CN110183441A - A kind of preparation method of OLED electron transport material NBphen - Google Patents
A kind of preparation method of OLED electron transport material NBphen Download PDFInfo
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- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
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Abstract
The invention discloses the preparation methods of OLED electron transport material NBphen a kind of.The preparation method includes: (1) in the presence of protective gas and the first organic solvent, and 2- bromonaphthalene and lithium metal are carried out haptoreaction, obtain 2- lithium naphthalene organic solution；(2) in the presence of protective gas, Bphen organic solution and 2- lithium naphthalene organic solution is subjected to haptoreaction, obtain reaction mixture；(3) reaction mixture is hydrolyzed with water and is reacted, obtain oil water mixture；(4) organic phase in the water layer of oil water mixture is extracted, organic phase and oxidant are then subjected to haptoreaction, obtain the NBphen.Method of the invention is reacted more convenient and energy saving without being cooled to -78 DEG C；That reacts is highly-safe, is convenient for being prepared on a large scale.
Description
Technical field
The invention belongs to electron transport material synthesis technical fields, more particularly, to a kind of OLED electron transport material
The preparation method of NBphen.
Background technique
In recent years, Organic Light Emitting Diode (organic light-emitting diodes, OLED) is the organic of representative
Photoelectric material shows huge commercial applications prospect, be widely used in FPD and lighting area [J.Smith,
E.Bawolek, Y.K.Lee, Electron.Lett., 2015,51 (17), 1312.], cause the extensive of academia and industrial circle
Concern.Luminous organic material is the important component that OLED device is constructed, the exploitation pair of novel efficient luminous organic material
In the raising of OLED device performance play it is conclusive effect [Chen Bin, Zhao Zujin, Tang Benzhong Science Bulletin, 2016,61 (32),
3435.]。
The OLED device of early stage generallys use single layer structure, and electron-transport, hole transport and luminescent material concentrate on one kind
In material, brightness is extremely low.1987, Deng Qingyun study group introduced bi-layer devices, using Alq3It is also served as electron-transport luminous
Layer, TPD are hole transmission layer, and device brightness under the low driving voltage less than 10V is more than 1000cd/m2[C.W.Tang,
S.A.Vanslyke,Appl.Phys.Lett.,1987,51(12),913.].1988, Japan proposed 3-tier architecture, device again
Electron-transport, shine, hole transport [C.Adachi, S.Tokito, T.Tsutsui, Jpn are respectively formed by different materials
J.Appl.Phys.,1988,27(2),L269.].Even to this day, with various doping means and new diseases, researcher
More diversified device architecture can be developed, so that the luminescent properties of OLED are greatlyd improve, between metal electrode and ITO
Can there are electron injecting layer, electron transfer layer, organic luminous layer, hole transmission layer, hole injection layer etc..
In OLED device, the mobility of most of hole mobile material is 10-3~10-4cm2/ (Vs), and electronics passes
The mobility of defeated material is usually 10-4~10-6cm2/(V·s)[Z.Q.Zhang,Q.Wang,Y.F.Dai,
Org.Electron.,2009,10(3),491.].The electron mobility of electron transport material is relatively low, transmittability is poor and transmission
The stronger cavitation material mismatch of ability is to cause one of the main reason for device efficiency is low, stability is poor.In order to enhance electricity
Sub- transmittability constructs the balance of electronics and hole, to improve OLED device performance, it is desirable to the higher, property using mobility
The more stable electron transport material of energy, and construct structurally reasonable, level-density parameter electron transfer layer.
Must have high film stability, thermal stability and electron-transporting for making the material of electron transfer layer.
Common electron transport material includes Alq3, Liq, PBD, Bebq, TAZ, Bphen etc., chemical structure is respectively such as 1 institute of following formula
Show.Recent studies have indicated that using Bphen and the device and traditional devices phase after other materials doping as electron transfer layer
Improve 3.5 times than, brightness, current efficiency improve 1.1~2.5 times [Yuan Taoli, Wang Xiufeng, Mu Qiang shine journal, 2017,38
(8), 1069.], illustrate Bphen and its derivative is a kind of excellent electron transport material.
