CN106892865A - A kind of synthetic method of the chloro- 6- p-methylphenyls quinoline of 2,4- bis- - Google Patents
A kind of synthetic method of the chloro- 6- p-methylphenyls quinoline of 2,4- bis- Download PDFInfo
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- CN106892865A CN106892865A CN201510962975.7A CN201510962975A CN106892865A CN 106892865 A CN106892865 A CN 106892865A CN 201510962975 A CN201510962975 A CN 201510962975A CN 106892865 A CN106892865 A CN 106892865A
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- quinoline
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- bis
- methylphenyls
- methyl
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/18—Halogen atoms or nitro radicals
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
Abstract
The invention belongs to electroluminescent organic material technical field, disclose a kind of 2, the synthetic method of the chloro- 6- p-methylphenyls quinoline of 4- bis-, the present invention is to obtain intermediate 4- -4 '-nitrobiphenyls of methyl by Suzuki coupling reactions by 4- methylphenylboronic acids and the bromo- 4- nitrobenzene of 1-, the intermediate obtains intermediate 4- -4 '-amidos of methyl biphenyl and obtains target compound 2 with cyclization in malonic acid, POCl3 again through hydrogen reducing, the chloro- 6- p-methylphenyls quinoline of 4- bis-, product formula is C16H11Cl2N.Of the invention 2, the chloro- 6- p-methylphenyls quinoline of 4- bis-, its synthetic method is simple, it is easy to industrialized production, and there is the features such as emission wavelength is long, fluorescence intensity is high by its zinc, aluminum complex and derivative for preparing, requirement at this stage to color OLED luminescent material can preferably be met, notable economic worth can be created in terms of photo-electroluminescence device or Electro-Optical Display is prepared.
Description
Technical field
The invention belongs to electroluminescent organic material technical field, and in particular to chloro- 6- couples of 2,4- of one kind bis-
The synthetic method of tolyl quinoline.
Background technology
Organic electroluminescent refers to luminescence phenomenon of the organic material under the excitation of electric current or electric field, is
Electric energy, to the non-hot-cast socket of luminous energy, is progressively to tend to ripe in current field of photoelectric devices and have huge
A kind of new Display Technique of practical prospect.Electroluminescent organic material by its glow color it is adjustable,
Actively luminous, high brightness, high efficiency, wide viewing angle, low energy consumption, preparation process is simple, can prepare it is curved
Excellent specific property and the potential applications in large-area flat-plate total colouring field such as bent soft screen, attract
The extensive concern of scientific circles and playing an active part in for world renowned company, are generally considered display of new generation
Most competitive technology in technology.Document (Visco R E, Chandross E A.
Electroluminescence in Solutions of Aromatic Hydrocarbons.J.Am.Chem.Soc.,
1964,86:5350-5351.) report including naphthalene, anthracene, phenanthrene, aphthacene, quinone, carbazole, fluorenes, connection
Organic material that benzene, terphenyl etc. are made up of the main body containing conjugated structure with the activator containing conjugated structure
The electro optical phenomenon of material, U.S. Kodak Company Tang (Tang C W, Vanslyke S A. in 1987
Organic Electroluminescent Diodes.AppL Phys.Lett.,1987,51:913-915.) etc. use
Aromatic diamine (TPD) with hole transmission characteristic is used as hole transmission layer (HTL), fluorescence efficiency
It is very high, have electron transport property and the organic molecule -8-hydroxyquinoline (Alq of vacuum evaporation can be used3)
The organic electroluminescence of sandwich structure is prepared for as electron transfer layer (ETL) and luminescent layer (ELL)
Part, the device drive voltage is low (only 10V), and brightness is high (more than l000cd/m2), luminous efficiency it is high
(1.5Im/W), service life so far, brings organic electroluminescent in more than l00h, function admirable
The research boom of material, indicates that field of organic electroluminescence is entered and breeds the practical epoch.
