CN112341391B - Naphthalimide organic dye, electrowetting display ink and electrowetting display - Google Patents

Naphthalimide organic dye, electrowetting display ink and electrowetting display Download PDF

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CN112341391B
CN112341391B CN202011321073.2A CN202011321073A CN112341391B CN 112341391 B CN112341391 B CN 112341391B CN 202011321073 A CN202011321073 A CN 202011321073A CN 112341391 B CN112341391 B CN 112341391B
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electrowetting display
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organic dye
naphthalimide
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CN112341391A (en
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邓勇
叶德超
周国富
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Shenzhen Guohua Optoelectronics Co Ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
    • C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
    • C07D221/04—Ortho- or peri-condensed ring systems
    • C07D221/06—Ring systems of three rings
    • C07D221/14—Aza-phenalenes, e.g. 1,8-naphthalimide
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B57/00—Other synthetic dyes of known constitution
    • C09B57/08—Naphthalimide dyes; Phthalimide dyes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D11/00—Inks
    • C09D11/02—Printing inks
    • C09D11/03—Printing inks characterised by features other than the chemical nature of the binder
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B26/00—Optical devices or arrangements for the control of light using movable or deformable optical elements
    • G02B26/004—Optical devices or arrangements for the control of light using movable or deformable optical elements based on a displacement or a deformation of a fluid
    • G02B26/005—Optical devices or arrangements for the control of light using movable or deformable optical elements based on a displacement or a deformation of a fluid based on electrowetting
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom

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Abstract

The invention discloses a naphthalimide organic dye, electrowetting display ink and an electrowetting display, wherein the chemical structural general formula of the naphthalimide organic dye is shown as (I):
Figure DDA0002792893590000011
wherein R is1Is selected from C4～C20Substituted or unsubstituted alkyl, oxaalkyl, alkylphenyl; x is selected from N, NH; r2Is selected from C4～C20Substituted or unsubstituted alkyl, alicyclic group, phenyl, alkylphenyl, oxaalkyl. The naphthalimide organic dye used in the invention has good fluorescence emission performance and higher solubility in a non-polar solvent, and can be effectively applied to an electrowetting display device to prepare the electrowetting display device with high brightness.

Description

Naphthalimide organic dye, electrowetting display ink and electrowetting display
Technical Field
The invention relates to the field of electrowetting display, in particular to naphthalimide organic dye, electrowetting display ink and an electrowetting display.
Background
The electrowetting display technology (EFD), also called electrowetting display technology, is a display prototype based on electrowetting display, which was first developed by philips in the netherlands in 2003. Different from the display principle that black-white particles migrate under an electric field in the traditional electrophoretic electronic paper display technology, the display principle is that the surface performance of the hydrophobic layer is controlled by changing voltage, and the contact angle of the ink layer on the hydrophobic layer is changed: when no voltage is applied, the ink uniformly wets the insulating layer to form a colored pixel point; when voltage is applied, the surface performance of the hydrophobic layer is changed under the action of the electric field, so that the interfacial tension between the three phases of the ink, the polar liquid and the hydrophobic layer is changed, the ink is compressed, and transparent or substrate ground color pixel points are formed, thereby obtaining the image display effect. Electrowetting adopts an electric field to control spreading and contraction of a dyeing oil film on a hydrophobic interface to form an image, and has the advantages of high response speed, easiness in colorization and the like, so that wide attention and continuous research are always paid.
The color ink as the core material of the electrowetting display determines the display performance and the visual experience of the electrowetting display technology. The existing electrowetting display ink material is a soluble reflective organic dye, and realizes colorized display by absorbing partial waveband ambient light and reflecting residual ambient light. The working principle determines that the brightness of the conventional electrowetting display device completely depends on ambient light, so that the display contrast is low and the visual experience is poor under low-brightness external ambient light, and at the moment, the display brightness and the contrast of the conventional electrowetting display device need to be improved by means of a front light source. However, the application of the front light source will greatly increase the power consumption of the display device, so the application thereof is limited.
Disclosure of Invention
The present invention is directed to solving at least one of the problems of the prior art. Therefore, the invention provides a naphthalimide organic dye, electrowetting display ink and an electrowetting display.
