CN107098931B - Multi-functional amphipathic conjugated molecular material of one kind and the preparation method and application thereof - Google Patents
Multi-functional amphipathic conjugated molecular material of one kind and the preparation method and application thereof Download PDFInfo
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- 239000000463 material Substances 0.000 title claims abstract description 39
- 238000002360 preparation method Methods 0.000 title claims abstract description 10
- 150000001875 compounds Chemical class 0.000 claims abstract description 50
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 claims abstract description 14
- 238000007641 inkjet printing Methods 0.000 claims abstract description 12
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 claims abstract description 9
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 5
- 238000003786 synthesis reaction Methods 0.000 claims abstract description 5
- -1 phosphonate ester Chemical class 0.000 claims abstract description 4
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 29
- 239000002904 solvent Substances 0.000 claims description 25
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 24
- 238000006243 chemical reaction Methods 0.000 claims description 20
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 17
- 239000000376 reactant Substances 0.000 claims description 17
- 239000010410 layer Substances 0.000 claims description 16
- 229910052757 nitrogen Inorganic materials 0.000 claims description 15
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 claims description 14
- YMWUJEATGCHHMB-UHFFFAOYSA-N dichloromethane Natural products ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 13
- 239000000243 solution Substances 0.000 claims description 9
- ZZPNDIHOQDQVNU-UHFFFAOYSA-N 2-hydroxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane Chemical compound CC1(C)OB(O)OC1(C)C ZZPNDIHOQDQVNU-UHFFFAOYSA-N 0.000 claims description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 8
- 238000004528 spin coating Methods 0.000 claims description 8
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 claims description 8
- 235000011056 potassium acetate Nutrition 0.000 claims description 7
- 239000002356 single layer Substances 0.000 claims description 7
- 238000010129 solution processing Methods 0.000 claims description 7
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 claims description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 6
- GPAYUJZHTULNBE-UHFFFAOYSA-N diphenylphosphine Chemical compound C=1C=CC=CC=1PC1=CC=CC=C1 GPAYUJZHTULNBE-UHFFFAOYSA-N 0.000 claims description 6
- KTWOOEGAPBSYNW-UHFFFAOYSA-N ferrocene Chemical compound [Fe+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 KTWOOEGAPBSYNW-UHFFFAOYSA-N 0.000 claims description 6
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 6
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 claims description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 5
- 239000007864 aqueous solution Substances 0.000 claims description 5
- 238000004090 dissolution Methods 0.000 claims description 5
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 claims description 5
- SODQFLRLAOALCF-UHFFFAOYSA-N 1lambda3-bromacyclohexa-1,3,5-triene Chemical compound Br1=CC=CC=C1 SODQFLRLAOALCF-UHFFFAOYSA-N 0.000 claims description 4
- 238000005401 electroluminescence Methods 0.000 claims description 4
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 claims description 3
- 235000019441 ethanol Nutrition 0.000 claims description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 3
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 230000003287 optical effect Effects 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 11
- 238000004519 manufacturing process Methods 0.000 abstract description 5
- 230000008569 process Effects 0.000 abstract description 5
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 abstract description 2
- 125000003545 alkoxy group Chemical group 0.000 abstract description 2
- 125000003118 aryl group Chemical group 0.000 abstract description 2
- 239000000126 substance Substances 0.000 abstract 2
- 125000003983 fluorenyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 abstract 1
- 238000004020 luminiscence type Methods 0.000 abstract 1
- 239000007777 multifunctional material Substances 0.000 abstract 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 16
- 239000000047 product Substances 0.000 description 12
- 229910052739 hydrogen Inorganic materials 0.000 description 8
- 238000005160 1H NMR spectroscopy Methods 0.000 description 6
- 238000000605 extraction Methods 0.000 description 6
- 150000003384 small molecules Chemical class 0.000 description 6
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 238000000921 elemental analysis Methods 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 3
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 3
- SGRHVVLXEBNBDV-UHFFFAOYSA-N 1,6-dibromohexane Chemical compound BrCCCCCCBr SGRHVVLXEBNBDV-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- 229940126062 Compound A Drugs 0.000 description 2
