CN107383928A - A kind of di-azo dyes, ink and electric moistening display - Google Patents

A kind of di-azo dyes, ink and electric moistening display Download PDF

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Publication number
CN107383928A
CN107383928A CN201710523209.XA CN201710523209A CN107383928A CN 107383928 A CN107383928 A CN 107383928A CN 201710523209 A CN201710523209 A CN 201710523209A CN 107383928 A CN107383928 A CN 107383928A
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China
Prior art keywords
phenyl
base
ink
azo dyes
hexyl
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CN201710523209.XA
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CN107383928B (en
Inventor
邓勇
叶德超
蒋洪伟
郭媛媛
李楠
周国富
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Shenzhen Guohua Optoelectronics Co Ltd
Academy of Shenzhen Guohua Optoelectronics
Shenzhen Guohua Optoelectronics Research Institute
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Shenzhen Guohua Optoelectronics Co Ltd
Shenzhen Guohua Optoelectronics Research Institute
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    • 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
    • C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
    • C09B35/02—Disazo dyes
    • C09B35/021—Disazo dyes characterised by two coupling components of the same type
    • C09B35/03—Disazo dyes characterised by two coupling components of the same type in which the coupling component is a heterocyclic compound
    • 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
    • C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
    • C09B35/02—Disazo dyes
    • C09B35/039—Disazo dyes characterised by the tetrazo component
    • C09B35/04—Disazo dyes characterised by the tetrazo component the tetrazo component being a benzene derivative
    • 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
    • C09D11/037—Printing inks characterised by features other than the chemical nature of the binder characterised by the pigment

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Electrochromic Elements, Electrophoresis, Or Variable Reflection Or Absorption Elements (AREA)
  • Inks, Pencil-Leads, Or Crayons (AREA)

Abstract

The invention discloses a kind of di-azo dyes, ink and electric moistening display, such dyestuff is the bisazo class organic dyestuff of the structure containing bis-pyrazolone, in orange, such organic dyestuff contains 2 pyrazolone heterocycle chromonic structures, with higher molar absorption coefficient, there is higher solubility in non-polar solven, dissolve in non-polar solven, ink is made, gained ink colors are bright-coloured, saturation degree is high, coloring intensity superelevation, it is highly suitable for electrowetting to show, the ink is filled into electric moistening display part, electric moistening display part has the relatively low switch response time, and the no reflow phenomenon under constant voltage.

