CN107353891A - It is a kind of using three indenes fluorenes units as star-like bipolarity small molecule emitter material of core and preparation method and application - Google Patents
It is a kind of using three indenes fluorenes units as star-like bipolarity small molecule emitter material of core and preparation method and application Download PDFInfo
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Abstract
The invention discloses a kind of using three indenes fluorenes units as star-like bipolarity small molecule emitter material of core and preparation method and application.Electrophilic unit and electron unit, by Suzuki coupling reactions, are connected in turn on three indenes fluorenes units by the preparation method successively using three indenes fluorenes units as core, obtain the star-like bipolarity small molecule emitter material using three indenes fluorenes units as core.The present invention has good dissolubility, film forming and film morphology stability by the star-like bipolarity small molecule emitter material of core of three indenes fluorenes units in common organic solvents, with the luminescent layer of its making can in balancing device electronics and hole injection and transmission, make acquisition efficient while simplify device preparation technology.
Description
Technical field
The present invention relates to organic photoelectric technologic material field, and in particular to a kind of small as the bipolarity of core using three indenes fluorenes units
Molecular ligh-emitting materials and preparation method and application.
Background technology
Organic Light Emitting Diode (OLED) is because with efficient, low voltage drive, being easy to the advantages that prepared by large area and obtaining 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, which is have developed, with sandwich device architecture can reach 1000cd/m2, make
OLED obtains epoch-making development.OLED is made up of negative electrode, anode and the organic layer of centre, and organic layer generally comprises electricity
Sub- transport layer, luminescent layer and hole transmission layer, first electronics and hole inject from negative and positive the two poles of the earth respectively, and respectively in functional layer
Migrated, then electronics and hole form exciton in place, and exciton is migrated within the specific limits, last exciton
It is luminous.
In order to realize the commercialization of organic/polymer electroluminescent device early, except that should meet that full color can be realized
Outside display, the requirement such as monochromatic purity is high, thermo-chemical stability is good and service life is grown, it is also desirable to which device has high luminous effect
Rate.One of the principal element for influenceing OLED efficiency at present is the imbalance of material electronics in itself and hole transport injection.
Therefore, in order to obtain efficient OLED, it is necessary to the balance of the electrons transmission and injection of reasonable adjusting material.In recent years
Come, bipolar materials have attracted people extensive because of the hole with balance and electronic carrier stream in field of organic electroluminescence
Concern, and the material causes the structure of device to simplify.This new technology is not only in theoretical research field by scientist
Favored, and the production that progressively moves towards the industrialization, thus exploitation bipolar materials have practical value.
The content of the invention
It is an object of the invention to provide a kind of star-like bipolarity small molecule emitter material using three indenes fluorenes units as core, and
Three indenes fluorenes units contain polar group；The introducing of three indenes fluorenes units, advantageously reduce the highest occupied molecular orbital of monomer
(HOMO) while energy level, the injection and transmission in hole in organic electroluminescence device are substantially improved.
The present invention also aims to provide a kind of described star-like bipolarity small molecule hair using three indenes fluorenes units as core
The preparation method of luminescent material.
The present invention also aims to provide a kind of described star-like bipolarity small molecule hair using three 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 realized by following concrete technical scheme.
A kind of star-like bipolarity small molecule emitter material using three indenes fluorenes units as core, there is following chemical structural formula：
In formula, Ar1For electrophilic unit, Ar2For electron unit；R is carbon number 1-20 straight or branched alkyl,
Or the alkoxy for carbon number 1-20.
Further, the electrophilic unit Ar1For any one in following structural formula：
Wherein, n=1-3；R1For carbon number 1-20 straight or branched alkyl, or the alcoxyl for carbon number 1-20
Base.
Further, the electron unit Ar2For any one in following structural formula：
A kind of described preparation method using three indenes fluorenes units as the star-like bipolarity small molecule emitter material of core, main bag
Include the preparation of three indenes fluorenes units of center polar functionalities.
A kind of described preparation method using three indenes fluorenes units as the star-like bipolarity small molecule emitter material of core, including such as
Lower step：
Using the three indenes fluorenes units of the R containing group as core, by Suzuki coupling reactions, by electrophilic unit A1With electron list
First A2It is connected in turn on three indenes fluorenes units, obtains described using three indenes fluorenes units as the luminous material of the star-like bipolarity small molecule of core
Material.
Further, the temperature of the Suzuki coupling reactions is 110 DEG C~160 DEG C.
Further, the time of the Suzuki coupling reactions is 18~32 hours.
