CN106478672A - A kind of indoloquinoxalines derivant material and its electroluminescent device - Google Patents
A kind of indoloquinoxalines derivant material and its electroluminescent device Download PDFInfo
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Abstract
Indoloquinoxalines derivative preparation method is related to Minute Organic Synthesis and photoelectric material application, and indoloquinoxalines are applied to organic electroluminescent, photovoltaic cell, Organic Electricity storage, nonlinear optical organic, chemistry and the Material Field such as bio-sensing and organic laser as important intermediate.The present invention is a kind of indoloquinoxalines derivative preparation method and its electroluminescent device, and tool advantage is：(1) route of synthesizing halogen indoloquinoxalines monomer is simple, easily pass through to introduce saturation or unsaturated aliphatic hydrocarbyl moiety group realize can spin coating derivant；(2) pass through to introduce aromatic rings, be effectively improved injection and the transmittability in hole, improve device efficiency, and be possibly used for carrier injection or transmission layer material；(3) high glass transition temperature and the high thermal stability of indoloquinoxalines are maintained；(4) fluorescence emission spectrum and triplet have effectively been modulated, thus forming good material of main part.
Description
Technical field
The invention belongs to organic photoelectrical material sciemtifec and technical sphere and in particular to a class indoloquinoxalines derivant material and its
Preparation method, and by this materials application in organic electroluminescent, organic integrated circuits, organic solar batteries, organic effect
The organic electronics such as pipe, dye laser, organic non linear optical material and fluorescent probe field.
Background technology
Tang with Kodak in 1987 et al. uses 8-hydroxyquinoline aluminum first using ultra-thin membrane technology
(Alq3) make double-deck organic electroluminescence device (LED) [Appl.Phys.Lett.1987,51,913.] as luminescent layer,
The epoch-making progress of organic electroluminescent starts.Nineteen ninety, Britain's all one's life laboratory Friend [Nature 1990,
347,539.] et al. the reported first electroluminescent of polystyrene support (PPV), Heeger group in 1991
[Appl.Phys.Lett 1991,58,1982] is made for salmon pink LED made with spin-coating film, has opened macromolecule from this
Electroluminescent material and the research of device (PLED).Drive because organic electroluminescence device has actively luminous, low-voltage direct-current
The advantages of dynamic, all solidstate, wide viewing angle, low-power, fast response time, low cost, all these inorganic semiconductor materials are not comparable
Intend, thus have broad application prospects.But compared with inorganic electroluminescence device, organic electroluminescence device stability
Difference, driving voltage is high, and the thickness of organic layer affects greatly on the driving voltage of device, and organic layer carrier mobility is relatively low.Cause
This, reduce driving voltage, improves Carrier Injection Efficiency and efficiency of transmission is most important.
Very well, and heat stability is strong for the planar conjugate of indoloquinoxalines molecule, but due to its HOMO, LUMO and
The anode of LED, the work function of negative electrode do not match that, thus result in hole and the injection of electronics is difficult and uneven.Therefore design,
Synthesis and exploitation have hole and electric charge injection and are particularly important with the indoloquinoxalines class material of transmission performance.By virtue
The indoloquinoxalines derivant that ring is coupled, enhances conjugacy, and intermolecular π-π effect, has the work(of transporting holes
Can, but up to the present, seldom have the paper in organic electronic field for the indoloquinoxalines system and patent report.
Content of the invention
It is an object of the invention to proposing a kind of hole injection layer material for efficient and long life OLED and its conjunction
One-tenth method.Big conjugate planes molecule indoloquinoxalines are connected by aromatic ring, modifies from material and electronic structure modulates two
Angle considers that synthesis has high performance organic photoelectrical material.Study such material in electroluminescent organic material, organic simultaneously
Integrated circuit, organic solar batteries, organic field-effect tube, dye laser, organic non linear optical material and fluorescent probe etc.
The application in organic electronics field.
