CN106892872A - A kind of synthetic method of 2- (4- bromophenyls) -4- xenyl -6- phenyl pyrimidines - Google Patents
A kind of synthetic method of 2- (4- bromophenyls) -4- xenyl -6- phenyl pyrimidines Download PDFInfo
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- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/26—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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Abstract
The invention belongs to electroluminescent organic material technical field, disclose a kind of synthetic method of 2 (4 bromophenyl) phenyl pyrimidines of 4 xenyl 6, organic matter of the present invention is with parabromoacetophenone as raw material, prepare 4-acetylbiphenyl, then chalcone is prepared with benzaldehyde again, prepared chalcone again and prepare to obtaining target product 2 (4 bromophenyl) phenyl pyrimidine of 4 xenyl 6 after bromobenzene amitraz hydrochloride cyclization, target product molecular formula is C28H19BrN2.The product of present invention synthesis is a kind of off-white powder, it is a kind of electron transport material with cavity transmission ability and exciton blocking ability, can be widely used for OLED phosphor materials, while reducing device voltage, improving device efficiency, make device architecture more simple, the purpose of cost of manufacture is reduced so as to reach.
Description
Technical field
The invention belongs to electroluminescent organic material technical field, it is related to a kind of 2- (4- bromophenyls) -4- to join
The synthetic method of phenyl -6- phenyl pyrimidines.
Background technology
By the development of more than 30 years, the luminescence theory of OLED obtained further improving and development.
It is generally acknowledged that the luminescence mechanism of OLED is under the driving of external electrical field, noted by negative electrode and anode respectively
The electronics and hole for entering are combined in organic layer migration and give off energy, and transfer energy to organic molecule,
It is excited, from ground state transition to excitation state, the spoke when molecule being stimulated returns to ground state by excitation state
Penetrate decay, the luminescence phenomenon that the energy of decay is emitted in the form of light.Generally include 5 stages：
It is the injection of carrier, the migration of carrier, the formation of exciton, the migration of exciton, luminous.
Current electroluminescent field one focus is phosphorescent light-emitting materials, and phosphorescence is excitation state radiation transistion
Another important kind, is that the different low-energy state of multiplet is quenched is discharged spoke to excited state molecule
Penetrate.The phosphorescence being typically observed all is from the first excited triplet state (T1) radiation that is discharged to ground state.
General phosphorescence is weaker than fluorescence a lot, because the T of transmitting phosphorescence1State is generally difficult from S0State is straight
Connect absorption photon and formed, T1State is typically from S1State is formed through intersystem crossing.Due to by glimmering
The competition of transfer process in light, by S1State is to T1The yield of state intersystem crossing is greatly lowered.1998
Year M.A.Baldo et al. (Baldo, M.；O'brien,D.；You,Y.；et al."Highly efficient
phosphorescent emission from organic electroluminescent devices",Nature 1998,
395,151.) for the first time to atom centered on Pt
2,3,7,8,12,13,17,18-octaethyl-21H, 23H-phorpine platinum (II) (PtOEP) complex
Since being made red electrophosphorescence device, because the internal quantum efficiency of electroluminescent phosphorescence can reach 100%,
OLED phosphorescence develops very fast in terms of material.Conventional central metal atom have Pt, Os, Ir,
Ru, Eu etc., wherein that most is Ir, form respectively red phosphorescence material, green phosphorescent material,
The series material such as blue phosphor materials and yellow phosphorescence material.But phosphorescence luminous organic material faces mainly
Problem：Sandwiched hole and exciton barrier-layer are needed between luminescent layer and electron transfer layer, to prevent from lighting
The excited state energy that layer is formed diffuses to other layers and triggers photochromic impure and delustring.
The content of the invention
It is an object of the invention to provide a kind of while having cavity transmission ability and exciton blocking ability
Electron transport material, while reducing device voltage, improving device efficiency, makes device architecture more
Simply, the purpose of cost of manufacture is reduced so as to reach.