A kind of described star-like bipolarity small molecule emitter material using three indenes fluorenes units as core is applied to prepare organic hair
The luminescent layer of optical diode, the star-like bipolarity small molecule emitter material using three indenes fluorenes units as core is dissolved with organic solvent
Afterwards, spin coating, inkjet printing or printing film forming, the luminescent layer of obtained Organic Light Emitting Diode are passed through；Luminescent layer group based on preparation
The Organic Light Emitting Diode of dress can be used for making flat-panel monitor.
Further, the organic solvent includes toluene.
Compared with prior art, the present invention has advantages below：
(1) centered on the present invention uses three indenes fluorenes units first, bipolarity small molecule emitter material, and synthesis side have been synthesized
Method is simple, is easily purified, and is advantageous to industrial applications；
(2) star-like bipolarity small molecule emitter material of the present invention using three indenes fluorenes units as core has good electronics and sky
Cave transmission performance, can be with the injection and transmission of equilbrium carrier so that more holes and electronics effectively compound generation exciton,
So as to improve the luminous efficiency of luminescent device；
(3) star-like bipolarity small molecule emitter material of the present invention using three indenes fluorenes units as core has good in organic solvent
Good dissolubility, film forming and film morphology stability, the sky in electroluminescent device can be balanced with the luminescent layer of its making
Cave and the injection and transmission of electronics, simplify device preparation technology while improving device efficiency.
Brief description of the drawings
Fig. 1 is uv-visible absorption spectra spectrograms of the bipolarity small molecule emitter material P1 under filminess；
Fig. 2 is uv-visible absorption spectra spectrograms of the bipolarity small molecule emitter material P2 under filminess；
Fig. 3 is luminous efficiency-current density plot of the electroluminescent device based on bipolarity small molecule emitter material P3
Figure.
Embodiment
The present invention is described in further detail with reference to embodiment and accompanying drawing, but embodiments of the present invention are unlimited
In this.
Embodiment 1
The preparation of compound 1
Indone (11g, 83.3mmol), 4mL hydrochloric acid and 8mL acetic acid are added in two-mouth bottle, after reacting 20h, by frozen water
Reaction solution is added, has precipitation to produce, is filtered successively with water, acetone, dichloromethane.Washed product dioxane is molten
Solution, heat, stir, cooling, filtered, then washed with tetrahydrofuran solution, obtain final product, yield 60%.1H NMR
、13Compound obtained by CNMR, MS and elementary analysis result show is target product 1, the following institute of its chemical equation
Show：
Embodiment 2
The preparation of compound 2
Under an argon atmosphere, compound 1 (5g, 14mmol) is added in the two mouthfuls of flasks dried and with 100mL without
Water tetrahydrofuran dissolves, and is cooled to -78 DEG C, and 53.76mL n-BuLis are slowly added dropwise, and stirs two hours, and it is pungent to add 17.6mL bromines
Alkane, after reacting 20h, with dichloromethane extractive reaction liquid, subnatant is taken, column chromatography for separation is carried out by eluant, eluent of n-hexane.
Products therefrom is dissolved in acetone, with ethyl alcohol recrystallization, obtains final product.Yield：65%.1H NMR、13CNMR, MS and element
Compound obtained by analysis result shows is target product 2, and its chemical equation is as follows：
Embodiment 3
The preparation of compound 3
Compound 2 (3g, 3.54mmol) is dissolved in 10mL chloroforms, adds iron powder (0.1g, 0.175mmol), ice bath to 5
DEG C, the mixed liquor of bromine (0.64mL, 12.39mmol) and 30mL chloroforms is slowly added dropwise, lucifuge, is added dropwise, is warmed to room temperature anti-
After answering 10 hours, the solution of sodium bisulfite of saturation is added, removes unnecessary unreacted bromine.The crude product stone obtained after filtering
Oily ether：Dichloromethane=10：3 (v/v) carry out column chromatography for separation, obtain final product, yield：58%.1H NMR、13CNMR、MS
Compound obtained by showing with elementary analysis result is target product 3, and its chemical equation is as follows：
Embodiment 4
The preparation of compound 4
Under an argon atmosphere, compound 3 (10g, 7.98mmol) is dissolved in the refined anhydrous tetrahydro furans of 180mL
(THF) in, 1.6mol L are gradually added dropwise at -78 DEG C-1N-BuLi 28mL, react 2 hours, then add 2- isopropyl oxygen
Base -4,4,5,5- tetramethyls -1,3,2- dioxaborinate 25mL, continue reaction 1 hour at -78 DEG C, be warming up 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, adds anhydrous sulphur
