CN107162984A - A kind of bipolarity small molecule emitter material using the indenes fluorenes unit of two phenanthro- 2,8 as core and preparation method and application - Google Patents
A kind of bipolarity small molecule emitter material using the indenes fluorenes unit of two phenanthro- 2,8 as core and preparation method and application Download PDFInfo
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- 0 *C(C=C)c1ccc(C(C2c3ccccc3)C=Cc3c2cccc3)cc1 Chemical compound *C(C=C)c1ccc(C(C2c3ccccc3)C=Cc3c2cccc3)cc1 0.000 description 1
- AVXFJPFSWLMKSG-UHFFFAOYSA-N Brc(cc1)cc(Cc2c3)c1-c2ccc3Br Chemical compound Brc(cc1)cc(Cc2c3)c1-c2ccc3Br AVXFJPFSWLMKSG-UHFFFAOYSA-N 0.000 description 1
- CYKLQIOPIMZZBZ-UHFFFAOYSA-N CCCCCCCCC1(CCCCCCCC)c2cc(Br)ccc2-c(cc2)c1cc2Br Chemical compound CCCCCCCCC1(CCCCCCCC)c2cc(Br)ccc2-c(cc2)c1cc2Br CYKLQIOPIMZZBZ-UHFFFAOYSA-N 0.000 description 1
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Abstract
The invention discloses a kind of bipolarity small molecule emitter material using the indenes fluorenes unit of two phenanthro- 2,8 as core and preparation method and application.Electron donor unit and electron acceptor unit, for core, the indenes fluorenes unit both sides of two phenanthro- 2,8 are connected to by Suzuki coupling reactions by the present invention with the indenes fluorenes of two phenanthro- 2,8, obtain described with bipolarity small molecule emitter material of the indenes fluorenes unit of two phenanthro- 2,8 for core.Synthetic method of the present invention is simple, is easily purified, is conducive to industrial applications.The bipolarity small molecule emitter material has good dissolubility, film forming and film morphology stability, and the luminescent layer based on the bipolarity small molecule emitter material is when preparing device without annealing so that preparation technology is simple.
Description
Technical field
The present invention relates to organic photoelectrical material technical field, and in particular to one kind is with two phenanthro- -2,8- indenes fluorenes units for core
Bipolarity small molecule emitter material and preparation method and application.
Background technology
Organic Light Emitting Diode (OLED) is because with efficient, low voltage drive, it is easy to which prepared by large area the advantages of obtains people
Extensive concern.OLED research is started from the 1950s, until doctor Deng Qingyun of Kodak in 1987 adopts
OLED luminosity under 10V direct voltage drives is have developed with sandwich device architecture and can reach 1000cdm-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
And hole transmission layer, electronics and hole inject from negative and positive the two poles of the earth respectively first, and are migrated respectively in functional layer, Ran Hou electricity
Son and hole form exciton in place, and exciton is migrated within the specific limits, last excitonic luminescence.
In order to realize the commercialization of organic/polymer electroluminescent device early, panchromatic show can be realized except that should meet
Show, monochromatic purity is high, thermo-chemical stability is good and service life length etc. is required outside, it is also desirable to which device has high luminous efficiency.
One of principal element of influence OLED efficiency is the imbalance of material electronics in itself and hole transport injection at present.Cause
This, in order to obtain efficient OLED, it is necessary to the balance of the electron hole transmission and injection of reasonable adjusting material.
In recent years, bipolar materials are inhaled because of the hole with balance and electronic carrier stream in field of organic electroluminescence
Draw people widely to pay close attention to, and the material causes the structure of device to simplify.This new technology is not only in theoretical research
Field is favored by scientist, and the production that progressively moving towards the industrialization, thus exploitation bipolar materials have practical valency
Value.
The content of the invention
It is an object of the invention to provide a kind of luminous material of bipolarity small molecule using two phenanthro- -2,8- indenes fluorenes units as core
Material, the material has good electronics and hole transport performance, is conducive to the injection and transmission of equilbrium carrier so that more
Hole is effectively combined with electronics and produces exciton, so as to improve the luminous efficiency of device.
The present invention also aims to provide a kind of described small point of bipolarity using two phenanthro- -2,8- indenes fluorenes unit as cores
The preparation method of sub- luminescent material.
The present invention also aims to provide a kind of bipolarity small molecule using two phenanthro- -2,8- indenes fluorenes units as core
Application of the luminescent material in the luminescent layer of Organic Light Emitting Diode is prepared.