To achieve these goals, the technical solution adopted in the present invention is：A kind of 2- (4- bromophenyls)
The synthetic method of -4- xenyl -6- phenyl pyrimidines, comprises the following steps：
Step 1, heating response in solvent, warp are dissolved in by parabromoacetophenone, phenyl boric acid, alkali and catalyst
Post processing obtains 4-acetylbiphenyl；
Step 2,4-acetylbiphenyl, benzaldehyde and alkali soluble obtain chalcone in solvent heating response, post processing；
Step 3, will be dissolved in solvent to bromobenzylcyanide, be passed through hydrogen chloride gas, and reaction obtains 4BrBzOEt；
Step 4, obtains to bromobenzene amitraz hydrochloride to ammonia is led in 4BrBzOEt；
Heating response is closed during step 5 will be dissolved in solvent to bromobenzene amitraz hydrochloride, chalcone, sodium methoxide
Ring, the target product of high-purity is obtained by post processing purifying；Synthetic route is as follows：
The target product is 2- (4- bromophenyls) -4- xenyl -6- phenyl pyrimidines, and molecular formula is
C28H19BrN2。
A kind of synthetic method of above-mentioned 2- (4- bromophenyls) -4- xenyl -6- phenyl pyrimidines, the step 1
Carry out under nitrogen protection, wherein, solvent toluene, the volume ratio of second alcohol and water are 2: 1: 1；Reaction
The mol ratio 1: 1.13 of thing parabromoacetophenone, phenyl boric acid, alkali, TBAB and tetrakis triphenylphosphine palladium:
2: 0.5: 0.01, the alkali is at least one in potassium carbonate, potassium acetate, sodium carbonate or potassium phosphate；
70 DEG C of reaction temperature, reaction time 4h.
A kind of synthetic method of above-mentioned 2- (4- bromophenyls) -4- xenyl -6- phenyl pyrimidines, the step 1
Last handling process is specially washes the extraction of reaction solution toluene, crosses chromatographic column, and concentration is filtered, done
It is dry to obtain final product high-purity 4-acetylbiphenyl.
A kind of synthetic method of above-mentioned 2- (4- bromophenyls) -4- xenyl -6- phenyl pyrimidines, the step 2
The mol ratio 1: 1.1: 1.47 of middle 4-acetylbiphenyl, benzaldehyde and alkali；Solvent in the step 2 is first
Alcohol and water, its volume ratio 1: 0.14；50~55 DEG C of step 2 reaction temperature, reaction time
14~16h；The alkali is at least one in potassium carbonate, potassium acetate, sodium carbonate or potassium phosphate.
A kind of synthetic method of above-mentioned 2- (4- bromophenyls) -4- xenyl -6- phenyl pyrimidines, the step 2
Last handling process is filtered, is drying to obtain high-purity chalcone (1- to be washed with ethanol rinse and boiling respectively
Biphenyl -4- base -3- phenyl-acryloyls ketone).
A kind of synthetic method of above-mentioned 2- (4- bromophenyls) -4- xenyl -6- phenyl pyrimidines, the step 3
In to ratio 1g: 5ml of bromobenzylcyanide and ethanol；After hydrogen chloride is dried through the concentrated sulfuric acid in the step 3
It is passed through in system；0~18 DEG C of reaction temperature in the step 3,15~20h of reaction time；The step
3 reaction solutions are concentrated under reduced pressure to give 4BrBzOEt (4- bromobenzene formimidic acid ethyl esters hydrochloride).
A kind of synthetic method of above-mentioned 2- (4- bromophenyls) -4- xenyl -6- phenyl pyrimidines, the step 4
0 DEG C~20 DEG C of reaction temperature, reaction time 16h.
A kind of synthetic method of above-mentioned 2- (4- bromophenyls) -4- xenyl -6- phenyl pyrimidines, the step 4
Last handling process be：Reaction solution is directly concentrated under reduced pressure, and filtering is drained, and obtains solid to bromobenzene carbonamidine
Hydrochloride.