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 229920000144 PEDOT:PSS Polymers 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- 238000000137 annealing Methods 0.000 description 2
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 2
- JNGZXGGOCLZBFB-IVCQMTBJSA-N compound E Chemical compound N([C@@H](C)C(=O)N[C@@H]1C(N(C)C2=CC=CC=C2C(C=2C=CC=CC=2)=N1)=O)C(=O)CC1=CC(F)=CC(F)=C1 JNGZXGGOCLZBFB-IVCQMTBJSA-N 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- 229940072033 potash Drugs 0.000 description 2
- 235000015320 potassium carbonate Nutrition 0.000 description 2
- 235000011181 potassium carbonates Nutrition 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- AVXFJPFSWLMKSG-UHFFFAOYSA-N 2,7-dibromo-9h-fluorene Chemical class BrC1=CC=C2C3=CC=C(Br)C=C3CC2=C1 AVXFJPFSWLMKSG-UHFFFAOYSA-N 0.000 description 1
- NPJKQTVHTXPSTH-UHFFFAOYSA-M CC([O-])=O.CC(O)=O.CC(O)=O.CC(O)=O.N.[K+] Chemical compound CC([O-])=O.CC(O)=O.CC(O)=O.CC(O)=O.N.[K+] NPJKQTVHTXPSTH-UHFFFAOYSA-M 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 241001062472 Stokellia anisodon Species 0.000 description 1
- 238000006069 Suzuki reaction reaction Methods 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 description 1
- 150000002220 fluorenes Chemical class 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000011229 interlayer Substances 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 238000002386 leaching Methods 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 150000002829 nitrogen Chemical class 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 238000010422 painting Methods 0.000 description 1
- 238000000059 patterning Methods 0.000 description 1
- 125000004437 phosphorous atom Chemical group 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 238000003672 processing method Methods 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 238000005019 vapor deposition process Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
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- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4018—Esters of cycloaliphatic acids
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- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4006—Esters of acyclic acids which can have further substituents on alkyl
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- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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- H10K71/13—Deposition of organic active material using liquid deposition, e.g. spin coating using printing techniques, e.g. ink-jet printing or screen printing
- H10K71/135—Deposition of organic active material using liquid deposition, e.g. spin coating using printing techniques, e.g. ink-jet printing or screen printing using ink-jet printing
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Abstract
The invention discloses a kind of multi-functional amphipathic conjugated molecular materials and the preparation method and application thereof, the material is made of the fluorenes and pyrene substance of High Efficiency Luminescence, phosphonate ester selects the linear molecule compound of different alkyl chains as polarity side group, and general structure is shown below:Wherein, R is one of C1-C30 alkyl, alkoxy, alkane phenyl, alkane phenoxy group, aryl.Advantages that the material has that chemical structure is simple, synthesis cost is cheap etc., while there are good solution processability energy, filming performance and multifunctional light electrical characteristics, can be used as multifunctional material and meanwhile realize high brightness blue emission and efficient embellishing cathode interface.Using the material simultaneously as the Organic Light Emitting Diode of luminescent layer and boundary layer, excellent photoelectric characteristic can be realized by solution processes or inkjet printing mode using simplified device architecture, overcome the production obstacle in conventional multilayer device.
Description
Technical field
The invention belongs to photoelectric materials and applied technical field, and in particular to a kind of multi-functional amphipathic conjugated molecular material and
Preparation method and application.
Background technique
Organic Light Emitting Diode (OLED) has been widely used for full color flat panel display, solid state lighting and large area flexible
The fields such as electronic device.Due to its significant progress on materials chemistry and device physics, vacuum with multi-layer structure is heavy
Product small molecule OLED comes into business application.However, vacuum deposition method manufacturing process is complicated, at high cost and stock utilization
It is low.In addition, the use of shadow mask limits scalability and resolution ratio of the device in vapor deposition processes.In contrast,
The OLED of solution processing has been received significant attention with the material use of its cost-effective manufacture and low loss.
