Perylene compound and preparation method thereof, organic dye, printing ink and electrowetting display

Abstract

The invention discloses a perylene compound and a preparation method thereof, an organic dye, ink and an electrowetting display. The perylene compound has a structural formula as shown in a formula I or a formula II: # imgabs0 #. The perylene compound provided by the invention has a relatively pure green phase, a relatively high molar absorption coefficient and stability, has extremely high solubility in a non-polar organic solvent, and can be dissolved in the organic solvent to obtain printing ink suitable for electrowetting display; the method can be used for preparing high-contrast green electrowetting devices.

Description

Technical Field

[0001] The present invention relates to the technical field of electrowetting display, and in particular to a perylene compound and a preparation method thereof, an organic dye, ink and an electrowetting display. Background Art

[0002] Electrowetting display (EFD), also known as electrowetting display technology, is a prototype display based on the principle of electrowetting display first developed by Philips of the Netherlands in 2003. The display principle is to control the surface properties of the hydrophobic layer by changing the voltage, thereby changing the contact angle of the ink layer on the hydrophobic layer. When no voltage is applied, the ink uniformly wets the insulating layer to form a colored pixel; when voltage is applied, the electric field changes the surface properties of the hydrophobic layer, causing the interfacial tension between the three phases of ink-polar liquid-hydrophobic layer to change, and the ink is compressed to form transparent or substrate-colored pixels, thereby obtaining a display image effect.

[0003] Electrowetting display ink materials are proprietary materials for electrowetting display colors, so they have high requirements for the solubility of dyes in non-polar solvents, color saturation, and color intensity. Disclosed in the related art are ink materials based on anthraquinone structures. The advantage of anthraquinone-structured ink materials for electrowetting display is that they have low polarity and most dyes have excellent light resistance, but their disadvantage is that the color intensity is low. Therefore, researchers have gradually shifted their attention to the development of azo dyes with high color intensity. However, the existing azo electrowetting display green phase organic dyes have poor photostability and are difficult to meet the application requirements of electrowetting display devices in outdoor applications.

[0004] Therefore, it is necessary to develop a perylene-based compound with high photostability and a green phase. Summary of the invention

[0005] The present invention aims to solve at least one of the technical problems existing in the prior art. To this end, the first aspect of the present invention provides a perylene compound, which has a green phase and high light stability when used in an organic dye.

[0006] The second aspect of the present invention also provides a method for preparing a perylene compound.

[0007] The third aspect of the present invention also provides an organic dye.

[0008] The fourth aspect of the present invention also provides an ink.

[0009] A fifth aspect of the present invention also provides an electrowetting display.

[0010] According to a first aspect of the present invention, there is provided a perylene compound having a structural formula shown in Formula I or Formula II:

[0011]

[0012] Among them, R 1 and R 2 Each independently selected from unsubstituted or substituted with halogen, hydroxyl, C 1～10 C substituted with at least one of an alkoxy group or a nitro group 1～30 Alkyl, unsubstituted or substituted with halogen, hydroxyl, C 1～10 Alkoxy, nitro substituted C 3～30 Cycloalkyl, unsubstituted or substituted with halogen, hydroxyl, C 1～10 Alkyl, nitro substituted C 1～30 Alkoxy, unsubstituted or replaced by C 1～10 an alkyl-substituted phenyl group;

[0013] R 3 , R 4 , R 5 , R 6 Each independently selected from C 1～30 Alkyl, unsubstituted or replaced by C 1～30 Alkoxy, C 1～30 The phenyl group is substituted with an alkyl group.

[0014] According to a preferred embodiment of the present invention, there are at least the following beneficial effects:

[0015] The perylene compound provided by the present invention has a relatively pure green phase, a high molar absorption coefficient and light stability, and has extremely high solubility in non-polar organic solvents. When dissolved in an organic solvent, an ink suitable for electrowetting display can be obtained, and can be used to prepare a high-contrast green phase electrowetting device.

[0016] According to some preferred embodiments of the present invention, R 1 and R 2 Each independently selected from C 5～20 Alkyl, unsubstituted or replaced by C 1～10 The phenyl group is substituted with an alkyl group.