Description

A kind of di-azo dyes, ink and electric moistening display
Technical field
The present invention relates to electric moistening display field, more particularly to a kind of di-azo dyes, ink and electrowetting to show Device.
Background technology
Electrowetting Display Technique (EFD, Electrofluide display), also referred to as electricity moistening Display Technique, are Holland The display prototype that principle is shown as with electrowetting that PHILIPS Co. developed first in 2003.The displaying principle is to utilize Change voltage so as to control the surface property of hydrophobic layer, change contact angle of the ink layer on hydrophobic layer：When being not powered on pressure, oil Ink forms a Colored pixels point to insulating barrier uniform wet；When applying voltage, the effect of electric field changes the surface of hydrophobic layer Performance makes the interfacial tension between ink-polar liquid-hydrophobic layer three-phase change, and ink is compressed, and forms transparent or base The pixel of plate background color, so as to obtain display image effect.
Electrowetting shows that ink material is the proprietary material that electrowetting shows color, therefore to dyestuff in non-polar solven Solubility, color saturation, coloring intensity etc. all have higher requirements.Patent WO 2003/071346, WO 2010/031860, Patent protection, anthracene all have been carried out to the ink material based on anthraquinone ring in US 2011/0226998, US 20130241815 The ink material of quinone structure is used for the advantage that electrowetting is shown and is that its polarity is relatively low, and the light fastness of most of dyestuff is excellent, But its inferior position is that coloring intensity is relatively low.Therefore, notice has progressively been transferred to exploitation by researchers has intensity of colour occurred frequently Azo dyes on, as patent US 8143382 to bisazo class pyrazolone series weld structure carry out Patent protection.
Existing published yellow electrowetting shows that organic dyestuff comprises only a pyrazolone heterocycle structure, mole suction Backscatter extinction logarithmic ratio is relatively low.
The content of the invention
The technical problems to be solved by the invention are to provide a kind of orange shown available for electrowetting, a kind of electricity profit Wet display orange ink.
The technical solution used in the present invention is：
A kind of di-azo dyes, shown in the general structure such as formula (I) of the di-azo dyes：
Wherein, R1、R2、R3、R4For any substituent.
In some preferred embodiments, R1、R2、R3、R4The alkyl for being 1-12 for substitution or unsubstituted carbon number Or phenyl.
In some preferred embodiments, R1For methyl, ethyl, propyl group, normal-butyl, n-pentyl, n-hexyl, normal heptane Base, normal octane base, isooctane base, nonyl, decane base, n-undecane base, dodecyl, phenyl, aminomethyl phenyl, ethylo benzene Any of base, propyl group phenyl, butyl phenyl, amyl group phenyl, hexyl phenyl, alkyl phenyl in heptan, octyl phenyl.
In some preferred embodiments, R2For methyl, ethyl, propyl group, normal-butyl, n-pentyl, n-hexyl, normal heptane Base, normal octane base, isooctane base, nonyl, decane base, n-undecane base, dodecyl, phenyl, aminomethyl phenyl, ethylo benzene Any of base, propyl group phenyl, butyl phenyl, amyl group phenyl, hexyl phenyl, alkyl phenyl in heptan, octyl phenyl.
In some preferred embodiments, R3For methyl, ethyl, propyl group, normal-butyl, n-pentyl, n-hexyl, normal heptane Base, normal octane base, isooctane base, nonyl, decane base, n-undecane base, dodecyl, phenyl, aminomethyl phenyl, ethylo benzene Any of base, propyl group phenyl, butyl phenyl, amyl group phenyl, hexyl phenyl, alkyl phenyl in heptan, octyl phenyl.
In some preferred embodiments, R4For methyl, ethyl, propyl group, normal-butyl, n-pentyl, n-hexyl, normal heptane Base, normal octane base, isooctane base, nonyl, decane base, n-undecane base, dodecyl, phenyl, aminomethyl phenyl, ethylo benzene Any of base, propyl group phenyl, butyl phenyl, amyl group phenyl, hexyl phenyl, alkyl phenyl in heptan, octyl phenyl.
Present invention also offers a kind of ink, the ink is dissolved in organic solvent by di-azo dyes as described above to be obtained Arrive.