Solution processing is a kind of simple and cheap method, is more suitable for the large-scale production of OLED, includes spin coating, leaching
The processing technologys such as painting, blade coating, inkjet printing, intaglio printing and silk-screen printing.Wherein inkjet printing is a kind of promising
Technology is conducive to patterning because saving material, convenient for production large area film.Although light emitting polymer is deemed applicable to spray
Ink print, but the charge unbalance problem in the impurity in polymer and the device based on polymer may will be greatly reduced efficiency
And the service life.In contrast, small molecule structure is clear, is easy to purify, it is easier to realize practical efficient stable device.Cause
This, it is quite attractive and in demand for manufacturing small molecule OLED by inkjet printing.
However, the small molecule OLED of ink jet printing is challenging.On the one hand, commercially common OLED small molecule
Solubility and film form are all very poor usually in solution processes.On the other hand, due to interface attack phenomenon, it is difficult to be printed by ink-jet
Brush building multilayer device structure, which is injected and transmitted with balancing charge, obtains Efficient devices.Therefore, exploitation has multi-functional characteristic
Novel printable OLED material has especially important meaning to simplify device architecture.
Summary of the invention
Technical problem: the present invention provides a kind of multi-functional amphipathic conjugated molecular material and the preparation method and application thereof,
To solve current solution processing OLED device, structure is complicated, electron injecting layer can not the problems such as solution processing.
Technical solution: to achieve the above object, the invention adopts the following technical scheme:
A kind of multi-functional amphipathic conjugated molecular material, for the material with fluorene structured for skeleton, pyrene is end-capping group, phosphonate ester
As polarity side group, the linear conjugate molecular compound of different alkyl chains is selected, there is the general structure as shown in following formula 1:
Wherein, R is one of C1-C30 alkyl, alkoxy, alkane phenyl, alkane phenoxy group, aryl；C is carbon atom；O is
Oxygen atom；P is phosphorus atoms.
Specifically, when R selects hexyl or benzene oxygen hexyl, which is compound represented by the following Expression 2 or formula 3:
A kind of preparation method of multi-functional amphipathic conjugated molecular material, including following synthetic route and synthesis step:
Wherein 1≤n≤30, and be natural number；
Reactant (a), reactant (b) and smelling of tetrabutyl ammonium, potassium carbonate are added in reaction vessel by step (1), are added
Enter solvent to make it dissolve, reacts 4-12h under counterflow condition, obtain compound (c)；
Step (2) is by the product Compound (c) of step (1), connection boric acid pinacol ester, potassium acetate, [1,1 '-bis- (diphenyl
Phosphine) ferrocene] palladium chloride dichloromethane complex are added in reaction vessel, and solvent is added and makes it dissolve, under nitrogen protection
100 DEG C are protected from light for 24 hours, obtain compound (d)；
Step (3) adds the product Compound (d) of step (2), 1- bromine pyrene (e), tetrabutylammonium bromide, tetra-triphenylphosphine palladium
Enter into reaction vessel, solvent dissolution is added, is protected from light 8-16h at 90-120 DEG C of nitrogen protection, obtains compound (f)；
The product Compound (f) of step (3), triethyl phosphite are added in microwave tube by step (4) is dissolved in solvent
In, 0.5-1h is reacted at 100-150 DEG C in microwave reactor, obtains compound (g).
Solvent used in the step (1) is acetone or potassium hydroxide aqueous solution, reactant (a) and reactant (b)
Molar ratio is 1:(3-5)；
Solvent used in the step (2) is one kind of toluene, dioxane, the product Compound (c) of step 1): connection
Boric acid pinacol ester: potassium acetate: the molar ratio of [1,1 '-bis- (diphenylphosphine) ferrocene] palladium chloride dichloromethane complex is
1:(2.4-4): (6-9): (0.03-0.1)；
Solvent used in the step (3) be one or more of tetrahydrofuran, toluene, chlorobenzene, o-dichlorohenzene, instead
Answer object (d): reactant (e): tetrabutylammonium bromide: the molar ratio of tetra-triphenylphosphine palladium is 1:(2.4-4): (0.2-0.4):
(0.03-0.1)；
In the step (4), the molar ratio of compound (f) and triethyl phosphite is 1:(10-30).
