CN105542507A - Red dye and red dye composition - Google Patents

Red dye and red dye composition Download PDF

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Publication number
CN105542507A
CN105542507A CN201510687946.4A CN201510687946A CN105542507A CN 105542507 A CN105542507 A CN 105542507A CN 201510687946 A CN201510687946 A CN 201510687946A CN 105542507 A CN105542507 A CN 105542507A
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China
Prior art keywords
orchil
formula
nhc
substrate
hydrogen atom
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CN201510687946.4A
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Chinese (zh)
Inventor
黄群佑
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T&t Industries Corp
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T&t Industries Corp
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Publication of CN105542507A publication Critical patent/CN105542507A/en
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    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09BORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B1/00Dyes with anthracene nucleus not condensed with any other ring
    • C09B1/16Amino-anthraquinones
    • C09B1/20Preparation from starting materials already containing the anthracene nucleus
    • C09B1/26Dyes with amino groups substituted by hydrocarbon radicals
    • C09B1/28Dyes with amino groups substituted by hydrocarbon radicals substituted by alkyl, aralkyl or cyclo alkyl groups
    • C09B1/285Dyes with no other substituents than the amino groups
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09BORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0071Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
    • C09B67/0083Solutions of dyes
    • GPHYSICS
    • G02OPTICS
    • G02BOPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B26/00Optical devices or arrangements for the control of light using movable or deformable optical elements
    • G02B26/004Optical devices or arrangements for the control of light using movable or deformable optical elements based on a displacement or a deformation of a fluid
    • G02B26/005Optical 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

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Electrochromic Elements, Electrophoresis, Or Variable Reflection Or Absorption Elements (AREA)

Abstract

The present invention provides a red dye and a red dye composition for an electrowetting display device, the red dye comprising a plurality of compounds represented by the formula (formula 1):(formula 1), wherein X, Y in the compound respectively and independently represent hydrogen atom, substituted or unsubstituted alkyl with 2-20 carbon atoms, R1、R2Each independently represents a hydrogen atom or-NHCnH2n+1N is a positive integer, R1、R2May or may not be the same. The red dye and the red dye composition provided by the invention have high light fastness.

