Perylene-based compounds, methods for their preparation, organic dyes, inks and electrowetting displays

Abstract

The application discloses a perylene compound and a preparation method, an organic dye, an ink and an electrowetting display thereof; the perylene compound has a structural formula shown in formula I or formula II; the perylene compound has a pure green phase, a high molar absorption coefficient and stability, has a very high solubility in a non-polar organic solvent, and can be dissolved in an organic solvent to obtain an ink suitable for the electrowetting display, and can be used for preparing a high-contrast green electrowetting device.

Description

Technical Field

[0001] This invention relates to the field of electrowetting display technology, and in particular to a perylene compound and its preparation method, organic dyes, inks and electrowetting displays. Background Technology

[0002] Electrofluide display (EFD), also known as electrowetting display technology, is a prototype display first developed by Philips in 2003. This display principle involves changing the voltage to control the surface properties of a hydrophobic layer, thereby altering the contact angle of the ink layer on the hydrophobic layer. Without voltage, the ink uniformly wets the insulating layer, forming a colored pixel. When voltage is applied, the electric field changes the surface properties of the hydrophobic layer, causing a change in the interfacial tension between the ink, polar liquid, and hydrophobic layer phases. The ink is compressed, forming transparent or substrate-colored pixels, thus achieving the displayed image effect.

[0003] Electrowetting display inks are proprietary materials for electrowetting display colors, thus requiring high standards for dye solubility, color saturation, and color intensity in non-polar solvents. Currently disclosed technologies primarily utilize anthraquinone-based inks. While anthraquinone inks offer advantages in electrowetting displays due to their low polarity and excellent lightfastness of most dyes, their disadvantage lies in low color intensity. Therefore, researchers have gradually shifted their focus to developing azo dyes with high color intensity. However, existing azo-based green organic dyes for electrowetting displays exhibit poor photostability, making it difficult to meet the outdoor application requirements of electrowetting display devices.

[0004] Therefore, it is necessary to develop a perylene compound that has high photostability and is in the green phase. Summary of the Invention

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

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

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

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

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

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

[0011]

[0012] R1 and R2 are each independently selected from unsubstituted or halogenated, hydroxyl, C 1～10 At least one of the alkoxy and nitro groups of C 1～30 Alkyl, unsubstituted or halogenated, hydroxyl, C 1～10 alkoxy, nitro-substituted C 3～30 cycloalkyl, unsubstituted or halogenated, hydroxyl, C 1～10 Alkyl, nitro-substituted C 1～30 alkoxy, unsubstituted or C 1～10 Alkyl-substituted phenyl;

[0013] R3, R4, R5, and R6 are each independently selected from C. 1～30 Alkyl, unsubstituted or C 1～30 alkoxy, C 1～30 Alkyl-substituted phenyl groups.

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

[0015] The perylene compounds provided by this invention have a relatively pure green phase, a high molar absorptivity and photostability, and extremely high solubility in nonpolar organic solvents. When dissolved in organic solvents, they can yield an ink suitable for electrowetting displays, which can be used to formulate high-contrast green phase electrowetting devices.

[0016] According to some preferred embodiments of the present invention, R1 and R2 are each independently selected from C. 5～20 Alkyl, unsubstituted or C 1～10 Alkyl-substituted phenyl groups.

[0017] According to some preferred embodiments of the present invention, R3, R4, R5, and R6 are each independently selected from C. 1～30 Alkyl, unsubstituted or C 1～10 Alkyl-substituted phenyl groups.

[0018] According to some preferred embodiments of the present invention, 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-pentadecanyl, n-hexadecyl, n-heptadecyl, n-octadecyl, n-nonadecanyl, 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, 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-pentadecanyl, n-hexadecyl, n-heptadecyl, n-octadecyl, n-nonadecanyl, n-eicosyl, 2-nonyldecyl, 2-pentylhexyl, 2-heptyloctyl, 2-octyldodecyl, 4-butylphenyl, 4-octylphenyl, and 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] A second aspect of the present invention provides a method for preparing the perylene compounds, comprising the following steps:

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

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

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

[0027]

[0028] The definitions of R1, R2, R3, R4, R5, and R6 correspond to the definitions described in the first aspect of this invention.

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

[0030] Since the preparation method employs all the technical solutions of the perylene compounds described in the above embodiments, it possesses at least all the beneficial effects brought about by the technical solutions of the above embodiments. Furthermore, the preparation method is simple in steps, has a 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 at least one of tetrakis(triphenylphosphine)palladium, ferrocene palladium dichloride, palladium acetate, or Pd2(dba)3. This results in better catalytic performance.