In a first aspect of the present invention, there is provided a naphthalimide organic dye, wherein the chemical structure of the naphthalimide organic dye is represented by the general formula (I):
Figure BDA0002792893570000021
wherein R is1Is selected from C4～C20Substituted or unsubstituted alkyl, oxaalkyl, alkylphenyl;
x is selected from N, NH;
R2is selected from C4～C20Substituted or unsubstituted alkyl, alicyclic group, phenyl, alkylphenyl, oxaalkyl.
The naphthalimide organic dye provided by the embodiment of the invention has at least the following beneficial effects:
the naphthalimide organic dye provided by the invention can be used as a dye for electrowetting display, and the dye is a typical fluorescent dye which can reflect part of visible light and can also attenuate absorbed light energy into visible light (fluorescence) in a long wave band to be emitted. Therefore, organic fluorescent dyes exhibit a superposition of emitted fluorescence and reflected light with vivid bright colors. The reflective display prepared by the dye can work under wider ambient brightness, and has more excellent contrast and better visual experience. The structure of the naphthalimide organic dye used in the invention introduces the long-chain alkyl, so that the naphthalimide organic dye has good lipid solubility while ensuring good fluorescence emission performance, has high solubility in a non-polar solvent, is not easy to crystallize and separate out in the non-polar solvent, and can be effectively applied to an electrowetting display device to prepare the electrowetting display device with high brightness. Meanwhile, the X group is regulated and controlled to be a nitrogen atom and a nitrogen-hydrogen atom, the electron donating capability of the X group is changed, the Stokes shift of the fluorescence emission spectrum of the dye can be regulated and controlled, and the color light and the brightness of the dye can be regulated and controlled.
"Oxoalkyl" refers to a radical formed by substituting a carbon atom in an alkyl chain with an oxygen atom, and has the structure shown as-R3-O-R4Both R3 and R4 are alkyl groups.
Naphthalimide-based organic dyes according to some embodiments of the present invention, R1In (1), the alkyl is C13～C20Substituted or unsubstituted alkyl, preferably C15～C20Substituted or unsubstituted alkyl; r1In (1), the oxaalkyl group is C4～C20Substituted or unsubstituted oxaalkyl, preferably C8～C15Substituted or unsubstituted oxaalkyl, more preferably 3- (2-ethylhexyloxy) propyl; r1In (1), the alkylphenyl is C7～C20Substituted or unsubstituted alkylphenyl, preferably C7～C13A substituted or unsubstituted alkylphenyl group,more preferably alkylphenyl is C7～C10Substituted or unsubstituted alkylphenyl.
Naphthalimide-based organic dyes according to some embodiments of the present invention, R2Wherein the alicyclic group is C4～C20A substituted or unsubstituted alicyclic group, preferably C4～C10A substituted or unsubstituted alicyclic group, more preferably the alicyclic group is C5A substituted or unsubstituted alicyclic group; r2In (1), the phenyl is C7～C20Substituted or unsubstituted alkylphenyl, preferably C7～C10Substituted or unsubstituted alkylphenyl; r2In (1), the oxaalkyl is C4～C20Substituted or unsubstituted oxaalkyl, preferably C5～C15Substituted or unsubstituted oxaalkyl, more preferably 3- (2-ethylhexyloxy) propyl.
Naphthalimide-based organic dyes according to some embodiments of the present invention, R1Selected from the group consisting of butyl, pentyl, hexyl, heptyl, octyl, 2-ethylhexyl, nonyl, n-decyl, undecyl, 3- (2-ethylhexyloxy) propyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, eicosyl, 2-octyldodecyl.
Naphthalimide-based organic dyes according to some embodiments of the present invention, R2Selected from the group consisting of butyl, cyclobutyl, pentyl, cyclopentylene, hexyl, cyclohexylene, heptyl, octyl, 2-ethylhexyl, nonyl, n-decyl, undecyl, 3- (2-ethylhexyloxy) propyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, eicosyl, 2-octyldodecyl, phenyl, methylphenyl, ethylphenyl, propylphenyl, butylphenyl, pentylphenyl, hexylphenyl, heptylphenyl, octylphenyl, nonylphenyl, decylphenyl, undecylphenyl, dodecylphenyl, tridecylphenyl, tetradecylphenyl.