[0017] According to some preferred embodiments of the present invention, R 3 , R 4 , R 5 , R 6 Each independently selected from C 1～30 Alkyl, unsubstituted or replaced by C 1～10 The phenyl group is substituted with an alkyl group.

[0018] According to some preferred embodiments of the present invention, R 1and R 2 Each is independently selected from n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, n-nonadecyl, n-eicosyl, 2-nonyldecyl, 2-pentylhexyl, 2-heptyloctyl, 2-octyldodecyl, 4-butylphenyl, 4-octylphenyl, 4-(2-ethylhexyl)phenyl, and 2,6-diisopropylphenyl.

[0019] According to some preferred embodiments of the present invention, R 3 , R 4 , R 5 , R 6 Each is independently selected from n-butyl, n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, n-nonadecyl, n-eicosyl, 2-nonyldecyl, 2-pentylhexyl, 2-heptyloctyl, 2-octyldodecyl, 4-butylphenyl, 4-octylphenyl, 4-(2-ethylhexyl)phenyl.

[0020] According to some preferred embodiments of the present invention, the perylene compound is selected from one of the following structural formulas:

[0021]

[0022]

[0023] The second aspect of the present invention provides a method for preparing the perylene compound, comprising the following steps:

[0024] Under anaerobic conditions, compound A, a solvent, an inorganic base, compound C, compound D and a catalyst are mixed and heated to react; or,

[0025] Under anaerobic conditions, compound B, a solvent, an inorganic base, compound C, compound D and a catalyst are mixed and heated to react;

[0026] The structural formulas of compound A, compound B, compound C and compound D are as follows:

[0027]

[0028] R 1 , R 2 , R 3 , R 4 , R 5 , R 6 The definition of is the same as that described in the first aspect of the present invention.

[0029] The method for preparing the perylene-based compound according to the preferred embodiment of the present invention has at least the following beneficial effects:

[0030] Since the preparation method adopts all the technical solutions of the perylene compounds of the above embodiments, it has at least all the beneficial effects brought by the technical solutions of the above embodiments. Furthermore, the preparation method has simple steps, high yield, and is easy to mass produce.

[0031] According to some preferred embodiments of the present invention, the inorganic base is selected from at least one of potassium carbonate, sodium carbonate or cesium carbonate.

[0032] According to some preferred embodiments of the present invention, the catalyst comprises a palladium catalyst.

[0033] According to some preferred embodiments of the present invention, the palladium catalyst is selected from tetrakis(triphenylphosphine)palladium, ferrocenepalladium dichloride, palladium acetate or Pd 2 (dba) 3 At least one of the above. Thus, the catalytic effect is better.

[0034] According to some preferred embodiments of the present invention, the reaction temperature of the heating reaction is 70-150° C. Thus, a high yield is achieved within the above temperature range.

[0035] According to some preferred embodiments of the present invention, the reaction time of the heating reaction is 6 to 24 hours. A reaction time shorter than 6 hours may easily lead to incomplete reaction, and a reaction time exceeding 24 hours may easily waste resources.

[0036] According to some preferred embodiments of the present invention, the solvent is selected from at least one of toluene, xylene, trimethylbenzene and ethylbenzene, thereby promoting the dissolution of the raw material.

[0037] According to a third aspect of the present invention, there is provided an organic dye, comprising the perylene compound according to the first aspect of the present invention.

[0038] Therefore, the organic dye adopts all the technical solutions of the perylene-based compounds of the above preferred embodiments, and thus has at least all the beneficial effects brought by the technical solutions of the above preferred embodiments.

[0039] The fourth aspect of the present invention provides an ink comprising the perylene compound described in the first aspect of the present invention or the organic dye described in the second aspect of the present invention; and a non-polar solvent.

[0040] Therefore, the ink adopts all the technical solutions of the perylene-based compounds of the above preferred embodiments, and thus has at least all the beneficial effects brought about by the technical solutions of the above preferred embodiments.

