CN106187908A - One class can use small molecule emitter material containing naphtho-indenes fluorenes unit that environmentally friendly solvent processes and preparation method and application - Google Patents

One class can use small molecule emitter material containing naphtho-indenes fluorenes unit that environmentally friendly solvent processes and preparation method and application Download PDF

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CN106187908A
CN106187908A CN201610489630.9A CN201610489630A CN106187908A CN 106187908 A CN106187908 A CN 106187908A CN 201610489630 A CN201610489630 A CN 201610489630A CN 106187908 A CN106187908 A CN 106187908A
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naphtho
environmentally friendly
small molecule
indenes fluorenes
preparation
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应磊
赵森
彭俊彪
杨伟
曹镛
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South China University of Technology SCUT
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Abstract

The invention discloses small molecule emitter material containing naphtho-indenes fluorenes unit that a class can use environmentally friendly solvent to process and preparation method and application.This small molecule emitter material, with naphtho-indenes fluorenes as core cell, has the group of electric transmission unit by selection, it is thus achieved that the small molecule material centered by naphtho-indenes fluorenes.This kind of material can carry out solution processing with environmentally friendly solvent, and the small molecule material prepared by the present invention can be used for making the luminescent layer of Organic Light Emitting Diode.

Description

The little molecule containing naphtho-indenes fluorenes unit that one class can use environmentally friendly solvent to process is sent out Luminescent material and preparation method and application
Technical field
The invention belongs to organic photoelectric technical field, be specifically related to that a class can use that environmentally friendly solvent processes containing naphtho- Small molecule emitter material of indenes fluorenes unit and preparation method and application.
Background technology
Organic Light Emitting Diode (OLED) because having efficiently, low voltage drive, it is easy to large area the advantage such as is prepared and is obtained people Pay close attention to widely.The research of OLED starts from the 1950's, until doctor Deng Qingyun of Kodak in 1987 adopts Have developed OLED luminosity under 10V direct voltage drive with sandwich device architecture and can reach 1000cd m-2, make OLED obtains epoch-making development.
OLED is made up of the organic layer of negative electrode, anode and centre, and organic layer generally comprises electron transfer layer, luminescent layer With hole transmission layer, first electronics and hole inject from negative and positive the two poles of the earth respectively, and migrate in functional layer respectively, then electricity Son and hole form exciton in place, and exciton migrates within the specific limits, last excitonic luminescence.
In order to realize the commercialization of organic/polymer electroluminescent device early, it is capable of panchromatic showing except meeting Show, monochromatic purity is high, thermo-chemical stability is good and outside the requirement such as length in service life, it is also desirable to device has high luminous efficiency. One of principal element affecting OLED efficiency is electronics and the imbalance of hole transport injection of material itself at present.Cause This, in order to obtain efficient OLED, it is necessary to electron hole transmission and the balance injected of reasonable adjusting material.
In recent years, bipolar materials, because having hole and the electronic carrier stream of balance, is inhaled in field of organic electroluminescence Draw people to pay close attention to widely, and the structure that this material makes device has simplified.This novel technology is not only in theoretical research Field is favored by scientist, and the production that the most progressively moves towards the industrialization, thus exploitation bipolar materials has practical valency Value.Introduce oxyalkyl chain in the molecule simultaneously, make molecule have good dissolubility and film property inside environmentally friendly solvent, Can be processed with environmentally friendly solvent.
Summary of the invention
Present invention aims to the deficiencies in the prior art, it is provided that a class can use what environmentally friendly solvent processed to contain The small molecule emitter material of naphtho-indenes fluorenes unit, this small molecule emitter material has good electronics and cavity transmission ability, can Transmission with equilbrium carrier so that more exciton is the most compound, and then improves luminous efficiency.
The present invention also aims to provide the preparation method of described small molecule emitter material.
The present invention also aims to provide the application in the light emitting diode of described small molecule emitter material.
The purpose of the present invention is achieved through the following technical solutions.
One class can use the small molecule emitter material containing naphtho-indenes fluorenes unit that environmentally friendly solvent is processed, its chemical constitution As follows:
Further, R is-(CH2)n-O-(CH2)m-X, wherein, n=1-10, m=1-10, X are appointing in following structure Meaning one:
The structural formula of Ar is any one in following structure:
In formula: n is 1-6, R1For straight chain that carbon number is 1-20 or branched alkyl or alkoxyl or aryl or three Aniline etc..