A kind of preparation method of multi-functional amphipathic conjugated molecular material, including following synthetic route and synthesis step:
Wherein 1≤n≤30, and be natural number；
Reactant (a), reactant (b), methane sulfonic acid are added in reaction vessel by step (1), and solvent, which is added, keeps its molten
It solves, reacts 36-48h under counterflow condition, obtain compound (c)；
The product Compound (c) of step (1), reactant (d) and smelling of tetrabutyl ammonium, potassium carbonate are added to by step (2)
In reaction vessel, solvent is added and makes it dissolve, reacts 4-12h under counterflow condition, obtains compound (e)；
Step (3) is by the product Compound (e) of step (2), connection boric acid pinacol ester, potassium acetate, [1,1 '-bis- (diphenyl
Phosphine) ferrocene] palladium chloride dichloromethane complex are added in reaction vessel bottle, and solvent is added and makes it dissolve, nitrogen protection
Under, 100 DEG C of reactions for 24 hours, obtain compound (f)；
The product (f) of step (3), (g), tetrabutylammonium bromide, tetra-triphenylphosphine palladium are added in reactor by step (4)
Dissolution in a solvent, is protected from light 8-16h for 80-120 DEG C under nitrogen protection, obtains compound (h)；
The product Compound (h) of step (4), triethyl phosphite are added in microwave tube by step (5) is dissolved in solvent
In, 0.5-1h is reacted at 100-150 DEG C in microwave reactor, obtains compound (i).
Solvent used in the step (1) is chloroform；
Solvent used in the step (2) is acetone or potassium hydroxide aqueous solution, reactant (c) and reactant (d)
Molar ratio is 1:(3-5)；
Solvent used in the step (3) is one kind of toluene, dioxane, compound (e): connection boric acid pinacol
Ester: potassium acetate: the molar ratio of [1,1 '-bis- (diphenylphosphine) ferrocene] palladium chloride dichloromethane complex is 1:(2.4-4):
(5-9): (0.03-0.1)；
Solvent used in the step (4) be one or more of tetrahydrofuran, toluene, chlorobenzene, o-dichlorohenzene, instead
Answer object (g): reactant (e): tetrabutylammonium bromide: the molar ratio of tetra-triphenylphosphine palladium is 1:(2.4-4): (0.2-0.5):
(0.03-0.13)；
In the step (5), the molar ratio of compound (h) and triethyl phosphite is 1:(10-30).
Application of the above-mentioned multi-functional amphipathic conjugated molecular material in organic electroluminescence device, specifically: the material
Material is separately as electron injecting layer, structure are as follows: anode/luminescent layer/electron injecting layer/cathode；Or simultaneously as luminescent layer with
Electron injecting layer, structure are as follows: anode/luminescent layer/cathode.
Multi-functional amphipathic conjugated molecular material of the invention has alcohol-soluble, can prepare single layer by solution processing
Or multilayer organic light emitting diode device, including spin coating and inkjet printing two ways.It is made by inkjet printing mode organic
When electroluminescent device, ink is configured using one or more of ethylene glycol monomethyl ether, ethylene glycol ethyl ether, ethyl alcohol solution.
The utility model has the advantages that the present invention provides a kind of multi-functional amphipathic conjugated molecular materials, with fluorene structured for skeleton, pyrene is made
For end group, phosphate is as polarity side.Such material has been synthesized by a series of processes such as Suzuki coupling, phosphating reactions
Material, the material have synthesis process it is simple and easy to control, it is low in cost, be easily purified, the advantages such as yield height.The combination of pyrene and fluorenes assigns
The good thermal stability of small molecule, fluorescence quantum efficiency, light emission luminance, it is molten that phosphate polar group then assigns the excellent alcohol of material
Property, electron injection ability and filming performance.The material is suitable for the processing methods such as spin coating, inkjet printing, can with it is regular activated
The solvent of layer shows orthogonal property to avoid intermixing, and the blue emission and active cathodic circle of high brightness can be achieved at the same time
Face is modified to simplify device architecture.The material in environmental-friendly alcoholic solvent have good solubility, can with it is regular activated
The casting solution of layer shows orthogonal property, thus interface attack phenomenon when solwution method being avoided to prepare multilayer device.The material
Possess multifunctional light electrical characteristics, the blue emission and active cathodic modifying interface of high brightness can be achieved at the same time, solves molten at present
Liquid process OLED device structure is complicated, electron injecting layer can not solution processing etc. problems.
