CN107098931A - A kind of multi-functional amphipathic conjugated molecular material and preparation method and application - Google Patents
A kind of multi-functional amphipathic conjugated molecular material and preparation method and application Download PDFInfo
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- 239000000463 material Substances 0.000 title claims abstract description 44
- 238000002360 preparation method Methods 0.000 title claims abstract description 12
- 150000001875 compounds Chemical class 0.000 claims abstract description 60
- 238000007641 inkjet printing Methods 0.000 claims abstract description 12
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 5
- -1 phosphonate ester Chemical class 0.000 claims abstract description 5
- 238000003786 synthesis reaction Methods 0.000 claims abstract description 5
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 4
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 3
- 125000003118 aryl 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 34
- 239000002904 solvent Substances 0.000 claims description 34
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 30
- 238000006243 chemical reaction Methods 0.000 claims description 28
- 239000000376 reactant Substances 0.000 claims description 24
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 20
- YMWUJEATGCHHMB-UHFFFAOYSA-N dichloromethane Natural products ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 17
- 229910052757 nitrogen Inorganic materials 0.000 claims description 17
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 claims description 16
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 claims description 12
- 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 10
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 10
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 claims description 10
- 239000000243 solution Substances 0.000 claims description 9
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 claims description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 8
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 8
- GPAYUJZHTULNBE-UHFFFAOYSA-N diphenylphosphine Chemical compound C=1C=CC=CC=1PC1=CC=CC=C1 GPAYUJZHTULNBE-UHFFFAOYSA-N 0.000 claims description 8
- 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 8
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 claims description 8
- 235000011056 potassium acetate Nutrition 0.000 claims description 8
- 238000004528 spin coating Methods 0.000 claims description 8
- 238000010129 solution processing Methods 0.000 claims description 7
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 6
- 239000007864 aqueous solution Substances 0.000 claims description 6
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-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
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 5
- 238000005401 electroluminescence Methods 0.000 claims description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 4
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 claims description 3
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 claims description 2
- SODQFLRLAOALCF-UHFFFAOYSA-N 1lambda3-bromacyclohexa-1,3,5-triene Chemical compound Br1=CC=CC=C1 SODQFLRLAOALCF-UHFFFAOYSA-N 0.000 claims description 2
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 230000003287 optical effect Effects 0.000 claims 1
- 229910052700 potassium Inorganic materials 0.000 claims 1
- 239000011591 potassium Substances 0.000 claims 1
- 239000000052 vinegar Substances 0.000 claims 1
- 235000021419 vinegar Nutrition 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 10
- 150000002220 fluorenes Chemical class 0.000 abstract description 2
- 238000004020 luminiscence type Methods 0.000 abstract 1
- 239000007777 multifunctional material Substances 0.000 abstract 1
- 150000003220 pyrenes Chemical class 0.000 abstract 1
- 239000000126 substance 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
- 239000010410 layer Substances 0.000 description 14
- 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
- 239000003054 catalyst Substances 0.000 description 4
- 238000000921 elemental analysis Methods 0.000 description 4
- 239000002356 single layer Substances 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 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
- 229920000144 PEDOT:PSS Polymers 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- 238000000137 annealing Methods 0.000 description 2
- 230000009286 beneficial effect Effects 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
- 239000007788 liquid Substances 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 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
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 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
- 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
- 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
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000001816 cooling Methods 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
- 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
- 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
- 238000007650 screen-printing Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000000967 suction filtration Methods 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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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- 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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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- 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
- C07F9/4006—Esters of acyclic acids which can have further substituents on alkyl
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
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- H10K50/17—Carrier injection layers
- H10K50/171—Electron injection layers
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
- H10K71/10—Deposition of organic active material
- H10K71/12—Deposition of organic active material using liquid deposition, e.g. spin coating
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- H10K71/12—Deposition of organic active material using liquid deposition, e.g. spin coating
- 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 multi-functional amphipathic conjugated molecular material of one kind and preparation method and application, the material is the fluorenes and pyrene class material composition by High Efficiency Luminescence, phosphonate ester is as polarity side base, and from the linear molecule compound of different alkyl chains, its general structure is shown below：Wherein, R is one kind in C1 C30 alkyl, alkoxy, alkane phenyl, alkane phenoxy group, aryl.The material has the advantages such as chemical constitution is simple, synthesis is with low cost, while having good solution processability energy, filming performance and multifunctional light electrical characteristics, can realize the blue emission and efficient embellishing cathode interface of high brightness simultaneously as multifunctional material.Using the material simultaneously as luminescent layer and the Organic Light Emitting Diode of boundary layer, excellent photoelectric characteristic can be realized by solution processes or inkjet printing mode using simplified device architecture, overcome the making obstacle in conventional multilayer device.