As the derivative of Bphen, and NBphen (2,9- bis- (2- naphthalene) -4,7- diphenyl -1,10- ferrosins, 2,9-
Bis (naphthalen-2-yl) -4,7-diphenyl-1,10-phenanthroline) it is a kind of Novel electronic transmission material,
Its molecular structure is as shown in following formula 2.NBphen has thermal stability more better than Bphen.Its glass transition temperature is 105
DEG C, Bphen is 63 DEG C；In thermogravimetric analysis, NBphen thermal weight loss at 370 DEG C reaches 0.5%, and Bphen is 260 DEG C.Phase
Closing research confirms, NBphen and common dopant material such as Cs radical derivative are formed by N-shaped electron transfer layer, is improving electronics
Also have many advantages, such as to be easy to be deposited while efficiency of transmission, the OLED device prepared with this brightness in 14V can reach
39820cd·m-2, hence it is evident that better than the brightness (25000cdm under traditional devices the same terms-2)[L.-Y.Shen,X.-M.Wu,
Y.-L.Hua,Acta Phys.-Chim.Sin.,2012,28(6),1497.]。
With the arriving of OLED material commercialization spring tide, NBphen is very wide as the market prospects of electron transport material
It is wealthy, but preparation method has not been reported in open source literature at present, and external related patents quantity is seldom, and uses tradition
Butyl lithium route, synthetic method as shown in following formula 3, the disadvantages of the method are as follows butyl lithium be weak solution, in air can not be steady
Existing calmly and inflammable and explosive, reaction needs stringent anaerobic waterless operation, need to be in -78 DEG C of low-temp reaction, cumbersome and risk is high,
It is only suitable in laboratory repeatedly a small amount of preparations.
Formula 3, the synthetic route of NBphen in existing foreign patent
Summary of the invention
The object of the present invention is to provide the synthetic methods of OLED electron transport material NBphen a kind of, to overcome traditional fourth
Butyl lithium existing for base lithium route is inflammable and explosive, and reaction needs stringent anaerobic waterless operation that need to carry out under -78 DEG C of low temperature to react
Etc. cumbersome and high risk problem, so that preparation method convenience and high-efficiency, is conducive to large scale preparation.
To achieve the goals above, the present invention provides the preparation methods of OLED electron transport material NBphen a kind of, should
Preparation method includes:
(1) in the presence of protective gas and the first organic solvent, 2- bromonaphthalene and lithium metal is subjected to haptoreaction, obtained
2- lithium naphthalene organic solution；
(2) in the presence of protective gas, Bphen organic solution and the 2- lithium naphthalene organic solution are subjected to haptoreaction,
Obtain reaction mixture；
(3) reaction mixture is hydrolyzed with water and is reacted, obtain oil water mixture；
(4) organic phase in the water layer of the oil water mixture is extracted, then connects the organic phase with oxidant
Touching reaction, obtains the NBphen.
Technical solution of the present invention has the following beneficial effects:
(1) method of the invention using lithium metal replace the organolithium reagents such as n-BuLi (tert-butyl lithium) to 2- bromonaphthalene into
Row lithiation, lithium metal are weighed in air, are handled in which can be convenient；Lithiation can be carried out at 0~50 DEG C, be not necessarily to
- 78 DEG C are cooled to, makes to react more convenient and energy saving；It, will not be as butyl lithium even if lithiation liquid touches air
Equally there is the danger burnt, increase the safety of reaction, is convenient for being prepared on a large scale；
(2) method of the invention, operation is simple with post-processing step, without being suitble to industrialized production through column Chromatographic purification；
(3) it is reacted in the prior art using butyl lithium, the overall productivity of NBphen only has 50~70%, and of the invention
Method, the overall productivity of NBphen can reach 89~92%.
Other features and advantages of the present invention will then part of the detailed description can be specified.
Specific embodiment
The preferred embodiment of the present invention is described in more detail below.Although the following describe preferred implementations of the invention
Mode, however, it is to be appreciated that may be realized in various forms the present invention without that should be limited by the embodiments set forth herein.Phase
Instead, these embodiments are provided so that the present invention is more thorough and complete, and can be by the scope of the present invention completely
It is communicated to those skilled in the art.