[0041] According to some preferred embodiments of the present invention, the content of the perylene compound or the organic dye described in the third aspect of the present invention is 1 to 30 parts by weight; and the content of the non-polar solvent is 70 to 99 parts by weight.

[0042] According to some preferred embodiments of the present invention, the non-polar solvent is selected from at least one of n-decane, n-dodecane, n-tetradecane, n-hexadecane, fluorinated alkanes, silane, cyclohexane or dimethyladamantane.

[0043] A fifth aspect of the present invention provides an electrowetting display, comprising the ink described in the fourth aspect of the present invention.

[0044] Therefore, the electrowetting display adopts all the technical solutions of the ink of the above preferred embodiment, and thus has at least all the beneficial effects brought by the technical solutions of the above preferred embodiment.

[0045] Definitions and general terms

[0046] “C 1-10 "Alkyl" means an alkyl group having 1 to 10 carbon atoms, including C 1～10 The straight chain alkyl and C 1～10 The branched alkyl group may be, for example, a straight-chain alkyl group having 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10 carbon atoms, or a branched-chain alkyl group having 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10 carbon atoms, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, n-hexyl, etc. 1-30 Alkyl", "C 5～20 The "alkyl" has a similar explanation, except that the number of carbon atoms is different.

[0047] “C 3-30 The term "cycloalkyl" refers to a cycloalkyl group having 3 to 30 carbon atoms, for example, cyclopropyl, methylcyclopropyl, ethylcyclopropyl, cyclopentyl, methylcyclopentyl, cyclohexyl, etc.

[0048] “C 1～10 "Alkoxy" means an alkoxy group having a total of 1 to 10 carbon atoms, including C 1～10 The straight chain alkoxy and C 1～10 The branched alkoxy group may be, for example, a straight chain alkoxy group having a total number of carbon atoms of 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10, or a branched alkoxy group having a total number of carbon atoms of 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10, such as a methoxy group, an ethoxy group, a n-propoxy group, an isopropoxy group, or the like. 1-30 The "alkoxy group" has a similar explanation, except that the number of carbon atoms is different.

[0049] Other features and advantages of the present invention will be set forth in the description which follows, and in part will be apparent from the description, or may be learned by practice of the present invention. BRIEF DESCRIPTION OF THE DRAWINGS

[0050] The above and / or additional aspects and advantages of the present invention will become apparent and easily understood from the description of the embodiments in conjunction with the following drawings, in which:

[0051] Figure 1 is the ultraviolet absorption spectrum of the green ink prepared in Example 6 of the present invention;

[0052] Figure 2 is a working curve diagram of the green ink prepared in Example 6 of the present invention;

[0053] Figure 3 is an aging resistance performance graph of the green ink prepared in Example 6 of the present invention;

[0054] Figure 4 Schematic diagram of the switching of ink of the electrowetting device under voltage drive in an embodiment of the present invention;

[0055] Figure 5 is an EFD device diagram of the green ink prepared in Example 6 of the present invention;

[0056] Figure 6 This is a diagram of the green ink EFD device prepared in Example 6 of the present invention shrinking into a droplet (driven to open) under voltage driving;

[0057] Figure 7 This is a response speed diagram of the green ink prepared in Example 6 of the present invention when driven by a voltage of 18V;

[0058] Figure 8 This is a diagram showing the green ink prepared in Example 6 of the present invention maintaining a stable shrinking droplet without backflow under a constant voltage. DETAILED DESCRIPTION

[0059] The following are specific embodiments of the present invention, and the technical solutions of the present invention are further described in conjunction with the embodiments, but the present invention is not limited to these embodiments.

[0060] Unless otherwise specified, the reagents, methods and equipment used in the present invention are conventional reagents, methods and equipment in the art.