8- hydroxyl quinoline beautiful jades contain acidic groups-OH and dentate N, are formed with metal ion complexation
Complex with molecule " inner complex salt " structure, with the excellent characteristic for preparing device.Kodak is public
Department is earliest by 8-hydroxyquinoline aluminium (Alq3) in El element, justifying because its spatial molecular configuration is presented
It is spherical, be conducive to preventing forming exciplex or charge-transfer complex with the organic molecule of interface；
With Tg higher, filming performance is good, with carrier mobility speed higher, with Alq3It is luminous
Layer green device stability very fortunately theoretical research and industry in widely used (the bright .10- hydroxyls of Dong Zhen
The synthesis of benzoquinoline derivative and performance study University Of Shanxi, 2012.).Document (Amy Meyers,
Marcus Week.Solution and Solid-State Characterization of Alq3-Functionalized
Polymers,Chem.Mater.,2004,16:1183-1188.), by 8-hydroxyquinoline derivative and A13+
The serial complex of formation is grafted onto the polymer architecture formed in macromolecular material has dissolving well
Property, the luminosity and 8-hydroxyquinoline of these polymer replace base directly related, when substitution base is drawing
During electron group, its blue spectral shift, when being electron donating group, spectral red shift；Document (Mei Qunbo,
Du Naiying, the full in heptan of Lv can producing high-molecular small molecule 8- hydroxyl quinoline beautiful jade metal complexs synthesis with characterize
Fine chemistry industry .2005,22:728-731.) report that dissolubility is excellent, the 8- hydroxyls with polymerizable segment
Quinoline coordination compound monomer, its thermodynamic property stabilization, can prepare device with the method for spin coating.It is comprehensive
The research and development of organic electroluminescence device, synthesis electroluminescent organic material is the focus in the field
One of.
The content of the invention
It is an object of the invention to provide the synthetic method of one kind chloro- 6- p-methylphenyls quinoline of 2,4- bis-, molecule
Formula is C16H11Cl2N, by doing chemical modification on quinoline ring, improves the film-forming type of material, thermally-stabilised
Property, finally give high performance OLED material.
To achieve these goals, the technical solution adopted in the present invention is：A kind of chloro- 6- couples of 2,4- bis-
The synthetic method of tolyl quinoline, comprises the following steps：
The first step, 4- methylphenylboronic acids and the bromo- 4- nitrobenzene of 1- obtain centre by Suzuki coupling reactions
Body 4- -4 '-nitrobiphenyls of methyl；
Second step, intermediate -4 '-nitrobiphenyl of 4- methyl through hydrogen reducing obtain intermediate 4- methyl -4 ' -
Amido biphenyl；
3rd step, 4- -4 '-amido of methyl biphenyl obtains target chemical combination with malonic acid cyclization in POCl3
The chloro- 6- p-methylphenyls quinoline of thing 2,4- bis-；Reaction equation is as follows：
The final product molecular formula is C16H11Cl2N。
A kind of synthetic method of the above-mentioned chloro- 6- p-methylphenyls quinoline of 2,4- bis-, the specific conjunction of the first step
It is as follows into process：To nitrogen is led in system, reactant 4- methylphenylboronic acids, the bromo- 4- nitrobenzene of 1- are added
And catalyst four (triphenylphosphine) closes palladium, potassium carbonate, TBAB；Add toluene, ethanol and
Water, insulation reaction after heating to 70~72 DEG C, reaction terminate after point liquid, washing, drying, subtract
Pressure is concentrated to give crude product 1；Crude product 1 is heated to backflow dissolving through toluene, normal heptane, crosses post, crosses post liquid
It is chilled, filtering drain, baking material can obtain 4- -4 '-nitrobiphenyls of methyl.