Description

Orchil and orchil component
Technical field
The present invention relates to a kind of orchil and orchil component, particularly relate to a kind of orchil for electric moisten display device and orchil component.
Background technology
In recent years, Electronic Paper (E-paper) and e-book (E-book) are just flourish, and having more frivolously will become the trend of following main development with the indicating meter of deflection characteristic.Electric moistening display (ElectrowettingDisplayDevice, EWD) is then a kind of display panel that can be applicable to e-book and Electronic Paper.
Generally speaking, electric moistening display comprises top electrode, lower electrode and the polar fluid be sandwiched between two electrodes and non-polar fluid.The working method of electric moistening display is, when no voltage is applied, ink layer (non-polar fluid) is covered with pixel cell.Incident light so can be made to be presented on state of by reflective layer reflects.In addition, when making pixel cell present on state of, then to its upper and lower two electrode application voltage, with the edge making ink layer be contracted in described pixel region, and then expose the reflecting layer be positioned at below ink layer.Incident light so can be made to be presented on state of by reflective layer reflects.
On the other hand, if make electric moistening display color display, generally coloured dye can be mixed in the ink layer of electric moistening display.When not applying a voltage to upper/lower electrode, the ink layer being mixed with coloured dye is covered with pixel cell, the ink layer that incident light can be made to be perforated through be mixed with coloured dye and make described pixel cell present coloured image.Otherwise, when making pixel cell present dark-state, then to its upper and lower two electrode application voltage, with the edge making ink layer be retracted to described pixel region.But the fastness to light (lightfastness) of conventional color dyestuff is not good, and must pass through complicated purge process and just can use, the development of colored electroweting indicating meter is still had and manyly improves part.
Summary of the invention
The invention provides a kind of orchil, it has high fastness to light.
The invention provides a kind of orchil component, it comprises above-mentioned orchil, and this orchil component can have high fastness to light.
The present invention proposes a kind of orchil, and for electric moisten display device, this orchil comprises the multiple compound represented by chemical formula (formula 1):
X, Y in wherein said compound represent being substituted or being unsubstituted alkyl, R of hydrogen atom, carbon number 2 ~ 20 independently of one another 1, R 2represent hydrogen atom or-NHC independently of one another nh 2n+1, n is positive integer, R 1, R 2can identical also can not be identical.
The present invention proposes a kind of orchil component, and for electric moisten display device, this orchil component comprises orchil and at least one nonpolar or low polar solvent.Above-mentioned orchil comprises the multiple compound represented by chemical formula (formula 1):
X, Y in wherein said compound represent being substituted or being unsubstituted alkyl, R of hydrogen atom, carbon number 2 ~ 20 independently of one another 1, R 2represent hydrogen atom or-NHC independently of one another nh 2n+1, n is positive integer, R 1, R 2can identical also can not be identical.
The present invention proposes another kind of orchil component, and for electric moisten display device, this orchil component comprises orchil and at least one in the compound that represented by chemical formula (formula 2) or (formula 3):
Above-mentioned orchil comprises the multiple compound represented by chemical formula (formula 1):
X, Y in wherein said compound represent being substituted or being unsubstituted alkyl, R of hydrogen atom, carbon number 2 ~ 20 independently of one another 1, R 2represent hydrogen atom or-NHC independently of one another nh 2n+1, n is positive integer, R 1, R 2can identical also can not be identical.
Based on above-mentioned, the orchil comprising the multiple compound represented by chemical formula (formula 1) according to an embodiment of the invention has high fastness to light.In addition, at least one of being arranged in pairs or groups by this orchil in the compound represented by chemical formula (formula 2) or (formula 3) uses, and the electric moisten display device of this orchil component of application can be made more to meet the fixed gamut standards of TSC-system.
For above-mentioned feature and advantage of the present invention can be become apparent, special embodiment below, and coordinate accompanying drawing to be described in detail below.
Accompanying drawing explanation
Fig. 1 is the diagrammatic cross-section of the electric moisten display device of one embodiment of the invention.
Description of reference numerals:
100: first substrate;
102,202: substrate;
104,204: electrode layer;
106: dielectric layer;
108: hydrophobic layer;
110: hydrophilic curtain wall structure;
112: unit area;
130: polar solvent layer;
140: non-polar color solution layer;
150: seal gum;
200: second substrate.
Embodiment
Fig. 1 is the diagrammatic cross-section of the electric moisten display device of one embodiment of the invention.Please refer to Fig. 1, the electric moisten display device of the present embodiment comprises first substrate 100, second substrate 200, polar solvent layer 130 and non-polar color solution layer 140.