In a second aspect of the invention, there is provided an electrowetting display ink comprising naphthoyliumAmine organic dye and non-polar solvent, wherein the chemical structure general formula of the naphthalimide organic dye is shown as (I):
Figure BDA0002792893570000031
wherein R is1Is selected from C4～C20Substituted or unsubstituted alkyl, oxaalkyl, alkylphenyl;
x is selected from N, NH;
R2is selected from C4～C20Substituted or unsubstituted alkyl, alicyclic group, phenyl, alkylphenyl, oxaalkyl.
Electrowetting display inks, R, according to some embodiments of the invention1In (1), the alkyl is C13～C20Substituted or unsubstituted alkyl, preferably C15～C20Substituted or unsubstituted alkyl; r is1In (1), the oxaalkyl group is C4～C20Substituted or unsubstituted oxaalkyl, preferably C8～C15Substituted or unsubstituted oxaalkyl, more preferably 3- (2-ethylhexyloxy) propyl; r1In (1), the alkylphenyl is C7～C20Substituted or unsubstituted alkylphenyl, preferably C7～C13Substituted or unsubstituted alkylphenyl, more preferably alkylphenyl is C7～C10Substituted or unsubstituted alkylphenyl.
Electrowetting display inks, R, according to some embodiments of the invention2Wherein the alicyclic group is C4～C20A substituted or unsubstituted alicyclic group, preferably C4～C10A substituted or unsubstituted alicyclic group, more preferably the alicyclic group is C5A substituted or unsubstituted alicyclic group; r2In (1), the phenyl is C7～C20Substituted or unsubstituted alkylphenyl, preferably C7～C10Substituted or unsubstituted alkylphenyl; r2In (1), the oxaalkyl group is C4～C20Substituted or unsubstituted oxaalkyl, preferably C5～C15Substituted or unsubstituted oxygenThe heteroalkyl group is more preferably a 3- (2-ethylhexyloxy) propyl group.
Electrowetting display inks, R, according to some embodiments of the invention1Selected from the group consisting of butyl, pentyl, hexyl, heptyl, octyl, 2-ethylhexyl, nonyl, n-decyl, undecyl, 3- (2-ethylhexyloxy) propyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, eicosyl, 2-octyldodecyl.
Electrowetting display inks, R, according to some embodiments of the invention2Selected from the group consisting of butyl, cyclobutyl, pentyl, cyclopentyl, hexyl, cyclohexylene, heptyl, octyl, 2-ethylhexyl, nonyl, n-decyl, undecyl, 3- (2-ethylhexyloxy) propyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, eicosyl, 2-octyldodecyl, phenyl, methylphenyl, ethylphenyl, propylphenyl, butylphenyl, pentylphenyl, hexylphenyl, heptylphenyl, octylphenyl, nonylphenyl, decylphenyl, undecylphenyl, dodecylphenyl, tridecylphenyl, tetradecylphenyl.
According to some embodiments of the present invention, the electrowetting display ink includes 1 to 30 parts by mass of the naphthalimide organic dye and 5 to 100 parts by mass of the non-polar solvent, and preferably, the non-polar solvent is at least one of n-decane, n-dodecane, n-tetradecane, n-hexadecane, fluorine-containing alkane, and silane.
In a third aspect of the invention, there is provided an electrowetting display comprising an electrowetting display ink as described above.
Drawings
The invention is further described with reference to the following figures and examples, in which:
FIG. 1 is a graph showing the luminance of a device formed of Dye-4 and Y20 Dye in effect example 1 as a function of the concentration of the Dye.
Detailed Description
The concept and technical effects of the present invention will be clearly and completely described below in conjunction with the embodiments to fully understand the objects, features and effects of the present invention. It is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all embodiments, and those skilled in the art can obtain other embodiments without inventive effort based on the embodiments of the present invention, and all embodiments are within the protection scope of the present invention.
Example 1
2.0g (7.22mmol,277g/mol) of 4-bromo-1, 8-naphthalic anhydride are weighed out
Figure BDA0002792893570000041
Adding the mixture into a 50ml round-bottom flask, measuring 40ml of absolute ethyl alcohol as a reaction solvent, and heating to 50 ℃. 3.7g (187g/mol, 0.02mol) of 3- (2-ethylhexyloxy) propylamine were weighed out
Figure BDA0002792893570000051
The reaction was continued for 8h, the solvent was removed by rotary evaporation and the mixture was passed through a column to give 3.08g of intermediate 1 as a colorless oil
Figure BDA0002792893570000052
The yield thereof was found to be 95.6%.