The present invention has synthesized a series of conjugate derivative material of indoloquinoxalines, and the molecular structural formula of compound is such as
Under：
Wherein, R is hydrogen or straight chain, side chain or the cyclic alkyl chain with 1 to 22 carbon atom；Or for have 2 to
The thiazolinyl of 40 carbon atoms, alkynyl, aryl, wherein one or more carbon atoms can be taken by hetero atom Si, Se, O, S, N, sulfone
In generation, the hydrogen on one or more carbon atoms can be replaced by fluorine or cyano group；
Ar is aromatic rings, can be following any one：
Wherein R is hydrogen or straight chain, side chain or the cyclic alkyl chain with 1 to 22 carbon atom；Or for having 2 to 40
The thiazolinyl of individual carbon atom, alkynyl, aryl, wherein one or more carbon atoms can be taken by hetero atom Si, Se, O, S, N, sulfone
In generation, the hydrogen on one or more carbon atoms can be replaced by fluorine or cyano group.
N is 1 or 2 or 3 or 4 or 5 or 6.
The preparation method of this indoloquinoxalines derivant material, its step is as follows：
The first step：By halogeno indole -2 of 1 times of equivalent, 3- diketone, 1.2-1.5 times of equivalent o-phenylenediamine, noble gases are protected
Shield, acetic acid makees solvent, 80-90 DEG C of reaction 8-10h, and standing or recrystallization or column chromatography or thin layer chromatography purification obtain second step
Raw material；
Second step：By 1 times work as content of starting materials, solvent DMF or dioxane or 2- methyltetrahydrofuran, 1.5-2 times of equivalent 1
To halo saturation or the unsaturated fatty chain base of 40 carbon atoms, 150 DEG C of backflow 5-8 hours, reaction adds dichloro after terminating
Methane or ethyl acetate, sodium-chloride water solution or potassium chloride solution mix and blend 20 minutes -1 hour, merge organic faciess, standing
Or recrystallization or column chromatography or thin layer chromatography purification obtain the 3rd step raw material；
3rd step：1 times is worked as content of starting materials, the copper of 0.01-0.05 times of equivalent or copper powder or iodate Asia ketone or Schweinfurt green or palladium
Or palladium or [1,1 '-bis- (diphenylphosphine) ferrocene] palladium chloride or four triphenyl phosphorus palladiums or diacetyl two (triphenylphosphine)
Palladium or double (triphenylphosphine) palladium of dichloro or [1,1 '-bis- (diphenylphosphino) ferrocene] palladium chloride, the Ar of 1-6 times of equivalent or halogen
The tin reagent of the Grignard reagent of the borate of the boric acid for Ar or Ar or Ar or Ar or Ar, potassium carbonate or cesium carbonate or lithium carbonate or
Sodium sulfate or potassium sulfate or potassium acetate or Sodium Acetate Trihydrate, atmospheric atmosphere or inert gas shielding, DMA or toluene or dimethylbenzene or front three
Solvent made by benzene or chlorobenzene or dichloro-benzenes or dioxane, 90-150 DEG C, reacts 10-24h under 1 atmospheric pressure, reaction terminates
Add dichloromethane or ethyl acetate, sodium-chloride water solution or potassium chloride solution mix and blend 20 minutes -1 hour afterwards, merge
Organic faciess, standing or recrystallization or column chromatography or thin layer chromatography purification obtain indoloquinoxalines derivant material.
Compound-material proposed by the present invention can serve as electroluminescent organic material, organic integrated circuits, organic laser
Material, the semi-conducting material of organic field-effect tube, organic solar battery material, organic non linear optical material etc..
By nuclear magnetic resonance, NMR (NMR), chromaticness online (GC-MS), Matrix-assisted laser desorption ionization
(MALDI-TOF-MS) the halogen monomer of intermediate and coupled derivative material structure are characterized, by thermogravimetric analysiss and heating differential analysis
Test the heat stability of material, characterize their electrochemical properties by cyclic voltammetry.
On this basis, Preliminary design device is evaluating 8 or 9 indoloquinoxalines coupled derivative materials.
Main advantages of the present invention are：
1, the route of synthesizing halogen indoloquinoxalines monomer is simple, easily passes through to introduce saturation or unsaturated aliphatic hydrocarbyl moiety
Group with realize can spin coating derivant.
2, by introducing aromatic rings Effective Regulation, the injection improving hole and transmittability, improve device efficiency, and
It is possibly used for carrier injection or transmission layer material.
3, maintain high glass transition temperature and the high thermal stability of indoloquinoxalines.
4, effectively modulate fluorescence emission spectrum and triplet, thus forming good material of main part.
