CN105742514A - Method for improving alcohol/water solubility and electronic injection characteristics of electron transport material - Google Patents

Method for improving alcohol/water solubility and electronic injection characteristics of electron transport material Download PDF

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CN105742514A
CN105742514A CN201610060650.4A CN201610060650A CN105742514A CN 105742514 A CN105742514 A CN 105742514A CN 201610060650 A CN201610060650 A CN 201610060650A CN 105742514 A CN105742514 A CN 105742514A
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acid
electron
alcohol
nitrogenous
nitrogen
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CN105742514B (en
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杨楚罗
尹校君
相烨鹏
周涛
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Wuhan University WHU
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    • H—ELECTRICITY
    • 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]
    • H10K50/14—Carrier transporting layers
    • H10K50/16—Electron transporting layers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
    • C07D213/127—Preparation from compounds containing pyridine rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
    • C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
    • C07D271/10—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles
    • C07D271/107—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles with two aryl or substituted aryl radicals attached in positions 2 and 5
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D498/04—Ortho-condensed systems
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/656—Aromatic compounds comprising a hetero atom comprising two or more different heteroatoms per ring
    • H10K85/6565—Oxadiazole compounds
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole

Abstract

The invention provides a simple acid treatment method to improve the alcohol/water solubility and the interface modification characteristics of a traditional evaporation-type electron transport material. The traditional evaporation-type nitrogen-containing heterocyclic electron transport material is relatively poor in solubility in an alcohol or water solution in general, and is not suitable for preparation of an all-solution processing organic light-emitting device. By the simple acid treatment method, a nitrogen-containing aromatic heterocycte is protonized, so that the alcohol/water solubility is improved; and meanwhile, these protonized nitrogen-containing salts have good interface modification characteristics. These nitrogen-containing salts are applied to the organic light-emitting device prepared by a solution processing method as an electron injection/transport layer, so that the efficiency of the device can be significantly improved; and the efficiency attenuation of the device is relieved. Furthermore, the structure of the device can be simplified, so that the production cost is reduced. The simple acid treatment method has the advantages that the dual-functional (electron injection and transport) material with the alcohol/water solubility can be obtained only by simple conventional acid treatment; and the simple acid treatment method has practicability.

