CN104277064A - Compound containing solubilization structure unit and application of compound in electronic device - Google Patents

Compound containing solubilization structure unit and application of compound in electronic device Download PDF

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CN104277064A
CN104277064A CN201410289149.6A CN201410289149A CN104277064A CN 104277064 A CN104277064 A CN 104277064A CN 201410289149 A CN201410289149 A CN 201410289149A CN 104277064 A CN104277064 A CN 104277064A
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slg
emitting diode
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潘才法
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    • C—CHEMISTRY; METALLURGY
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    • C09D11/00—Inks
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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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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
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    • 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
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/30—Coordination compounds
    • H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
    • H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
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    • 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
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    • 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
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
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    • C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
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Abstract

The invention relates to a novel compound containing a solubilization structure unit. The compound is composed of an organic functional structure unit A and a solubilization structure unit SLG, wherein the SLG contains at least one inorganic aromatic ring. According to the compound disclosed by the invention, the solubility and the coating performance are greatly improved, and meanwhile, high performance of an apparatus is kept. The invention also relates to a composition containing the compound as a paint or printing ink, and use of the composition in preparation of an organic electronic device. The invention further relates to an organic electronic device, particularly an organic light-emitting device, which comprises one or more functional films, wherein at least one film comprises the compound disclosed by the invention.

Description

A kind ofly comprise the compound of solubilising structural unit and the application in electron device thereof
Art:
The present invention relates to a kind of novel compound including solubilising structural unit and application in organic electronic devices particularly in organic luminescent device, and the production method of organic electronic devices and the application in illumination and technique of display and other occasions thereof.
Background technology:
Organic luminescent device, particularly Organic Light Emitting Diode (OLED) is (see Appl.Phys.Lett.1987 such as TANG, 51, p913), because it is from main light emission, high brightness, abundant by the adjustability of chemosynthesis to color, flexible etc. become current most promising next generation's display and lighting engineering.Particularly they can by the method printed, as spray ink Printing (InkJet Printing), technology film forming from solution such as silk screen printing (Screen Printing), thus greatly can reduce manufacturing cost, therefore just attractive especially to large screen display and luminaire.
Based on micromolecular OLED excellent performance, reached the business-like stage, but it obtains method preparation by vacuum evaporation usually.In order to make full use of the advantage of Method of printing, first under the prerequisite not reducing device performance, the solubleness of small molecule material must be improved.This type of solution is also few at present, is a urgent problem.
Summary of the invention
In order to solve existing OLED in sum, the particularly shortcoming of small molecules OLED, the invention provides a kind of novel compound including solubilising structural unit, it is made up of organic functions structural unit A and solubilising structural unit SLG, and wherein SLG includes at least one inorganic aromatic ring.According to compound of the present invention, solubleness and film performance improve a lot, simultaneously the high-performance of retainer member.Second object of the present invention be to provide comprise this compound composition as coating or printing-ink, and preparing the purposes of organic electronic devices.3rd object of the present invention is to provide a kind of organic electronic devices, particularly organic luminescent device, includes one or more layers organic functional thin film, wherein has at least thin film to include according to compound of the present invention.
The detailed description of invention
Will be appreciated that, the concrete enforcement of description done below and display is example of the present invention, and does not mean that another by any way
Limit the scope of the invention outward.In fact, for succinct object, may not describe conventional electronics, manufacture method, semiconducter device in detail at this, and relevant organic materials, and other function of system.
The invention provides a kind of novel compound according to following general formula 1:
Wherein: A is an organic functions structural unit, and n is the integer from 1 to 10, and SLG is solubilising structural unit, SLG at least includes an electroneutral inorganic planar ring, and described inorganic planar ring includes 4m+2 π-electronics, and wherein m is the integer of 1 to 6.
In a preferential embodiment, SLG includes at least one inorganic aromatic ring.In the present invention, inorganic planar ring or inorganic aromatic ring refer to that non-C and C atomicity ratio is greater than 1:1, and namely non-C total atom number is greater than C atomicity.Preferably, inorganic planar ring or inorganic aromatic ring are made up of non-C element completely.In a preferential embodiment, non-C element is selected from main group element B, N, O, S, P and aluminium, more preferably be main group element B, N, O, S.