1.5g (446g/mol, 0.00336mol) of intermediate 1 are weighed out
Figure BDA0002792893570000053
Dissolving in 30ml of ethylene glycol monomethyl ether, transferring 2ml of piperidine
Figure BDA0002792893570000054
The temperature is increased to 125 ℃ and the reaction is continued for 12 h. Column chromatography to obtain 1.2g of yellow-green dye 1,
Figure BDA0002792893570000055
(Dye-1) in a yield of 80%.
Nuclear magnetic hydrogen spectrum characterization data:1H NMR(400MHz,CDCl3):δ＝8.558-8.546(d,J＝4.8Hz,1H),δ＝ 8.485-8.471(d,J＝5.6Hz,1H),δ＝8.380-8.366(d,J＝5.6Hz,1H),7.669-7.643(t,J＝10.4Hz, 1H),7.167-7.151(d,J＝6.4Hz,1H),4.272-4.243(t,J＝11.6Hz,2H),3.550-3.528(t,J＝8.8Hz, 2H),3.279-3.264(q,J＝6Hz,2H),3.218(s,4H),2.037-1.991(m,J＝18.4Hz,2H),1.891-1.875(m, J＝6.4Hz,4H),1.424-1.375(m,J＝19.6Hz,1H),1.212(m,8H),0.870-0.847(t,J＝9.2Hz,3H), 0.823-0.798(t,J＝10Hz,3H).13C NMR(400MHz,CDCl3):164.573,164.096,157.174,132.580, 130.948,130.492,129.928,126.274,125.340,123.209,116.093,114.704,73.786,69.206,54.558, 39.653,37.959,30.518,29.116,28.387,26.234,24.356,23.808,23.071,14.129,11.065.
example 2
2.0g (7.22mmol,277g/mol) of 4-bromo-1, 8-naphthalic anhydride are weighed out
Figure BDA0002792893570000056
Adding the mixture into a 50ml round-bottom flask, measuring 40ml diethylene glycol butyl ether as a reaction solvent, and heating to 120 ℃. 7.4g (187g/mol, 0.04mol) of 3- (2-ethylhexyloxy) propylamine were weighed out
Figure BDA0002792893570000057
Continuously reacting for 8h, removing the solvent by rotary evaporation, passing through a column to obtain 4.2g of yellow-green dye 2,
Figure BDA0002792893570000061
(Dye-2) in a yield of 75.6%.
Characterization data of nuclear magnetic spectrum:1H NMR(400MHz,CDCl3):δ＝8.567(m,1H),8.429(m,1H),8.067(m, 1H),7.525(m,1H),6.640(m,1H),6.465(m,1H),4.264-4.253(d,J＝4.4Hz,2H),3.703(s,2H), 3.554-3.508(d,J＝18.4Hz,4H),3.389(s,2H),3.287(s,2H),2.098(s,2H),2.031(s,2H),1.439(s, 2H),1.266(m,16H),0.905(m,12H).13C NMR(400MHz,CDCl3):164.756,164.184,149.922, 134.612,130.996,129.829,126.327,124.327,123.064,120.318,103.753,74.764,73.747,71.247, 69.250,43.458,39.895,39.641,37.781,30.561,29.113,28.453,23.857,23.070,14.127,11.058.
example 3
2.77g (0.01mmol,277g/mol) 4-bromo-1, 8-naphthalic anhydride are weighed out
Figure BDA0002792893570000062
Adding the mixture into a 50ml round-bottom flask, measuring 40ml of glacial acetic acid as a reaction solvent, and heating to 50 ℃. 4.47g (149g/mol, 0.03mol) of p-n-butylaniline are weighed
Figure BDA0002792893570000063
Heating to reflux reaction for 12h, removing solvent by rotary evaporation, and passing through column to obtain 2.5g colorless oily intermediate 1
Figure BDA0002792893570000064
The yield thereof was found to be 62.5%.