[0061] Some of the raw materials in the present invention are as follows:

[0062] Compound 2-1 :N,N-dibutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline synthesis:

[0063]

[0064] Weigh p-bromoaniline (106-40-1, 5.12 g, 30 mmol, McLean's reagent) and anhydrous potassium carbonate (60 mmol, 10.07 g) and transfer to a 500 mL reaction bottle, add DMF 100 mL and bromobutyl (150 mmol, 20.55 g, McLean's reagent), replace the air with nitrogen, and heat to 100 ° C for 12 hours. After the reaction is completed, remove potassium carbonate by vacuum filtration, then wash with 100 mL of water 3 times to remove DMF, and then remove bromobutyl by vacuum distillation, and then purify by chromatography to obtain 4.26 g of N, N-dibutyl-4-bromoaniline, with a yield of 50%.

[0065] In a 500 mL double-necked reaction bottle, N,N-dibutyl-4-bromoaniline (4.26 g, 15 mmol), bis-pinacol diborane (CAS: 73183-34-3, 18 mmol, 4.57 g, MacLean reagent), potassium acetate (30 mmol, 2.94 g, MacLean reagent), 1,4-dioxane 100 mL were added, stirred and the air was replaced with nitrogen, and [PdCl 2 (dPPf)] (CAS: 72287-26-4, 1mmol, 0.2g, Anergy reagent), heated to 80°C for 18 hours. After the reaction, the mixture was cooled to room temperature, and then 200mL of water and 100mL of petroleum ether were added for extraction and washing, and then washed twice with 100mL of saturated brine, dried with anhydrous sodium sulfate, and passed through a chromatography column to obtain 4.5g of compound 2-1 with a yield of 90%.

[0066] Compound 2-2 Compound 2-2 was synthesized by the same method as above, except that isooctane bromide (purchased from MacLean Biochemical Technology Co., Ltd.) was used to replace the above-mentioned butyl bromide. The structural formula of compound 2-2 is as follows:

[0067]

[0068] Compound 2-3 :Synthesis of N,N-di[4-(2-ethylhexyl)phenyl]-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline

[0069]

[0070] After filling a 100 mL double-necked reaction flask with a magnetic stirrer with argon, 0.058 g of tri-tert-butylphosphonium tetrafluoroborate (CAS No.: 131274-22-1, Aladdin), 0.2 mmol, and Pd 2(DBA) (CAS No.: 351364-51-3, Aladdin) 0.0916g, 0.1mmol, then add anhydrous toluene 10mL and stir to dissolve for 10min, add aniline (0.93g, 10mmol), 4-(2-ethylhexyl) bromobenzene (CAS No.: 883903-22-8, Nanjing Zhiyan Technology, 30mmol, 8g) and toluene 30mL, stir for 0.5 hours under argon protection. Then add sodium tert-butoxide (CAS No.: 865-48-5, McLean, 30mmol, 2.88g), stir and heat to 107℃ for 40 hours. After the reaction is completed, cool to room temperature, filter with diatomaceous earth, add 1M dilute hydrochloric acid 100mL to wash once, then wash once with saturated brine, dry with anhydrous sodium sulfate, distill to remove toluene, and then purify by column chromatography to obtain N,N-di[4-(2-ethylhexyl)phenyl]-aniline.

[0071] The purified N,N-di[4-(2-ethylhexyl)phenyl]-aniline product was dissolved in 50 mL of chloroform under argon protection, and NBS (10 mmol, 1.78 g) was added at 0°C for 3 hours and then stirred at room temperature for 12 hours. After the reaction was completed, it was extracted with 50 mL of n-hexane, filtered with diatomaceous earth, and concentrated for later use.

[0072] The obtained product was dissolved in 50 mL of dioxane, and bis-pinacol diborane (CAS No.: 73183-34-3, Aladdin 10 mmol, 2.54 g) and potassium acetate (24 mmol, 3 g) were added, stirred and dissolved, and [PdCl 2 (dPPf)] (CAS No.: 72287-26-4, McLean, 0.21 mmol, 90 mg), heated to 78 ° C under argon protection for 12 hours, after the reaction, washed with ethyl acetate 50 mL and water 50 mL and concentrated to obtain compound 2-3.