The example of electroneutral inorganic planar ring has, but is not limited to:
In a preferential embodiment, SLG at least includes an electroneutral inorganic planar ring, and described inorganic planar environmental protection contains 6 or 10 π-electronics
In a preferential embodiment, SLG can independently be selected from following general formula:
Wherein
Ar 1, Ar 2be independently from each other aryl or heteroaryl groups separately, described group can be replaced by the group of one or more any type;
R 1, R 2hydrogen independently of one another separately; there is the straight chained alkyl of 1 to 20 C atom, alkoxyl group or thio alkoxy group; or there is the alkyl of the side chain of 3 to 20 C atoms or ring-type, alkoxyl group or thio alkoxy group or silyl-group; or there is the keto group of replacement of 1 to 20 C atom; there is the alkoxycarbonyl groups of 2 to 20 C atoms; there is the aryloxycarbonyl group of 7 to 20 C atoms; cyano group (-CN), carbamoyl group (-C (=O) NH 2); halogen formyl group (-C (=O)-X wherein X represents halogen atom); formyl group (-C (=O)-H); isocyano-group; isocyanate groups; thiocyanic ester group or lsothiocyanates group, oh group, nitryl group; CF3 group; Cl, Br, F; crosslinkable group or there is substituted or unsubstituted aromatics or the heteroaromatic ring system of 5 to 40 annular atomses; or there is aryloxy or the heteroaryloxy group of 5 to 40 annular atomses, or the combination of these systems, wherein one or more radicals R 1, R 2can each other and/or with described radicals R 1the ring of bonding forms aliphatic series or the aromatics ring system of monocycle or many rings; And
M is 0,1,2,3 or 4;
Wherein said dotted line key represents the key with functional architecture unit A bonding.
In a more preferential embodiment, SLG can independently be selected from following three way type:
Wherein
R 1, R 2and m as in general formula 2 define,
O, p are 0,1,2,3,4 or 5 separately independently of one another, and
Wherein said dotted line key represents the key with functional architecture unit A bonding.
In the present invention, Small molecule organic materials refers to that molecular weight is at most the material of 5000g/mol, and molecular weight is referred to as superpolymer higher than the material of 5000g/mol.In a preferential embodiment, described composition comprises one or more organic molecule functional materialss.
In a preferential embodiment, be little point of material according to compound of the present invention.In certain embodiments, the molecular weight of this compound is at least 800g/mol, is better be at least 900g/mol, is more preferably and is at least 1000g/mol, be preferably at least 1100g/mol,
In the present invention, organic functional material refers to the organic materials with an electronics or optical property, include but not limited to, hole (also claiming electric hole) is injected or transport material (HIM/HTM), hole barrier materials (HBM), electron injection or transport material (EIM/ETM), electron-blocking materials (EBM), organic host material (Host), singlet emitters (fluorescent illuminant), heavy state twinkler (phosphorescent emitter), particularly luminescent organometallic complex compound, and dyestuff.In the present invention, Host, material of main part, body material and substrate material have identical implication, and they can exchange.Organic functions structural unit A includes the structure of above-described functional materials.In a preferential embodiment, organic functions structural unit A includes the structure of a material of main part.In the embodiment that another is preferential, organic functions structural unit A includes the structure of HTM or ETM.The organic functional material be applicable to has detailed description after this paper.The embodiment preferential to some is made an explanation now.
Below be listed in some preferential embodiments, the condition that SLG should meet:
1) T1 of solubilising structural unit SLG is greater than the T1 of organic functions structural unit A
2) S1 of solubilising structural unit SLG is greater than the S1 of organic functions structural unit A
3) HOMO of solubilising structural unit SLG is lower than the HOMO of organic functions structural unit A
4) LUMO of solubilising structural unit SLG is higher than the LUMO of organic functions structural unit A
5) △ (HOMO-LUMO) of solubilising structural unit SLG is greater than the △ (HOMO-LUMO) of organic functions structural unit A.
In the embodiment that some are more preferential, the condition that SLG should meet: 1)+3), or 1)+4), or 1)+5), or 2)+3), or 2)+4), or 2)+5), or 3)+4).
In more preferential embodiment, SLG should meet: 1)+3)+4), or 2)+3)+4).
In certain embodiments, according to compound of the present invention, its second-order transition temperature is at least 90 DEG C, is better be at least 100 DEG C, is more preferably and is at least 120 DEG C, be preferably at least 140 DEG C.
