0.8g of pigment and wrap it with filter paper, soak it in the corresponding solvent at room temperature for 24 hours, then take out the pigment, compare the color of the solvent with the color of the color card, and visually determine the solvent resistance grade, where grade 5 is the best and grade 1 is the worst.

[0208] The results of the solvent resistance of the pigments are shown in Table 2.

[0209] Table 2

[0210] Solvent resistance test Ethanol 2-Butanone Butyl acetate Xylene Example 1 5 4 5 4

[0211] As can be seen from Table 2, the pigment of the present invention has excellent solvent resistance.

[0212] Acid and alkali resistance

[0213] The acid and alkali resistance test method is the same as the solvent resistance test method, except that the solvent in the solvent resistance test method is replaced with a 2% hydrochloric acid aqueous solution or a 2% NaOH aqueous solution.

[0214] The acid and alkali resistance of the pigments is shown in Table 3, where grade 5 is the best and grade 1 is the worst.

[0215] Table 3

[0216] Acid and alkali resistance test 2% HCl 2% NaOH Example 1 5 4

[0217] As can be seen from Table 3, the pigment of the present invention has excellent acid and alkali resistance.

[0218] Heat resistance

[0219] The test pigment was formulated into an alkyd resin (Xinhua Resin 3150) coating, sprayed on a metal plate and dried (drying temperature 130°C, time 30 minutes), and the hue value was tested. The metal plate was placed in a blast oven at 150°C and 200°C for 30 minutes, then taken out and the hue value was tested again to obtain the color difference value △E before and after.

[0220] The heat resistance results of the pigments are shown in Table 4.

[0221] Table 4

[0222]

[0223] As can be seen from Table 4, the pigment of the present invention has excellent heat resistance.

Claims

1. A perylene compound having the general formula (I): in: Ar groups are independently C6-C 18 Aryl, the C6-C 18 The aryl group may be optionally substituted by a substituent selected from the group consisting of halogen, C1-C 20 Alkyl, C1-C 20 Alkoxy, C1-C 20 Alkylthio, -NO2, -CN, C3-C 10 Cycloalkyl, C4-C 20 Cycloalkylalkyl, C4-C 20 Cycloalkylalkoxy, C4-C 20 Cycloalkylalkylthio, C4-C 20 Alkylcycloalkyl or sulfonic acid group; wherein C1-C 20 Alkyl, C1-C 20 Alkoxy, C1-C 20 Alkylthio, C3-C 10 Cycloalkyl, C4-C 20 Cycloalkylalkyl, C4-C 20 Cycloalkylalkoxy, C4-C 20 Cycloalkylalkylthio or C4-C 20 The alkylcycloalkyl group may be optionally substituted with one or more groups independently selected from the group consisting of halogen, -NO2, -CN, hydroxyl, thiol, sulfonic acid, carboxyl or amino; The R1 groups are independently halogen, C1-C 20 Alkyl, C1-C 20 Alkoxy, C1-C 20 Alkylthio, -NO2, -CN, C3-C 10 Cycloalkyl, C4-C 20 Cycloalkylalkyl, C4-C 20 Cycloalkylalkoxy, C4-C 20 Cycloalkylalkylthio, C4-C 20 Alkylcycloalkyl or sulfonic acid group; wherein C1-C 20 Alkyl, C1-C 20 Alkoxy, C1-C 20 Alkylthio, C3-C 10 Cycloalkyl, C4-C 20 Cycloalkylalkyl, C4-C 20 Cycloalkylalkoxy, C4-C 20 Cycloalkylalkylthio or C4-C 20 The alkylcycloalkyl group may be optionally substituted with one or more groups independently selected from the group consisting of halogen, -NO2, -CN, hydroxyl, thiol, sulfonic acid, carboxyl or amino; The R2 radicals are independently halogen, C1-C 20 Alkyl, C1-C 20 Alkoxy, C1-C 20 Alkylthio, -NO2, -CN, C3-C 10 Cycloalkyl, C4-C 20 Cycloalkylalkyl, C4-C 20 Cycloalkylalkoxy, C4-C 20 Cycloalkylalkylthio, C4-C 20 Alkylcycloalkyl or sulfonic acid group; wherein C1-C 20 Alkyl, C1-C 20 Alkoxy, C1-C 20 Alkylthio, C3-C 10 Cycloalkyl, C4-C 20 Cycloalkylalkyl, C4-C 20 Cycloalkylalkoxy, C4-C 20 Cycloalkylalkylthio or C4-C 20 The alkylcycloalkyl group may be optionally substituted with one or more groups independently selected from the group consisting of halogen, -NO2, -CN, hydroxyl, thiol, sulfonic acid, carboxyl or amino; n is 0, 1, 2, 3 or 4; m is 0, 1, 2, 3, 4, 5, 6, 7 or 8; and q is 0 or 1.