Description

A kind of method improving electron transport material alcohol/water solublity and Electron Injection Characteristics
Technical field
The invention belongs to field of organic electroluminescent materials, particularly to a kind of method improving electron transport material alcohol/water solublity and Electron Injection Characteristics.
Background technology
Organic electroluminescent LED (OLED) with its flexibility, self-luminous, visual angle is wide, response is fast, energy consumption is low and the many merits such as potential low cost has attracted concern (Nature2000,403,750) widely.The preparation method of OLED is generally divided into two kinds, i.e. vacuum evaporation and solution spin coating.Compared to the device fabrication mode of vacuum evaporation, adopt the mode of solution processing to prepare organic electroluminescence device and be easier to realize large area and prepare, thus reducing production cost (Org.Lett.2014,16,1140 and Adv.Mater.2015,27,1327 etc.).
It is limited to solution spin coating and prepares the selection rule of orthogonal solvents in the middle of device, generally require that electron transfer layer or cathode interface layer material have alcohol/water solublity, but the material of this respect is little, the electron transfer layer of therefore spin coating type device and electron injecting layer generally still adopt the mode that vacuum steaming is crossed to prepare (Adv.Mater.2013,25,596 and Adv.Mater.2015,27,93).
Although having been reported that the electron transport material for nitrogen-containing hetero lopps can adopt the processing mode spin coating electron transfer layer (Adv.Mater.2010 of formic acid/water mixed solvent, 22,4744 and Macromol.RapidCommun.2015,36,1658), it is contemplated that luminescent layer can be existed certain destruction thus reducing stability and the efficiency of device by formic acid.Particularly, between the electron transfer layer of spin coating and cathode electrode (being generally aluminum), yet suffer from a bigger electronics injection barrier, therefore need for one layer of electron injecting layer of evaporation between electron transfer layer and electrode.In this case, existing method, particularly material solution need further to improve and development.
Summary of the invention
In view of above-mentioned the deficiencies in the prior art, the technical problem to be solved is to provide a kind of method improving electron transport material alcohol/water solublity and Electron Injection Characteristics.The method to improve alcohol/water solublity and the Electron Injection Characteristics of conventional electrical transmission material by simple acid treatment method, thus realizing complete solution treatment process to prepare OLED, being improved device efficiency simultaneously, simplifying device architecture.
Technical scheme is as follows:
Nitrogen heterocyclic ring electron-like is transmitted material and is placed in the middle of aqueous acid, room temperature～50 DEG C are stirred 6～8 hours, then the mode adopting decompression distillation removes unnecessary acid and water, remaining solid residue namely be generate nitrogen heterocyclic ring electron-like transmission material containing nitrogen salt, then adopt the way separation purification of recrystallization.
The acid used is conventional organic acid or inorganic acid such as hydrochloric acid, hydrobromic acid, hydroiodic acid, Tetrafluoroboric acid, hexafluorophosphoric acid or trifluoromethanesulfonic acid etc..
Here the good solvent selected in recrystallization process is generally the big polar solvent such as methanol, ethanol, water or DMF, and poor solvent generally selects oxolane, normal hexane equal solvent.
Described nitrogen heterocyclic ring electron-like transmission material is one or more in nitrogenous five-ring heterocycles, nitrogenous hexa-member heterocycle or nitrogenous polynary condensed ring.
Traditional evaporation type nitrogen heterocyclic ring electron-like transmission material dissolubility in the middle of alcohols or aqueous solution is generally poor, is not suitable for preparing the organic electroluminescence device of whole soln processing.The inventive method adopts simple acid treatment method by the protonation of nitrogenous heteroaromatic and then to improve its alcohol/water solublity, has good modifying interface characteristic containing nitrogen salt after these protonations simultaneously.These are used as electronics injection/transport layer containing nitrogen salt and are applied to can not only be obviously improved in the middle of organic electroluminescence device prepared by solution processing method the efficiency of device, slow down device efficiency decay, but also the structure of device can be simplified thus reducing cost of manufacture.
Advantages of the present invention is exactly simple to operate, and what obtain has good alcohol/water solublity containing nitrogen salt, it is easy to accomplish prepared by the OLED of whole soln processing.In addition these containing nitrogen salt with good modifying interface characteristic, it is possible to as electron injection material.The material so having electronics injection and transport property concurrently is beneficial to simplify device architecture, thus reducing element manufacturing cost.
Accompanying drawing explanation
Fig. 1, the current efficiency of the device B1-B6 function relation figure to electric current density.Wherein the electronics of device B1-B5 injects/transmits material PBD-HCl, TmPyPB-TfOH, Tm3PyDPB-HCl, BCP-HBr and 3Py-DBBO-HCl respectively, and B6 is control device.
Fig. 2, the power efficiency of the device B1-B6 function relation figure to electric current density.Wherein the electronics of device B1-B5 injects/transmits material PBD-HCl, TmPyPB-TfOH, Tm3PyDPB-HCl, BCP-HBr and 3Py-DBBO-HCl respectively, and B6 is control device.
Fig. 3, the external quantum efficiency of the device B1-B6 function relation figure to electric current density.Wherein the electronics of device B1-B5 injects/transmits material PBD-HCl, TmPyPB-TfOH, Tm3PyDPB-HCl, BCP-HBr and 3Py-DBBO-HCl respectively, and B6 is control device.
Detailed description of the invention
It is exemplified below several examples the present invention is described in more detail.