First substrate 100 is positioned opposite to each other with second substrate 200.In the present embodiment, first substrate 100 comprises substrate 102, electrode layer 104, dielectric layer 106, hydrophobic layer 108 and hydrophilic curtain wall structure 110.
Substrate 102 is mainly used for carrying display unit, and substrate 102 can be transparency carrier, and its material is such as glass, quartz or organic polymer.Substrate 102 also can be reflection substrate.In addition, substrate 102 can be hard substrate also can be soft substrate plate.
Electrode layer 104 is positioned at the side of substrate 102.In the present embodiment, electrode layer 104 comprises pixel electrode that multiple active member and active member be electrically connected to form pel array layer.In other embodiments, electrode layer 104 can be simple Passive electrode pattern.In addition, electrode layer 104 can comprise the metallic substance with high reverse--bias character.If electrode layer 104 uses transparent conductive material, then the lower of electrode layer 104 can arrange one deck reflecting layer further.
Dielectric layer 106 is positioned on electrode layer 104.The material of dielectric layer 106 can be silicon oxide, silicon nitride or other dielectric materials.
Hydrophobic layer 108 is positioned on dielectric layer 106.In the present embodiment, the method forming hydrophobic layer 108 can be carries out hydrophobic surface process to the surface of dielectric layer 106, forms hydrophobic layer 108 so that hydrophobic upgrading is carried out on the surface of dielectric layer 106.According to another embodiment, the method forming hydrophobic layer 108 can be directly carries out coating processes, plating run or deposition procedure, to form hydrophobic layer 108 on dielectric layer 106.
Hydrophilic curtain wall structure 110 is positioned on hydrophobic layer 108, to define multiple unit area 112 on first substrate 100.Described unit area 112 is corresponding display pixel cells.Therefore, if the electrode layer of first substrate 100 104 is pel array layer, then the electrode layer 104 in each unit area 112 is that correspondence is provided with at least one active member and at least one pixel electrode.
In addition, second substrate 200 comprises substrate 202 and electrode layer 204.Second substrate 200 also can be described as subtend substrate.The substrate 202 of second substrate 200 can be glass, quartz or organic polymer substrate.Substrate 202 can be hard substrate also can be soft substrate plate.
Electrode layer 204 is positioned at the side of substrate 202.Electrode layer 204 also can be described as counter electrode.Therefore, electrode layer 204 and electrode layer 104 are used to manipulate the liquid level between first substrate 100 and second substrate 200, use the object reaching display.In general, electrode layer 204 can be transparent electrode layer, and its material comprises metal oxide, such as, be indium tin oxide or indium-zinc oxide etc.
In addition, between first substrate 100 and second substrate 200, also comprise seal gum 150, together with being sticked together with second substrate 200 by first substrate 100, and form a spatial accommodation between first substrate 100 and second substrate 200.
Polar solvent layer 130 is between first substrate 100 and second substrate 200.In more detail, polar solvent layer 130 is in the spatial accommodation between first substrate 100 and second substrate 200.Polar solvent layer 130 can be water or other polar liquid.
Non-polar color solution layer 140 fills in the unit area 112 that hydrophilic curtain wall structure 110 defines.The non-polar color solution layer 140 being positioned at unit area 112 can comprise the color solution of multiple color.In the present embodiment, a kind of color solution of color can be inserted in each unit area 112.For example, non-polar color solution layer 140 can comprise the color solutions such as black, red, yellow, blue, and is insert the color solutions such as black, red, yellow or blue separately in unit area 112, so the present invention is not limited thereto.
Specifically, above-mentioned non-polar color solution layer 140 comprises orchil component according to some embodiments of the invention.Above-mentioned orchil component can comprise orchil and at least one nonpolar or low polar solvent.Above-mentioned orchil comprises the multiple compound represented by chemical formula (formula 1):
In the present embodiment, X, the Y of (formula 1) can represent being substituted or being unsubstituted alkyl of hydrogen atom, carbon number 2 ~ 20 independently of one another, so the present invention is not limited thereto.Abovementioned alkyl can be straight chain, side chain or ring-type.
In the present embodiment, the R of (formula 1) 1, R 2hydrogen atom or-NHC can be represented independently of one another nh 2n+1, n is positive integer.R 1, R 2can identical also can not be identical.For example, R 1, R 2-NHC can be represented independently of one another 8h 17,-NHC 12h 25or-NHC 18h 37.
It is worth mentioning that, compared to conventional color dyestuff, the orchil comprising the multiple compound represented by chemical formula (formula 1) of the present invention has high fastness to light, therefore be conducive to application in the display, particularly be applied in colored electroweting indicating meter, so the present invention is not limited thereto.