Brief description
Fig. 1 is the UV-PL spectrogram of IQ1；
Fig. 2 is the UV-PL spectrogram of IQ2；
Fig. 3 is the current-voltage-brightness curve chart of device prepared by with IQ2 as hole injection layer；
Fig. 4 is the electric current-efficiency curve diagram of device prepared by with IQ2 as hole injection layer.
Specific embodiment
The content of patent for a better understanding of the present invention, to further illustrate this below by specific embodiment
Bright technical scheme.Specifically include synthesis, property testing and device preparation.But these embodiments are not intended to limit the present invention.
Embodiment 1：8,8- (phenyl tetrafluoride)-two (6- (2- ethylhexyl) indoloquinoxalines 8,8 '-(perfluoro-
Isosorbide-5-Nitrae-phenylene) bis (6- (2-ethylhexyl) -6H-indolo [2,3-b] quinoxaline) (IQ1) synthesis
(1) 8- bromo- 6- hydrogen-indoloquinoxalines
6- bromo-isatin (9.04g, 60mmol) and o-phenylenediamine (9.72g, 90mmol) are dissolved in 150mL acetic acid solution
In, then it is heated to 120 DEG C of backflow 8-10h in a nitrogen environment.Through being recrystallized to give 8.6 yellow solids in ethanol, produce
Rate 72%.The solid obtaining does not need to process further, is directly entered next step reaction.
(2) the bromo- 6- of 8- (2- ethylhexyl) indoloquinoxalines
Above-mentioned yellow solid (5.96g, 20mmol) and bromo-iso-octane (6.21g, 30mmol) are dissolved in the DMF of 50mL
In, it is subsequently adding potassium carbonate (11.04g, 80mmol), phase transfer catalyst tetrabutylammonium iodide (0.74g, 2mmol), stirring adds
To 140 DEG C, flow back heat 5h.Reaction adds q. s. methylene chloride and excessive saturated aqueous common salt extraction, the organic faciess obtaining after terminating
It is dried with anhydrous magnesium sulfate.With petrol ether/ethyl acetate=30: 1 obtains yellow solid 5.17 as eluant silica gel column chromatography
(63%).1H NMR (400MHz, CDCl3) δ 8.33 (d, J=8.2Hz, 1H), 8.29 (d, J=8.3,1.5Hz, 1H), 8.13
(d, J=8.4, Hz, 1H), 7.77 (t, J=8.4Hz, 1H), 7.69 (t, J=8.3Hz, 1H), 7.61 (s, 1H), 7.51 (d, J
=8.2Hz, 1H), 4.34 (d, J=7.6Hz, 2H), 2.21-2.13 (m, 1H), 1.52-1.32 (m, 4H), 1.26 (m, 4H),
0.96 (t, J=7.5Hz, 3H), 0.86 (t, J=7.2Hz, 3H)；GC-MS calculated for C22H24BrN3, 410.35；
found410.9.
(3) 8,8- (phenyl tetrafluoride)-two (6- (2- ethylhexyl) indoloquinoxalines
The bromo- 6- of 8- (2- ethylhexyl) indoloquinoxalines (0.82g, 2mmol), phenyl tetrafluoride (0.21g, 1.4mmol), second
Sour palladium (0.023g, 0.1mmol), PtBu2Me-HBF4(0.494g, 0.2mmol) and potassium carbonate (0.691g, 5mmol) are blended in
In flask containing DMA20mL.Reaction system is heated to 150 DEG C in a nitrogen environment, reacts 12h.Reaction adds suitable after terminating
Amount dichloromethane and excessive saturated aqueous common salt extraction, the organic faciess anhydrous magnesium sulfate obtaining is dried.Use petrol ether/ethyl acetate
As eluant silica gel column chromatography obtain yellow solid 0.53g (65%) at=30: 1.1H NMR (400MHz, CDCl3) δ 8.64 (d,
J=8.0Hz, 2H), 8.34 (d, J=8.4Hz, 2H), 8.21-8.11 (m, 2H), 7.80 (t, J=8.4Hz, 2H), 7.72 (t, J
=8.4Hz, 2H), 7.66 (s, 2H), 7.58 (d, J=8.0Hz, 2H), 4.45 (d, J=7.4Hz, 4H), 2.31-2.17 (m,
2H), 1.52-1.35 (m, 8H), 1.34-1.20 (m, 8H), 0.98 (t, J=7.4Hz, 6H), 0.86 (t, J=7.2Hz, 6H)；
MALDI-TOF-MS：calcd for C50H48F4N6808.95, found 809.26.Structural formula is as follows：
Embodiment 2：8 indoloquinoxalines coupled derivative IQ1's (product in embodiment 1) containing aromatic rings
Ultra-violet absorption spectrum, fluorescence spectrum
IQ1 is dissolved in chloroform diluted solution, using Tianjin island UV-1750 ultraviolet-visual spectrometer and Hitachi's F-4600 fluorescence
Spectrogrph is tested.Fluorescence spectrum is to measure in excitation wavelength 350nm.The stone by spin coating of the fluorescence spectrum of solid film
English piece is carried out.