In some preferred embodiments, the ink is dissolved in non-polar solven by the di-azo dyes to be obtained Arrive.
In some preferred embodiments, the non-polar solven is decane, n-dodecane, n-tetradecane, positive ten At least one of six alkane, fluorine-containing alkane, silane.
Present invention also offers a kind of electric moistening display, the electric moistening display includes ink as described above.
The beneficial effects of the invention are as follows：
The invention provides a kind of bisazo class organic dyestuff of structure containing bis-pyrazolone, in orange, such has engine dyeing Material contains 2 pyrazolone heterocycle chromonic structures, has higher molar absorption coefficient, good light stability, in non-polar solven With higher solubility, dissolve in non-polar solven, ink is made, gained ink colors are bright-coloured, saturation degree is high, color development is strong Superelevation is spent, is highly suitable for electrowetting and shows, the ink is filled into electric moistening display part, electric moistening display part tool There are relatively low switch response time, and the no reflow phenomenon under constant voltage.
Brief description of the drawings
Fig. 1 is Dyestuff synthesis flow chart in embodiment 1.
Embodiment
Embodiment 1：
Synthetic schemes shown in reference picture 1, prepares dyestuff：
Weigh 6.6g (132g/mol, 0.05mol) tertbutyloxycarbonyl hydrazine and be dissolved in 50mL n-hexanes, weigh 6.7g (114g/ Mol, 0.058mol) different octanal is slowly dropped in above-mentioned solution, it is warming up to back flow reaction 2h.Reaction is evaporated removing after terminating molten Agent, obtain compound 1, yield 100%.
Compound 1 is cooled to 0~5 DEG C, weigh 1mol/L borine tetrahydrofuran solutions 100mL be slowly dropped to it is above-mentioned anti- Answer in device, solvent is dichloromethane/petroleum ether=1：1,2h is reacted, obtains compound 2.15mL concentrated hydrochloric acids are measured, slowly It is added drop-wise in above-mentioned solution, is heated to flowing back after producing without obvious bubble, reacts 0.5h.Cool down after completion of the reaction, suction filtration removes The boric acid separated out is removed, solution is rotated into drying.Obtain compound 3, yield 78%.
Weigh 1.44g (144g/mol, 0.01mol) compound 3, sodium methoxide 0.54g (54g/mol, 0.01mol) is dissolved in In 20mL absolute ethyl alcohols, half an hour is stirred at room temperature, is filtered to remove inorganic salts.Filtrate is warming up to 60~75 DEG C.Weigh 1.3g (130g/mol, 0.01mol) ethyl acetoacetate is dissolved in 20mL ethanol, in being slowly dropped in 1h in above-mentioned solution, is incubated 6h.N-hexane extraction is used after completion of the reaction, is washed 2 times with 10% aqueous hydrochloric acid solution, is washed with water to neutrality.Collected organic layer, Drying is rotated, obtains the following compound 4 of structural formula, yield 57.2%.
Weigh 4- nitroanilines (138g/mol, 0.01mol) 1.38g to be dissolved in 50mL water, add concentrated hydrochloric acid 4mL, heating To 70 degrees Celsius of dissolvings, 0~5 DEG C is rapidly cooled to, natrium nitrosum 0.75g (69g/mol, 0.011mol) is weighed and is dissolved in 5mL water In, disposably it is added in above-mentioned solution, diazotising 30min.2.52g (252g/mol, 0.01mol) compound 4 is weighed to be dissolved in In 50mL ethanol, 0~5 DEG C is cooled to, above-mentioned diazol is slowly dropped in above-mentioned solution, using sodium hydrate aqueous solution control PH value of solution processed is 9.Filtered after coupling, dry, obtain compound 5, yield 76.7%.
Weigh Compound 5 (359g/mol, 0.00919mol) 3.3g is dissolved in 50mL toluene, is warming up to 80 DEG C.Weigh nine Hydrated sodium sulfide (240g/mol, 0.0459mol) 11.0g is added in above-mentioned reaction solution.React 2h.Reaction terminates rear water Wash, be layered, take oil reservoir revolving to dry and remove solvent, obtain compound 6, yield 95.4%.
Weigh Compound 6 (329g/mol, 0.0052mol) compound 6 is dissolved in 10mL acetic acid and 5mL propionic acid, is cooled to 0 ~5 DEG C, disposably add natrium nitrosum (69g/mol, 0.015mol) 1g, diazotising 1h.Weigh Compound 4 (210g/mol, 0.0052mol) 1.1g is dissolved in 100mL ethanol, is cooled to -10~0 DEG C, and above-mentioned diazol is slowly added into Coupling Solution Coupling, it is 9 with sodium hydrate aqueous solution regulation pH value of solution.Rear coupling reaction 2h is added dropwise.Filtering, dry compound A, i.e., For orange A, yield 70%.