The present invention also relates to a mixture, wherein include at least one according to compound of the present invention, and the organic functional material of at least one.Organic functional material can be selected from hole-injecting material (HIM) or hole mobile material (HTM) or electron-blocking materials (EBM), electron injection material (EIM) or electron transport material (ETM) or hole barrier materials (HBM), material of main part (Host), fluorescent illuminant or phosphorescent emitter, or their various combinations.
In a preferential embodiment, described mixture includes at least one according to compound of the present invention, and the organic luminophor of at least one, is wherein material of main part according to compound of the present invention.
In a more preferential embodiment, described mixture includes at least one according to compound of the present invention, and the phosphorescent emitter of at least one, is wherein phosphorescent light body material according to compound of the present invention.
In the embodiment that another is more preferential, described mixture includes at least one according to compound of the present invention, and the fluorescent illuminant of at least one, is wherein fluorescent host material according to compound of the present invention.
In certain embodiments, described mixture also includes high polymer material.All structures including the small molecule material of above or the following stated are herein all suitable materials as the high polymer material of repeating unit.In a preferential embodiment, composition in the present invention includes conjugated highpolymer, suitable conjugated highpolymer has polyfluorene (polyfluorene), poly-spiral shell-difluorene (poly (spiro-bifluorene)), poly-indenofluorene (polyindenofluorene), poly-(p-phenylene vinylene) (poly (p-phenylen-vinylene)), poly-(to phenylene) (poly (para-phenylene)), and derivative.
The invention still further relates to a kind of according to the application of compound of the present invention in organic electronic devices.
The invention still further relates to a composition, wherein include at least one according to compound of the present invention, at least one organic solvent.The example of organic solvent, includes, but is not limited to, methyl alcohol, ethanol, 2-methyl cellosolve, methylene dichloride, trichloromethane, chlorobenzene, orthodichlorobenzene, tetrahydrofuran (THF), methyl-phenoxide, morpholine, toluene, o-Xylol, m-xylene, p-Xylol, Isosorbide-5-Nitrae dioxane, acetone, methyl ethyl ketone, 1,2 ethylene dichloride, 3-phenoxytoluene, 1,1,1-trichloroethane, 1,1,2,2-tetrachloroethane, vinyl acetic monomer, N-BUTYL ACETATE, dimethyl formamide, N,N-DIMETHYLACETAMIDE, dimethyl sulfoxide (DMSO), naphthane, naphthalane, indenes and/or their mixture.
In a preferential embodiment, be a solution according to composition of the present invention.In another embodiment, be a suspension according to composition of the present invention.
Composition of the present invention can comprise 0.01 to 20wt%, preferably 0.1 to 15wt%, more preferably 0.2 to 10wt%, most preferably the organic functional material of 0.25 to 5wt%.Described percent data relates to solvent or the solvent mixture of 100%.
In a preferential embodiment, in described composition, organic solvent comprises the dimethylanisole of at least 60% weight.In the embodiment of some, in described composition, comprise the following Chinese gloomy (Hansen) solubility parameter: H according to compound of the present invention d17.0 to 20.0MPa 0.5, H p2 to 10.0MPa 0.5, H h0.0 to 15.0MPa 0.5, be more preferably H d17.5 to 19.0MPa 0.5, H p3.5 to 8.0MPa 0.5, H h3.0 to 10.0MPa 0.5.
In a preferential embodiment, comprise at least 3.0MPa according to compound of the present invention 0.5the solubleness radius determined according to the gloomy Hansen solubility parameter of the Chinese, be more preferably at least 4.5MPa 0.5, preferably at least 4.5MPa 0.5.
Hansen Solubility Parameter can be determined according to software and user manual thereof: Hansen Solubility Parameters in Practice HSPiP 3 rdedition, (Software version3.0.38) with reference to the Hansen Solubility Parameters:A User ' s Handbook, Second Edition, C.M.Hansen (2007), Taylor and Francis Group, LLC) as supplied by Hanson and Abbot et al.
In the embodiment of some, described composition its viscosity 25 DEG C time arrives 100mPas 1.0.
The invention still further relates to described composition as coating or printing-ink the purposes when preparing organic electronic devices, especially for print or coating preparation method, process.