Detailed description of the invention
Fig. 1 is the compound PEP's in embodiment 11HNMR spectrogram.
Fig. 2 is the compound PEP's in embodiment 113C NMR spectra.
Fig. 3 is the compound POEP's in embodiment 21HNMR spectrogram.
Fig. 4 is the compound POEP's in embodiment 213C NMR spectra.
Fig. 5 is the uv absorption spectra of compound PEP and POEP.
Fig. 6 is the fluorescence emission spectrogram of compound of compound PEP and POEP.
Fig. 7 is the brightness-voltage curve of the Organic Light Emitting Diode in embodiment 3.
Fig. 8 is the Current efficiency-voltage curve of the Organic Light Emitting Diode in embodiment 3.
Specific embodiment
The present invention will be further described combined with specific embodiments below.
Embodiment 1: reaction route is as follows.
Specific step is as follows:
Ith step: 2,7- dibromo fluorenes (20g, 61.7mmol), 1,6- dibromo-hexane (35.5mL, 246.9mmol), the tetrabutyl
The mass fraction that 50g is added in smelling ammonium (TBAB) (2g) is in 50% potassium hydroxide aqueous solution, and 65 DEG C of reactions are overnight.Extraction, rotation
Dry, 100~200 mesh cross column, obtain 32g compound A, yield 160%.
IIth step: compound A (6g, 9.23mmol), connection boric acid pinacol ester (9.36g, 36.9mmol) substitute nitrogen three
Potassium acetate (9.34g, 64.6mmol) is added after secondary, substitutes nitrogen, is protected from light and catalyst Pd (pddf) is added2Cl2(0.4g,
It 0.524mmol) is dissolved in the dioxane of 45mL, the lower 100 DEG C of reactions of nitrogen protection are for 24 hours.Extraction was spin-dried for pillar, obtained
4.93g compound B, yield 82%.
IIIth step: compound B (1g, 1.34mmol), 1- bromine pyrene (1.51g, 5.37mmol) are substituted nitrogen and are added afterwards three times
Smelling of tetrabutyl ammonium (0.12g, 0.37mmol), substitutes nitrogen, is protected from light and catalyst Pd (PPh is added3)4(0.1g, 0.08mmol) is molten
Solution is protected from light 12 hours in the potash water dissolution of the toluene and 7mL of 21mL at 95 DEG C.Extraction was spin-dried for pillar, obtained
0.459g compound C, yield 46%.
IVth step: compound C (0.2g, 0.224mmol) is dissolved in triethyl phosphite (0.74g, 4.48mmol), micro-
140 DEG C of reaction 1h in wave reactor.Vacuum distillation crosses column, obtains 0.183g target product PEP, yield 92%.
Compound C:1H NMR(400MHz,CDCl3):δ8.28-8.22(m,8H),8.14(m,7H),8.07-8.01(m,
5H),7.67(d,4H),3.33(t,4H),2.11(m,4H),1.75(m,4H),1.32-1.20(m,8H),0.96(m,4H).13C
NMR(100MHz,CDCl3):δ151.0,140.2,140.1,138.2,131.6,131.0,130.6,129.7,128.7,
127.8,127.5,126.1,125.3,125.2,125.0,124.9,124.8,119.9,55.4,40.4,31.2,30.5,
29.7,26.3,24.9,24.2,22.5.MS m/z:892.14(M+)(calcd:892.82).Elemental Analysis:C
76.76%, H 5.39% (calcd:C 76.68%, H 5.42%)
Target product PEP:1H NMR(400MHz,CDCl3):δ8.32-8.25(m,4H),8.25-8.17(t,4H),
8.16-8.09(m,6H),8.09-8.04(m,4H),8.03-7.98(d,2H),7.72-7.63(t,4H),4.0(m,12H),
1.44(s,13H)1.23(m,22H).13C NMR(100MHz,CDCl3):δ151.0,140.2,140.1,138.2,131.6,
131.0,130.6,129.7,128.7,127.8,127.5,126.1,125.3,125.2,125.0,124.9,124.8,
119.9,61.4,55.4,40.4,30.6,30.5,29.7,26.3,24.9,24.2,22.5,16.5.MS m/z:1006.40(M+) (calcd:1007.2) .Elemental analysis:C 77.62%, H 6.77% (calcd:C 77.51%, H
6.81%)
Embodiment 2: reaction route is as follows.