An above-described class can use the little mulecular luminescence of the indenes fluorenes containing naphtho-(NIF) unit that environmentally friendly solvent processes The preparation method of material, mainly includes the preparation of naphtho-indenes fluorenes nuclear unit, then with naphtho-indenes fluorenes as core, by Suzuki coupling It is connected to a series of in naphtho-indenes fluorenes nuclear unit by body unit Ar.The preparation method of described small molecule emitter material, main Intramolecular to be included is simultaneously introduced to electronic unit and the injection of electrophilic unit, beneficially carrier and transmission, thus favorably In improving luminous efficiency.
An above-described class can use the small molecule emitter material containing naphtho-indenes fluorenes unit that environmentally friendly solvent is processed Application in light emitting diode, flat faced display.
Further, small molecule emitter material is applied to the luminescent layer of light emitting diode, with environment amenable organic molten Liquid dissolves, then by spin coating, inkjet printing or printing process film forming.
Yet further, described environment amenable organic solution is water or alcohol etc..
The small molecule emitter material of the present invention is with fluorenes as raw material, and fluorenes has higher fluorescence quantum yield, it is easy to carry out molten Liquid is processed, and is the most promising blue light material of a class.And introduce oxyalkyl chain in the molecule, make molecule have water/ The characteristic that alcohol is molten, therefore this micromolecular is when being used as the luminescent layer of Organic Light Emitting Diode, can be with environmentally friendly molten Agent is processed, such as water, alcohol etc..
Compared with prior art, the invention have the advantages that
(1) present invention is first centered by naphtho-indenes fluorenes, is re-introduced into electric transmission unit, forms A-D-A type bipolarity little Molecular ligh-emitting materials.This kind of material is owing to containing electric transmission unit and hole transporting unit, beneficially device efficiency simultaneously Improve.
(2) small molecule emitter material based on naphtho-indenes fluorenes prepared by the present invention, owing to there being higher fluorescence quantum yield, The device efficiency being conducive to material improves.
(3) little molecule prepared by the present invention is inside environmentally friendly solvent, has preferable dissolubility, using it as luminescence Layer need not make annealing treatment when preparing device so that preparation technology is simpler.
Accompanying drawing explanation
Fig. 1 is compound P1 electroluminescent light spectrogram.
Fig. 2 is compound P1 luminescence generated by light spectrogram in toluene solution.
Fig. 3 is that compound P1 is at toluene solution medium ultraviolet-visible absorption spectra spectrogram.
Fig. 4 is cyclic voltammetric (CV) spectrogram of compound P2.
Fig. 5 is the luminous efficiency-current density plot curve chart of compound P3.
Fig. 6 is the luminous efficiency-current density plot figure of compound P4.
Fig. 7 is the luminous efficiency-current density plot figure of compound P5.
Detailed description of the invention
Below in conjunction with embodiment, the present invention is described in further detail, but embodiments of the present invention are not limited to this.
The preparation of embodiment 1 2-bromine fluorenes
In 250mL there-necked flask, add fluorenes (16.6g, 0.1mol), iron powder (88mg, 1.57mmol), chloroform 100mL.Ice-water bath cools down, dropping bromine (17.6g, 0.1mol)/chloroform mixed solution 35mL.During dropping, in bottle, temperature does not surpasses Cross 5 DEG C.After reacting 16 hours, stopped reaction, filtration, Gossypol recrystallized from chloroform, obtain white solid 19.3g, productivity 84%.1H NMR、13CNMR, MS and elementary analysis result show that obtained compound is target product, and its chemical equation is as follows:
The preparation of embodiment 2 2-bromo-9,9-bis-(2-hydroxyethyl)-9H-fluorenes