The purpose of the present invention is achieved through the following technical solutions.
One kind is with the bipolarity small molecule emitter material that two phenanthro- -2,8- indenes fluorenes units are core, and chemical structural formula is as follows：
In formula, Ar1For electron donor unit, Ar2For electron acceptor unit；
R1-R10The straight chain or branched alkyl for being 1-20 for H atom, aryl, triphenylamine, carbon number, or be carbon atom
Number 1-20 alkoxy.
Further, the electron acceptor unit Ar2For any one in following structural formula：
Wherein, n=1-3；R1The straight chain or branched alkyl for being 1-20 for carbon number, or be carbon number 1-20 alkane
Epoxide.
Further, the electron donor unit Ar1For any one in following structural formula：
Described one kind is prepared in method of two phenanthro- -2, the 8- indenes fluorenes units for the bipolarity small molecule emitter material of core,
Mainly include the preparation of the phenanthro- -2,8- indenes fluorenes units of center two.
Described one kind is prepared in method of two phenanthro- -2, the 8- indenes fluorenes units for the bipolarity small molecule emitter material of core,
Comprise the following steps：
Under argon atmosphere, with two phenanthro- -2,8- indenes fluorenes for core, by Suzuki coupling reactions by electron donor unit and electricity
Sub- receptor unit is connected to two phenanthro- -2,8- indenes fluorenes unit both sides, and it is the double of core with two phenanthro- -2,8- indenes fluorenes units to obtain described
Polar micromolecules luminescent material.
Further, the temperature of the Suzuki coupling reactions is 110~150 DEG C, and the time of reaction is 16~18h.
A kind of described bipolarity small molecule emitter material using two phenanthro- -2,8- indenes fluorenes units as core is preparing organic hair
Application in the luminescent layer of optical diode, will be described with bipolarity small molecule luminous material of two phenanthro- -2, the 8- indenes fluorenes units for core
Material is dissolved in common organic solvents, by spin coating, inkjet printing or printing process film forming, obtains the hair of Organic Light Emitting Diode
Photosphere.
Further, the common organic solvents include chlorobenzene.
Further, by the luminescent layer of preparation, further assembling prepares light emitting diode and flat-panel monitor.
Compared with prior art, the present invention has advantages below：
(1) present invention is used centered on two phenanthro- -2,8- indenes fluorenes units first, has synthesized the luminous material of bipolarity small molecule
Material, synthetic method is simple, is easily purified, is conducive to industrial applications.
(2) bipolarity small molecule emitter material prepared by the present invention has good dissolubility, film forming and film morphology
Stability, the luminescent layer based on the bipolarity small molecule emitter material is when preparing device without annealing so that prepare work
Skill is simple.
Brief description of the drawings
Fig. 1 is compound D1 thermogravimetric analysis (TGA) spectrogram；
Fig. 2 is UV-visible absorption spectrums of the compound D2 under filminess；
Fig. 3 is the luminescence generated by light spectrogram based on compound D3 under filminess；
Fig. 4 is the luminescence generated by light spectrogram based on compound D4 under filminess.
Embodiment
With reference to embodiment, the present invention is described in further detail, but the implementation of the present invention is not limited to this.
Embodiment 1
The preparation of the bromo- 2- phenanthrenecarboxylic acids methyl esters of 1-
Chemical equation is as follows：
Under an argon atmosphere, the bromo- 2- phenanthrenecarboxylic acids (10g, 39.83mmol) of 1- are added in two-mouth bottle, adds 100mL first
Alcohol, is then added dropwise the concentrated sulfuric acid (39.06mg, 398.29umol), is heated to 110 DEG C, reacts 18h；Reactant mixture is fallen
Enter in water, be extracted with ethyl acetate, after organic layer is washed completely with saline solution, plus anhydrous magnesium sulfate is dried；After solution concentration, obtain
To crude white solid, (eluant, eluent selects petroleum ether/dichloromethane=3/1, v/v) is purified with silica gel column chromatography, when product is long
Between place refrigerator in obtain white solid, yield 85%.1H NMR、13CNMR, MS and elementary analysis result show resulting change
Compound is target product.
Embodiment 2
The preparation of 2,7- dibromo fluorenes
Chemical equation is as follows：
In 250mL there-necked flasks, fluorenes (24.5g, 0.1mol), iron powder (88mg, 1.57mmol) and chloroform are added
100mL；Ice-water bath is cooled down, and bromine (17.6g, 0.1mol)/chloroform mixed solution 35mL is added dropwise, and temperature does not surpass in bottle during dropwise addition
Cross 5 DEG C；Reaction is finished, filtering, Gossypol recrystallized from chloroform, obtains white solid 20.3g, yield 83%.1HNMR、13CNMR, MS and element
Compound obtained by analysis result shows is target product.