Sour magnesium is dried；After solution concentration, thick pale yellow shape crude product is obtained, (eluant, eluent selection petroleum ether/second is purified with silica gel column chromatography
Acetoacetic ester=20/1, v/v), obtain white solid, yield 70%.1H NMR、13CNMR, MS and elementary analysis result show gained
The compound arrived is target product 4, and its chemical equation is as follows：
Embodiment 5
The preparation of compound 5
Under argon atmosphere, by compound 4 (5g, 3.59mmol) and S, S- dioxo-dibenzothiophene (4.03g,
10.76mmol) be added in two-mouth bottle, add 100ml toluene and be completely dissolved, add sodium carbonate (1.90g,
17.94mmol), TBAB (312.01mg, 967.86umol) and four triphenyl phosphorus palladiums (109.77umol,
126.84mg), 18h is reacted at 110 DEG C；Reactant mixture is poured into water, is extracted with ethyl acetate, organic layer saline solution
Completely after washing, anhydrous magnesium sulfate is added to dry；After solution concentration, (eluant, eluent selection petroleum ether/dichloro is purified with silica gel column chromatography
Methane=6/1, v/v), finally give white solid, yield 80%.1H NMR、13CNMR, MS and elementary analysis result show institute
Obtained compound is target product 5, and its chemical equation is as follows：
Embodiment 6
Compound P1 preparation
Under argon atmosphere, by compound 5 (1g, 526.67umol) and triphenylamine borate (587.74mg,
1.58mmol) be added in two-mouth bottle, add 100mL toluene and be completely dissolved, add sodium carbonate (481.57mg,
4.54mmol), TBAB (312.01mg, 967.86umol) and four triphenyl phosphorus palladiums (21mg, 18.17umol),
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,
Anhydrous magnesium sulfate is added to dry；After solution concentration, purified with silica gel column chromatography (eluant, eluent selects petroleum ether/dichloromethane=6/1,
V/v), white solid, yield 80% are finally given.1H NMR、13CNMR, MS and elementary analysis result show resulting chemical combination
Thing is target product P1, and its chemical equation is as follows：
Uv-visible absorption spectra spectrograms of the obtained star-like bipolarity small molecule emitter material P1 under filminess is such as
Shown in Fig. 1, from figure 1 it appears that maximum absorption bands of the bipolarity small molecule emitter material P1 under filminess exists
365nm。
Embodiment 7
Compound P2 preparation
Under argon atmosphere, compound 5 (1g, 526.67umol) and carbazole (264.69mg, 1.58mol) are added to
In 100mL two-mouth bottles, add 100mL toluene and be completely dissolved, add palladium (4.08mg, 18.17umol) and three uncles
Butyl phosphorus (7.35mg, 36.35umol), reacts 18h at 110 DEG C；Reactant mixture is poured into water, extracted with ethyl acetate
Take, after organic layer is washed completely with saline solution, add anhydrous magnesium sulfate to dry；After solution concentration, (elution is purified with silica gel column chromatography
Agent selects petroleum ether/dichloromethane=4/1, v/v), finally give white solid, yield 80%.1H NMR、13CNMR, MS and member
Compound obtained by plain analysis result shows is target product P2, and its chemical equation is as follows：
UV-visible absorption spectrums of the obtained star-like bipolarity small molecule emitter material P2 under filminess is as schemed
Shown in 2, from figure 2 it can be seen that absworption peak 381nms of the bipolarity small molecule emitter material P2 under filminess.
Embodiment 8
Compound P3 preparation
Under argon atmosphere, compound 5 (1g, 526.67umol) and tert-butyl carbazole (284.69mg, 1.58mol) are added
Enter into 100ml two-mouth bottles, add 100ml toluene be completely dissolved, add palladium (4.08mg, 18.17umol) and
Tri-tert phosphorus (7.35mg, 36.35umol), reacts 18h at 110 DEG C；Reactant mixture is poured into water, uses ethyl acetate
Extraction, after organic layer is washed completely with saline solution, adds anhydrous magnesium sulfate to dry；After solution concentration, purified and (washed with silica gel column chromatography
De- agent selection petroleum ether/dichloromethane=4/1, v/v), finally give white solid, yield 80%.1H NMR、13CNMR, MS and
Compound obtained by elementary analysis result shows is target product P3, and its chemical equation is as follows：
Embodiment 9
The preparation of electroluminescent device based on small molecule
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 is doped with polystyrolsulfon acid on ITO
Polyethoxy thiophene (PEDOT:PSS=1:1, w/w) film, thickness 150nm；PEDOT:PSS films are in vacuum drying oven at 80 DEG C
Dry 8 hours, bipolarity small molecule emitter material P1, P2, P3 ethanol solution (1wt%) is then spin-coated on PEDOT respectively:
The surface of PSS films, thickness 80nm, obtains luminescent layer；Finally be deposited successively on luminescent layer the thick thin layer CsF of 1.5nm and
Metal Al layer thick 120nm, obtain the electroluminescent device that structure is ITO/PEDOT/EML/CsF/Al.