Description
Technical field
The invention belongs to photoelectric material and applied technical field, and in particular to a kind of multi-functional amphipathic conjugated molecular material and
Its preparation method and application.
Background technology
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, the vacuum with sandwich construction is sunk
Product small molecule OLED comes into business application.However, vacuum deposition method manufacturing process is complicated, cost height 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.By 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 OLED large-scale production, includes spin coating, leaching
The processing technologys such as painting, scraper for coating, inkjet printing, intaglio printing and silk-screen printing.Wherein inkjet printing is a kind of promising
Technology, because saving material, beneficial to patterning, is easy to make large area film.Although light emitting polymer is deemed applicable to spray
Charge unbalance problem in impurity in ink print, but polymer and the device based on polymer may substantially reduce efficiency
And the life-span.By contrast, small molecule structure is clear and definite, be easy to purifying, it is easier to realize practical efficient stable device.Cause
This, it is quite attractive and in demand to manufacture small molecule OLED by inkjet printing.
However, the small molecule OLED of ink jet printing is challenging.On the one hand, commercial common OLED small molecules
Solubility and film form are all very poor generally in solution processes.On the other hand, due to interface attack phenomenon, it is difficult to printed by ink-jet
Brush is built multilayer device structure and acquisition Efficient devices is injected and transmitted with balancing charge.Therefore, exploitation has multi-functional characteristic
New printable OLED material is to simplify device architecture, with especially important meaning.
The content of the invention
Technical problem：The invention provides multi-functional amphipathic conjugated molecular material of one kind and preparation method and application,
To solve that current solution processing OLED is complicated, electron injecting layer can not the problem such as solution processing.
Technical scheme：To achieve the above object, the present invention uses following technical scheme：
A kind of multi-functional amphipathic conjugated molecular material, the material is with fluorene structured for skeleton, and pyrene is end-capping group, phosphonate ester
As polarity side base, from the linear conjugate molecular compound of different alkyl chains, with the general structure as shown in following formula 1：
Wherein, R is one kind in 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, the material is with the compound represented by following formula 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), plus
Entering solvent dissolves it, 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- (diphenyl
Phosphine) ferrocene] palladium chloride dichloromethane complex are added in reaction vessel, and adding solvent dissolves it, under nitrogen protection
100 DEG C of lucifuges react 24h, obtain compound (d)；
Step (3) adds the product Compound (d) of step (2), 1- bromine pyrenes (e), TBAB, tetra-triphenylphosphine palladium
Enter into reaction vessel, add solvent dissolving, lucifuge reaction 8-16h, obtains compound (f) in the case where nitrogen protects 90-120 DEG C；
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, compound (g) is obtained.
The solvent used in the step (1) is acetone or potassium hydroxide aqueous solution, reactant (a) and reactant (b)
Mol ratio is 1：(3-5)；
The solvent used in the step (2) be toluene, one kind of dioxane, step 1) product Compound (c)：Connection
Boric acid pinacol ester：Potassium acetate：The mol ratio of [1,1 ＇-bis- (diphenylphosphine) ferrocene] palladium chloride dichloromethane complex is
1:(2.4-4):(6-9)：(0.03-0.1)；
The solvent used in the step (3) is the one or more in tetrahydrofuran, toluene, chlorobenzene, o-dichlorohenzene, instead
Answer thing (d)：Reactant (e)：TBAB：The mol ratio of tetra-triphenylphosphine palladium is 1:(2.4-4):(0.2-0.4)：
(0.03-0.1)；
In the step (4), the mol 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), pyrovinic acid are added in reaction vessel by step (1), and adding solvent makes its molten
36-48h is reacted under solution, counterflow condition, compound (c) is obtained；
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, adding solvent dissolves it, 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 be added to reaction vessel bottle in, add solvent dissolve it, nitrogen protection
Under, 100 DEG C of reaction 24h obtain compound (f)；
The product (f) of step (3), (g), TBAB, tetra-triphenylphosphine palladium are added in reactor by step (4)
In a solvent, 80-120 DEG C of lucifuge reaction 8-16h, obtains compound (h) under nitrogen protection for dissolving；
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, compound (i) is obtained.