In there-necked flask add 2-bromine fluorenes (7.4g, 0.03mol), benzyltriethylammoinium chloride (0.07g, 0.3mmol), two Methyl sulfoxide 90mL, 45mL sodium hydrate aqueous solution (50wt%).Under room temperature, stirring forms suspension.Dropping ethylene bromohyrin (11.5g, 65mmol), after continuing stirring 3 hours, extracts with ether.Ether phase, anhydrous sulfur is washed with saturated sodium-chloride water solution Acid magnesium is dried.Boiling off solvent, product petroleum ether is made eluant column chromatography and is purified, and obtains white solid.1H NMR、13CNMR, MS and Elementary analysis result shows that obtained compound is target product, and its chemical equation is as follows:
Embodiment 3 2-borate-9, the preparation of 9-bis-(2-hydroxyethyl) fluorenes
Under an argon atmosphere, by bromo-for 2-9,9-bis-(2-hydroxyethyl) fluorenes (5g, 9.82mmol) is dissolved in 180mL and refines Anhydrous THF in, at-78 DEG C, gradually drip 1.6mol.L-1N-BuLi 28mL, react 2 hours, be subsequently adding 2-isopropyl Epoxide-4,4,5,5-tetramethyl-1,3,2-dioxaborinate 25mL, continue reaction 1 hour at-78 DEG C, are warming up to room temperature anti- Answer 24 hours.Reactant mixture is poured into water, is extracted with ethyl acetate, after organic layer saline solution washs completely, add anhydrous Magnesium sulfate is dried.Solution concentrate after, obtain thick pale yellow shape crude product, with silica gel column chromatography purify (eluant select petroleum ether/ Ethyl acetate=20/1, v/v), obtain white solid, productivity 70%.1H NMR、13CNMR, MS and elementary analysis result show institute The compound obtained is target product, and its chemical equation is as follows:
The preparation of embodiment 4 1-bromo-2-naphthoyl chloride
Under an argon atmosphere, 1-bromine two naphthoic acid (10g, 39.83mmol) is added in two-mouth bottle, adds 100ml N, Dinethylformamide, is then added dropwise over thionyl chloride (20ml), at room temperature reacts 18h.Pour reactant mixture into water In, it is extracted with ethyl acetate, after organic layer saline solution washs completely, adds anhydrous magnesium sulfate and be dried.After solution concentrates, obtain white Color solid crude product, purifies (eluant selects petroleum ether/dichloromethane=3/1, v/v) with silica gel column chromatography, and product is put for a long time Put and refrigerator obtains white solid, productivity 70%.1H NMR、13CNMR, MS and elementary analysis result show obtained compound For target product, its chemical equation is as follows:
The preparation of embodiment 5 compound M1
Under argon atmosphere, by 2-borate-9,9-bis-(2-hydroxyethyl) fluorenes (5g, 13.15mmol) and 1-bromine dinaphthyl Formyl chloride (3.54g, 13.15mmol) joins in two-mouth bottle, adds 100ml toluene and makes it be completely dissolved, adds carbonic acid Sodium (6.97g, 65.74mmol) and tetrabutyl ammonium bromide (312.01mg, 967.86umol), add tetra-triphenylphosphine palladium (303.87,026mmol), react 18h at 110 DEG C.Reactant mixture is poured into water, is extracted with ethyl acetate, organic layer After washing completely with saline solution, add anhydrous magnesium sulfate and be dried.After solution concentrates, purify (eluant selection stone with silica gel column chromatography Oil ether/dichloromethane=5/1, v/v), finally give white solid, productivity 70%.1H NMR、13CNMR, MS and elementary analysis knot Fruit shows that obtained compound is target product, and its chemical equation is as follows:
The preparation of embodiment 6 compound M2
Under argon atmosphere, M1 (5g, 8.70mmol) is added in single port bottle, adds 50ml anhydrous methylene chloride and be allowed to It is completely dissolved.Reactant liquor reacting at 0 DEG C 1h again, adds aluminum chloride (10g, 16.5mmol), mixed liquor is the most anti- Answer 18h.Add water to reactant liquor comes cancellation reaction, be extracted with ethyl acetate, after organic layer saline solution washs completely, add Anhydrous magnesium sulfate is dried.After solution concentrates, purify (eluant selection petroleum ether/dichloromethane=2/1, v/ with silica gel column chromatography V), product is placed for a long time in refrigerator and is obtained white solid, productivity 85%.1H NMR、13CNMR, MS and elementary analysis result table Compound obtained by bright is target product, and its chemical equation is as follows:
The preparation of embodiment 7 compound M3