A kind of synthetic method of the above-mentioned chloro- 6- p-methylphenyls quinoline of 2,4- bis-, the specific conjunction of the second step
It is as follows into process：- 4 '-nitrobiphenyl of 4- methyl and palladium carbon and solvents tetrahydrofurane are added, after replacing hydrogen
Be heated to 40~52 DEG C and in this temperature range insulation reaction, reaction terminate after by post separation,
It is concentrated under reduced pressure to give 4- -4 '-aminobphenyls of methyl.
A kind of synthetic method of the above-mentioned chloro- 6- p-methylphenyls quinoline of 2,4- bis-, the specific conjunction of the 3rd step
It is as follows into process：4- -4 '-amido of methyl biphenyl and malonic acid are added to being connected with the container of nitrogen, is added
POCl3, heats to backflow, and reaction terminates rear reaction solution and is slowly added in water, filtering, water
Wash, post separation, be concentrated under reduced pressure to give solid, as final product 2, the chloro- 6- p-methylphenyls quinoline of 4- bis-.
Beneficial effects of the present invention：The chloro- 6- p-methylphenyls quinoline products of 2,4- bis- prepared by the present invention are
A kind of light yellow solid, is soluble in toluene, dichloroethanes, is slightly soluble in water, ethanol, normal heptane, its
Synthetic method is simple, it is easy to industrialized production, and the zinc that is prepared by it, aluminum complex spread out
Biology has the features such as emission wavelength is long, fluorescence intensity is high, can preferably meet at this stage to color OLED
The requirement of luminescent material, can create significantly economy in terms of photo-electroluminescence device or Electro-Optical Display is prepared
Value.
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 liquid chromatogram (LC) figure of embodiment of the present invention 4- methyl -4 '-nitrobiphenyl purified products；
Fig. 2 is liquid chromatogram (LC) figure of embodiment of the present invention 4- methyl -4 '-amido biphenyl sterlings；
Fig. 3 is the liquid chromatogram of the chloro- 6- p-methylphenyls quinoline of embodiment of the present invention final product 2,4- bis-
(LC) figure；
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 building-up process of the synthetic method of the chloro- 6- p-methylphenyls quinoline of 2,4- bis- of the present invention is as follows：
1) synthetic operation of -4 '-nitrobiphenyl of 4- methyl：There are mechanical agitation, thermometer, condenser pipe to frame
The straight there-necked flasks of 10L in be passed through N2After sequentially add the bromo- 4- nitrobenzene of 4- methylphenylboronic acids 350.4g, 1-
404.0g, potassium carbonate 552.0g, TBAB 322.0g, toluene 3500.0ml, ethanol 2100ml,
Water 1400ml, adds four (triphenylphosphines) to close palladium 11.6g after opening stirring 15min, opens heat temperature raising
To 70 DEG C~72 DEG C, start to be sampled every 1h after rear insulation reaction (70 DEG C~72 DEG C) 4h, work as original
Stop reaction during the material bromo- 4- nitrobenzenes LC ＜ 1.0% of 1-；Reaction equation is as follows：
2) post processing of -4 '-nitrobiphenyl of 4- methyl：Reaction solution cools to 40 DEG C~50 DEG C, adds first
Benzene 3500.0ml, stirs 30min, adds hot water 4000.0ml, point liquid, and water is with toluene 1000.0ml
Extract, aqueous phase discarded, merge organic phase and be washed till neutral (pH=7), sulfuric acid for 4000ml/ times with hot water
Magnesium 30.0g dries 1h, filtering, discarded after filter cake toluene 200.0ml drip washing, filtrate in -0.08MPa,
Dripless in 2min is concentrated at 55 DEG C~65 DEG C to ooze, obtain crude product black solid 560.0g；
Above-mentioned crude product 560.0g adds toluene 2100.0ml, normal heptane 6300.0ml to be heated to backflow dissolving
(1.5 DEG C/min, 100 DEG C~102 DEG C), cross post, cross post liquid standing and are naturally cooling to 30 DEG C after refrigerator
Middle freezing (- 20 DEG C) 12h, filtering, filter cake obtains yellow brilliant in 6h is dried at -0.08MPa, 75 DEG C
Body shape solid 411.7g, content LC ＞ 98.0%, as high-purity -4 '-nitrobiphenyl of 4- methyl (see
Accompanying drawing 1, main peak content LC=98.9267%).