[0073] Compound 1-1 :The structural formula and preparation method are as follows:

[0074]

[0075] Add 250mL of NMP solution to a 500mL three-necked flask and stir; weigh 0.03mol, 17.5g of 1,7-dibromo-3,4,9,10-perylenetetracarboxylic dianhydride (CAS: 118129-60-5, McLean) and transfer to the three-necked flask, then add 0.18mol, 10.8g of acetic acid; stir at room temperature. Then add 0.066mol, 19.639g of 2-octyldodecylamine (CAS: 62281-06-5, McLean); exclude air, pass nitrogen protection, and react at 110℃ for 8 hours. After the reaction is completed and cooled to room temperature, pour the reaction solution into 1000mL of ethanol and stir for 20min, then let it stand for 1 hour, pour out the upper clear night, and vacuum dry to obtain 25g of crude product. Finally, purify by chromatography column to obtain compound 1-1.

[0076] Generally, compound 1-1 includes a small amount of isomer 1-1*, and the two can be separated by column chromatography or by recrystallization from toluene.

[0077]

[0078] Compound 1-2 : The synthesis method is the same as compound 1-1, except that 2-ethylhexylamine is used instead of 2-octyldodecylamine. The structural formula of compound 1-2 is as follows:

[0079]

[0080] Compound 1-3 : The synthesis method is the same as compound 1-1; the difference is that 2,6-diisopropylaniline is used to replace 2-octyldodecylamine. The structural formula of compound 1-3 is as follows:

[0081]

[0082] Example 1

[0083] This example provides a perylene compound, the structural formula and preparation method of which are as follows:

[0084]

[0085] In a 100mL double-necked reaction bottle, weigh the compound 1-1 (1.11 g, 1 mmol, 1109.2 g / mol) prepared above, add 50mL of toluene and stir to dissolve, weigh potassium carbonate (2.8 g, 20 mmol) and dissolve it in 20mL of water and then add it, weigh compound 2-1 (2mmol, 0.55 g) and tetrakistriphenylphosphine palladium (0.05mmol, 58 mg) and add them, exclude air, pass argon, heat to 120°C under argon protection and react for 8 hours, after the reaction is completed, cool to room temperature, pour the reaction solution into 200mL of ethanol and stir, let stand to precipitate solid, filter, add n-hexane to extract, purify by chromatography column to obtain 0.78g of perylene compound I-1; yield 62.6%.

[0086] The data analysis of compound I-1 is as follows:

[0087] 1 HNMR,600HZ,20℃:8.516(d,2H),8.108-8.122(d,2H),7.987-8.02(d,2H )7.341-7.361(d,4H)6.668-6.685(d,4H),4.129-4.141(d,4H)3.329-3. 354(m,8H),1.973-1.993(m,2H),1.628-1.651(m,8H),1.383-1.418(m, 8H),1.223-1.238(m.64H),0.986-1.121(m,12H),0.830-0.883(m,12H).

[0088] 13 CNMR (400MHz, CDCl 3 ):164.6,145.8,137.6,133.7,130.4,129.0,128.9,128.5,126.1,125.2,123.3,123.1,121.1,113.2,57.7,44.3,37.9,32.1,30.7,29.6,28.6,23.1,20.8,14.1,13.8.

[0089] MS(MALDI-TOF)(DIF)m / z(%):1358.06.

[0090] The isomeric compound 1-1* of compound 1-1 was obtained by column chromatography separation; the same method was used to synthesize compound I-1*:

[0091] 1HNMR,600HZ,20℃:8.516(d,2H),8.138-8.182(d,2H),7.989-8.05(d,2 H)7.341-7.361(d,4H)6.668-6.685(d,4H),4.129-4.141(d,4H)3.329-3 .354(m,8H),1.973-1.993(m,2H),1.628-1.651(m,8H),1.383-1.418(m ,8H),1.223-1.238(m.64H),0.986-1.121(m,12H),0.830-0.883(m,12H)

[0092] 13CNMR(400MHz, CDCl3):164.6,145.8,137.6,133.7,130.4,129.0,128.9,128.5,126.1,125.2 ,123.3,123.1,121.1,113.2,57.7,44.3,37.9,32.1,30.7,29.6,28.6,,23.1,20.8,14.1,13.8

[0093] MS(MALDI-TOF)(DIF)m / z(%):1358.06.