[0034] According to some preferred embodiments of the present invention, the reaction temperature of the heating reaction is 70–150°C. Therefore, a high yield is achieved within this 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 of less than 6 hours is prone to incomplete reaction, while a reaction time of more than 24 hours is prone to wasting 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. This effectively promotes the dissolution of the raw materials.

[0037] According to a third aspect of the present invention, an organic dye is provided, comprising the perylene compounds described in the first aspect of the present invention.

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

[0039] A fourth aspect of the present invention provides an ink comprising the perylene compounds described in the first aspect of the present invention or the organic dyes described in the second aspect of the present invention; and a nonpolar solvent.

[0040] Therefore, the ink adopts all the technical solutions of the perylene compounds of the above-mentioned preferred embodiments, and thus has at least all the beneficial effects brought about by the technical solutions of the above-mentioned 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; the content of the nonpolar solvent is 70 to 99 parts by weight.

[0042] According to some preferred embodiments of the present invention, the nonpolar solvent is selected from at least one of n-decane, n-dodecane, n-tetradecane, n-hexadecane, fluorinated alkanes, silanes, 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-mentioned preferred embodiments, and thus has at least all the beneficial effects brought about by the technical solutions of the above-mentioned preferred embodiments.

[0045] Definitions and general terms

[0046] “C 1-10 "alkyl" refers to an alkyl group with a total number of carbon atoms of 1 to 10, including C14 and C24. 1～10 straight-chain alkyl and C 1～10 Branched alkyl groups can be, for example, straight-chain alkyl groups with a total number of carbon atoms of 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10, or branched alkyl groups with a total number of carbon atoms of 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, n-hexyl, etc. Regarding "C 1-30 Alkyl group, C 5～20 "alkyl" has a similar interpretation, except that the number of carbon atoms is different.

[0047] “C 3-30 "Cycloalkyl" indicates a cycloalkyl group with a total number of carbon atoms of 3 to 30; for example, cyclopropyl, methylcyclopropyl, ethylcyclopropyl, cyclopentyl, methylcyclopentyl, cyclohexyl, etc.

[0048] “C 1～10 "Alkoxy group" refers to an alkoxy group with a total number of carbon atoms of 1 to 10, including C. 1～10 straight-chain alkoxy groups and C 1～10 Branched alkoxy groups can be, for example, straight-chain alkoxy groups with a total number of carbon atoms of 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10, or branched-chain alkoxy groups with a total number of carbon atoms of 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10, such as methoxy, ethoxy, n-propoxy, isopropoxy, etc. Regarding "C 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 invention will be set forth in the description which follows, and will be apparent in part from the description, or may be learned by practicing the invention. Attached Figure Description

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

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

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

[0053] Figure 3 This is a graph showing the aging resistance of the green ink prepared in Example 6 of this invention;

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

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

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

[0057] Figure 7 This is a graph showing the response speed of the green ink prepared in Example 6 of the present invention under a voltage of 18V.

[0058] Figure 8 This is a diagram showing the state of the green ink prepared in Example 6 of the present invention, which maintains stable shrinkage droplets without backflow under constant voltage. Detailed Implementation

[0059] The following are specific embodiments of the present invention, and the technical solutions of the present invention will be 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 this invention are all conventional reagents, methods and equipment in this technical field.

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

[0062] Compound 2-1 Synthesis of N,N-dibutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxapentoborane-2-yl)aniline:

[0063]

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

[0065] In a 500 mL two-necked reaction flask, N,N-dibutyl-4-bromoaniline (4.26 g, 15 mmol), dipinalanoyl diborane (CAS: 73183-34-3, 18 mmol, 4.57 g, Maclean's reagent), potassium acetate (30 mmol, 2.94 g, Maclean's reagent), and 100 mL of 1,4-dioxane were added. The mixture was stirred and the air was purged with nitrogen. Then, [PdCl2(dPPf)] (CAS: 72287-26-4, 1 mmol, 0.2 g, Anegiete reagent) was added, and the mixture was heated to 80 °C and reacted for 18 hours. After the reaction was complete, the mixture was cooled to room temperature and extracted and washed with 200 mL of water and 100 mL of petroleum ether. The mixture was then washed twice with 100 mL of saturated brine, dried over anhydrous sodium sulfate, and purified by column chromatography to give compound 2-1 4.5 g, with a yield of 90%.