The solvent used in the step (1) is chloroform；
The solvent used in the step (2) is acetone or potassium hydroxide aqueous solution, reactant (c) and reactant (d)
Mol ratio is 1：(3-5)；
The solvent used in the step (3) is toluene, one kind of dioxane, compound (e)：Join boric acid pinacol
Ester：Potassium acetate：The mol ratio of [1,1 ＇-bis- (diphenylphosphine) ferrocene] palladium chloride dichloromethane complex is 1:(2.4-4):
(5-9)：(0.03-0.1)；
The solvent used in the step (4) is the one or more in tetrahydrofuran, toluene, chlorobenzene, o-dichlorohenzene, instead
Answer thing (g)：Reactant (e)：TBAB：The mol ratio of tetra-triphenylphosphine palladium is 1:(2.4-4):(0.2-0.5)：
(0.03-0.13)；
In the step (5), the mol 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, be specially：The material
Material is separately as electron injecting layer, and its structure is：Anode/luminescent layer/electron injecting layer/negative electrode；Or simultaneously as luminescent layer with
Electron injecting layer, its structure is：Anode/luminescent layer/negative electrode.
The multi-functional amphipathic conjugated molecular material of the present invention, with alcohol-soluble, can prepare individual layer by solution processing
Or multilayer organic light emitting diode device, including spin coating and inkjet printing two ways.Make organic by inkjet printing mode
During electroluminescent device, ink is configured using one or more of solution in ethylene glycol monomethyl ether, ethylene glycol ethyl ether, ethanol.
Beneficial effect：The invention provides the multi-functional amphipathic conjugated molecular material of one kind, with fluorene structured for skeleton, pyrene is made
For end group, phosphate is used as polarity side.It is coupled by Suzuki, a series of processes such as phosphating reaction have synthesized such material
Material, the advantage such as the material has that building-up process is simple and easy to control, with low cost, is easily purified, yield height.The combination of pyrene and fluorenes is assigned
The good heat endurance of small molecule, fluorescence quantum efficiency, luminosity, it is molten that phosphate polar group then assigns the excellent alcohol of material
Property, electron injection ability and filming performance.The material is applied to the processing mode 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 realized simultaneously
Face is modified to simplify device architecture.The material in environment-friendly alcoholic solvent have good solubility, can with it is regular activated
The casting solution of layer shows orthogonal property, so that interface attack phenomenon when avoiding the solwution method from preparing multilayer device.The material
Possess multifunctional light electrical characteristics, the blue emission and active cathodic modifying interface of high brightness can be realized simultaneously, solve molten at present
OLED is complicated for liquid processing, electron injecting layer can not the problem such as solution processing.
Brief description of the drawings
Fig. 1 is the compound PEP in embodiment 11HNMR spectrograms.
Fig. 2 is the compound PEP in embodiment 113C NMR spectras.
Fig. 3 is the compound POEP in embodiment 21HNMR spectrograms.
Fig. 4 is the compound POEP in embodiment 213C NMR spectras.
Fig. 5 is compound PEP and POEP uv absorption spectra.
Fig. 6 is compound PEP and POEP fluorescence emission spectrogram of compound.
Fig. 7 be embodiment 3 in Organic Light Emitting Diode brightness-voltage curve.
Fig. 8 be embodiment 3 in Organic Light Emitting Diode Current efficiency-voltage curve.
Embodiment
With reference to specific embodiment, the present invention will be further described.
Embodiment 1：Reaction scheme is as follows.
Comprise the following steps that：
Ith step：2,7- dibromo fluorenes (20g, 61.7mmol), 1,6- dibromo-hexane (35.5mL, 246.9mmol), the tetrabutyl
Smelling ammonium (TBAB) (2g) adds 50g mass fraction in 50% potassium hydroxide aqueous solution, 65 DEG C of reactions are stayed overnight.Extraction, rotation
Dry, 100~200 mesh cross post, obtain 32g compound A, yield 160%.
IIth step：Compound A (6g, 9.23mmol), connection boric acid pinacol ester (9.36g, 36.9mmol) substitutes nitrogen three
Potassium acetate (9.34g, 64.6mmol) is added after secondary, nitrogen is substituted, lucifuge adds catalyst Pd (pddf)2Cl2(0.4g,
0.524mmol) it is dissolved in 45mL dioxane, the lower 100 DEG C of reactions 24h of nitrogen protection.Extraction was spin-dried for pillar, obtained
4.93g compound B, yield 82%.
IIIth step：Compound B (1g, 1.34mmol), 1- bromines pyrene (1.51g, 5.37mmol) is substituted to be added after nitrogen three times
Smelling of tetrabutyl ammonium (0.12g, 0.37mmol), substitutes nitrogen, and lucifuge adds catalyst Pd (PPh3)4(0.1g, 0.08mmol) is molten
Solution is reacted 12 hours in the potash water dissolving of 21mL toluene and 7mL in 95 DEG C of lucifuges.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 ripple reactor.Vacuum distillation, crosses post, 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
(the calcd of 76.76%, H 5.39%: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:(the calcd of C 77.62%, H 6.77%:C 77.51%, H
6.81%)
Embodiment 2：Reaction scheme is as follows.