[0094] Example 2

[0095] This example provides a perylene compound I-2, the structural formula of which is as follows:

[0096]

[0097] The preparation method is basically the same as that of Example 1, except that compound 2-2 is used instead of compound 2-1 in Example 1.

[0098] The data of the prepared perylene compound I-2 are as follows:

[0099] 1 HNMR,600HZ,20℃:8.526(d,2H),8.118-8.127(d,2H),7.97-8.00(d,2H)7.345-7.366(d,4H)

[0100] 6.566-6.678(d,4H),4.119-4.131(d,4H)3.329-3.354(m,8H),1.973-1.993(m,2H),1.734-1.74 2(m,4H)1.341-1.368(m,32H)1.223-1.238(m.64H),0.988-1.131(m,24H),0.830-0.883(m,12H).

[0101] 13 CNMR (400MHz, CDCl 3 ):165.5,145.8,137.6,133.7,130.4,129.0,128.9,128.5,126.1,125.2,123.3,123.1,121.1,113.2,62.2,44.3,40.2,37.9,32.1,30.7,29.6,28.6,25.5,23.1,20.8,14.1,10.8.

[0102] MS(MALDI-TOF)(DIF)m / z(%):1582.48.

[0103] Example 3

[0104] This example provides a perylene compound I-3, the structural formula of which is as follows:

[0105]

[0106] The preparation method is basically the same as that of Example 1, except that compound 2-3 is used to replace compound 2-1 in Example 1.

[0107] The data of the prepared perylene compound I-3 are as follows:

[0108] 1 HNMR, 600HZ, 20℃: 8.522(d,2H),8.138-8.147(d,2H),7.87-8.10(d,2H)7.35 6-7.386(d,4H)7.06-7.086(d,8H)6.476-6.782(d,12H),4.11-4.134(d,4H), 3.129-3.254(m,8H),1.993-2.118(m,2H),1.788-1.824(m,4H),1.331-1.37 8(m,32H)1.220-1.258(m.64H),0.986-1.135(m,24H),0.831-0.883(m,12H).

[0109] 13 CNMR (400MHz, CDCl 3 ):165.1,141.8,140.5,137.6,133.7,131.4,130.1,129.2,128.9,128.5,128.3,128.1,127.1,125.2,123.3,123.1,122.0,121.1,44.3,40.2,39.8,34.2,32.1,30.7,29.6,28.6,27.4,25.5,23.4,23.1,14.1,11.8.

[0110] MS(MALDI-TOF)(DIF)m / z(%):1886.87.

[0111] Example 4

[0112] This example provides a perylene compound I-4, the structural formula of which is as follows:

[0113]

[0114] The preparation method is basically the same as that of Example 2, except that compound 1-2 is used instead of compound 1-1 in Example 2.

[0115] The data of the prepared perylene compound I-4 are as follows:

[0116] 1 H NMR, 600HZ, 20℃: 8.522(d,2H),8.108-8.121(d,2H),7.857-7.988(d,2 H)7.345-7.366(d,4H)6.576-6.68(d,4H),4.109-4.13(d,4H)3.329-3. 354(m,8H),1.973-1.993(m,2H),1.734-1.742(m,4H)1.341-1.368(m, 32H)1.223-1.238(m.24H),0.988-1.131(m,24H),0.830-0.883(m,12H)

[0117] 13 CNMR (400MHz, CDCl 3):164.5,143.8,137.6,133.7,130.4,129.0,128.9,128.5,126.1,125.2,123.3,123.1,121.1,113.2,62.2,44.3,40.2,37.9,32.1,30.7,29.6,28.6,25.5,23.1,20.8,14.1,10.8

[0118] MS(MALDI-TOF)(DIF)m / z(%):1245.84.

[0119] Example 5

[0120] This example provides a perylene compound I-5, the structural formula of which is as follows:

[0121]

[0122] The preparation method is basically the same as that of Example 2, except that compound 1-3 is used instead of compound 1-1 in Example 2.