Example one: the hcl acidifying of nitrogenous five-ring heterocycles electron transport material PBD processes
PBD has been widely used in the electron transfer layer in the middle of vacuum evaporation type organic electroluminescence device (Chem.Mater.2004,16,4556) as classical electron transport material.Weigh PBD20mg and be placed among the round-bottomed flask of 25ml, add concentrated hydrochloric acid 10ml, airtight, it is stirred at room temperature 6～8 hours, decompression is distilled off excessive hydrochloric acid solution.Solid residue is dissolved in alcoholic solution, then dropwise transfers to the hydrochlorate (PBD-HCl, quantitative response) that the white solid obtaining precipitating out in the middle of the hexane solution of quickly stirring is PBD.Anal.calcdforC24H24Cl2N2O (%): C67.45, H5.66, N6.55；foundC67.25,H5.88,N6.55.
Example two: the trifluoromethanesulfonic acid acidification of nitrogenous hexa-member heterocycle electron-like transmission material TmPyPB
Compound TmPyPB is electron transport material (Adv.Funct.Mater.2009,19,1260) conventional in the middle of OLED.Weighing 500mg compound TmPyPB and be placed in the round-bottomed flask of 25ml, add the deionized water of 10ml, 1～2ml trifluoromethanesulfonic acid, seal, after being stirred at room temperature 6～8 hours, decompression is distilled off unnecessary trifluoromethanesulfonic acid aqueous solution.Being dissolved in the middle of methanol by the solid residue obtained, be then slowly added in poor solvent ether, the fluoroform sulphonate (TmPyPB-TfOH) that quickly stirring obtains precipitating out is white solid (reaction is quantitative response).Anal.calcdforC42H30F9N3O9S3(%): C51.06, H3.06, N4.25, S9.74；foundC51.36,H3.17,N4.33,S9.58.
Example three: the hcl acidifying of electron transport material Tm3PyDPB processes
Weighing 500mg compound Tm3PyDPB and be placed in the round-bottomed flask of 25ml, add the concentrated hydrochloric acid of 10ml, seal, after being stirred at room temperature 6～8 hours, decompression is distilled off unnecessary hydrochloric acid.The solid residue obtained is dissolved in the middle of ethanol, is slowly added to poor solvent normal hexane, adopt solvent diffusion method recrystallization to obtain pure hydrochlorate (Tm3PyDPB-HCl) for faint yellow solid (reaction is quantitative response).Anal.calcdforC60H46Cl6N6(%): C67.74, H4.36, N7.90；foundC67.62,H4.66,N7.88.
Example four: the hydrobromic acid acidification of nitrogenous polynary condensed ring electron-like transmission material BCP
Weigh 500mg compound BCP and be placed in the round-bottomed flask of 25ml, add 10ml 48% hydrobromic acid aqueous solution, seal, 50 DEG C stirring 6～8 hours after decompression unnecessary hydrobromic acid is distilled off.The solid residue obtained is dissolved in the middle of ethanol, is slowly added to poor solvent normal hexane, adopt solvent diffusion method recrystallization to obtain pure hydrobromate (BCP-HBr) for white solid (reaction is quantitative response).Anal.calcdforC26H22Br2N2(%): C59.79, H4.25, N5.36；foundC59.67,H4.28,N5.47.
Example five: the hcl acidifying containing the electron transport material 3Py-DBBO of different azacyclo-s processes
Weighing 200mg compound 3Py-DBBO (J.Mater.Chem.C.2015,3,7589) and be placed in the round-bottomed flask of 25ml, add the concentrated hydrochloric acid of 10ml, seal, after being stirred at room temperature 6～8 hours, decompression is distilled off unnecessary hydrochloric acid.The solid residue obtained is dissolved in the middle of ethanol, is slowly added to poor solvent normal hexane, adopt solvent diffusion method recrystallization to obtain pure hydrochlorate (3Py-DBBO-HCl) for faint yellow solid (reaction is quantitative response).Anal.calcdforC42H34Cl6N6O2(%): C58.15, H3.95, N9.69；foundC58.18,H4.12,N9.77.
The modifying interface performance test of nitrogen heterocyclic ring salt:
In order to test these nitrogen heterocyclic rings salt compounds (PBD-HCl, TmPyPB-TfOH, Tm3PyDPB-HCl, BCP-HBr, 3Py-DBBO-HCl) the modifying interface ability to electrode, we test its work function (WF) on metal aluminium electrode and ito glass surface, and test condition is atmospheric exposure condition, method of testing is Kai Erwen probe, and detailed data is shown in following table.The device architecture of test is: electrode/nitrogen heterocyclic ring salt thin film (～10nm).It can be seen that electrode ITO and aluminum are respectively provided with good modifying interface ability by the nitrogen heterocyclic ring salt compounds after these protonations, so can effectively reduce interface potential barrier, make electronics be easier to from electrode injection to organic luminous layer.
a)Work content relative to ITO reduces number,b)Number is reduced relative to the work content of aluminum.
The application in the middle of organic electroluminescence device of the nitrogen heterocyclic ring salt.
The electron transport material that these nitrogen heterocyclic ring compounds are inherently good, the salt that acidifying is subsequently formed has good Electron Injection Characteristics concurrently, and these nitrogen heterocyclic ring salt can be dissolved in the middle of alcohol or water kind solvent.It is the organic electroluminescence device of fluorescent light-emitting layer that the processing method adopting whole soln spin coating is prepared for being electronics injections/transport layer, superyellow based on nitrogen heterocyclic ring salt, and its structure is: ITO/PEDOT:PSS/SuperYellow/ electronics injection transport layer/Al.Wherein the electronics of device B1-B5 injects/transmits material PBD-HCl, TmPyPB-TfOH, Tm3PyDPB-HCl, BCP-HBr and 3Py-DBBO-HCl respectively, and B6 is control device.Current efficiency/power efficiency/the external quantum efficiency of the device function relation figure such as Fig. 1,2,3 to electric current density.Can be seen that relative to comparative device B6, the efficiency of B1-B5 obtains and is obviously improved, wherein maximum current efficiency has exceeded 18.7cd/A, outer quantum is more than 5.7%, and along with the increase efficiency of brightness decays also very slow, it was shown that acid treatment nitrogen heterocyclic ring electron-like is transmitted material modification simple effectively.