The present invention provides the preparation method of OLED electron transport material NBphen a kind of, which includes:
(1) in the presence of protective gas and the first organic solvent, 2- bromonaphthalene and lithium metal is subjected to haptoreaction, obtained
2- lithium naphthalene organic solution；
(2) in the presence of protective gas, Bphen organic solution and the 2- lithium naphthalene organic solution are subjected to haptoreaction,
Obtain reaction mixture；
(3) reaction mixture is hydrolyzed with water and is reacted, obtain oil water mixture；
(4) organic phase in the water layer of the oil water mixture is extracted, then connects the organic phase with oxidant
Touching reaction, obtains the NBphen.
In accordance with the present invention it is preferred that the Bphen organic solution is the Bphen organic solution after degassing processing.
In accordance with the present invention it is preferred that in step (1), first organic solvent be ether, tetrahydrofuran, benzene, toluene,
At least one of methylene chloride, chloroform, DMF and carbon tetrachloride；First organic solvent is the first dry organic solvent；
The 2- bromonaphthalene is added drop-wise to anti-in the form of the organic solution for the 2- bromonaphthalene that 2- bromonaphthalene and the first organic solvent are formed
It answers in container；Wherein, in the organic solution of the 2- bromonaphthalene, the mass ratio of 2- bromonaphthalene and the first organic solvent is 1:3-10；
The catalytic reaction temperature is 25-45 DEG C, reaction time 1-8h.
In accordance with the present invention it is preferred that in the organic solution of the 2- bromonaphthalene, the mass ratio of 2- bromonaphthalene and the first organic solvent
For 1:4-5.
In the present invention, in step (1), reactant lithium metal is to be excessively added, after reaction, by excessive lithium metal mistake
Elimination removes.
In accordance with the present invention it is preferred that solvent used in the Bphen organic solution is ether, tetrahydro furan in step (2)
It mutters, at least one of benzene, toluene, methylene chloride, chloroform, DMF and carbon tetrachloride, the solvent is dry solvent, Bphen
Mass ratio with the solvent is 1:3-6；
The molar ratio of Bphen and 2- lithium naphthalene is 1:2-5, preferably 1:2.5；
The haptoreaction is first then to be warming up to 40-60 DEG C in 0 DEG C of reaction 1-8h the reaction was continued 8-12h.
In accordance with the present invention it is preferred that the mass ratio of the Bphen and the solvent is 1:8-10.
In accordance with the present invention it is preferred that the reaction mixture is cooled to 0 DEG C in step (3), water then is carried out with water
Solution reaction.
In the present invention, in step (3), water is preferably deionized water, and water is to be excessively added.
In accordance with the present invention it is preferred that the oxidant is manganese dioxide, SeO in step (4)2, dichlorodicyanobenzoquinone
(DDQ) and at least one of potassium permanganate；Preferably manganese dioxide；
The extraction is carried out with methylene chloride；
The catalytic reaction temperature is 20-50 DEG C, reaction time 6-12h.
In the present invention, in step (4), extract preferably multiple；Oxidant is to be excessively added；Contact in step (4) is anti-
The reaction answered carries out degree, and it is preferable to use TLC monitorings.
In accordance with the present invention it is preferred that the protective gas is nitrogen.
In the present invention, it is filtered to remove solid matter after reaction, is collected by filtration after filtrate concentration generated faint yellow
Solid is recrystallized in ethanol after dry with cold ethanol washing, is obtained target product.
In the present invention, preparing each raw material used in NBphen can be commercially available.
The preparation method of NBphen of the invention, it is theoretically, every to use 1g metal lithium sheet, it can be instead of 70ml 2mol/l's
The butyl lithium solution of butyl lithium solution or 90ml 1.6mol/l is not necessarily to special reaction vessel in laboratory conditions, can be with
The reaction of 5~10g lithium metal scale is easily operated, obtained 30~60g of NBphen product, both reduces cost of material every time,
Also facilitate carry out enlarged experiment.It is such as operated using reaction kettle, only need to simply scale up and preparative-scale can be mentioned
Height arrives feather weight.