[0123] The data of the prepared perylene compound I-5 are as follows:

[0124] 1 HNMR, 600HZ, 20℃: 8.522(d,2H),8.108-8.121(d,2H),7.875-7.988(d, 2H)7.345-7.366(d,4H)7.022-7.112(d,4H)6.810-6.905(d,2H),6.56- 6.63(d,4H),3.329-3.354(m,8H),2.73-2.93(m,4H),1.734-1.742(m, 4H)1.341-1.368(m,32H),1.138-1.158(m,24H),0.988-1.131(m,24H).

[0125] 13 CNMR(400MHz, CDCl3):163.5,143.8,140.3,137.9,137.3,133.8,131.9,130.9,129.2,128.7,

[0126] 128.3,128.1,126.1,123.7,123.5,123.2,121.1,113.2,61.2,37.9,32.1,30.7,25.6,25.5,24.4,23.1,20.8,14.1,10.8.

[0127] MS(MALDI-TOF)(DIF)m / z(%):1341.93.

[0128] Example 6

[0129] This example provides a green ink, and its preparation method is as follows:

[0130] 0.2 g of the perylene compound I-1 prepared in Example 1 was dissolved in 2 g of n-decane to obtain a product.

[0131] Example 7

[0132] This example provides a green ink, and its preparation method is as follows:

[0133] 1 g of the perylene compound I-2 prepared in Example 2 was dissolved in 4 g of n-decane to obtain the product.

[0134] Example 8

[0135] This example provides a green ink, and its preparation method is as follows:

[0136] 1 g of the perylene compound I-3 prepared in Example 3 was dissolved in 5 g of n-decane to obtain the compound.

[0137] Example 9

[0138] This example provides a green ink, and its preparation method is as follows:

[0139] 0.5 g of the perylene compound I-4 prepared in Example 4 was dissolved in 6 g of n-decane to obtain the product.

[0140] Example 10

[0141] This example provides a green ink, and its preparation method is as follows:

[0142] Take 0.5 g of the perylene compound I-5 prepared in Example 5 and dissolve it in 8 g of n-decane to obtain the product.

[0143] Performance Testing

[0144] The green ink prepared in Example 6 of the present invention was tested by ultraviolet spectrophotometer to obtain the absorption spectrum of the green ink and the working curve of the green ink. The results are as follows: Figure 1 and Figure 2 As shown in the test results, the green ink prepared in Example 6 has maximum absorption peaks at 483nm and 633nm, and the corresponding molar absorption coefficients are 37223cm -1 (mol / L) -1 ; 19232cm -1 (mol / L) -1 .

[0145] Furthermore, the green ink prepared in Example 6 of the present invention was subjected to a weather resistance test. After aging for 100 hours in a xenon lamp weatherproof box (50°C, 364nm, 0.55W / h) to simulate sunlight, the change in its absorption spectrum was tested. The results are as follows: Figure 3 As shown, the light stability of the green ink prepared in Example 6 is as follows: after 100 hours of testing, the absorbance changes of the ink are ΔA (λ＝483nm) =-0.05%; ΔA (λ＝633nm) =-0.03%; the test results show that the light stability of the green ink is very excellent.

[0146] Further, the green ink and water of Example 6 were packaged into an EFD device (eg Figure 5 As shown in FIG. 1 ), by injecting conductive silver paste into the EFD device, turning on the power supply, and adjusting the driving voltage to increase slowly from 0 to 18 V, it can be observed that the pixel ink liquid in the EFD device slowly shrinks from the spreading state (as shown in FIG. 1 ). Figure 4 When the voltage is stabilized at 18V, the ink shrinks and gathers at the corners of the pixel. The opening ratio of the ink is calculated by software (as shown in Figure 6 The device is placed under a colorimeter, and a 5Hz square wave is applied to the device to turn it on and off. The colorimeter is used to collect the brightness changes of the on and off. The software calculates that the time required from the lowest brightness to 90% of the highest brightness is the on time, and the time required from the highest brightness to 10% of the lowest brightness is the off time, thereby obtaining the response speed of the ink in the device (as shown in Figure 2). Figure 7 Place the device under an inverted microscope, power it on, and slowly change the voltage from 0V to 18V. Observe through the microscope that the transmittance of the device is at its maximum. Keep the voltage at 18V unchanged and test the change in transmittance. Figure 8 As shown, the transmittance of the device is basically unchanged in 120s, indicating that the ink in the device pixel can maintain the droplet shape unchanged without spreading back under a constant voltage, that is, there is no reflux phenomenon. Examples 7 to 10 use the same test method, and the results are shown in Table 1.