The printing be applicable to or coating technique include, but is not limited to spray ink Printing, letterpress, silk screen printing, dip-coating, rotary coating, scraper for coating, roller printing, torsion roller printing, lithography, flexographic printing, rotary printing, spraying, brushes or bat printing, slit-type extruding type coating etc.It is preferred that both intaglio printing, silk screen printing and ink jet printing.Intaglio printing, ink jet printing will be applied in an embodiment of the present invention.Solution or suspension can comprise one or more component such as surface active cpd, lubricant, wetting agent, dispersion agent, hydrophobizing agent, caking agent etc. in addition, and for adjusting viscosity, film forming properties, improves tack etc.Relevant printing technique, and to the related request about solution, as solvent and concentration, viscosity etc., details refer to Helmut Kipphan edit " print media handbook: technology and production method " (Handbook of Print Media:Technologies and Production Methods), ISBN3-540-67326-1.
The invention further relates to an organic electronic devices, include one or more layers organic functional thin film, wherein have at least thin film to include according to compound of the present invention.
Suitable organic electronic devices includes but not limited to Organic Light Emitting Diode, organic light emission battery, organic photovoltaic battery, organic field-effect tube, organic light-emitting field effect pipe, organic sensor and organic phasmon emitting diode (Organic Plasmon Emitting Diode).Preferred organic electronic devices has Organic Light Emitting Diode, organic light emission battery.
In above-described organic luminescent device, comprise a substrate, an anode, at least one luminescent layer, a negative electrode.Substrate can be opaque or transparent.Transparent substrate can be used for the transparent emitting components of manufacture one.Such as can be see, the Nature1996 such as Bulovic, 380, p29, and Gu etc., Appl.Phys.Lett.1996,68, p2606.Base material can be rigidity or elastic.Substrate can be plastics, metal, semiconductor wafer or glass.Preferably substrate has a level and smooth surface.The substrate of free of surface defects is selection desirable especially.In a preferential embodiment, substrate is optional in polymeric film or plastics, and its second-order transition temperature Tg is more than 150 DEG C, is better above 200 DEG C, is more preferably more than 250 DEG C, preferably more than 300 DEG C.The example of suitable substrate has poly-(ethylene glycol terephthalate) (PET) and polyoxyethylene glycol (2,6-naphthalene) (PEN).
Anode can comprise a conducting metal or metal oxide, or conductive polymers.Anode can easily injected hole in HIL or HTL or luminescent layer.In the embodiment of, inorganic semiconductor twinkler or be less than 0.5eV as the absolute value of the HOMO energy level of the p-type semiconductor material of HIL or HTL or EBL or the difference of valence-band level in the work function of anode and luminescent layer, be better be less than 0.3eV, be preferably less than 0.2eV.The example of anode material includes but not limited to, Al, Cu, Au, Ag, Mg, Fe, Co, Ni, Mn, Pd, Pt, ITO, aluminium-doped zinc oxide (AZO) etc.Other suitable anode materials are known, and those of ordinary skill in the art can easily choice for use.Anode material can use any suitable deposition techniques, as a suitable physical vaporous deposition, comprises rf magnetron sputtering, vacuum thermal evaporation, electron beam (e-beam) etc.
In certain embodiments, anode is patterning.The ITO electrically-conductive backing plate of patterning can commercially have been bought, and can be used for preparation according to device of the present invention.
Negative electrode can comprise a conducting metal or metal oxide.Negative electrode easily can inject electronics to EIL or ETL or directly to luminescent layer.In the embodiment of, inorganic semiconductor twinkler or be less than 0.5eV as the absolute value of the lumo energy of the n-type semiconductor of EIL or ETL or HBL or the difference of conduction level in the work function of negative electrode and luminescent layer, be better be less than 0.3eV, be preferably less than 0.2eV.In principle, all materials that can be used as the negative electrode of OLED all may as the cathode material of device of the present invention.The example of cathode material includes but not limited to, Al, Au, Ag, Ca, Ba, Mg, LiF/Al, MgAg alloy, BaF 2/ Al, Cu, Fe, Co, Ni, Mn, Pd, Pt, ITO etc.Cathode material can use any suitable deposition techniques, as a suitable physical vaporous deposition, comprises rf magnetron sputtering, vacuum thermal evaporation, electron beam (e-beam) etc.
In a preferential embodiment, according in luminescent device of the present invention, its luminescent layer is prepared from by printing note inventive composition.
The invention still further relates to according to luminescent device of the present invention application in electronic equipment of various, include, but not limited to display equipment, set lights, light source, sensor etc.