In the present embodiment, above-mentioned nonpolar or low polar solvent can be the alkane (such as hexane, heptane, octane, nonane, decane, undecane, dodecane, tridecane, the tetradecane, pentadecane, n-Hexadecane etc.) of carbon number 1 ~ 30, naphthenic hydrocarbon (such as naphthalane), oil (such as silicone oil) or its mixture, so the present invention is not limited thereto.
Specifically, based on the viewpoint reducing colour cast, orchil component of the present invention also can comprise at least one in the compound represented by chemical formula (formula 2) or (formula 3):
More specifically, orchil component of the present invention can comprise following three kinds of compositions: the orchil comprising the multiple compound represented by (formula 1) the arrange in pairs or groups compound (forming two) represented by (formula 3), the orchil comprising the multiple compound represented by (formula 1) of the compound (forming) represented by (formula 2), the orchil comprising the multiple compound represented by (formula 1) of arranging in pairs or groups is arranged in pairs or groups the compound represented by chemical formula (formula 2) and the compound (forming three) represented by chemical formula (formula 3).Based on the viewpoint reducing colour cast, tetrazo kind solvent.In the orchil component of above-mentioned three kinds of compositions, more meet with (composition three) gamut standards formulated by NTSC (NationalTelevisionSystemCommittee, NTSC) again.
Optionally, the such as multiple additives such as viscosity adjusting control agent, other oil additives can be added, in orchil component, so the present invention is not limited thereto.
In the present embodiment, with the total weight of orchil component, the content comprising the orchil of the multiple compound represented by chemical formula (formula 1) is 5 ~ 30wt%, the content of the compound represented by chemical formula (formula 2) or (formula 3) is 95 ~ 70wt%, and content that is nonpolar or low polar solvent is 60 ~ 99wt%.
The preparation method of orchil, orchil component and electric moisten display device is according to an embodiment of the invention further illustrated below with several experimental example.
< experimental example >
The preparation of orchil
First, prepare the 1-nitroanthraquinone (1-nitro-anthraquinone) of 0.5 ~ 10 mole, the aniline (aniline) of 0.5 ~ 10 mole, the n-octyl amine (n-octylamine) of 0.5 ~ 10 mole, the n-dodecylamine (n-dodecylamine) of 0.5 ~ 10 mole, the octadecyl amine (n-octadecylamine) of 0.5 ~ 10 mole and the NaOH of 0.5 ~ 10 mole, mixed and be dissolved in toluene.Then, reflux after 0.5 ~ 5 hour at 100 ~ 120 DEG C.Subsequently, the said mixture reacted is filtered, a solid can be obtained.Finally, with deionized water, the cleaning of this solid is presented to deionized water colourless, the orchil comprising the multiple compound represented by (formula 1) can be obtained.
In this experimental example, X, Y in those compounds are hydrogen atom, R 1comprise-NHC 8h 17,-NHC 12h 25and-NHC 18h 37, R 2be hydrogen atom, so the present invention is not limited thereto.
The preparation of orchil component
First, orchil obtained in above-mentioned experimental example is mixed with at least one in the compound represented by following chemical formula (formula 2) or (formula 3).Then, said mixture is dissolved in such as decane or dodecane, the orchil component of one embodiment of the invention can be obtained.With the total weight of orchil component, the content of orchil is 15wt%, and the content of the compound represented by chemical formula (formula 2) or (formula 3) is 85wt%.
The preparation of electric moisten display device
First, sequentially on substrate, electrode layer and dielectric layer is made.After above-mentioned two retes of formation, utilize coating process, hydrophobic material is coated on dielectric layer.Then, photoresist is coated on dielectric layer, and utilize exposure imaging processing procedure, patterning program is carried out to photoresistance, to form multiple curtain wall structure.Subsequently, utilize coating process, the orchil component obtained by above-mentioned experimental example is inserted between multiple curtain wall structure.Finally, after adding polar liquid, carry out group and stand and encapsulation procedure, electric moisten display device according to an embodiment of the invention can be obtained.
It is worth mentioning that, according to the standard colour cast measuring basis of indicating meter, when △ Eab value is less than 3, represent that human eye cannot tell heterochromia, and the △ Eab value of the electric moisten display device obtained according to above-mentioned experimental example is 2.29.It can thus be appreciated that electric moisten display device of the present invention does not almost have the problem of colour cast.
Last it is noted that above each embodiment is only in order to illustrate technical scheme of the present invention, be not intended to limit; Although with reference to foregoing embodiments to invention has been detailed description, those of ordinary skill in the art is to be understood that: it still can be modified to the technical scheme described in foregoing embodiments, or carries out equivalent replacement to wherein some or all of technical characteristic; And these amendments or replacement, do not make the essence of appropriate technical solution depart from the scope of various embodiments of the present invention technical scheme.