[0147] Table 1

[0148]

[0149]

[0150] The green ink prepared from the perylene compounds provided in Examples 1 to 5 of the present invention has a high molar absorption coefficient and stability, and has extremely high solubility in non-polar organic solvents. It can be seen from the data in Table 1 that it has the advantages of fast response speed, high stability and no reflux when used in green electrowetting devices.

[0151] The above is a detailed description of the embodiments of the present invention, but the present invention is not limited to the above embodiments. Various changes can be made within the knowledge scope of ordinary technicians in the relevant technical field without departing from the purpose of the present invention.

Claims

1. A perylene compound, characterized in that: It has the structural formula shown in Formula I or Formula II: Wherein, R1 and R2 are each independently selected from unsubstituted or substituted with halogen, hydroxyl, C 1～10 C substituted with at least one of an alkoxy group or a nitro group 1～30 Alkyl, unsubstituted or substituted with halogen, hydroxyl, C 1～10 Alkoxy, nitro substituted C 3～30 Cycloalkyl, unsubstituted or substituted with halogen, hydroxyl, C 1～10 Alkyl, nitro substituted C 1～30 Alkoxy, unsubstituted or replaced by C 1～10 an alkyl-substituted phenyl group; R3, R4, R5, and R6 are each independently selected from C 1～30 Alkyl, unsubstituted or replaced by C 1～30 Alkoxy, C 1～30 The phenyl group is substituted with an alkyl group.

2. The perylene compound according to claim 1, characterized in that R1 and R2 are each independently selected from C 5～20 Alkyl, unsubstituted or replaced by C 1～10 The phenyl group is substituted with an alkyl group.

3. The perylene compound according to claim 1, characterized in that: R3, R4, R5, and R6 are each independently selected from C 1～30 Alkyl, unsubstituted or replaced by C 1～10 The phenyl group is substituted with an alkyl group.

4. The perylene compound according to claim 1 or 2, characterized in that: R1 and R2 are each independently selected from n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, n-nonadecyl, n-eicosyl, 2-nonyldecyl, 2-pentylhexyl, 2-heptyloctyl, 2-octyldodecyl, 4-butylphenyl, 4-octylphenyl, 4-(2-ethylhexyl)phenyl, and 2,6-diisopropylphenyl.

5. The perylene compound according to claim 1 or 3, characterized in that: R3, R4, R5, and R6 are each independently selected from n-butyl, n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, n-nonadecyl, n-eicosyl, 2-nonyldecyl, 2-pentylhexyl, 2-heptyloctyl, 2-octyldodecyl, 4-butylphenyl, 4-octylphenyl, and 4-(2-ethylhexyl)phenyl.

6. The perylene compound according to claim 1 or 2, characterized in that: Select one of the following structural formulas:

7. A method for preparing the perylene compound according to any one of claims 1 to 6, characterized in that: The steps include: Under anaerobic conditions, compound A, a solvent, an inorganic base, compound C, compound D and a catalyst are mixed and heated to react; or, Under anaerobic conditions, compound B, a solvent, an inorganic base, compound C, compound D and a catalyst are mixed and heated to react; The structural formulas of compound A, compound B, compound C and compound D are as follows: The definitions of R1, R2, R3, R4, R5, and R6 are the same as those in any one of claims 1 to 6.

8. An organic dye, characterized in that The invention comprises the perylene compound according to any one of claims 1 to 6.

9. An ink, characterized in that: The invention comprises a non-polar solvent and the perylene compound according to any one of claims 1 to 6 or the organic dye according to claim 8.

10. An electrowetting display, characterized in that: Comprising the ink according to claim 9.

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