3) synthetic operation of -4 '-amido of 4- methyl biphenyl：To sequentially adding 4- methyl in the straight there-necked flasks of 5L
- 4 '-nitrobiphenyl 380.0g, palladium carbon 38.0g, tetrahydrofuran 3800.0ml, replacing hydrogen (- 0.08MPa,
5min vacuumizing, logical hydrogen 1min) heating water bath is warming up to 40 DEG C~52 DEG C after three times, and in this temperature
After the interval insulation reaction 72h of degree every 3h samplings once, when raw material 4- methyl -4 '-nitrobiphenyl contents
Stop reaction when LC ＜ 0.5% and main peak content LC ＞ 85.0%；Reaction equation is as follows：
4) post processing of -4 '-amido of 4- methyl biphenyl：Reaction solution Temperature fall is filtered to remove palladium to 30 DEG C
Carbon, filtrate crosses post, crosses post liquid and oozes in being concentrated into 2mim dripless under 45 DEG C, -0.08MPa, dense
Contracting residue is transferred in drip pan and in 6h is dried under 60 DEG C, -0.08MPa, obtains gray solid 318.0g
As 4- methyl -4 '-amido biphenyl of high-purity, content LC ＞ 98.0% are (see accompanying drawing 2, main peak content
LC=98.0768%).
5) synthetic operation of the chloro- 6- p-methylphenyls quinoline of 2,4- bis-：To frame have mechanical agitation, thermometer,
N is passed through in condenser pipe, the straight there-necked flasks of 2L of device for absorbing tail gas2After sequentially add POCl3
786.67ml, 4- methyl -4 '-amido biphenyl 100.0g, malonic acid 85.07g, heat to backflow
After (90 DEG C~122 DEG C) 4h every 1h samplings once, when raw material 4- methyl -4 '-amido diphenyl contents
Stop reaction when LC ＜ 1.0% and main peak content LC ＞ 75.0%；Reaction equation is as follows：
6) post processing of the chloro- 6- p-methylphenyls quinoline of 2,4- bis-：Reaction solution Temperature fall is to slow after 30 DEG C
4h is poured into frozen water 7866.7ml and stirs, filtering is drained, water phase highly acid need to be collected separately, filter cake
Filtering is drained to pH=4~5 after being washed with water 3433ml, and filter cake removes remaining three with wet chemical
Chlorethoxyfos and its accessory substance (pH=9~10), filter after stirring 30min and drain, and are washed with water 3433ml
Filter cake to neutral (pH=7) is washed, filtering is drained, and filter cake is obtained in 6h is dried under 80 DEG C, -0.08MPa
Dark brown solid 200.0g is the chloro- 6- p-methylphenyls quinoline crude products of 2,4- bis-, and (see accompanying drawing 3, main peak contains
Amount LC=72.6692%)；
Above-mentioned dark brown solid 200.0g adds toluene 3147.5ml stirring 4h, filtering, filter cake to discard,
Filtrate crosses post, crosses post liquid and oozes in being concentrated into dripless in 2min under 60 DEG C, -0.08MPa, concentrates
Residue is transferred in drip pan, in 12h is dried under 85 DEG C, -0.08MPa, obtains buff white solid 76.4g,
The chloro- 6- p-methylphenyls quinoline of final product 2,4- bis- of as high-purity.
The above is preferred exemplary applications of the invention, not limitation of the present invention, every according to this
Simple modification that inventive technique main points are made, structure change change belong to protection scope of the present invention it
It is interior.