Embodiment 3
The preparation of 2,7- bis- bromo- 9,9- dioctyl fluorenes
Chemical equation is as follows：
Added in there-necked flask 2,7- dibromos fluorenes (9.7g, 0.03mol), benzyltriethylammoinium chloride (0.07g,
0.3mmol), dimethyl sulfoxide (DMSO) 90mL and 45mL sodium hydrate aqueous solutions (50wt%), at room temperature stirring form suspension；Add
1- bromines normal octane (12.5g, 65mmol), continues after stirring 3 hours, is extracted with ether, second is washed with saturated sodium-chloride water solution
Ether phase, anhydrous magnesium sulfate is dried, and boils off solvent, and product petroleum ether makees the purification of eluant, eluent column chromatography, obtains white solid.1H
NMR、13Compound obtained by CNMR, MS and elementary analysis result show is target product.
Embodiment 4
The preparation of 2,7- diborate -9,9- dioctyl fluorenes
Chemical equation is as follows：
Under an argon atmosphere, bromo- 9, the 9- dioctyl fluorenes (5g, 9.12mmol) of 2,7- bis- are dissolved in refined four of 180mL
In hydrogen furans (THF), 1.6mol.L is gradually added dropwise at -78 DEG C-1N-BuLi 28mL, react 2 hours, then add 2- it is different
Propoxyl group -4,4,5,5- tetramethyls -1,3,2- dioxaborinate 25mL continue to react 1 hour at -78 DEG C, then heated to
Room temperature reaction 24 hours；Reactant mixture is poured into water, is extracted with ethyl acetate, after organic layer is washed completely with saline solution,
Plus anhydrous magnesium sulfate is dried；After solution concentration, thick pale yellow shape crude product is obtained, (eluant, eluent selection is purified with silica gel column chromatography
Petrol ether/ethyl acetate=15/1, v/v), product is placed in refrigerator obtain white solid, yield 70% for a long time.1H NMR、13Compound obtained by CNMR, MS and elementary analysis result show is target product.
Embodiment 5
Compound M1 preparation
Chemical equation is as follows：
Under argon atmosphere, by 2,7- diborates -9,9- dioctyl fluorene (5g, 7.78mmol) and the bromo- 2- phenanthrenecarboxylic acids of 1-
Methyl esters (6.19g, 23.34mmol) is added in two-mouth bottle, is added 100ml toluene and is completely dissolved, adds sodium carbonate
(4.12g, 38.91mmol), TBAB (312.01mg, 967.86umol) and four triphenyl phosphorus palladiums (179.84mg,
155.63umol), 18h is reacted at 110 DEG C；Reactant mixture is poured into water, is extracted with ethyl acetate, organic layer salt
After water washing completely, plus anhydrous magnesium sulfate is dried.After solution concentration, (eluant, eluent selection petroleum ether/bis- are purified with silica gel column chromatography
Chloromethanes=8/1, v/v), finally give white solid, yield 80%.1H NMR、13CNMR, MS and elementary analysis result show
Resulting compound is target product M1.
Embodiment 6
Compound M2 preparation
Chemical equation is as follows：
Under argon atmosphere, M1 (10g, 13.17mmol) is added in single port bottle, the anhydrous THF of 50ml are added until complete
Fully dissolved, then reaction solution is reacted into 1h at 0 DEG C, then n-octyl magnesium bromide (C is added dropwise8H17MgBr, 16.65g,
76.60mmol), mixed liquor reacts 18h at room temperature；Add water in reaction solution that reaction is quenched, be extracted with ethyl acetate,
After organic layer is washed completely with saline solution, plus anhydrous magnesium sulfate is dried；After solution concentration, (eluant, eluent is purified with silica gel column chromatography
Select petroleum ether/dichloromethane=3/1, v/v), product is placed in refrigerator obtain white solid, yield 80% for a long time.1H
NMR、13Compound obtained by CNMR, MS and elementary analysis result show is target product M2.