Wherein, the electroluminescent device based on star-like bipolarity small molecule emitter material P3, device architecture：ITO/PEDOT/
EML/CsF/Al, its luminous efficiency-current density plot figure is as shown in figure 3, from figure 3, it can be seen that the maximum lumen of device
Efficiency is 1.68cd/A.
The photoelectric properties test result of electroluminescent device based on star-like bipolarity small molecule emitter material P1, P2, P3
As shown in table 1.
The photoelectric properties test result of electroluminescent device of the table 1 based on material P1, P2, P3
As shown in Table 1, the electroluminescent device efficiency highest prepared based on P2, maximum lumen efficiency is 2.4cd/A, and
It is 100cd/m in brightness2When, luminous efficiency still may remain in 2.0cd/A, and it is smaller to illustrate that device efficiency roll-offs, and
Electroluminescent device based on P1 and P3 shows small efficiency roll-off, illustrates the electroluminescent device based on bipolar materials
Hole and electron injection and transmission with balance.
Above-described embodiment is the preferable embodiment of the present invention, but embodiments of the present invention are not by above-described embodiment
Limitation, it is other it is any without departing from the present invention Spirit Essences with made under principle change, modification, replacement, combine, simplification all should
For equivalent substitute mode, it is included within protection scope of the present invention.
Claims (7)
1. a kind of star-like bipolarity small molecule emitter material using three indenes fluorenes units as core, it is characterised in that there is following chemistry
Structural formula：
In formula, Ar1For electrophilic unit, Ar2For electron unit；R is carbon number 1-20 straight or branched alkyl, or is
Carbon number 1-20 alkoxy.
2. a kind of star-like bipolarity small molecule emitter material using three indenes fluorenes units as core according to claim 1, it is special
Sign is, the electrophilic unit Ar1For any one in following structural formula：
Wherein, n=1-3；R1For carbon number 1-20 straight or branched alkyl, or the alkoxy for carbon number 1-20.
3. a kind of star-like bipolarity small molecule emitter material using three indenes fluorenes units as core according to claim 1, it is special
Sign is, the electron unit Ar2For any one in following structural formula：
4. prepare a kind of star-like bipolarity small molecule using three indenes fluorenes units as core described in any one of claims 1 to 3 to light
The method of material, it is characterised in that comprise the following steps：
Using the three indenes fluorenes units of the R containing group as core, by Suzuki coupling reactions, by electrophilic unit A1With electron unit A2
It is connected in turn on three indenes fluorenes units, obtains the star-like bipolarity small molecule emitter material using three indenes fluorenes units as core.
A kind of 5. system using three indenes fluorenes units as the star-like bipolarity small molecule emitter material of core according to claim 4
It is standby, it is characterised in that the temperature of the Suzuki coupling reactions is 110 DEG C~160 DEG C；The time of the Suzuki coupling reactions
For 18~32 hours.
A kind of 6. star-like bipolarity small molecule emitter material using three indenes fluorenes units as core described in any one of claims 1 to 3
Applied to the luminescent layer for preparing Organic Light Emitting Diode, it is characterised in that will be small as the star-like bipolarity of core using three indenes fluorenes units
After molecular ligh-emitting materials are dissolved with organic solvent, by spin coating, inkjet printing or printing film forming, Organic Light Emitting Diode is made
Luminescent layer.
7. application according to claim 6, it is characterised in that the organic solvent includes toluene.
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| CN109020978A (en) * | 2018-07-31 | 2018-12-18 | 华南协同创新研究院 | A kind of star-like fluorescent molecule and the preparation method and application thereof |
| CN114094023A (en) * | 2021-11-16 | 2022-02-25 | 上海八亿时空先进材料有限公司 | Organic electroluminescent element containing triphenyltriindene-based compound |
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| CN101219921A (en) * | 2008-01-18 | 2008-07-16 | 北京大学 | Conjugation arborization electroinduced ethereal blue light material, preparation method and application thereof |
| CN102464650A (en) * | 2010-11-17 | 2012-05-23 | 海洋王照明科技股份有限公司 | Organic semiconductor material containing anthracene, thiofuran and truxene and preparation method and application of organic semiconductor material |
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| CN106675551A (en) * | 2016-12-09 | 2017-05-17 | 华南理工大学 | Bipolar small molecular luminescent material capable of being processed by adopting environment-friendly solvent and taking naphtho-indenofluorene unit as core as well as production method and application of bipolar small molecular luminescent material |
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