Under argon atmosphere, by M2 (5g, 12.30mmol), hydrazine hydrate 10mL and potassium hydroxide (3.45g, 61.50mmol), join in the two-mouth bottle of 250ml, be subsequently adding diethylene glycol and be allowed to be completely dissolved, be then heated to reflux, reaction Overnight.Add water to reactant liquor comes cancellation reaction, be extracted with ethyl acetate, after organic layer saline solution washs completely, add Anhydrous magnesium sulfate is dried.After solution concentrates, purify (eluant selection petroleum ether/dichloromethane=1/1, v/ with silica gel column chromatography V), product is placed for a long time in refrigerator and is obtained white solid, productivity 85%.1H NMR、13CNMR, MS and elementary analysis result table Compound obtained by bright is target product, and its chemical equation is as follows:
The preparation of embodiment 8 compound M4
M3 (5g, 12.74mmol), benzyltriethylammoinium chloride (0.07g, 0.3mmol), dimethyl is added in there-necked flask Sulfoxide 90mL, 45mL sodium hydrate aqueous solution (50wt%).Under room temperature, stirring forms suspension.Dropping ethylene bromohyrin (4.78g, 38.2mmol), after continuing stirring 3 hours, extract with ether.Ether phase, anhydrous magnesium sulfate is washed with saturated sodium-chloride water solution It is dried.Boiling off solvent, product petroleum ether is made eluant column chromatography and is purified, and obtains white solid.1H NMR、13CNMR, MS and element Analysis result shows that obtained compound is target product, and its chemical equation is as follows:
The preparation of embodiment 9 compound M5
Under argon atmosphere, compound M4 (5g, 10.40mmol) is dissolved in N,N-dimethylacetamide, adds carbon Acid potassium (7.19g, 52mmol), is heated to backflow, after stirring 2 hours, adds glycol dibromide (20ml) under argon shield, Reacting 24 hours, then cool the temperature to room temperature, be filtered to remove potassium carbonate, filtrate is poured in frozen water, extracts with dichloromethane, nothing Water magnesium sulfate is dried, and purifies (eluant selects petroleum ether/dichloromethane=3/1, v/v) with silica gel column chromatography, and product is long-time Place in refrigerator and obtain white solid, productivity 80%.1H NMR、13CNMR, MS and elementary analysis result show obtained chemical combination Thing is target product, and its chemical equation is as follows:
The preparation of embodiment 10 compound M6
Under argon atmosphere, M5 (5g, 5.50mmol) is dissolved in 50mL dichloromethane, add iron powder (185.35mg, 3.32mmol), then it is added dropwise over bromine (1.76g, 11.1mmol), at room temperature reacts 18h.It is extracted with ethyl acetate, organic After layer saline solution washs completely, add anhydrous magnesium sulfate and be dried.After solution concentrates, purify (eluant selection with silica gel column chromatography Petroleum ether/dichloromethane=2/1, v/v), product is placed for a long time in refrigerator and is obtained white solid, productivity 75%.1H NMR、13CNMR, MS and elementary analysis result show that obtained compound is target product, and its chemical equation is as follows:
The preparation of embodiment 11 compound M7
Under argon atmosphere, 250ml there-necked flask adds compound M6 (5g, 4.69mmol), is dissolved in N, N- Adding the diethanolamine of excess in dimethylformamide, at room temperature reaction 48 hours, pour the mixture in water, use dichloromethane Alkane extracts, and anhydrous magnesium sulfate is dried, and obtains white solid after concentration after product acetone/water mixed liquor recrystallization,1H NMR 、13CNMR, MS and elementary analysis result show that obtained compound is target product, and its chemical equation is as follows:
The preparation of the bromo-S of embodiment 12 2-, S-dioxydibenze bithiophene
The preparation of the bromo-dibenzothiophenes of 2-(1)
Dibenzothiophenes (10g, 54.2mmol) and 0.1g iron powder are dissolved in 50mL chloroform, lucifuge, add at 0 DEG C Bromine (8.6g, 54.2mmol), reacts 40 hours under room temperature.Add saturated NaHSO3Aqueous solution removes unnecessary bromine, filters Obtain faint yellow solid, and wash twice with methanol, obtain white solid.Productivity: 50%.1H NMR、13CNMR, MS and element Analysis result shows that obtained compound is target product.