A kind of synthetic method of above-mentioned 2- (4- bromophenyls) -4- xenyl -6- phenyl pyrimidines, the step 5
Middle reactant chalcone, the mol ratio 1: 0.93: 1.6 to bromobenzene amitraz hydrochloride and sodium methoxide；It is described
Reaction temperature is 74 DEG C, reaction time 7h in step 5；It is ethanol that the step 5 uses solvent.
A kind of synthetic method of above-mentioned 2- (4- bromophenyls) -4- xenyl -6- phenyl pyrimidines, the step 5
Post-process and be：Respectively final product is obtained with ethanol, toluene and water wash, excessively silicagel column, concentrate drying
2- (4- bromophenyls) -4- xenyl -6- phenyl pyrimidines.
Beneficial effects of the present invention：The present invention provides a kind of high-purity 2- (4- bromophenyls) -4- xenyls -6-
The synthetic method of phenyl pyrimidine, synthesis material is simple, cheap, and building-up process is simple to operate, easy
In realizing industrialized production, with short production cycle；Prepared product has good stability, molten
Solution property and film forming, can be used to prepare OLED, be passed because triphen yl pyrimidines are provided simultaneously with hole
Defeated layer and exciton blocking ability, can replace the electron transfer layer and sky commonly used in device with a kind of material
Cave, exciton barrier-layer, so that device architecture is more simple.
Brief description of the drawings
The present invention is specifically described below by accompanying drawing and in conjunction with the embodiments, wherein content is only used shown in accompanying drawing
In explanation of the present invention, without constituting to the limitation gone up in all senses of the invention.
Fig. 1 is embodiment of the present invention 4-acetylbiphenyl reaction end gas-chromatography GC figures；
Fig. 2 is embodiment of the present invention chalcone reaction end gas-chromatography GC figures；
Fig. 3 is that the embodiment of the present invention is schemed to bromobenzene amitraz hydrochloride reaction end liquid chromatogram LC；
Fig. 4 is the reaction of embodiment of the present invention final products 2- (4- bromophenyls) -4- xenyl -6- phenyl pyrimidines
Terminal liquid chromatogram LC schemes.
Specific embodiment
Embodiments of the invention are elaborated below：The present embodiment is being with technical solution of the present invention
Under the premise of implemented, give detailed implementation method and specific operating process.It should be understood that
It is to those skilled in the art, without departing from the inventive concept of the premise, may be used also
To make some variations and modifications, these belong to the scope of the present invention.
A kind of specific synthesis of the synthetic method of 2- (4- bromophenyls) -4- xenyl -6- phenyl pyrimidines of the present invention
Process is as follows：
1) synthetic operation of 4-acetylbiphenyl：The there-necked flask of device 1L, mechanical agitation, thermometer and return
Flow cooling device, is then passed through nitrogen in there-necked flask, and parabromoacetophenone 50g, benzene are added after 10min
Boric acid 34.6g, potassium carbonate 69.4g, TBAB 40.5g, tetrakis triphenylphosphine palladium 2.9g, toluene 400ml,
Ethanol 200ml, water 200ml, open stirring, heat temperature raising (2 DEG C/min) to backflow (71 DEG C),
Every 1h sampling analyses after 3h, as main content 4-acetylbiphenyl GC>When 90.0%, stop reaction (see attached
Fig. 1, main content GC=95.7910%)；Reaction equation is as follows：
Post processing：Reaction solution is cooled to after not flowing back, and point liquid, organic phase is temporarily put, and water mutually uses 400ml
Toluene is extracted, point liquid, merges organic phase, and is washed till neutrality with hot water, then organic phase 80g
Anhydrous magnesium sulfate is dried 0.5h under 60 DEG C, stirring, filters, drains, filter cake 80ml toluene
Carry out drip washing, drain, prepare peroxidating aluminium-silica gel heat-insulation column, collected post liquid it is concentrated under reduced pressure (65 DEG C,
- 0.085MPa) stop concentration when 100ml toluene is about remained, ethanol 250ml is added, heating for dissolving is complete
Entirely, after being cooled to room temperature, refrigerator freezing (- 20 DEG C) overnight (about 12h) is put into, filters, drains,
100ml ethanol rinses are used, after draining, room temperature (12 DEG C) hangs 3h, obtains GC>95.0% is faint yellow
Solid 46g is 4-acetylbiphenyl.