Separated using column chromatography chromatogram, carry out nuclear magnetic spectrogram analysis after purification, its spectral data is：1H NMR(CDCl3)： 13.56(s,2H),7.432(s,4H),3.665-3.585(m,4H),2.269(s,6H),1.861(m,2H),1.305(16H, m),0.929-0.876(12H,m).Spectral data certification structure is correct.
The dyestuff good light stability that the present embodiment is prepared, and there is high solubility, it can be dissolved in organic molten Ink is prepared in agent.Especially in non-polar organic solvent, such as decane, n-dodecane, n-tetradecane, positive 16 In alkane, fluorine-containing alkane, silane etc., the dyestuff is respectively provided with high solubility, and dyestuff is dissolved in non-polar organic solvent, prepares Obtained ink colors are bright-coloured, saturation degree is high, coloring intensity superelevation, are highly suitable for electrowetting and show.
Embodiment 2：
Compound B is synthesized using the same synthetic method of same embodiment 1, its structural formula is：
Analyzed using nuclear magnetic spectrogram, its spectral data is：1H NMR(CDCl3)：13.26(s,2H),7.433(s,4H), 3.605-3.385(m,4H),2.551(m,4H),1.787(m,4H),1.305-1.289(32H,m),0.950-0.856(24H, m).Spectral data certification structure is correct.
The dyestuff good light stability that the present embodiment is prepared, and there is high solubility, it can be dissolved in organic molten Ink is prepared in agent.Especially in non-polar organic solvent, such as decane, n-dodecane, n-tetradecane, positive 16 In alkane, fluorine-containing alkane, silane etc., the dyestuff is respectively provided with high solubility, and dyestuff is dissolved in non-polar organic solvent, prepares Obtained ink colors are bright-coloured, saturation degree is high, coloring intensity superelevation, are highly suitable for electrowetting and show.
Embodiment 3：
Compound C is synthesized using the same synthetic method of same embodiment 1, its structural formula is：
Analyzed using nuclear magnetic spectrogram, its spectral data is：1H NMR(CDCl3)：13.86(s,2H),7.333(s,4H), 7.213(d,4H),7.103(d,4H),2.585(m,8H),1.878(m,2H),1.787(m,4H),1.385-1.289(20H, m),0.900-0.856(18H,m).Spectral data certification structure is correct.
The dyestuff good light stability that the present embodiment is prepared, and there is high solubility, it can be dissolved in organic molten Ink is prepared in agent.Especially in non-polar organic solvent, such as decane, n-dodecane, n-tetradecane, positive 16 In alkane, fluorine-containing alkane, silane etc., the dyestuff is respectively provided with high solubility, and dyestuff is dissolved in non-polar organic solvent, prepares Obtained ink colors are bright-coloured, saturation degree is high, coloring intensity superelevation, are highly suitable for electrowetting and show.
Embodiment 4：
The dyestuff that 0.1g embodiments 1-3 is prepared is weighed respectively, is dissolved in 10mL decanes, is prepared into electrowetting respectively Show ink I, II, III.The color of prepared ink material, maximum absorption wavelength (λ max), solubility C at 25 DEG C, mole Absorptivity ε and ε C are as shown in table 1.
The ink material results of property of table 1
Sample Color λmax(nm) C solubility (molL-1) ε(L.mol-1·cm-1) ε·C
Ink I It is orange 475 0.018 43386 780
Ink I I It is orange 475 0.115 40768 4688
Ink I II It is red 490 0.100 48763 4876
As shown in Table 1, using electrowetting ink material made of the dyestuff of invention have high solubility and Molar extinction coefficient, ε C values are also higher, bright-colored, and saturation degree is high.The ink of preparation is filled into electric moistening display part In, its electrical response performance energy is tested, obtains result such as table 2.
Table 2 uses the electrical response performance energy of the electric moistening display of ink material
As shown in Table 2, the electric moistening display part filled using the ink material of invention has relatively low switch Response time, and the no reflow phenomenon under constant voltage, ink made from dyestuff of the present invention are highly suitable for electrowetting and shown Show.