The preparation of the bromo-S of 2-, S-dioxydibenze bithiophene (2)
Bromo-for 2-dibenzothiophenes 5g is dissolved in 50mL acetic acid, adds 15mL H2O2, 100 DEG C of reaction 2h.Course of reaction In, there is white solid to separate out, be washed out, filter, be dried, thick product chlorobenzene recrystallization, obtain white needles.Produce Rate: 75%.1H NMR、13CNMR, MS and elementary analysis result show that obtained compound is target product, its chemical reaction Equation is as follows:
Embodiment 13 2,7-diborate-9,9-dioctyl fluorene
(1) by 2,7-dibromo fluorenes (10g, 30.86mmol), KOH (8.66g, 154.32mmol) join two mouthfuls of 250ml In Ping, add 100ml DMF and be allowed to be completely dissolved, after being stirred at room temperature one hour, then one Secondary property adds bromooctane (17.88g, 92.59mmol), is stirred at room temperature, overnight.Being extracted with ethyl acetate, organic layer is eaten After saline washs completely, add anhydrous magnesium sulfate and be dried.After solution concentrates, purify (eluant selection oil with silica gel column chromatography Ether), the product acetone obtained carries out recrystallization, finally gives white solid.Productivity 75%.1H NMR、13CNMR, MS and unit Element analysis result shows that obtained compound is target product, and its chemical equation is as follows:
(2) under an argon atmosphere, by 2,7-bis-bromo-9,9-dioctyl fluorene (5g, 10.65mmol) is dissolved in 180mL and refines THF in, at-78 DEG C, gradually drip 1.6mol L-1N-BuLi 28mL, react 2 hours, be subsequently adding 2-isopropyl oxygen Base-4,4,5,5-tetramethyl-1,3,2-dioxaborinate 25mL, continue reaction 1 hour at-78 DEG C, are warming up to room temperature reaction 24 hours.Reactant mixture is poured into water, is extracted with ethyl acetate, after organic layer saline solution washs completely, add anhydrous sulfur Acid magnesium is dried.After solution concentrates, obtain thick pale yellow shape crude product, purify (eluant selection petroleum ether/second with silica gel column chromatography Acetoacetic ester=20/1, v/v), product is placed for a long time in refrigerator and is obtained white solid, productivity 70%.1H NMR、13CNMR, MS and Elementary analysis result shows that obtained compound is target product, and its chemical equation is as follows:
The preparation of embodiment 14 compound M8
Under an argon atmosphere, by bromo-for 2-S, S-dioxydibenze bithiophene (5g, 16.94mmol), 2-borate-9,9-bis- Octyl group fluorenes (21.77g, 33.88mmol), Na2CO3(8.98g, 84.70mmol) and tetrabutyl ammonium bromide 1g, join 250ml In two-mouth bottle, after it fully dissolves, add Pd (PPh3)4(391.51mg, 338.81umol), reacts 16h at 110 DEG C.With Ethyl acetate extracts, and after organic layer saline solution washs completely, adds anhydrous magnesium sulfate and is dried.After solution concentrates, use silica gel column layer Analysis purifies (eluant selects petroleum ether/dichloromethane=4/1, v/v), and product is placed for a long time in refrigerator and obtained white solid, Productivity 70%.1H NMR、13CNMR, MS and elementary analysis result show that obtained compound is target product, its chemical reaction Equation is as follows:
The preparation of embodiment 15 compound P1
Under argon atmosphere, by M7 (5g, 5.42mmol), 1-phenyl-2 (4-phenylboric acid)-benzimidazole (3.61g, 11.53mmol), tetrabutyl ammonium bromide (176.93mg, 548.83umol), Na2CO3(2.91g, 27.44mmol) joins In 150ml two-mouth bottle, after it fully dissolves, add Pd (PPh3)4(317.10mg, 274.42umol), reacts at 110 DEG C 16h. is extracted with ethyl acetate, and after organic layer saline solution washs completely, adds anhydrous magnesium sulfate and is dried.After solution concentrates, use silicon Plastic column chromatography purifies (eluant selects petroleum ether/dichloromethane=1/1, v/v), and product is placed for a long time in refrigerator and obtained white Solid, productivity 80%.1H NMR、13CNMR, MS and elementary analysis result show that obtained compound is target product, and it is changed Reaction equation is as follows:
The electroluminescent spectrogram of bipolarity small molecule material P1 that the present embodiment obtains, luminescence generated by light spectrogram and ultraviolet- Visible absorbance spectrogram, as shown in Figure 1, Figure 2, Figure 3 shows.Therefrom we can see that the electroluminescent spectrum of small molecule material M5 exists 470nm.Little molecule P1 uv-visible absorption spectra spectrogram inside toluene solution as it is shown on figure 3, it can be seen that The absworption peak of little molecule P1 is at 318nm and 380nm, and the peak of the photoluminescence spectra of little molecule M5 is at 460nm.