2) synthetic operation of chalcone：To the 1L equipped with mechanical agitation, thermometer, the cooling device that flows back
Potassium hydroxide 19.3g, water 65.5ml are added in there-necked flask, after stirring and dissolving is complete, methyl alcohol 460ml is added,
After completely limpid, 4-acetylbiphenyl 46g, benzaldehyde 27.3g are added, it is then turned on being heated to 50~
55 DEG C of insulations, at this temperature every 2h sampling analyses after insulation 16h, when raw material 4-acetylbiphenyl
GC<3.0%, main content chalcone GC>When 85.0%, stop reaction (see accompanying drawing 2, main content
GC=89.0282%, raw material GC=1.2185%)；Reaction equation is as follows：
Post processing：After reaction solution is down to 14 DEG C, filters, drain, filter cake is drenched with 92ml/ times × 2 ethanol
Wash, boiled with 460ml ethanol after draining and wash (76 DEG C) 0.5h, after being naturally cooling to 12 DEG C, filtering,
Drain, filter cake is drained to main content GC with 92ml/ times × 2 times ethanol rinses>95.0%, hung
At night, obtain the faint yellow solid as chalcone (1- biphenyl -4- base -3- phenyl-acryloyls ketone) of 63.1g.
3) synthetic operation of 4BrBzOEt：To equipped with mechanical agitation, thermometer and heat sink
Dry and add to bromobenzylcyanide 80g, chloroform 1200ml, ethanol 400ml in 2L there-necked flasks, unlatching is stirred
After mixing dissolving completely, to being passed through in reaction system by the dried hydrogen chloride gas of the 80ml concentrated sulfuric acids,
There is obvious intensification, with ice-water bath temperature control at 0~18 DEG C, ice-water bath is removed in 5h recession, is warmed naturally to
12 DEG C, be further continued for ventilation 11h after every 1h sampling analyses, when being shown on silica gel plate without raw material stop
Reaction；Reaction equation is as follows：
Post processing：After stopping logical hydrogen chloride gas, reaction solution is directly concentrated under reduced pressure (55 DEG C, -0.085MPa)
It is dry, obtain white solid 120g as 4BrBzOEt (4- bromobenzene formimidic acid ethyl esters hydrochloride).
4) to the synthesis of bromobenzene amitraz hydrochloride：To equipped with mechanical agitation, thermometer, heat sink
Addition 4BrBzOEt 120g, ethanol 1600ml in 2L there-necked flasks are dried, after unlatching stirring and dissolving is complete
Be passed through ammonia, system has obvious heat release, temperature control at 0~20 DEG C, with time lengthening, reaction system face
Color is changed significantly, and starting is changed into red to white opacity from colourless from white opacity, then by red
Discoloration is red, transparent, every 1h sampling analyses after reacting 15h at this temperature (0~20 DEG C),
As main content LC>When 85.0%, raw material 4BrBzOEt LC<When 12.0% stop reaction (see accompanying drawing 3,
Main content LC=87.9361%, raw material LC=10.9626%)；Reaction equation is as follows：
Post processing：Ammonia is removed, changes heat sink for distilling apparatus, the ethanol in reaction solution is steamed,
After solvent about 1.4L is steamed, do not flow back (73 DEG C) are cooled to, to addition water 300ml in reaction system,
Distillation is further continued for, until being cooled to 70 DEG C after ethanol distillation is complete, reaction solution is poured into natural in beaker
Cooling, has a large amount of white solids to separate out, and after reaction solution is down to room temperature (about 10 DEG C), filters, takes out
Dry, filter cake uses 100ml ethanol rinses again with 100ml/ times × 2 times water wash after draining, drain to
LC>95.0%, room temperature hang overnight (about 13h) white solid 90.5g be to bromobenzene formamidine salt
Hydrochlorate.