Specific step is as follows:
Ith step: 2,7- dibromo, two Fluorenone (30.3g, 89.65mmol) is placed in 500mL there-necked flask, addition phenol (71mL,
591.18mmol), the CCl of 120mL4, temperature is adjusted to 80 DEG C, reacts 42h.Stop reaction, uses K after cooling2CO3Solution is quenched, and adds
It is fashionable slowly to have a large amount of bubbles and generate.After filter, waste liquid is purple.With DCM more times washings to powdered for pure white
Compound D about 28g, yield 93%.
IIth step: compound D (10g, 19.67mmol), 1,6- dibromo-hexane (19.20g, 78.71mmol), the tetrabutyl is smelt
Change ammonium (2g) to be added in the potassium hydroxide aqueous solution that the mass fraction of 50g is 50%, 65 DEG C of reactions are overnight.Extraction, is spin-dried for, 100
~200 mesh cross column.Obtain 13.2g compound E, yield 132%.
IIIth step: compound E (5.4g, 6.47mmol), connection boric acid pinacol ester (6.5614g, 25.89mmol) substitute nitrogen
Potassium acetate (3.81g, 33.8mmol) is added afterwards three times in gas, substitutes nitrogen, is protected from light and catalyst Pd (pddf) is added2Cl2(0.21g,
It 0.275mmol) is dissolved in the dioxane of 60mL, 100 DEG C of reactions are for 24 hours.Extraction was spin-dried for pillar, obtained 4.21g compound F,
Yield 78%.
IVth step: compound F (0.8g, 0.742mmol), after 1- bromine pyrene (0.626g, 2.23mmol) substitutes nitrogen three times
It is added smelling of tetrabutyl ammonium (0.11g, 0.34mmol), substitutes nitrogen, be protected from light and catalyst Pd (PPh is added3)4(0.1g,
It 0.09mmol) is dissolved in the potash water dissolution of toluene and 7mL of 21mL.It keeps being protected from light 12 hours at 95 DEG C.Extraction
It takes and was spin-dried for pillar, obtain 0.424g compound G, yield about 53%.
Vth step: compound G (0.2g, 0.198mmol) is dissolved in triethyl phosphite (0.659g, 3.972mmol),
140 DEG C of reactions are for 24 hours.Vacuum distillation crosses column and obtains 0.178g final product POEP, yield about 89%.