The preparation of embodiment 16 compound P2
Under argon atmosphere, by M7 (5g, 5.42mmol), M8 (8.42g, 11.53mmol), tetrabutyl ammonium bromide (176.93mg, 548.83umol), sodium carbonate (2.91g, 27.44mmol) joins in 250ml two-mouth bottle, treats that it fully dissolves After, add Pd (PPh3)4(317.10mg, 274.42umol), reacts 16 hours at 110 DEG C.It is extracted with ethyl acetate, organic After layer saline solution washs completely, add anhydrous magnesium sulfate and be dried.After solution concentrates, purify (eluant selection with silica gel column chromatography Petroleum ether/dichloromethane=2/1, v/v), product is placed for a long time in refrigerator and is obtained white solid, productivity 70%.1H NMR、13CNMR, MS and elementary analysis result show that obtained compound is target product, and its chemical equation is as follows:
As shown in Figure 4, we are tested the cyclic voltammetry curve of the bipolarity little molecule P2 that the present embodiment obtains by CV Calculate the highest occupied molecular orbital energy level (E of polymerHOMO) and minimum be not occupied molecular orbital energy level (ELUMO).Wherein, by There is the absolute vacuum energy level of a 4.8ev in ferrocene (Fc) oxidation-reduction potential, therefore Electrochemical Test Procedure is made with it On the basis of, by formula EHOMO=-e (EOX+4.8-Efer) and ELUMO=-(Ered+4.8-Efer) HOMO of polymer can be calculated And lumo energy, test figure from Fig. 4 it can be seen that the oxidation of bipolarity little molecule P2 and reduction potential be respectively 0.92ev and- 2.3ev, the E of ferrocenefer=0.4, therefore it is calculated HOMO=-5.32ev and LUMO=-2.1ev.
The preparation of embodiment 18 compound P3
Under argon atmosphere, by M7 (5g, 5.42mmol), 4-boric acid phenylate (2.1g, 11.53mmol), tetrabutyl phosphonium bromide Ammonium (176.93mg, 548.83umol), Na2CO3(2.91g, 27.44mmol) joins in 150ml two-mouth bottle, treats that it is the most molten Xie Hou, adds Pd (PPh3)4(317.10mg, 274.42umol), reacts 16h. at 110 DEG C and is extracted with ethyl acetate, organic layer After washing completely with saline solution, add anhydrous magnesium sulfate and be dried.After solution concentrates, purify (eluant selection stone with silica gel column chromatography Oil ether/dichloromethane=1/1, v/v), product is placed for a long time in refrigerator and is obtained white solid, productivity 80%.1H NMR、13CNMR, MS and elementary analysis result show that obtained compound is target product, and its chemical equation is as follows:
The compound P3 that the present embodiment obtains, based on device architecture: ITO/PEDOT/EML/CsF/Al, its luminous efficiency- Current density plot figure is as it is shown in figure 5, we can see that from Fig. 5 the maximum lumen efficiency of compound P3 is 1.64cd/A.
The preparation of embodiment 19 compound P4
Under argon atmosphere, by M7 (5g, 5.42mmol), 4-cyanophenylboronic acid (2.0g, 11.53mmol), tetrabutyl bromine Change ammonium (176.93mg, 548.83umol), Na2CO3(2.91g, 27.44mmol) joins in 150ml two-mouth bottle, treats that it is abundant After dissolving, add Pd (PPh3)4(317.10mg, 274.42umol), reacts 16h. at 110 DEG C and is extracted with ethyl acetate, organic After layer saline solution washs completely, add anhydrous magnesium sulfate and be dried.After solution concentrates, purify (eluant selection with silica gel column chromatography Petroleum ether/dichloromethane=1/1, v/v), product is placed for a long time in refrigerator and is obtained white solid, productivity 80%.1H NMR、13CNMR, MS and elementary analysis result show that obtained compound is target product, and its chemical equation is as follows:
The compound P4 that the present embodiment obtains, based on device architecture: ITO/PEDOT/EML/CsF/Al, its luminous efficiency- Current density plot figure as shown in Figure 6, we can see that from Fig. 6 the maximum lumen efficiency of compound P4 is 1.68cd/A.