Embodiment 7
Compound M3 preparation
Chemical equation is as follows：
Under argon atmosphere, compound M2 (5g, 8.68mmol) is dissolved in 50ml dichloromethane, added dropwise at room temperature
Enter BFEE (588.67mg, 8.68mmol) solution, react 18h；It is extracted with ethyl acetate, organic layer is complete with saline solution
After full washing, plus anhydrous magnesium sulfate is dried；After solution concentration, (eluant, eluent selection petroleum ether), product are purified with silica gel column chromatography
Place for a long time in refrigerator and obtain white solid, yield 90%.1H NMR、13Obtained by CNMR, MS and elementary analysis result show
Compound be target product M3.
Embodiment 8
Compound M4 preparation
Chemical equation is as follows：
Under argon atmosphere, compound M3 (5g, 4.48mmol) is dissolved in 50mL dichloromethane, iron powder is added
(185.35mg, 4.48mmol), then bromine (1.50g, 9.41mmol) is added dropwise, 18h is reacted at room temperature；Use ethyl acetate
Extraction, after organic layer is washed completely with saline solution, plus anhydrous magnesium sulfate is dried；After solution concentration, purified and (washed with silica gel column chromatography
De- agent selection petroleum ether), yield 70%.1H NMR、13Compound obtained by CNMR, MS and elementary analysis result show is mesh
Mark product M4.
Embodiment 9
Compound M6 preparation
Chemical equation is as follows：
Under argon atmosphere, compound M4 (5g, 3.93mmol) and benzimidazole boric acid (1.23g, 3.93mmol) are added
Enter into two-mouth bottle, add 100ml toluene and be completely dissolved, add sodium carbonate (2.08g, 19.63mmol), the tetrabutyl
Ammonium bromide (312.01mg, 967.86umol) and four triphenyl phosphorus palladiums (190.73mg, 78.5umol), react at 110 DEG C
18h；Reactant mixture is poured into water, is extracted with ethyl acetate, after organic layer is washed completely with saline solution, plus anhydrous magnesium sulfate
Dry；After solution concentration, (eluant, eluent selects petroleum ether/dichloromethane=6/1, v/v) is purified with silica gel column chromatography, is finally given
White solid, yield 80%.1H NMR、13Compound obtained by CNMR, MS and elementary analysis result show is target product
M6。
Embodiment 10
Compound D1 preparation
Chemical equation is as follows：
Under argon atmosphere, by compound M6 (1g, 683.51umol) and triphenylamine borate (253.77mg,
683.51umol) be added in two-mouth bottle, add 100ml toluene and be completely dissolved, add sodium carbonate (362.22mg,
3.42mmol), TBAB (312.01mg, 967.86umol) and four triphenyl phosphorus palladiums (15.08mg, 13.67umol),
18h is reacted at 110 DEG C；Reactant mixture is poured into water, is extracted with ethyl acetate, organic layer is washed completely with saline solution
Afterwards, plus anhydrous magnesium sulfate dry；After solution concentration, (eluant, eluent selection petroleum ether/dichloromethane=6/ is purified with silica gel column chromatography
1, v/v) white solid, yield 80%, are finally given.1H NMR、13CNMR, MS and elementary analysis result show resulting change
Compound is target product D1.
The compound D1 that the present embodiment is obtained TGA spectrograms are as shown in figure 1, as shown in Figure 1, compound D1 heat decomposition temperatures
(temperature during mass loss 5%) is 405 DEG C.
Embodiment 11
Compound D2 preparation
Chemical equation is as follows：
Under argon atmosphere, compound M6 (1g, 683.51umol) and carbazole (1114.29mg, 683.51umol) are added
Enter into 100ml two-mouth bottles, add toluene and be completely dissolved, add palladium (3.07mg, 13.67umol) and three tertiary fourths
Base phosphorus (5.53mg, 27.34umol), 18h is reacted at 110 DEG C；Reactant mixture is poured into water, is extracted with ethyl acetate,
After organic layer is washed completely with saline solution, plus anhydrous magnesium sulfate is dried；After solution concentration, (eluant, eluent is purified with silica gel column chromatography
Select petroleum ether/dichloromethane=4/1, v/v), finally give white solid, yield 80%.1H NMR、13CNMR, MS and element
Compound obtained by analysis result shows is target product D2.
Uv-visible absorption spectras of the target compound D2 that the present embodiment is obtained under filminess as shown in Fig. 2 from
As can be seen that compound D2 absworption peak is located at 245nm and 388nm in Fig. 2.