The present invention is further illustrated by the following examples:
The synthetic route of the reaction of following embodiment is as shown in formula I.
Embodiment 1
The present embodiment provides the preparation methods of OLED electron transport material NBphen a kind of, specifically comprise the following steps:
(1) under nitrogen protection, by the dry ether solution (30ml) of 2- bromonaphthalene (8.28g, 40mmol) in 25 DEG C in 2h
Interior to be added in the 100ml round-bottomed flask equipped with the 1.3g metal lithium sheet and 20ml dry ether shredded by dropping funel, drop finishes
Continue to stir 2h for 25 DEG C afterwards, filtering removes the solid matters such as remaining metal lithium sheet, obtains 2- lithium naphthalene organic solution；
(2) Bphen (3.32g, 10mmol) is dissolved in the dry ether of 20ml, degasification uses ice water after operating three circulations
Bath is cooled to 0 DEG C, and above-mentioned 2- lithium naphthalene organic solution is added by dropping funel in 1.5h under nitrogen protection, and drop continues after finishing
After reacting 1h, reaction is warming up to 40 DEG C through 30min and keeps 8h, obtains reaction mixture；
(3) after above-mentioned reaction mixture being cooled to room temperature, it further is cooled to 0 DEG C with ice-water bath, then in 20min
20ml deionized water is added altogether in three times, stirs 30min, obtains oil water mixture；
(4) by after above-mentioned oil-aqueous mixtures liquid separation, (25ml x 3) is extracted with dichloromethane in water layer, and organic phase is merged,
And 50g activated manganese dioxide is added, 25 DEG C of stirring 10h.It is filtered to remove black solid after reaction, is filtered after filtrate is concentrated
Faint yellow solid caused by collecting is recrystallized in ethanol after dry with cold ethanol washing, is obtained target product NBphen
5.39g, yield 92.1%.1H NMR(600MHz,CDCl3)δ9.03(s,2H),8.79-8.81(dd,2H),8.31(s,2H),
8.11-8.13(dd,2H),8.08-8.10(m,2H),7.95-7.96(m,2H),7.88(s,2H),7.67(d,2H),7.65-
7.66(m,2H),7.54-7.62(m,10H)。
Embodiment 2
(1) under nitrogen protection, by the dry ether solution (100ml) of 2- bromonaphthalene (20.70g, 100mmol) in 25 DEG C
It is added drop-wise in the 500ml round-bottomed flask equipped with the 3.3g metal lithium sheet shredded and 60ml dry ether in 4h by dropping funel,
40 DEG C of reflux 2h after drop finishes, filtering remove the solid matters such as remaining metal lithium sheet, obtain 2- lithium naphthalene organic solution；
(2) Bphen (13.28g, 40mmol) is dissolved in the dry toluene of 60ml, degasification uses ice after operating three circulations
Above-mentioned 2- lithium naphthalene organic solution is added by dropping funel in 2h under nitrogen protection to 0 DEG C in water-bath cooling, and drop continues after finishing
After reacting 2h, reaction is warming up to 45 DEG C through 30min and keeps 12h, obtains reaction mixture；
(3) after above-mentioned reaction mixture being cooled to room temperature, it further is cooled to 0 DEG C with ice-water bath, then in 45min
50ml deionized water is added altogether in three times, stirs 1h, obtains oil water mixture；
(4) by after above-mentioned oil-aqueous mixtures liquid separation, (50ml x 3) is extracted with dichloromethane in water layer, and organic phase is merged,
And 200g activated manganese dioxide is added, 40 DEG C of stirring 8h.It is filtered to remove black solid after reaction, is filtered after filtrate is concentrated
Faint yellow solid caused by collecting is recrystallized in ethanol after dry with cold ethanol washing, is obtained target product NBphen
20.95g yield 89.5%.1H NMR(600MHz,CDCl3)δ9.03(s,2H),8.79-8.81(dd,2H),8.31(s,2H),
8.11-8.13(dd,2H),8.08-8.10(m,2H),7.95-7.96(m,2H),7.88(s,2H),7.67(d,2H),7.65-
7.66(m,2H),7.54-7.62(m,10H)。
Embodiment 3
(1) under nitrogen protection, by the dry THF solution (250ml) of 2- bromonaphthalene (62.20g, 300mmol) in 25 DEG C
It is added drop-wise in the 500ml round-bottomed flask equipped with the 10g metal lithium sheet shredded and 100ml dry THF, is dripped by dropping funel in 4h