The preparation of embodiment 20 compound P5
Under argon atmosphere, by M7 (5g, 5.42mmol), compound M9 (8.42g, 11.53mmol), tetrabutyl ammonium bromide (176.93mg, 548.83umol), Na2CO3(2.91g, 27.44mmol) joins in 150ml two-mouth bottle, treats that it fully dissolves After, add Pd (PPh3)4(317.10mg, 274.42umol), reacts 16h. at 110 DEG C and is extracted with ethyl acetate, and organic layer is used After saline solution washs completely, add anhydrous magnesium sulfate and be dried.After solution concentrates, purify (eluant selection oil with silica gel column chromatography Ether/dichloromethane=1/1, v/v), product is placed for a long time in refrigerator and is obtained white solid, productivity 80%.1H NMR、13CNMR、 MS and elementary analysis result show that obtained compound is target product, and its chemical equation is as follows:
The compound P5 that the present embodiment obtains, based on device architecture: ITO/PEDOT/EML/CsF/Al, its luminous efficiency- Current density plot figure is as it is shown in fig. 7, we can see that from Fig. 7 the maximum lumen efficiency of compound P5 is 2.7cd/A.
The preparation of embodiment 21 electroluminescent device based on little molecule
On tin indium oxide (ITO) glass of well in advance, its square resistance is 10-20 Ω/, the most successively with acetone, Detergent, deionized water and isopropanol ultrasonic cleaning, plasma treatment 10 minutes.On ITO, spin coating is mixed polystyrene sulphur Polyethoxy thiophene (PEDOT:PSS) film of acid, thickness is 150nm.PEDOT:PSS film is dried 8 in vacuum drying oven at 80 DEG C Hour.The most respectively the ethanol solution (1wt%) of bipolarity small molecule emitter material P1, P2, P3, P4 and P5 is spin-coated on The surface of PEDOT:PSS film, thickness is 80nm；On luminescent layer, finally it is deposited with a thin layer CsF (1.5nm) successively and 120nm is thick Metal Al layer.
Table 1 is the photoelectric properties index of conjugated polymer based on naphtho-indenes fluorenes unit.
Table 1
Can be obtained by table 1, the small molecule emitter material containing naphtho-indenes fluorenes prepared by the present invention, the beneficially device efficiency of material Raising.
Above-described embodiment is the present invention preferably embodiment, but embodiments of the present invention are not by above-described embodiment Limit, the change made under other any spirit without departing from the present invention and principle, modify, substitute, combine, simplifying all should For equivalence substitute mode, within being included in protection scope of the present invention.

Claims (5)

1. a class can use the small molecule emitter material containing naphtho-indenes fluorenes unit that environmentally friendly solvent is processed, it is characterised in that The chemical structural formula of this luminescent material is as follows:
The little molecule containing naphtho-indenes fluorenes unit that a class the most according to claim 1 can use environmentally friendly solvent to process is sent out Luminescent material, it is characterised in that R is-(CH2)n-O-(CH2)m-X, wherein, n=1-10, m=1-10, X are appointing in following structure Meaning one:
The structural formula of Ar is any one in following structure:
In formula, n is 1-6, R1For straight chain that carbon number is 1-20 or branched alkyl or alkoxyl or aryl or triphenylamine.
3. the little molecule containing naphtho-indenes fluorenes unit that a preparation class described in claim 1 can use environmentally friendly solvent to process is sent out The method of luminescent material, it is characterised in that the method is with naphtho-indenes fluorenes as core, then will be connected by body unit Ar by Suzuki coupling In naphtho-indenes fluorenes nuclear unit.
4. can use that environmentally friendly solvent is processed little point containing naphtho-indenes fluorenes unit of the class described in any one of claim 1-3 Sub-luminescent material is applied to the luminescent layer of light emitting diode, it is characterised in that dissolve little point with environment amenable organic solvent Sub-luminescent material, then by spin coating, inkjet printing or printing process film forming.
Application the most according to claim 4, it is characterised in that described environment amenable organic solvent is water or alcohol.
CN201610489630.9A 2016-06-27 2016-06-27 One class can use small molecule emitter material containing naphtho-indenes fluorenes unit that environmentally friendly solvent processes and preparation method and application Pending CN106187908A (en)

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