Comprise the following steps that：
Ith step：The Fluorenone of 2,7- dibromo two (30.3g, 89.65mmol) is placed in 500mL there-necked flasks, addition phenol (71mL,
591.18mmol), 120mL CCl4, temperature is adjusted to 80 DEG C, reacts 42h.Stop reaction, K is used after cooling2CO3Solution is quenched, plus
It is fashionable slowly to have a large amount of bubbles and produce.Suction filtration afterwards, waste liquid is purple.With many washings of DCM 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) and add 50g mass fraction in 50% potassium hydroxide aqueous solution, 65 DEG C of reactions are stayed overnight.Extraction, is spin-dried for, 100
~200 mesh cross post.Obtain 13.2g compound E, yield 132%.
IIIth step：Compound E (5.4g, 6.47mmol), connection boric acid pinacol ester (6.5614g, 25.89mmol) substitutes nitrogen
Potassium acetate (3.81g, 33.8mmol) is added after gas three times, nitrogen is substituted, lucifuge adds catalyst Pd (pddf)2Cl2(0.21g,
0.275mmol) it is dissolved in 60mL dioxane, 100 DEG C of reaction 24h.Extraction was spin-dried for pillar, obtained 4.21g compound F,
Yield 78%.
IVth step：Compound F (0.8g, 0.742mmol), 1- bromines pyrene (0.626g, 2.23mmol) is substituted after nitrogen three times
Smelling of tetrabutyl ammonium (0.11g, 0.34mmol) is added, nitrogen is substituted, lucifuge adds catalyst Pd (PPh3)4(0.1g,
In the potash water dissolving for 0.09mmol) being dissolved in 21mL toluene and 7mL.Lucifuge is kept to react 12 hours at 95 DEG C.Extraction
Take and be 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 reaction 24h.Vacuum distillation, crosses post and obtains 0.178g end-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
(the calcd of 76.90%, H 5.23%: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:(the calcd of C 77.53%, H 6.44%:C 77.63%, H
6.43%)
Embodiment 3
The preparation of Organic Light Emitting Diode.
OLEDs single layer devices are prepared by spin-coating method：Its device architecture is ITO/PEDOT:PSS 35nm/ luminescent layers
65nm/Al 80nm.Solvent is done using chloroform, luminescent layer uses any one in compound PEP/POEP, prepares 15mg/mL's
Solution.The lower spin coating of nitrogen protection, rotating speed is 1500rpm, 80 DEG C of annealing 10min.
OLEDs single layer devices are prepared by ink-jet printing process：Its device architecture is ITO/PEDOT:PSS 35nm/PEP/Al
80nm.Ethylene glycol monomethyl ether is used for solution, 14mg/mL ink is configured.100 DEG C of annealing 20min.
Contrasted below for the electroluminescent properties of above-mentioned three kinds of individual layer organic light emitting diode devices：
aOpen bright voltage and be defined as brightness for 1cd m-2When operating voltage.bDuring high-high brightness.cPrepared by inkjet printing.
Three single layer devices are to use multi-functional amphiphilic conjugated molecule as illuminator and cathode interlayer.Analyze form
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 high-high 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 as little as 3.8V bright voltage that opens, and maximum current efficiency reaches 1.12cdA-1, have high-high brightness in 11.0V
8850.1cdm-2, performance is more preferably.Result above absolutely proves that this novel MOLECULE DESIGN is conducive to by simple device junction
Structure realizes excellent photoelectric characteristic.
Above-described embodiment is preferably embodiment, but embodiments of the present invention are not by above-described embodiment of the invention
The modifications and variations done under limitation, other any principles without departing from the present invention, should be equivalent substitute mode, all wrap
Containing within the scope of the present invention.
Claims (10)
1. a kind of multi-functional amphipathic conjugated molecular material, it is characterised in that：The material is with fluorene structured for skeleton, and pyrene is END CAPPED GROUP
Group, phosphonate ester is as polarity side base, from the linear conjugate molecular compound of different alkyl chains, with the knot as shown in following formula 1
Structure formula：
Wherein, R is one kind in C1-C30 alkyl, alkoxy, alkane phenyl, alkane phenoxy group, aryl.