Embodiment 12
Compound M7 preparation
Chemical equation is as follows：
Under an argon atmosphere, by the bromo- S of 2-, S- dioxydibenzes bithiophene (5g, 16.94mmol), 2- borates -9,9- bis-
Octyl group fluorenes (21.77g, 33.88mmol), Na2CO3(8.98g, 84.70mmol) and TBAB 1g are added to 250ml
In two-mouth bottle, after after abundant dissolving, Pd (PPh are added3)4(391.51mg, 338.81umol), 16h is reacted at 110 DEG C；Use second
Acetoacetic ester is extracted, after organic layer is washed completely with saline solution, plus anhydrous magnesium sulfate is dried；After solution concentration, silica gel column chromatography is used
Purification (eluant, eluent selects petroleum ether/dichloromethane=4/1, v/v), product is placed in refrigerator obtain white solid for a long time, produces
Rate 70%.1H NMR、13Compound obtained by CNMR, MS and elementary analysis result show is target product M7.
Embodiment 13
Compound M8 preparation
Chemical equation is as follows：
Under an argon atmosphere, by compound M4 (5g, 16.94mmol), compound M7 (21.77g, 33.88mmol),
Na2CO3(8.98g, 84.70mmol) and TBAB 1g, is added in 250ml two-mouth bottles, fully after dissolving, adds
Pd(PPh3)4(391.51mg, 338.81umol), 16h is reacted at 110 DEG C；It is extracted with ethyl acetate, organic layer saline solution
Completely after washing, plus anhydrous magnesium sulfate is dried；After solution concentration, (eluant, eluent selection petroleum ether/dichloro is purified with silica gel column chromatography
Methane=4/1, v/v), product is placed in refrigerator obtain white solid, yield 70% for a long time.1H NMR、13CNMR, MS and member
Compound obtained by plain analysis result shows is target product M8.
Embodiment 14
Compound D3 preparation
Chemical equation is as follows：
Under argon atmosphere, by compound M8 (1g, 583.51umol) and triphenylamine borate (253.77mg,
583.51umol) be added in two-mouth bottle, add 100ml toluene and be completely dissolved, add sodium carbonate (362.22mg,
3.42mmol), TBAB (312.01mg, 967.86umol) and four triphenyl phosphorus palladiums (15.08mg, 13.67umol),
18h is reacted at 110 DEG C；Reactant mixture is poured into water, is extracted with ethyl acetate, organic layer is washed completely with saline solution
Afterwards, plus anhydrous magnesium sulfate dry；After solution concentration, (eluant, eluent selection petroleum ether/dichloromethane=6/ is purified with silica gel column chromatography
1, v/v) white solid, yield 80%, are finally given.1H NMR、13CNMR, MS and elementary analysis result show resulting change
Compound is target product D3.
Photoluminescence spectra figures of the compound D3 that the present embodiment is obtained under filminess is as shown in figure 3, can from Fig. 3
To find out, compound D3 maximum emission peak is located at 515nm.
Embodiment 15
Compound D4 preparation
Chemical equation is as follows：
Under argon atmosphere, compound M8 (1g, 583.51umol) and carbazole (1114.29mg, 583.51umol) are added
Enter into 100ml two-mouth bottles, add toluene and be completely dissolved, add palladium (3.07mg, 13.67umol) and three tertiary fourths
Base phosphorus (5.53mg, 27.34umol), 18h is reacted at 110 DEG C；Reactant mixture is poured into water, is extracted with ethyl acetate,
After organic layer is washed completely with saline solution, plus anhydrous magnesium sulfate is dried；After solution concentration, (eluant, eluent is purified with silica gel column chromatography
Select petroleum ether/dichloromethane=4/1, v/v), finally give white solid, yield 80%.1H NMR、13CNMR, MS and element
Compound obtained by analysis result shows is target product D4.
Photoluminescence spectra figures of the compound D4 that the present embodiment is obtained under filminess is as shown in figure 4, can from Fig. 4
To find out, compound D4 maximum emission peak is located at 465nm.
Embodiment 16
The preparation of electroluminescent device based on bipolarity small molecule emitter material
It is on 20 Ω/ tin indium oxide (ITO) glass, first successively with acetone, washing in the square resistance of well in advance
Agent, deionized water and isopropanol are cleaned by ultrasonic, plasma treatment 10 minutes；Spin coating, which is mixed, on ITO polystyrolsulfon acid
Polyethoxy thiophene (mass ratio PEDOT:PSS=1:1) film, thickness is 150nm；PEDOT:PSS films are 80 DEG C in vacuum drying oven
Lower drying 8 hours；Then bipolarity small molecule emitter material D1, D2, D3, D4 chlorobenzene solution (1wt%) is spin-coated on respectively
PEDOT:The surface of PSS films, thickness is 80nm, is used as luminescent layer；A thin layer CsF is finally deposited successively on luminescent layer
(1.5nm) and 120nm thick metal Al layer.