IQ1 solution is having two absworption peaks, respectively 367nm and 409nm, the characteristic absorption of fluorescence spectrum more than 300nm
In 470nm.
The maximum absorption band of solid film is 369nm, and the characteristic absorption of fluorescence spectrum is in 475nm.It is specifically shown in accompanying drawing 1
Embodiment 3：9,9 '-(phenyl tetrafluoride)-two (6- (2- ethylhexyl) indoloquinoxalines 9,9 '-(perfluoro-
Isosorbide-5-Nitrae-phenylene) bis (6- (2-ethylhexyl) -6H-indolo [2,3-b] quinoxaline) (IQ2) synthesis and
Spectroscopic assay
Using the method similar with IQ1, simply 6- bromo-isatin is changed to 5-bromoisatin, the IQ2 of 45% yield can be obtained.
Method using similar IQ1 can measure ultra-violet absorption spectrum and fluorescence spectrum, and fluorescence spectrum is in excitation wavelength
350nm measures.
IQ2 solution is having two absworption peaks, respectively 357nm and 409nm, the characteristic absorption of fluorescence spectrum more than 300nm
In 471nm.
The absworption peak of solid film is 358nm and 409nm, and the characteristic absorption of fluorescence spectrum is in 475nm.It is specifically shown in accompanying drawing 2
The structural formula of IQ2 is as follows
Embodiment 4：IQ2 is the electroluminescent device test of hole injection layer
Device architecture adopts standard green device, and structure is ITO/IQ2/NPB (80nm)/Alq3 (60nm)/LiF
(0.7nm) thickness of/Al (120nm), IQ2 is respectively 0.5nm, 1nm, 1.5nm, 2nm.
(1) cleaning of ito glass substrate：By the ultrasonic detergent of ito glass heat with deionized water is ultrasonic is carried out,
Then it is placed on drying under infrared lamp.
(2) each organic function layer preparation：Cleaned ito glass substrate is put into vacuum intracavity, successively evaporation hole note
Enter a layer IQ2, thickness is respectively 0.5,1,1.5, and 2nm；Hole transmission layer NPB, thickness is 80nm；Luminescent layer Alq3, thickness is
60nm, Alq3Also serve as electron transfer layer.
(3) preparation of negative electrode：The Al being deposited with LiF and 120nm of 0.5nm on above-mentioned electron transfer layer successively is combined the moon
Pole layer.
(4) ready-made device takes out vacuum chamber, the current-voltage-brightness characteristic of test device and electroluminescent spectrum by force
Fig. 3 is the current-voltage-brightness curve chart of prepared device, and the starting voltage of device is respectively 3.1,3.5,4.9
And 6.5V, the thickness of corresponding IQ2 is 0.5,1,1.5, and 2nm.Fig. 4 is the current efficiency curve chart of device, the electric current effect of device
Rate is respectively 4.10,4.35,4.31 and 4.27cd A-1, the thickness of corresponding IQ2 is 0.5,1,1.5, and 2nm.Can from test result
To find out, when IQ2 is 1nm thickness, the combination property of device is best.