5) synthetic operation of 2- (4- bromophenyls) -4- xenyl -6- phenyl pyrimidines：To equipped with mechanical agitation,
Thermometer, backflow cooling device dry add in 1L there-necked flasks chalcone 40g, sodium methoxide 12.2g,
To bromobenzene amitraz hydrochloride 30.8g, ethanol 800ml, open agitating heating and be warming up to backflow (74 DEG C),
Every 1h sampling analyses after insulation 7h, as raw material chalcone LC<1.0%, main content LC>80.0%
When stop reaction (see accompanying drawing 4, main content LC=83.4027%, raw material chalcone LC=0.4391%)；
Reaction equation is as follows：
Post processing：After reaction solution is down to room temperature (about 8 DEG C), directly filter, filter cake 80ml ethanol
Drip washing is drained, after filter cake 1200ml toluene heats (60 DEG C) dissolvings completely, with hot water (60~65 DEG C)
Neutrality is washed to, 0.5h is dried at a temperature of 60~65 DEG C with the drying of 20g anhydrous magnesium sulfates, filtered,
Filter cake 80ml toluene drip washing, crosses silicagel column after merging filtrate, cross post liquid and collect, and be concentrated under reduced pressure drying
(55 DEG C, -0.085MPa), obtain faint yellow solid crude product 68.6g；
Upper crude product with 800ml ethanol boil and washes (74 DEG C) 1h main contents of raising, be down to room temperature
(12 DEG C) are filtered, drained afterwards, and filter cake carries out drip washing with 80ml ethanol, drained, are hung overnight (about
13h) obtain faint yellow crude product 52.8g；
After upper crude product is heated into 95 DEG C of dissolvings completely with 1200ml toluene, after being cooled to 25 DEG C, put
To enter filter after (- 20~-25 DEG C) of refrigerator freezing 3h, drain, filter cake freezed with 80ml after (- 20~-25 DEG C)
Toluene drip washing, drain, then with 80ml ethanol rinses once, drain rear baking material (45 DEG C, -0.08MPa,
4h), LC is obtained>98.0%, fugitive constituent<The 34.2g white fine work of 5000ppm is the final of high-purity
Product 2- (4- bromophenyls) -4- xenyl -6- phenyl pyrimidines.
The above is preferred exemplary applications of the invention, not limitation of the present invention, every basis
Simple modification that technical key point is made, structure change change belong to protection scope of the present invention
Within.
Claims (10)
1. a kind of synthetic method of 2- (4- bromophenyls) -4- xenyl -6- phenyl pyrimidines, it is characterised in that
Comprise the following steps：
Step 1, heating response in solvent, warp are dissolved in by parabromoacetophenone, phenyl boric acid, alkali and catalyst
Post processing obtains 4-acetylbiphenyl；
Step 2,4-acetylbiphenyl, benzaldehyde and alkali soluble obtain chalcone in solvent heating response, post processing；
Step 3, will be dissolved in solvent to bromobenzylcyanide, be passed through hydrogen chloride gas precursor reactant and obtain 4BrBzOEt；
Step 4, obtains to bromobenzene amitraz hydrochloride to ammonia is led in 4BrBzOEt；
Step 5, heating response is closed during solvent will be dissolved in bromobenzene amitraz hydrochloride, chalcone, sodium methoxide
Ring, the target product of high-purity is obtained by post processing purifying；Synthetic route is as follows：
The target product is 2- (4- bromophenyls) -4- xenyl -6- phenyl pyrimidines, and molecular formula is
C28H19BrN2。
2. a kind of 2- (4- bromophenyls) -4- xenyl -6- phenyl pyrimidines according to claim 1
Synthetic method, it is characterised in that the step 1 is carried out under nitrogen protection, wherein, solvent toluene,
The volume ratio of second alcohol and water is 2: 1: 1；Reactant parabromoacetophenone, phenyl boric acid, alkali, TBAB and
The mol ratio 1: 1.13: 2: 0.5: 0.01 of tetrakis triphenylphosphine palladium, the alkali is potassium carbonate, vinegar
At least one in sour potassium, sodium carbonate or potassium phosphate；70 DEG C of reaction temperature, reaction time 4h.