Continue to stir 1h for 25 DEG C after finishing, is heated to 45 DEG C and continues to stir 3h, filtering removes the solid matters such as remaining metal lithium sheet, obtains
2- lithium naphthalene organic solution；
(2) Bphen (39.85g, 120mmol) is dissolved in the dry THF of 200ml, degasification uses ice after operating three circulations
Above-mentioned 2- lithium naphthalene organic solution is added by dropping funel in 3h under nitrogen protection to 0 DEG C in water-bath cooling, and drop continues after finishing
After reacting 4h, reaction is warming up to 60 DEG C through 30min and keeps 12h, obtains reaction mixture；
(3) after above-mentioned reaction mixture being cooled to room temperature, it further is cooled to 0 DEG C with ice-water bath, then in 45min
120ml deionized water is added altogether in three times, stirs 3h, obtains oil water mixture；
(4) by after above-mentioned oil-aqueous mixtures liquid separation, (150ml x 3) is extracted with dichloromethane in water layer, is harmonious organic
And and 600g activated manganese dioxide, 45 DEG C of stirring 12h are added.It is filtered to remove black solid after reaction, after filtrate is concentrated
Generated faint yellow solid is collected by filtration, with cold ethanol washing, is recrystallized in ethanol twice after dry, obtains target production
Object NBphen 62.55g, yield 89.1%.1H NMR(600MHz,CDCl3)δ9.03(s,2H),8.79-8.81(dd,2H),
8.31(s,2H),8.11-8.13(dd,2H),8.08-8.10(m,2H),7.95-7.96(m,2H),7.88(s,2H),7.67
(d,2H),7.65-7.66(m,2H),7.54-7.62(m,10H)。
Embodiment 4
(1) under nitrogen protection, by the drying carbon tetrachloride solution (50ml) of 2- bromonaphthalene (10.35g, 50mmol) in 25 DEG C
The 250ml round bottom equipped with the 1.7g metal lithium sheet shredded and the dry carbon tetrachloride of 10ml is added drop-wise to by dropping funel in 2h to burn
In bottle, drips and continue to stir 2h for 35 DEG C after finishing, filtering removes the solid matters such as remaining metal lithium sheet, it is organic molten to obtain 2- lithium naphthalene
Liquid；
(2) Bphen (4.32g, 13mmol) is dissolved in the dry toluene of 30ml, degasification uses ice water after operating three circulations
Bath is cooled to 0 DEG C, and above-mentioned 2- lithium naphthalene organic solution is added by dropping funel in 1h under nitrogen protection, and drop continues anti-after finishing
After answering 2h, reaction is warming up to 45 DEG C through 30min and keeps 9h, obtains reaction mixture；
(3) after above-mentioned reaction mixture being cooled to room temperature, it further is cooled to 0 DEG C with ice-water bath, then in 30min
30ml deionized water is added altogether in three times, stirs 1h, obtains oil water mixture；
(4) by after above-mentioned oil-aqueous mixtures liquid separation, (40ml x 3) is extracted with dichloromethane in water layer, and organic phase is merged,
It is added to 50g potassium permanganate to be dissolved in the mixed solution of 400ml acetone/water (3:1, v:v) formation, 25 DEG C of stirring 8h.Reaction knot
It is filtered to remove black solid after beam, is redissolved in after filtrate is concentrated in 100ml methylene chloride, with saturated sodium thiosulfate solution
Washing 3 times, is concentrated into 20ml on a rotary evaporator, is placed in 4min in low speed centrifuge (4000r/min), collects centrifuge tube bottom
The faint yellow solid in portion is recrystallized in ethanol after dry with cold ethanol washing, is obtained target product NBphen 6.89g,
Yield 90.5%.1H NMR(600MHz,CDCl3)δ9.03(s,2H),8.79-8.81(dd,2H),8.31(s,2H),8.11-
8.13(dd,2H),8.08-8.10(m,2H),7.95-7.96(m,2H),7.88(s,2H),7.67(d,2H),7.65-7.66
(m,2H),7.54-7.62(m,10H)。
Various embodiments of the present invention are described above, above description is exemplary, and non-exclusive, and
It is not limited to disclosed each embodiment.Without departing from the scope and spirit of illustrated each embodiment, for this skill
Many modifications and changes are obvious for the those of ordinary skill in art field.