Claims (4)
1. a kind of indoloquinoxalines derivant material it is characterised in that：This compound is represented by below formula：
Wherein, R is hydrogen or straight chain, side chain or the cyclic alkyl chain with 1 to 22 carbon atom；Or for having 2 to 40
The thiazolinyl of carbon atom, alkynyl, aryl, wherein one or more carbon atoms can be replaced by hetero atom Si, Se, O, S, N, sulfone,
Hydrogen on one or more carbon atoms can be replaced by fluorine or cyano group；
Ar is aromatic rings, can be following any one：
Wherein R is hydrogen or straight chain, side chain or the cyclic alkyl chain with 1 to 22 carbon atom；Or for having 2 to 40 carbon
The thiazolinyl of atom, alkynyl, aryl, wherein one or more carbon atoms can be replaced by hetero atom Si, Se, O, S, N, sulfone, and one
Hydrogen on individual or multiple carbon atom can be replaced by fluorine or cyano group.
N is 1 or 2 or 3 or 4 or 5 or 6.
2. indoloquinoxalines derivant material as claimed in claim 1 is it is characterised in that Ar can be with and without replacement
Alkyl or alkoxyl, the wherein carbochain of alkyl or alkoxyl is the saturation of 1-40 or unsaturated aliphatic hydrocarbon for carbon number
Group.
3. a kind of preparation method of indoloquinoxalines derivant material as claimed in claim 1 or 2 is it is characterised in that be somebody's turn to do
The preparation method of indoloquinoxalines derivant material, its step is as follows：
The first step：By halogeno indole -2 of 1 times of equivalent, 3- diketone, 1.2-1.5 times of equivalent o-phenylenediamine, inert gas shielding, second
Solvent is made in acid, 80-90 DEG C of reaction 8-10h, and standing or recrystallization or column chromatography or thin layer chromatography purification obtain second step raw material；
Second step：By 1 times work as content of starting materials, solvent DMF or dioxane or 2- methyltetrahydrofuran, 1.5-2 times of equivalent 1 to 22
The halo saturation of individual carbon atom or unsaturated fatty chain base, 150 DEG C of backflow 5-8 hours, reaction adds dichloromethane after terminating
Or ethyl acetate, sodium-chloride water solution or potassium chloride solution mix and blend 20 minutes -1 hour, merge organic faciess, standing or weight
Crystallization or column chromatography or thin layer chromatography purification obtain the 3rd step raw material；
3rd step：1 times is worked as content of starting materials, the copper of 0.01-0.05 times of equivalent or copper powder or iodate Asia ketone or Schweinfurt green or palladium or vinegar
Sour palladium or [1,1 '-bis- (diphenylphosphine) ferrocene] palladium chloride or four triphenyl phosphorus palladiums or diacetyl two (triphenylphosphine) palladium or
Double (triphenylphosphine) palladium of dichloro or [1,1 '-bis- (diphenylphosphino) ferrocene] palladium chloride, the Ar of 1-6 times of equivalent or halo Ar
Or the tin reagent of the Grignard reagent of the boric acid of Ar or the borate of Ar or Ar or Ar, potassium carbonate or cesium carbonate or lithium carbonate or sulphuric acid
Sodium or potassium sulfate or potassium acetate or Sodium Acetate Trihydrate, atmospheric atmosphere or inert gas shielding, DMA or toluene or dimethylbenzene or trimethylbenzene or
Solvent made by chlorobenzene or dichloro-benzenes or dioxane, 90-150 DEG C, reacts 10-24h under 1 atmospheric pressure, reaction adds after terminating
Enter dichloromethane or ethyl acetate, sodium-chloride water solution or potassium chloride solution mix and blend 20 minutes -1 hour, merge organic
Phase, standing or recrystallization or column chromatography or thin layer chromatography purification obtain indoloquinoxalines derivant material.
4. the indoloquinoxalines derivant material as described in claim 1-3, electroluminescent material, organic integrated circuits,
In organic laser material, the semi-conducting material of organic field-effect tube, organic solar battery material, organic non linear optical material
Application.
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| CN109860430A (en) * | 2018-12-29 | 2019-06-07 | 江西冠能光电材料有限公司 | A kind of hole transport exciton blocking organic material and its application |
| CN109860430B (en) * | 2018-12-29 | 2021-08-06 | 江西冠能光电材料有限公司 | Hole-transport exciton-blocking organic material and application thereof |
| CN113402524A (en) * | 2021-07-26 | 2021-09-17 | 中国科学院宁波材料技术与工程研究所 | Thermal activation delayed fluorescence micromolecule material, organic electroluminescent device and manufacturing method |
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