Claims (10)

1. a kind of di-azo dyes, it is characterised in that shown in the general structure of the di-azo dyes such as formula (I)：
Wherein, R1、R2、R3、R4For any substituent.
2. di-azo dyes according to claim 1, it is characterised in that R1、R2、R3、R4For substitution or unsubstituted carbon Atomicity is 1-12 alkyl or phenyl.
3. di-azo dyes according to claim 1, it is characterised in that R1For methyl, ethyl, propyl group, normal-butyl, just Amyl group, n-hexyl, constructed from normal heptyl, normal octane base, isooctane base, nonyl, decane base, n-undecane base, dodecyl, benzene Base, aminomethyl phenyl, ethylphenyl, propyl group phenyl, butyl phenyl, amyl group phenyl, hexyl phenyl, alkyl phenyl in heptan, octyl benzene Any of base.
4. di-azo dyes according to claim 1, it is characterised in that R2For methyl, ethyl, propyl group, normal-butyl, just Amyl group, n-hexyl, constructed from normal heptyl, normal octane base, isooctane base, nonyl, decane base, n-undecane base, dodecyl, benzene Base, aminomethyl phenyl, ethylphenyl, propyl group phenyl, butyl phenyl, amyl group phenyl, hexyl phenyl, alkyl phenyl in heptan, octyl benzene Any of base.
5. according to the di-azo dyes described in claim any one of 1-4, it is characterised in that R3For methyl, ethyl, propyl group, just Butyl, n-pentyl, n-hexyl, constructed from normal heptyl, normal octane base, isooctane base, nonyl, decane base, n-undecane base, positive 12 It is alkyl, phenyl, aminomethyl phenyl, ethylphenyl, propyl group phenyl, butyl phenyl, amyl group phenyl, hexyl phenyl, alkyl phenyl in heptan, pungent Any of alkyl phenyl.
6. according to the di-azo dyes described in claim any one of 1-4, it is characterised in that R4For methyl, ethyl, propyl group, just Butyl, n-pentyl, n-hexyl, constructed from normal heptyl, normal octane base, isooctane base, nonyl, decane base, n-undecane base, positive 12 It is alkyl, phenyl, aminomethyl phenyl, ethylphenyl, propyl group phenyl, butyl phenyl, amyl group phenyl, hexyl phenyl, alkyl phenyl in heptan, pungent Any of alkyl phenyl.
7. a kind of ink, it is characterised in that the ink is dissolved in organic by any one of the claim 1-6 di-azo dyes Obtained in solvent.
8. ink according to claim 7, it is characterised in that the ink is dissolved in nonpolar by the di-azo dyes Obtained in solvent.
9. ink according to claim 8, it is characterised in that the non-polar solven is decane, n-dodecane, positive ten At least one of four alkane, hexadecane, fluorine-containing alkane, silane.
10. a kind of electric moistening display, it is characterised in that the electric moistening display is included described in claim any one of 7-9 Ink.
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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111534126A (en) * 2020-04-28 2020-08-14 深圳市国华光电科技有限公司 Multi-chromophore pyrazolone azo dyes, inks and electrowetting displays

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0580553A (en) * 1991-09-24 1993-04-02 Mita Ind Co Ltd Electrophotographic sensitive body
US5543259A (en) * 1993-12-13 1996-08-06 Xerox Corporation Developer compositions

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0580553A (en) * 1991-09-24 1993-04-02 Mita Ind Co Ltd Electrophotographic sensitive body
US5543259A (en) * 1993-12-13 1996-08-06 Xerox Corporation Developer compositions

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
HEMAL B. MEHTA ET AL.: "Synthesis and antimicrobial activities of new mono and bisphenyl linked bispyrazole and bispyrazolone derivatives", 《ARABIAN JOURNAL OF CHEMISTRY》 *
JALAL ISAAD ET AL.: "Simple route to a novel class of pyrazolidine-3,5-dione based azo dyes", 《TETRAHEDRON LETTERS》 *
JALAL ISAAD: "Highly water soluble dyes based on pyrazolone derivatives of carbohydrates", 《TETRAHEDRON》 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111534126A (en) * 2020-04-28 2020-08-14 深圳市国华光电科技有限公司 Multi-chromophore pyrazolone azo dyes, inks and electrowetting displays

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Application publication date: 20171124

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