The invention still further relates to the electronics included according to luminescent device of the present invention, include, but not limited to display equipment, set lights, light source, sensor etc.
Some more detailed descriptions (but being not limited thereto) are done to organic functional material below.In principle, all organic functional materials for OLEDs, comprise hole (also claiming electric hole) to inject or transport material (HIM/HTM), hole barrier materials (HBM), electron injection or transport material (EIM/ETM), electron-blocking materials (EBM), organic host materials (Host), singlet emitters (fluorescent illuminant), heavy state twinkler (phosphorescent emitter), particularly luminescent organometallic complex compound, dyestuff (Dye), in luminescent device all used in the present invention.Such as in WO 2010135519 A1, US 20090134784 A1 and WO 2011110277 A1, various organic functional material is described later in detail, hereby the full content in this 3 patent document is incorporated to herein as a reference.
1.HIM/HTM
The suitable optional compound including following structural unit of organic HTM material: phthalocyanine (phthlocyanine), porphyrin (porphyrine), amine (amine), aromatic amine, biphenyl class triaryl amine (triarylamine), thiophene (thiophene), thiophthene (fused thiophene) is as two thienothiophenes (dithienothiophene) and thiophthene (dibenzothiphene), pyrroles (pyrrole), aniline (aniline), carbazole (carbazole), indolocarbazole (indolocarbazole), and their derivative.The suitable HTM of another position also comprises the polymkeric substance containing fluorohydrocarbon (fluorohydrocarbon); Polymkeric substance containing conductiving doping; Conductive polymers, as PEDOT/PSS; Self-assembly monomer, as the compound containing phosphonic acids and sliane derivative; Metal oxide, as MoOx; Metal complex, and cross-linking compounds etc.
The example that can be used as the fragrant amine derivative compounds of cyclophane of HIM or HTM includes, but is not limited to following general structure:
Each Ar 1to Ar 9can independently be selected from aromatic hydrocarbon ring compound, as benzene, biphenyl, triphenyl, benzo, naphthalene, anthracene, phenalene, luxuriant and rich with fragrance, fluorenes, pyrene, Qu ， perylene, Azulene, heteroaromatic compound, as dibenzothiophene, diphenylene-oxide, furans, thiophene, cumarone, thionaphthene, carbazole, pyrazoles, imidazoles, triazole, isoxzzole, thiazole, oxadiazoles, oxatriazole, dioxazole, thiadiazoles, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazines, oxathiazine, oxadiazine, indoles, benzoglyoxaline, indazole, indoxazine, benzoxazoles, benzisoxazole, benzothiazole, quinoline, isoquinoline 99.9, cinnoline, quinazoline, quinoxaline, naphthalene, phthalein, pteridine, xanthene, acridine, azophenlyene, thiodiphenylamine, Phenazoxine, dibenzoselenophene, benzoselenophene, benzofuropyridine, indolocarbazole, pyridylindole, pyrrolodipyridine, furodipyridine, benzothienopyridine, thienodipyridine, benzoselenophenopyridine and selenophenodipyridine, include the group of 2 to 10 ring structures, they can be aromatic hydrocarbon ring group or the aromatic heterocycle group of identical or different type, and directly or by least one following group link together each other, as Sauerstoffatom, nitrogen-atoms, sulphur atom, Siliciumatom, phosphorus atom, boron atom, chain structure unit and aliphatic cyclic group.Wherein, each Ar can be substituted further, and substituting group is chosen as hydrogen, alkyl, alkoxyl group, amino, alkene, alkynes, aralkyl, assorted alkyl, aryl and heteroaryl.
In one aspect, Ar 1to Ar 9independently can be selected from the group comprising following group:
Wherein, n is the integer of 1 to 20; X 1to X 8cH or N; Ar 1aryl or heteroaryl.
The other example of the fragrant amine derivative compounds of cyclophane can see US3567450, US4720432, US5061569, US3615404, and US5061569.
The example that can be used as the metal complex of HTM or HIM includes, but is not limited to following general structure:
M is a metal, has the nucleidic mass being greater than 40;
(Y 1-Y 2) be one or two tooth part, Y 1and Y 2independently selected from C, N, O, P, and S; L is an assistant ligand; M is an integer, and its value is from 1 to the maximum coordination number of this metal; M+n is the maximum coordination number of this metal.
In one embodiment, (Y 1-Y 2) be a 2-phenylpyridine derivative.