Claims (4)
1. one kind 2, the synthetic method of the chloro- 6- p-methylphenyls quinoline of 4- bis-, it is characterised in that including following
Step：
The first step, 4- methylphenylboronic acids and the bromo- 4- nitrobenzene of 1- obtain centre by Suzuki coupling reactions
Body 4- -4 '-nitrobiphenyls of methyl；
Second step, intermediate -4 '-nitrobiphenyl of 4- methyl through hydrogen reducing obtain intermediate 4- methyl -4 ' -
Amido biphenyl；
3rd step, 4- -4 '-amido of methyl biphenyl obtains target chemical combination with malonic acid cyclization in POCl3
The chloro- 6- p-methylphenyls quinoline of thing 2,4- bis-；Reaction equation is as follows：
The final product molecular formula is C16H11Cl2N。
2. the synthetic method of the chloro- 6- p-methylphenyls quinoline of a kind of 2,4- bis- according to claim 1,
Characterized in that, the specific building-up process of the first step is as follows：To nitrogen is led in system, add anti-
The bromo- 4- nitrobenzene of thing 4- methylphenylboronic acids, 1- and catalyst four (triphenylphosphine) is answered to close palladium, potassium carbonate, four
Butylammonium bromide；Add toluene, second alcohol and water, insulation reaction after heating to 70~72 DEG C,
Reaction terminate after point liquid, washing, drying, be concentrated under reduced pressure to give crude product 1；Crude product 1 is through toluene, positive heptan
Alkane be heated to backflow dissolving, cross post, cross post liquid it is chilled, filtering drain, baking material can obtain 4- methyl
- 4 '-nitrobiphenyl.
3. the synthetic method of the chloro- 6- p-methylphenyls quinoline of a kind of 2,4- bis- according to claim 1,
Characterized in that, the specific building-up process of the second step is as follows：Add -4 '-nitrobiphenyl of 4- methyl and
Palladium carbon and solvents tetrahydrofurane, are heated to 40~52 DEG C and are protected in this temperature range after replacing hydrogen
Temperature reaction, reaction passes through post separation, is concentrated under reduced pressure to give 4- -4 '-aminobphenyls of methyl after terminating.
4. the synthetic method of the chloro- 6- p-methylphenyls quinoline of a kind of 2,4- bis- according to claim 1,
Characterized in that, the specific building-up process of the 3rd step is as follows：Added to being connected with the container of nitrogen
4- -4 '-amido of methyl biphenyl and malonic acid, add POCl3, heat to backflow, and reaction terminates
Reaction solution is slowly added in water afterwards, filtering, washing, post separation, is concentrated under reduced pressure to give solid, as
The chloro- 6- p-methylphenyls quinoline of final product 2,4- bis-.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109608341A (en) * | 2018-12-28 | 2019-04-12 | 西南交通大学 | A kind of aryl aniline compound and preparation method thereof |
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| US20130169148A1 (en) * | 2012-01-04 | 2013-07-04 | Universal Display Corporation | Highly efficient phosphorescent materials |
| WO2014185592A1 (en) * | 2013-05-13 | 2014-11-20 | 제일모직 주식회사 | Compound for organic optoelectric device, organic light-emitting diode including same, display device including organic light-emitting diode |
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2015
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2599771A1 (en) * | 2010-07-30 | 2013-06-05 | Daito Chemix Corporation | Naphthalene derivative |
| US20130169148A1 (en) * | 2012-01-04 | 2013-07-04 | Universal Display Corporation | Highly efficient phosphorescent materials |
| WO2014185592A1 (en) * | 2013-05-13 | 2014-11-20 | 제일모직 주식회사 | Compound for organic optoelectric device, organic light-emitting diode including same, display device including organic light-emitting diode |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN109608341A (en) * | 2018-12-28 | 2019-04-12 | 西南交通大学 | A kind of aryl aniline compound and preparation method thereof |
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