[0066] Compound 2-2 Compound 2-2 was synthesized using the same method as described above, except that isooctane bromo (purchased from Maclean Biotechnology Co., Ltd.) was used instead of butane bromo. The structural formula of compound 2-2 is as follows:

[0067]

[0068] Compounds 2-3 Synthesis of N,N-bis[4-(2-ethylhexyl)phenyl]-4-(4,4,5,5-tetramethyl-1,3,2-dioxapentoborane-2-yl)aniline

[0069]

[0070] After filling a 100 mL two-necked reaction flask equipped with a magnetic stirrer with argon gas, add 0.058 g (0.2 mmol) of tri-tert-butylphosphine tetrafluoroborate (CAS No.: 131274-22-1, Aladdin) and 0.0916 g (0.1 mmol) of Pd2(DBA) (CAS No.: 351364-51-3, Aladdin). Then add 10 mL of anhydrous toluene and stir to dissolve for 10 min. Add aniline (0.93 g, 10 mmol), 4-(2-ethylhexyl)bromobenzene (CAS No.: 883903-22-8, Nanjing Zhiyan Technology, 30 mmol, 8 g) and 30 mL of toluene. Stir for 0.5 h under argon protection. Then add sodium tert-butoxide (CAS No.: 865-48-5, Maclean, 30 mmol, 2.88 g), stir and heat to 107 °C, and maintain the reaction temperature for 40 h. After the reaction was completed, the mixture was cooled to room temperature, filtered with diatomaceous earth, washed once with 100 mL of 1M dilute hydrochloric acid, washed once with saturated brine, dried with anhydrous sodium sulfate, and then distilled to remove toluene. Finally, it was purified by column chromatography to obtain N,N-bis[4-(2-ethylhexyl)phenyl]-aniline.

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

[0072] The 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. The mixture was stirred and dissolved. After replacing the air with argon, [PdCl2(dPPf)] (CAS No.: 72287-26-4, Maclean, 0.21 mmol, 90 mg) was added. The mixture was heated to 78 °C under argon protection and reacted for 12 hours. After the reaction, the mixture was washed and extracted with 50 mL of ethyl acetate and 50 mL of water, and then concentrated to obtain compounds 2-3.

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

[0074]

[0075] Add 250 mL of NMP solution to a 500 mL three-necked flask and stir. Weigh 0.03 mol (17.5 g) of 1,7-dibromo-3,4,9,10-perylenetetracarboxylic dianhydride (CAS: 118129-60-5, Maclean's) and transfer it to the three-necked flask. Add 0.18 mol (10.8 g) of acetic acid and stir at room temperature. Then add 0.066 mol (19.639 g) of 2-octyldodecylamine (CAS: 62281-06-5, Maclean's). Remove air and react at 110 °C for 8 hours under nitrogen protection. After the reaction is complete, cool to room temperature and pour the reaction solution into 1000 mL of ethanol. Stir for 20 min, then let stand for 1 hour. Pour off the supernatant and dry under vacuum to obtain 25 g of crude product. Finally, purify by column chromatography to obtain compound 1-1.

[0076] Generally, compound 1-1 includes a small number of isomers 1-1*, which can be separated by column chromatography or by recrystallization from toluene.

[0077]

[0078] Compounds 1-2 The synthesis method for compound 1-2 is the same as that for compound 1-1; the difference is that 2-ethylhexylamine is used instead of 2-octyldodecylamine. The structural formula of compound 1-2 is as follows:

[0079]

[0080] Compounds 1-3 The synthesis method for compound 1-3 is the same as that for compound 1-1; the difference is that 2,6-diisopropylaniline is used instead of 2-octyldodecylamine. The structural formulas of compounds 1-3 are as follows:

[0081]

[0082] Example 1

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

[0084]

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

[0086] The data analysis for 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, 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.

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

[0090] The isomers of compound 1-1, 1-1*, were obtained by column chromatography; compound I-1* was synthesized using the same method.

[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; its structural formula is as follows:

[0096]

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

[0098] The data for 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, CDCl3):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; its structural formula is as follows:

[0105]

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

[0107] The data for 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] 13CNMR (400MHz, CDCl3):165.1,141.8,140.5,137.6,133.7,131.4,130.1,129.2,128.9,128.5,128.3,128.1,127.1,1 25.2,123.3,123.1,122.0,121.1,44.3,40.2,39.8,34.2,32.1,30.7,29.6,28.6,27.4,25.5,23.4,23.1,14.1,11.8.

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

[0111] Example 4

[0112] This example provides a perylene compound I-4; its structural formula is as follows:

[0113]

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

[0115] The data for 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, CDCl3):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; its structural formula is as follows:

[0121]

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

[0123] The data for 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):163.5,143.8,140.3,137.9,137.3,133.8,131.9,130.9,129.2,128.7,128.3,128.1, 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.

[0126] MS(MALDI-TOF)(DIF)m / z(%):1341.93.