In another embodiment, (Y 1-Y 2) be a carbenes.
In another embodiment, M selects in Ir, Pt, Os, and Zn.
In yet another aspect, the HOMO of metal complex is greater than-5.5eV (relative to vacuum level).
The suitable example that can be used as HIM/HTM compound is listed in table below:
2.EIM/ETM
In principle, suitable N-shaped organic semiconductor material is optional in all EIM/ETM for OLEDs.The example of EIM/ETM material is not particularly limited, and any metal complex or organic compound all may be used as ETM, as long as they can transmission electronic.Preferential organic ETM material can be selected from three (oxine) aluminium (AlQ 3), azophenlyene (Phenazine), phenanthroline (Phenanthroline), anthracene (Anthracene), luxuriant and rich with fragrance (Phenanthrene), fluorenes (Fluorene), two fluorenes (Bifluorene), spiral shell two fluorenes (Spiro-bifluorene), to phenylacetylene (Phenylene-vinylene), triazine (triazine), triazole (triazole), imidazoles (imidazole), pyrene (Pyrene), perylene (Perylene), anti-indenofluorene (trans-Indenofluorene), along indeno (cis-Indenonfluorene), dibenzo-indenofluorene (Dibenzol-indenofluorene), indeno naphthalene (Indenonaphthalene), benzanthrene (benzanthracene) and their derivative.
On the other hand, the compound that can be used as EIM/ETM is the molecule at least comprising less than one group:
R 1optional in following group: hydrogen, alkyl, alkoxyl group, amino, alkene, alkynes, aralkyl, assorted alkyl, aryl and heteroaryl, when they be aryl or heteroaryl time, the Ar in they and above-mentioned HTM 1and Ar 2same meaning;
Ar 1-Ar 5with the Ar described in HTM 1same meaning;
N be one from 0 to 20 integer;
X 1-X 8select in CH or N, wherein have at least one to be N.
On the other hand, the example that can be used as the metal complex of EIM/ETM includes, but is not limited to following general structure:
(O-N) or (N-N) be one or two tooth part, wherein metal and O, N or N, N coordination; L is an assistant ligand; M is an integer, and its value is from 1 to the maximum coordination number of this metal.
In the embodiment that another is preferential, organic alkali metal compound can be used as EIM.In the present invention, organic alkali metal compound is appreciated that the compound dug as following, wherein has basic metal, i.e. a lithium at least, sodium, potassium, rubidium, caesium, and comprises at least one organic ligand further.
Suitable organic alkali metal compound, comprises US7767317B2, the compound described in EP1941562B1 and EP1144543B1.
The organic alkali metal compound of prioritizing selection is the compound of following chemical formula:
Wherein R 1implication described above, camber line represents two or three atoms and keyed jointing, so as if desired form 5 yuan or six-ring with metal M, its Atom also can by one or more R 1replace, M is basic metal, is selected from lithium, sodium, potassium, rubidium, caesium.
Organic alkali metal compound can have the form of monomer, as previously discussed, or has the form of aggregate, such as, and two alkalimetal ions and two parts, 4 alkalimetal ions and 4 parts, 6 alkalimetal ions and 6 parts or the form at other.
The organic alkali metal compound of special prioritizing selection is the compound of following chemical formula:
The symbol wherein used is identical with aforementioned definitions, in addition: M is alkali metal
O, can be identical or different when occurring, be 0,1,2,3 or 4 at every turn;
P, can be identical or different when occurring, be 0,1,2 or 3 at every turn;
In a preferential embodiment, basic metal M is selected from lithium, sodium, potassium, is more preferably lithium or sodium, preferably lithium.
In a preferential embodiment, in organic alkali metal compound electron injecting layer. better, electron injecting layer is made up of organic alkali metal compound.
In the embodiment that another is preferential, organic alkali metal compound is doped in other ETM and is formed in electron transfer layer or electron injecting layer. and better, be electron transfer layer.
The example of suitable organic alkali metal compound is listed in table below:
3. triplet state substrate material (Triplet Host):
The example of triplet state substrate material is not particularly limited, and any metal complex or organic compound all may be used as matrix, as long as its triplet energies is than twinkler, particularly triplet emitters or phosphorescent emitter higher.