Claims (10)
1. a kind of preparation method of OLED electron transport material NBphen, which is characterized in that the preparation method includes:
(1) in the presence of protective gas and the first organic solvent, 2- bromonaphthalene and lithium metal is subjected to haptoreaction, obtain 2- lithium
Naphthalene organic solution；
(2) in the presence of protective gas, Bphen organic solution and the 2- lithium naphthalene organic solution is subjected to haptoreaction, obtained
Reaction mixture；
(3) reaction mixture is hydrolyzed with water and is reacted, obtain oil water mixture；
(4) organic phase in the water layer of the oil water mixture is extracted, then contact with oxidant by the organic phase anti-
It answers, obtains the NBphen.
2. preparation method according to claim 1, wherein the Bphen organic solution is after degassing processing
Bphen organic solution.
3. preparation method according to claim 1, wherein in step (1), first organic solvent is ether, tetrahydro
At least one of furans, benzene, toluene, methylene chloride, chloroform, DMF and carbon tetrachloride；First organic solvent is dry
First organic solvent；
The 2- bromonaphthalene is added drop-wise in the form of the organic solution for the 2- bromonaphthalene that 2- bromonaphthalene is formed with the first organic solvent reacts appearance
In device；Wherein, in the organic solution of the 2- bromonaphthalene, the mass ratio of 2- bromonaphthalene and the first organic solvent is 1:3-10；
The catalytic reaction temperature is 25-45 DEG C, reaction time 1-8h.
4. preparation method according to claim 3, wherein in the organic solution of the 2- bromonaphthalene, 2- bromonaphthalene has with first
The mass ratio of solvent is 1:4-5.
5. preparation method according to claim 1, wherein in step (2), solvent used in the Bphen organic solution
For at least one of ether, tetrahydrofuran, benzene, toluene, methylene chloride, chloroform, DMF and carbon tetrachloride, the solvent is dry
The mass ratio of dry solvent, Bphen and the solvent is 1:3-6；
The molar ratio of Bphen and 2- lithium naphthalene is 1:2-5；
The haptoreaction is first then to be warming up to 40-60 DEG C in 0 DEG C of reaction 1-8h the reaction was continued 8-12h.
6. preparation method according to claim 5, wherein the mass ratio of the Bphen and the solvent is 1:8-10.
7. preparation method according to claim 1, wherein in step (3), the reaction mixture is cooled to 0 DEG C, so
It is hydrolyzed and reacts with water afterwards.
8. preparation method according to claim 1, wherein in step (4), the oxidant is manganese dioxide, SeO2, two
At least one of chlorine dicyanobenzoquinone and potassium permanganate；
The extraction is carried out with methylene chloride；
The catalytic reaction temperature is 20-50 DEG C, reaction time 6-12h.
9. preparation method according to claim 8, wherein the oxidant is manganese dioxide.
10. preparation method according to claim 1, wherein the protective gas is nitrogen.
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| WO2015064969A2 (en) * | 2013-10-29 | 2015-05-07 | 덕산네오룩스 주식회사 | Compound for organic electroluminescent device, organic electroluminescent device using same, and electronic device using said organic electroluminescent device |
| WO2018206138A1 (en) * | 2017-05-08 | 2018-11-15 | Cynora Gmbh | Organic electroluminescent device |
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| WO2015064969A2 (en) * | 2013-10-29 | 2015-05-07 | 덕산네오룩스 주식회사 | Compound for organic electroluminescent device, organic electroluminescent device using same, and electronic device using said organic electroluminescent device |
| WO2018206138A1 (en) * | 2017-05-08 | 2018-11-15 | Cynora Gmbh | Organic electroluminescent device |
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