2. multi-functional amphipathic conjugated molecular material as claimed in claim 1, it is characterised in that：The material be with following formula 2 or
Compound represented by formula 3：
3. a kind of preparation method of multi-functional amphipathic conjugated molecular material as claimed in claim 1 or 2, 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 dissolves it, 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 adding solvent dissolves it, nitrogen protection lower 100
DEG C lucifuge reaction 24h, obtains compound (d)；
The product Compound (d) of step (2), 1- bromine pyrenes (e), TBAB, tetra-triphenylphosphine palladium are added to by step (3)
In reaction vessel, solvent dissolving is added, lucifuge reaction 8-16h, obtains compound (f) in the case where nitrogen protects 90-120 DEG C；
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, compound (g) is obtained.
4. the preparation method of multi-functional amphipathic conjugated molecular material according to claim 3, it is characterised in that：
The 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)；
The solvent used in the step (2) be toluene, one kind of dioxane, step 1) product Compound (c)：Join boric acid
Pinacol ester：Potassium acetate：The mol ratio of [1,1 ＇-bis- (diphenylphosphine) ferrocene] palladium chloride dichloromethane complex is 1:
(2.4-4):(6-9)：(0.03-0.1)；
The solvent used in the step (3) is the one or more in tetrahydrofuran, toluene, chlorobenzene, o-dichlorohenzene, reactant
(d)：Reactant (e)：TBAB：The mol ratio of tetra-triphenylphosphine palladium is 1:(2.4-4):(0.2-0.4)：(0.03-
0.1)；
In the step (4), the mol ratio of compound (f) and triethyl phosphite is 1:(10-30).
5. a kind of preparation method of multi-functional amphipathic conjugated molecular material as claimed in claim 1 or 2, it is characterised in that：
Including following synthetic route and synthesis step：
Reactant (a), reactant (b), pyrovinic acid are added in reaction vessel by step (1), and adding solvent dissolves it,
36-48h is reacted under counterflow condition, compound (c) is obtained；
The product Compound (c) of step (1), reactant (d) and smelling of tetrabutyl ammonium, potassium carbonate are added to reaction by step (2)
In container, adding solvent dissolves it, 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- (diphenylphosphine)
Ferrocene] palladium chloride dichloromethane complex be added to reaction vessel bottle in, add solvent dissolve it, nitrogen protection under,
100 DEG C of reaction 24h, obtain compound (f)；
The product (f) of step (3), (g), TBAB, tetra-triphenylphosphine palladium are added in reactor by step (4) to be dissolved
In a solvent, 80-120 DEG C of lucifuge reacts 8-16h under nitrogen protection, obtains compound (h)；
Step (5) product Compound (h) of step (4), triethyl phosphite are added in microwave tube dissolve in a solvent,
0.5-1h is reacted at 100-150 DEG C in microwave reactor, compound (i) is obtained.
6. the preparation method of multi-functional amphipathic conjugated molecular material according to claim 5, it is characterised in that：
The solvent used in the step (1) is chloroform；
The solvent used in the step (2) is acetone or potassium hydroxide aqueous solution, mole of reactant (c) and reactant (d)
Than for 1：(3-5)；
The solvent used in the step (3) is toluene, one kind of dioxane, compound (e)：Connection boric acid pinacol ester：Vinegar
Sour potassium：The mol ratio of [1,1 ＇-bis- (diphenylphosphine) ferrocene] palladium chloride dichloromethane complex is 1:(2.4-4):(5-
9)：(0.03-0.1)；
The solvent used in the step (4) is the one or more in tetrahydrofuran, toluene, chlorobenzene, o-dichlorohenzene, reactant
(g)：Reactant (e)：TBAB：The mol ratio of tetra-triphenylphosphine palladium is 1:(2.4-4):(0.2-0.5)：(0.03-
0.13)；
In the step (5), the mol ratio of compound (h) and triethyl phosphite is 1:(10-30).
7. a kind of multi-functional amphipathic conjugated molecular material as claimed in claim 1 or 2 is in organic electroluminescence device
Using.
8. application as claimed in claim 7, it is characterised in that：The material is separately as electron injecting layer, or is used as hair simultaneously
Photosphere and electron injecting layer, applied in organic electroluminescence device.
9. application as claimed in claim 7, it is characterised in that：The material prepares the organic hair of single or multiple lift by solution processing
Optical diode device, including spin coating and inkjet printing two ways.
10. application as claimed in claim 9, it is characterised in that：Organic electroluminescence device is made by inkjet printing mode
When, configure ink using one or more of solution in ethylene glycol monomethyl ether, ethylene glycol ethyl ether, ethanol.
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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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