Compound G:1H NMR(400MHz,CDCl3):δ8.30–8.15(m,8H),8.10(s,4H),8.07–7.90(m,
8H), 7.82-7.66 (m, 4H), 7.32 (d, J=8.4Hz, 4H), 6.80 (d, J=8.6Hz, 4H), 3.93 (s, 1H), 3.90
(t, J=6.3Hz, 4H), 3.38 (t, J=6.8Hz, 4H), 1.96-1.81 (m, 4H), 1.81-1.70 (m, 4H), 1.52-1.40
(m,8H).13C NMR(100MHz,CDCl3):δ157.9,152.5,140.6,138.9,137.9,137.8,135.8,131.5,
130.5,130.1,129.3,128.6,128.5,128.3,127.8,127.4,126.0,125.5,125.3,125.1,
125.0,124.8,124.7,120.3,114.2,67.7,64.5,33.9,32.7,29.7,29.1,27.9,25.3,31.3,
29.6,29.1,26.3,25.6.MS m/z:1077.20(M+)(calcd:1077.01).Elemental Analysis:C
76.90%, H 5.23% (calcd:C 76.95%, H 5.24%)
Target product POEP:1H NMR(400MHz,CDCl3):δ8.26-8.14(m,8H),8.10(s,4H),8.06-
7.99(m,8H),7.77-7.70(t,4H),7.30(d,4H),6.90(d,4H),4.11-3.99(m,8H),3.89(t,4H),
1.76-1.72(m,8H),1.76-1.66(m,8H),1.64-1.55(s,12H),0.89-0.80(m,12H).13C NMR
(100MHz,CDCl3):δ157.9,152.5,140.6,138.9,137.9,137.8,135.8,131.5,130.5,130.1,
129.3,128.6,128.5,128.3,127.8,127.4,126.0,125.5,125.3,125.1,125.0,124.8,
124.7,120.3,114.2,67.7,64.6,61.4,30.3,29.6,29.1,26.3,25.6,16.5.MS m/z:1911.99
(M+) (calcd:1191.39) .ElementalAnalysis:C 77.53%, H 6.44% (calcd:C 77.63%, H
6.43%)
Embodiment 3
The preparation of Organic Light Emitting Diode.
Prepare OLEDs single layer device by spin-coating method: its device architecture is ITO/PEDOT:PSS 35nm/ luminescent layer
65nm/Al 80nm.Solvent is done using chloroform, luminescent layer prepares 15mg/mL's using any one in compound PEP/POEP
Solution.Spin coating under nitrogen protection, revolving speed 1500rpm, 80 DEG C of annealing 10min.
Prepare OLEDs single layer device by ink-jet printing: its device architecture is ITO/PEDOT:PSS 35nm/PEP/Al
80nm.It uses ethylene glycol monomethyl ether for solution, configures the ink of 14mg/mL.100 DEG C of annealing 20min.
The following are the comparisons of the electroluminescent properties of above-mentioned three kinds of single layer organic light emitting diode devices:
aOpening bright voltage and being defined as brightness is 1cd m-2When operating voltage.bWhen maximum brightness.cIt is prepared by inkjet printing.
Three single layer devices are to use multi-functional amphiphilic conjugated molecule as illuminator and cathode interlayer.Analyze table
In device performance, when spin-coating method prepares single layer OLED devices, the device A current efficiency based on material PEP reaches 0.73cdA-1,
0.26cdA better than POEP-1.Wherein, device A maximum brightness reaches 3110.4cd m-2.High work function can be directly acted on
Aluminium electrode on, illustrate that the material has good cathodic modification ability.Compared with spin coating device, the ink-jet printer based on PEP
Part shows the bright voltage that opens down to 3.8V, and maximum current efficiency reaches 1.12cdA-1, have maximum brightness in 11.0V
8850.1cdm-2, performance is more preferably.Result above absolutely proves that this novel MOLECULE DESIGN is conducive to through simple device junction
Structure realizes excellent photoelectric characteristic.
The above embodiment is a preferred embodiment of the present invention, but embodiments of the present invention are not by above-described embodiment
Limitation, it is other any without departing from the modifications and variations done under the principle of the present invention, it should be equivalent substitute mode, all wrap
Containing within the scope of the present invention.