3. a kind of 2- (4- bromophenyls) -4- xenyl -6- phenyl pyrimidines according to claim 1
Synthetic method, it is characterised in that step 1 last handling process is specially and reaction solution is carried with toluene
Water intaking is washed, and crosses chromatographic column, and concentration is filtered, is drying to obtain high-purity 4-acetylbiphenyl.
4. a kind of 2- (4- bromophenyls) -4- xenyl -6- phenyl pyrimidines according to claim 1
Synthetic method, it is characterised in that the mol ratio 1 of 4-acetylbiphenyl, benzaldehyde and alkali in the step 2:
1.1∶1.47；Solvent in the step 2 is first alcohol and water, its volume ratio 1: 0.14；The step
50 DEG C~55 DEG C of reaction temperature, 14~16h of reaction time in rapid 2；The alkali be potassium carbonate, potassium acetate,
At least one in sodium carbonate or potassium phosphate.
5. a kind of 2- (4- bromophenyls) -4- xenyl -6- phenyl pyrimidines according to claim 1
Synthetic method, it is characterised in that step 2 last handling process to be washed with ethanol rinse and boiling respectively,
Filter, be drying to obtain high-purity chalcone.
6. a kind of 2- (4- bromophenyls) -4- xenyl -6- phenyl pyrimidines according to claim 1
Synthetic method, it is characterised in that to ratio 1g: 5ml of bromobenzylcyanide and ethanol in the step 3；
Hydrogen chloride is passed through in system after being dried through the concentrated sulfuric acid in the step 3；Reaction temperature in the step 3
0 DEG C~18 DEG C, 15~20h of reaction time；Step 3 reaction solution is concentrated under reduced pressure to give 4BrBzOEt.
7. a kind of 2- (4- bromophenyls) -4- xenyl -6- phenyl pyrimidines according to claim 1
Synthetic method, it is characterised in that 0 DEG C~20 DEG C of step 4 reaction temperature, reaction time 16h.
8. a kind of 2- (4- bromophenyls) -4- xenyl -6- phenyl pyrimidines according to claim 1
Synthetic method, it is characterised in that the last handling process of the step 4 is：Reaction solution directly depressurizes dense
Contracting, filtering is drained, and obtains solid to bromobenzene amitraz hydrochloride.
9. a kind of 2- (4- bromophenyls) -4- xenyl -6- phenyl pyrimidines according to claim 1
Synthetic method, it is characterised in that reactant chalcone in the step 5, to bromobenzene amitraz hydrochloride
With the mol ratio 1: 0.93: 1.6 of sodium methoxide；Reaction temperature is 74 DEG C in the step 5, during reaction
Between 7h；It is ethanol that the step 5 uses solvent.
10. a kind of 2- (4- bromophenyls) -4- xenyl -6- phenyl pyrimidines according to claim 1
Synthetic method, it is characterised in that the step 5 post-processes and is：Drenched with ethanol, toluene and water respectively
Wash, silicagel column, concentrate drying excessively obtains final product 2- (4- bromophenyls) -4- xenyl -6- phenyl pyrimidines.
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| CN111116493A (en) * | 2019-12-13 | 2020-05-08 | 上海工程技术大学 | Method for preparing Apabetalone, intermediate and preparation method of intermediate |
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| CN103396404A (en) * | 2013-07-31 | 2013-11-20 | 华南理工大学 | Compound using triphenylpyrimidine as core as well as preparation method and application thereof |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN111116493A (en) * | 2019-12-13 | 2020-05-08 | 上海工程技术大学 | Method for preparing Apabetalone, intermediate and preparation method of intermediate |
| CN111116493B (en) * | 2019-12-13 | 2021-07-27 | 上海工程技术大学 | Method for preparing Apabetalone, intermediate and preparation method of intermediate |
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