Claims (9)

1. the method improving electron transport material alcohol/water solublity and Electron Injection Characteristics, it is characterized in that: nitrogen heterocyclic ring electron-like is transmitted material and is placed in the middle of aqueous acid, room temperature～50 DEG C are stirred 6～8 hours, then the mode adopting decompression distillation removes unnecessary acid and water, remaining solid residue namely be generate nitrogen heterocyclic ring electron-like transmission material containing nitrogen salt, then adopt the way separation purification of recrystallization.
2. method according to claim 1, it is characterised in that the acid of use is organic acid or inorganic acid.
3. method according to claim 2, it is characterised in that the acid of use is hydrochloric acid, hydrobromic acid, hydroiodic acid, Tetrafluoroboric acid, hexafluorophosphoric acid or trifluoromethanesulfonic acid.
4. method according to claim 1, it is characterised in that the good solvent selected in recrystallization process is methanol, ethanol, water or DMF.
5. method according to claim 1, it is characterised in that the poor solvent selected in recrystallization process is oxolane or normal hexane.
6. method according to claim 1, it is characterised in that described nitrogen heterocyclic ring electron-like transmission material is one or more in nitrogenous five-ring heterocycles, nitrogenous hexa-member heterocycle or nitrogenous polynary condensed ring.
7. method according to claim 6, it is characterised in that described nitrogenous five-ring heterocycles includes
8. method according to claim 6, it is characterised in that described nitrogenous hexa-member heterocycle includes
9. method according to claim 6, it is characterised in that described nitrogenous polynary condensed ring includes
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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3674381A4 (en) * 2017-08-25 2021-08-18 Japan Science and Technology Agency Organic optical material

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US6344285B1 (en) * 1998-11-12 2002-02-05 Samsung Display Devices Co., Ltd. Organic electroluminescence device
CN102911204A (en) * 2012-10-26 2013-02-06 华南理工大学 Phosphate group based small-molecule water/alcohol soluble material and preparation method and application thereof
CN103360604A (en) * 2013-07-11 2013-10-23 华南理工大学 Conjugated metal polymer photoelectric material with functionalized polarity side-chain radicals and application thereof
CN104892641A (en) * 2015-05-27 2015-09-09 华南理工大学 Neutral cathode buffer layer molecular type material based on N-heterocycle groups as well as preparation method and application of neutral cathode buffer layer molecular type material

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US6344285B1 (en) * 1998-11-12 2002-02-05 Samsung Display Devices Co., Ltd. Organic electroluminescence device
CN102911204A (en) * 2012-10-26 2013-02-06 华南理工大学 Phosphate group based small-molecule water/alcohol soluble material and preparation method and application thereof
CN103360604A (en) * 2013-07-11 2013-10-23 华南理工大学 Conjugated metal polymer photoelectric material with functionalized polarity side-chain radicals and application thereof
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