The photoelectric properties index of electroluminescent device based on bipolarity small molecule emitter material D1~D4 is as shown in table 1.
The photoelectric properties index of electroluminescent device of the table 1 based on bipolarity small molecule emitter material D1~D4
As shown in Table 1, with target compound D1, D2, D3, D4 is the electroluminescent device of luminescent layer, based on device architecture：
ITO/PEDOT/Emitter/CsF/Al, the maximum lumen efficiency of target compound be followed successively by 2.02cd/A, 1.07cd/A,
0.78cd/A、1.2cd/A。
Above-described embodiment is preferably embodiment, but embodiments of the present invention are not by above-described embodiment of the invention
Limitation, it is other it is any without departing from Spirit Essences and the change made under principle of the present invention, modification, replacement, combine, simplification all should
For equivalent substitute mode, it is included within protection scope of the present invention.
Claims (7)
1. it is a kind of with bipolarity small molecule emitter material of two phenanthro- -2, the 8- indenes fluorenes units for core, it is characterised in that chemical constitution
Formula is as follows：
In formula, Ar1For electron donor unit, Ar2For electron acceptor unit；R1-R10For H atom, aryl, triphenylamine, carbon number
For 1-20 straight chain or branched alkyl, or it is the alkoxy that carbon number is 1-20.
2. it is according to claim 1 a kind of with the bipolarity small molecule emitter material that two phenanthro- -2,8- indenes fluorenes units are core,
Characterized in that, the electron acceptor unit Ar2For any one in following structural formula：
Wherein, n=1-3；R1The straight chain or branched alkyl for being 1-20 for carbon number, or be carbon number 1-20 alkoxy.
3. it is according to claim 1 a kind of with the bipolarity small molecule emitter material that two phenanthro- -2,8- indenes fluorenes units are core,
Characterized in that, the electron donor unit Ar1For any one in following structural formula：
4. prepare a kind of bipolarity small molecule using two phenanthro- -2,8- indenes fluorenes units as core described in any one of claims 1 to 3
The method of luminescent material, it is characterised in that comprise the following steps：
Under argon atmosphere, with two phenanthro- -2,8- indenes fluorenes for core, by Suzuki coupling reactions by electron donor unit and electronics by
Body unit is connected to two phenanthro- -2,8- indenes fluorenes unit both sides, obtains described with bipolarity of two phenanthro- -2, the 8- indenes fluorenes units for core
Small molecule emitter material.
5. a kind of bipolarity small molecule emitter material using two phenanthro- -2,8- indenes fluorenes units as core according to claim 4
Preparation method, it is characterised in that the temperature of the Suzuki coupling reactions is 110~150 DEG C, time of reaction for 16~
18h。
6. a kind of bipolarity small molecule using two phenanthro- -2,8- indenes fluorenes units as core described in any one of claims 1 to 3 lights
Application of the material in the luminescent layer of Organic Light Emitting Diode is prepared, it is characterised in that will be described with two phenanthro- -2,8- indenes fluorenes lists
Member is dissolved in common organic solvents for the bipolarity small molecule emitter material of core, passes through spin coating, inkjet printing or printing process
Film forming, obtains the luminescent layer of Organic Light Emitting Diode.
7. application according to claim 6, it is characterised in that the common organic solvents include chlorobenzene.
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| CN101679857A (en) * | 2007-07-27 | 2010-03-24 | 东丽株式会社 | Light-emitting device material and light-emitting device |
| CN105482813A (en) * | 2015-12-21 | 2016-04-13 | 南京邮电大学 | Novel fluorene bipolar fluorescent material based on anthraquinone group and application of novel fluorene bipolar fluorescent material in organic light emitting diodes |
| CN105636944A (en) * | 2013-10-14 | 2016-06-01 | 默克专利有限公司 | Materials for electronic devices |
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| CN101679857A (en) * | 2007-07-27 | 2010-03-24 | 东丽株式会社 | Light-emitting device material and light-emitting device |
| CN105636944A (en) * | 2013-10-14 | 2016-06-01 | 默克专利有限公司 | Materials for electronic devices |
| CN105482813A (en) * | 2015-12-21 | 2016-04-13 | 南京邮电大学 | Novel fluorene bipolar fluorescent material based on anthraquinone group and application of novel fluorene bipolar fluorescent material in organic light emitting diodes |
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