Claims (7)

1. an orchil, is characterized in that, for electric moisten display device, described orchil comprises the multiple compound represented by chemical formula (formula 1):
X, Y in wherein said compound are the R in hydrogen atom, described compound 1comprise-NHC 8h 17,-NHC 12h 25and-NHC 18h 37, the R in described compound 2for hydrogen atom.
2. an orchil component, is characterized in that, for electric moisten display device, described orchil component comprises:
One orchil, comprises the multiple compound represented by chemical formula (1):
X, Y in wherein said compound are the R in hydrogen atom, described compound 1comprise-NHC 8h 17,-NHC 12h 25and-NHC 18h 37, the R in described compound 2for hydrogen atom; And
At least one nonpolar or low polar solvent.
3. orchil component according to claim 2, is characterized in that, described at least one nonpolar or low polar solvent comprises the alkane of carbon number 1 ~ 30, naphthenic hydrocarbon, oil or its mixture.
4. orchil component according to claim 2, is characterized in that, with the total weight of described orchil component, the content of described orchil is 5 ~ 30wt%, and described content that is nonpolar or low polar solvent is 60 ~ 99wt%.
5. an orchil component, is characterized in that, for electric moisten display device, described orchil component comprises:
One orchil, comprises the multiple compound represented by chemical formula (formula 1):
X, Y in wherein said compound are the R in hydrogen atom, described compound 1comprise-NHC 8h 17,-NHC 12h 25and-NHC 18h 37, the R in described compound 2for hydrogen atom; And
At least one in the compound represented by chemical formula (formula 2) or (formula 3):
6. orchil component according to claim 5, is characterized in that, also comprises at least one nonpolar or low polar solvent.
7. orchil component according to claim 6, it is characterized in that, with the total weight of described orchil component, the content of described orchil is 5 ~ 30wt%, the content of the described compound represented by chemical formula (formula 2) or (formula 3) is 95 ~ 70wt%, and described content that is nonpolar or low polar solvent is 60 ~ 99wt%.
CN201510687946.4A 2014-10-23 2015-10-22 Red dye and red dye composition Pending CN105542507A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
TW103136648 2014-10-23
TW103136648A TW201615761A (en) 2014-10-23 2014-10-23 Red color dye compound and red color dye composition

Publications (1)

Publication Number Publication Date
CN105542507A true CN105542507A (en) 2016-05-04

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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1469177A (en) * 2002-07-17 2004-01-21 ϣ Method and composition for improving performance of cataphoresis display
CN102159651A (en) * 2008-09-19 2011-08-17 利奎阿维斯塔股份有限公司 Improvements in relation to electrowetting elements
CN103998529A (en) * 2011-12-26 2014-08-20 富士胶片株式会社 Colored composition and image display structure
CN104570605A (en) * 2013-10-17 2015-04-29 住友化学株式会社 Colored curable resin composition

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1469177A (en) * 2002-07-17 2004-01-21 ϣ Method and composition for improving performance of cataphoresis display
CN102159651A (en) * 2008-09-19 2011-08-17 利奎阿维斯塔股份有限公司 Improvements in relation to electrowetting elements
CN103998529A (en) * 2011-12-26 2014-08-20 富士胶片株式会社 Colored composition and image display structure
CN104570605A (en) * 2013-10-17 2015-04-29 住友化学株式会社 Colored curable resin composition

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
张淑芬 等: "含长碳链蒽醌型聚丙烯用红色染料的合成与应用", 《染料与染色》 *

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