[0127] Example 6

[0128] This example provides a green ink, the preparation method of which is as follows:

[0129] The perylene compound I-1 prepared in Example 1 is dissolved in 2g of n-decane to obtain the product.

[0130] Example 7

[0131] This example provides a green ink, the preparation method of which is as follows:

[0132] The perylene compound I-2 prepared in Example 2 is dissolved in 4g of n-decane to obtain the product.

[0133] Example 8

[0134] This example provides a green ink, the preparation method of which is as follows:

[0135] The perylene compound I-3 prepared in Example 3 is dissolved in 5g of n-decane to obtain the product.

[0136] Example 9

[0137] This example provides a green ink, the preparation method of which is as follows:

[0138] The perylene compound I-4 prepared in Example 4 was dissolved in 6g of n-decane to obtain the product.

[0139] Example 10

[0140] This example provides a green ink, the preparation method of which is as follows:

[0141] The perylene compound I-5 prepared in Example 5 is dissolved in 8g of n-decane to obtain the product.

[0142] Performance testing

[0143] The green ink prepared in Example 6 of this invention was tested using a UV spectrophotometer to obtain the absorption spectrum and working curve of the green ink. The results are as follows: Figure 1 and Figure 2 As shown: Test results indicate that the green ink prepared in Example 6 has maximum absorption peaks at 483 nm and 633 nm, with corresponding molar absorptivity of 37223 cm⁻¹. -1 ·(mol / L) -1 19232cm -1 ·(mol / L) -1 .

[0144] Furthermore, the green ink prepared in Example 6 of this invention was subjected to weather resistance testing. After 100 hours of accelerated aging under simulated sunlight in a xenon lamp weathering chamber (50℃, 364nm, 0.55W / h), the changes in its absorption spectrum before and after aging were measured, and the results are as follows. Figure 3 As shown, the photostability of the green ink prepared in Example 6 is as follows: after 100 hours of testing, the changes in ink absorbance are ΔA... (λ＝483nm) = -0.05%; ΔA (λ＝633nm) = -0.03%; the test results show that the green ink has excellent light stability.

[0145] Furthermore, the green ink and water from Example 6 are encapsulated into the EFD device (e.g., Figure 5 As shown in the figure, by injecting conductive silver paste into the EFD device, turning on the power, and slowly increasing the driving voltage from 0-18V, it can be observed that the pixel ink liquid in the EFD device slowly shrinks from a spread state (as shown in the figure). Figure 4 As shown), when the voltage stabilizes at 18V, the ink shrinks and gathers at the corners of the pixels. The aperture ratio of the ink is calculated by the software (e.g., Figure 6 (As shown). The device is placed under a colorimeter, and a 5Hz square wave is applied to it, causing it to switch on and off repeatedly. The colorimeter collects the brightness changes during these switching cycles. The software calculates the time required for the brightness to rise from its lowest to 90% of its highest level as the on-time, and the time required for the brightness to rise from its highest to 10% of its lowest level as the off-time. This allows the determination of the ink's response speed within the device (e.g., ...). Figure 7 (As shown). Place the device under an inverted microscope, power it on, and slowly change the voltage from 0V to 18V. Observe the device's transmittance at its maximum under the microscope. Keep the voltage at 18V constant and test the change in transmittance, as shown. Figure 8 As shown, the transmittance of the device remained essentially unchanged for 120 seconds, indicating that the ink in the device pixels could maintain its droplet shape under a constant voltage without spreading back, i.e., there was no backflow phenomenon. Examples 7-10 used the same test method, and the results are shown in Table 1.

[0146] Table 1

[0147]

[0148]

[0149] The green inks prepared from the perylene compounds provided in Examples 1-5 of this invention have high molar absorptivity and stability, and extremely high solubility in nonpolar organic solvents. As can be seen from the data in Table 1, they have the advantages of fast response speed, high stability and no backflow when used in green electrowetting devices.

[0150] The present invention has been described in detail above with reference to the embodiments of the present invention. However, the present invention is not limited to the above embodiments. Within the scope of knowledge possessed by those skilled in the art, various changes can be made without departing from the spirit of the present invention.

Claims

1. An electrowetting display, characterized in that, The non-polar solvent and the perylene-based compound having a structural formula of Formula I or Formula II: ； wherein R1and R2are each independently selected from the group consisting of 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-octylphenyl, 4-(2-ethylhexyl)phenyl, 2,6-diisopropylphenyl; R3, R4, R5, R6are each independently selected from the group consisting of 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-(2-ethylhexyl)phenyl.

2. The electrowetting display of claim 1, wherein, The perylene-based compound is selected from the following structural formula: 、 、 、 、 。

Images