2. The compound according to claim 1, wherein the Ar groups are independently phenyl, and the phenyl group may be optionally substituted by a substituent selected from the group consisting of halogen, C1-C 20 Alkyl, C1-C 20 Alkoxy, C1-C 20 Alkylthio, C3-C 10 Cycloalkyl or sulfonic acid group; wherein C1-C 20 Alkyl, C1-C 20 Alkoxy, C1-C 20 Alkylthio or C3-C 10 The cycloalkyl group may be optionally substituted with one or more groups independently selected from halogen.

3. compound according to claim 2, wherein Ar groups are independently phenyl, and the phenyl is optionally substituted by one or more groups selected from methyl, ethyl, n-propyl, isopropyl, fluorine, chlorine, bromine, iodine, sulfonic acid and methoxy.

4. The compound according to claim 1, wherein the R1 group is independently halogen, C1-C 20 Alkyl, C1-C 20 Alkoxy or sulfonic acid; wherein C1-C 20 Alkyl or C1-C 20 The alkoxy group may be optionally substituted with one or more groups independently selected from halogen; Preferably, the R1 radical is, independently of one another, fluorine, chlorine, bromine, iodine or sulfonic acid at each occurrence.

5. The compound according to claim 1, wherein the R2 group is independently halogen, C1-C 20 Alkyl, C1-C 20 Alkoxy or sulfonic acid; wherein C1-C 20 Alkyl or C1-C 20 The alkoxy group may be optionally substituted with one or more groups independently selected from the group consisting of halogen, -NO2 or -CN; Preferably, the R2 radicals are, independently of one another, methyl, ethyl, n-propyl, isopropyl, fluorine, chlorine, bromine, iodine, sulfonic acid or methoxy at each occurrence, More preferably, the R2 radicals are independently at each occurrence methyl or chlorine, The position of the R2 group is located at the ortho or meta position of the bridging oxygen atom.

6. The compound according to any one of claims 1 to 5, wherein n is 0 and m is 0.

7. The compound according to any one of claims 1 to 5, wherein n is 1 and m is 0.

8. A compound according to any one of claims 1 to 5, wherein: The Ar groups are independently phenyl, n is 0, and m is 0.

9. A compound according to any one of claims 1 to 5, wherein: The Ar groups are independently phenyl, The R2 groups are independently halogen or C1-C5 alkyl, n is 1, m is 0, and q is 0.

10. The compound according to claim 9, wherein: The Ar groups are independently phenyl, The R2 radicals are independently chlorine or methyl, n is 1, m is 0, and q is 0.

11. The compound according to any one of claims 1 to 5, wherein the perylene compound has formula (II), (III), (IV) or (V):

12. A method for preparing a perylene compound according to any one of claims 1 to 11, comprising making a compound of formula (VI): Reaction with a compound of formula (VII): wherein Ar, R1, R2, m, n and q are as defined in any one of claims 1-11.

13. The method according to claim 12, wherein the molar ratio of the compound of formula (VI) to the compound of formula (VII) is 1:2 to 1:10, preferably 1:2.5 to 1:5, and more preferably 1:3 to 1:

5.

14. The method according to claim 12 or 13, wherein the reaction is carried out in the presence of a catalyst selected from soluble zinc salts, such as zinc acetate, zinc chloride, zinc sulfate, zinc benzoate, zinc stearate.

15. Use of the perylene compound according to any one of claims 1 to 11 as a pigment.

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