1.5g (408g/mol,0.00367mol) of intermediate 1 are weighed out and dissolved in 30ml of ethylene glycol monomethyl ether, 2ml of piperidine are removed
Figure BDA0002792893570000065
Adding into the reaction solution, heating to reflux reaction for 24h, passing through a column to obtain 1.2g of yellow dye 2,
Figure BDA0002792893570000066
(Dye-3) in a yield of 83%.
Example 4
2.77g (0.01mol,277g/mol) 4-bromo-1, 8-naphthalic anhydride are weighed out
Figure BDA0002792893570000067
Adding the mixture into a 50ml round-bottom flask, measuring 40ml of absolute ethyl alcohol as a reaction solvent, and heating to 50 ℃. 7.4g (297g/mol, 0.025mol) of 2-octyldodecylamine are weighed out
Figure BDA0002792893570000071
The reaction was continued for 8h, the solvent removed by rotary evaporation and the column passed to give 5.1g of intermediate 1 as a colorless oil
Figure BDA0002792893570000072
The yield thereof was found to be 91.7%.
1.5g (446g/mol, 0.00336mol) of intermediate 1 are weighed out
Figure BDA0002792893570000073
Dissolving in 30ml of ethanolIn glycol methyl ether, 2ml of piperidine was transferred
Figure BDA0002792893570000074
The temperature is increased to 125 ℃ and the reaction is continued for 12 h. Passing through the column to obtain 1.2g of yellow-green dye 3,
Figure BDA0002792893570000075
(Dye-4) in a yield of 86%.
Nuclear magnetic hydrogen spectrum characterization data:1H NMR(400MHz,CDCl3):δ＝8.570(m,1H),8.497(m,1H),8.392(m, 1H),7.662(m,1H),7.178(m,1H),4.102-4.114(d,J＝4.8Hz,2H),3.320(s,4H),2.014-1.996(m, J＝7.2Hz,1H),1.891(s,4H),1.730(s,2H),1.224(m,32H),0.893-0.850(m,J＝17.2Hz,6H).13C NMR(400MHz,CDCl3):164.934,164.466,157.103,132.642,131.017,130.423,129.945, 126.270,125.365,123.222,116.111,114.734,54.555,44.361,36.626,31.897,31.750,30.068, 29.580,29.304,26.553,26.250,24.367,22.665,14.122.
effect example 1:
the fluorescent dye synthesized by the embodiment of the invention is compared with the common non-fluorescent dye to study the influence of the fluorescent dye on the brightness of the device. The structural formula of the adopted non-fluorescent dye Y-20 is shown as the following formula:
Figure BDA0002792893570000076
the non-fluorescent yellow dye Y-20 has a structural formula.
In the experiment, a dye and a nonpolar solvent n-decane are mixed to form electrowetting ink, the electrowetting ink is filled to form an electrowetting display device, the thickness of the ink is 65 micrometers, and then the brightness of the device is measured.
The luminance of the device formed by Dye-4 Dye and Y-20 Dye is related to the concentration of the Dye as shown in fig. 1, and it can be seen that the electrowetting display device prepared by the fluorescent Dye has a significant advantage in luminance over the non-fluorescent Dye.
The relationship between the brightness of the device formed by the dyes (Dye-1 to Dye-4) and the Y-20 Dye and the Dye concentration is shown in table 1, and the results show that the naphthalimide organic Dye of the embodiment of the invention has high solubility in a non-polar solvent, can be effectively applied to an electrowetting display device, and the prepared electrowetting display device has high brightness.
TABLE 1 relationship of dye concentration to device luminance
Figure BDA0002792893570000081
。

Claims (5)

1. The naphthalimide organic dye is characterized in that the chemical structural formula of the naphthalimide organic dye is as follows:
Figure 211464DEST_PATH_IMAGE001
or
Figure 991201DEST_PATH_IMAGE002
。
2. An electrowetting display ink comprising the naphthalimide-based organic dye according to claim 1 and a nonpolar solvent.
3. The electrowetting display ink according to claim 2, wherein said electrowetting display ink comprises 1 to 30 parts by mass of said naphthalimide-based organic dye and 5 to 100 parts by mass of said non-polar solvent.
4. The electrowetting display ink of claim 3, wherein said non-polar solvent is at least one of n-decane, n-dodecane, n-tetradecane, n-hexadecane, fluorinated alkanes, and silanes.
5. An electrowetting display comprising an electrowetting display ink according to any one of claims 2 to 4.
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