Claims (7)
1. a kind of multi-functional amphipathic conjugated molecular material, it is characterised in that: for the material with fluorene structured for skeleton, pyrene is END CAPPED GROUP
Group, phosphonate ester select the linear conjugate molecular compound of different alkyl chains as polarity side group, have and tie as shown in following formula 1
Structure general formula:
The material is specifically compound represented by the following Expression 2:
2. a kind of preparation method of multi-functional amphipathic conjugated molecular material as described in claim 1, it is characterised in that: including
Following synthetic route and synthesis step:
Reactant (a), reactant (b) and smelling of tetrabutyl ammonium, potassium carbonate are added in reaction vessel by step (1), are added molten
Agent makes it dissolve, and reacts 4-12h under counterflow condition, obtains compound (c)；
Step (2) is by the product Compound (c) of step (1), connection boric acid pinacol ester, potassium acetate, [1,1 '-bis- (diphenylphosphine)
Ferrocene] palladium chloride dichloromethane complex are added in reaction vessel, and solvent is added and makes it dissolve, 100 under nitrogen protection
It DEG C is protected from light for 24 hours, obtains compound (d)；
The product Compound (d) of step (2), 1- bromine pyrene (e), tetrabutylammonium bromide, tetra-triphenylphosphine palladium are added to by step (3)
In reaction vessel, solvent dissolution is added, is protected from light 8-16h at 90-120 DEG C of nitrogen protection, obtains compound (f)；
Step (4) product Compound (f) of step (3), triethyl phosphite are added in microwave tube dissolve in a solvent,
0.5-1h is reacted at 100-150 DEG C in microwave reactor, obtains compound (g).
3. the preparation method of multi-functional amphipathic conjugated molecular material according to claim 2, it is characterised in that:
Solvent used in the step (1) is acetone or potassium hydroxide aqueous solution, mole of reactant (a) and reactant (b)
Than for 1:(3-5)；
Solvent used in the step (2) is one kind of toluene, dioxane, the product Compound (c) of step 1): connection boric acid
Pinacol ester: potassium acetate: the molar ratio of [1,1 '-bis- (diphenylphosphine) ferrocene] palladium chloride dichloromethane complex is 1:
(2.4-4): (6-9): (0.03-0.1)；
Solvent used in the step (3) is one or more of tetrahydrofuran, toluene, chlorobenzene, o-dichlorohenzene, reactant
(d): reactant (e): tetrabutylammonium bromide: the molar ratio of tetra-triphenylphosphine palladium is 1:(2.4-4): (0.2-0.4): (0.03-
0.1)；
In the step (4), the molar ratio of compound (f) and triethyl phosphite is 1:(10-30).
4. a kind of multi-functional amphipathic conjugated molecular material answering in organic electroluminescence device as described in claim 1
With.
5. application as claimed in claim 4, it is characterised in that: the material is separately as electron injecting layer, or is used as hair simultaneously
Photosphere and electron injecting layer are applied in organic electroluminescence device.
6. application as claimed in claim 4, it is characterised in that: the material prepares the organic hair of single-layer or multi-layer by solution processing
Optical diode device, using spin coating and inkjet printing two ways.
7. application as claimed in claim 6, it is characterised in that: make organic electroluminescence device by inkjet printing mode
When, ink is configured using one or more of ethylene glycol monomethyl ether, ethylene glycol ethyl ether, ethyl alcohol solution.
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| CN104356004A (en) * | 2014-10-23 | 2015-02-18 | 江苏三月光电科技有限公司 | Synthesis of novel aromatic compound and application thereof to OLED (organic light emitting diode) device |
| CN104370752A (en) * | 2014-10-23 | 2015-02-25 | 江苏三月光电科技有限公司 | Synthesis of 1,3,5-tri(aryl amido) phenyl aromatic compound and application of 1,3,5-tri(aryl amido) phenyl aromatic compound on OLED (Organic Light-Emitting Diode) device |
| CN105418679A (en) * | 2015-10-29 | 2016-03-23 | 南京邮电大学 | Triphenylphosphine oxide unit bridged bipolar host material and application thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104356004A (en) * | 2014-10-23 | 2015-02-18 | 江苏三月光电科技有限公司 | Synthesis of novel aromatic compound and application thereof to OLED (organic light emitting diode) device |
| CN104370752A (en) * | 2014-10-23 | 2015-02-25 | 江苏三月光电科技有限公司 | Synthesis of 1,3,5-tri(aryl amido) phenyl aromatic compound and application of 1,3,5-tri(aryl amido) phenyl aromatic compound on OLED (Organic Light-Emitting Diode) device |
| CN105418679A (en) * | 2015-10-29 | 2016-03-23 | 南京邮电大学 | Triphenylphosphine oxide unit bridged bipolar host material and application thereof |
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