The example that can be used as the metal complex of triplet state matrix (Host) includes, but is not limited to following general structure:
M is a metal; (Y 3-Y 4) be one or two tooth part, Y 3and Y 4independently selected from C, N, O, P, and S; L is an assistant ligand; M is an integer, and its value is from 1 to the maximum coordination number of this metal; M+n is the maximum coordination number of this metal.
In a preferential embodiment, the metal complex that can be used as triplet state matrix has following form:
(O-N) be one or two tooth part, wherein metal and O and atom N coordination.
In some embodiments, M is optional in Ir and Pt.
The example that can be used as the organic compound of triplet state matrix is selected from the compound including aromatic hydrocarbon ring base, hinders as benzene, biphenyl, triphenyl, benzo, fluorenes, test, include the compound of fragrant heterocyclic radical, as dibenzothiophene, diphenylene-oxide, dibenzoselenophene, furans, thiophene, cumarone, thionaphthene, benzoselenophene, carbazole, indolocarbazole, pyridylindole, pyrrolodipyridine, pyrazoles, imidazoles, triazole species, oxazole, thiazole, oxadiazoles, oxatriazole, dioxazole, thiadiazoles, pyridine, pyridazine, pyrimidine, pyrazine, triazines, oxazines, oxathiazines, oxadiazines, indoles, benzoglyoxaline, indazole, indoxazine, bisbenzoxazoles, benzisoxazole, benzothiazole, quinoline, isoquinoline 99.9, cinnoline, quinazoline, quinoxaline, naphthalene, phthalein, pteridine, xanthene, acridine, azophenlyene, thiodiphenylamine, phenoxazines, benzofuropyridine, furodipyridine, benzothienopyridine, thienodipyridine, benzoselenophenopyridine and selenophenodipyridine, include the group of 2 to 10 ring structures, they can be aromatic hydrocarbon ring group or the aromatic heterocycle group of identical or different type, and directly or by least one following group link together each other, as Sauerstoffatom, nitrogen-atoms, sulphur atom, Siliciumatom, phosphorus atom, boron atom, chain structure unit and aliphatic cyclic group.Wherein, each Ar can be substituted further, and substituting group is chosen as hydrogen, alkyl, alkoxyl group, amino, alkene, alkynes, aralkyl, assorted alkyl, aryl and heteroaryl.
In a preferential embodiment, triplet state substrate material is optional in the compound comprising at least one following group:
Ar 1, Ar 2and Ar 3with the Ar in above-mentioned HIM/HTM 1and Ar 2same meaning, R 1-R 7can select independently of each other in following group: hydrogen, alkyl, alkoxyl group, amino, alkene, alkynes, aralkyl, assorted alkyl, aryl and heteroaryl, when they be aryl or heteroaryl time, the Ar in they and above-mentioned HIM/HTM 1and Ar 2same meaning;
N be one from 0 to 20 integer; X 1-X 8select in CH or N; X 9select in CR 1r 2or NR 1.
4. singlet state substrate material (Singlet Host):
The example of singlet state substrate material is not particularly limited, and any organic compound all may be used as matrix, as long as its singlet energy is than twinkler, particularly singlet emitters or fluorescent illuminant higher.
Example as the organic compound of singlet state substrate material use is optional from containing aromatic hydrocarbon ring compound, as benzene, and biphenyl, triphenyl, benzo, naphthalene, anthracene, phenalene, luxuriant and rich with fragrance, fluorenes, pyrene, bends, perylene, Azulene, heteroaromatic compound, as dibenzothiophene, diphenylene-oxide, dibenzoselenophene, furans, thiophene, cumarone, thionaphthene, benzoselenophene, carbazole, indolocarbazole, pyridylindole, Pyrrolodipyridine, pyrazoles, imidazoles, triazole, isoxzzole, thiazole, oxadiazoles, oxatriazole, dioxazole, thiadiazoles, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazines, oxathiazine, oxadiazine, indoles, benzoglyoxaline, indazole, indoxazine, benzoxazoles, benzisoxazole, benzothiazole, quinoline, isoquinoline 99.9, cinnoline, quinazoline, quinoxaline, naphthalene, phthalein, pteridine, xanthene, acridine, azophenlyene, thiodiphenylamine, Phenazoxine, benzofuropyridine, furodipyridine, benzothienopyridine, thienodipyridine, benzoselenophenopyridine and selenophenodipyridine, include the group of 2 to 10 ring structures, they can be aromatic hydrocarbon ring group or the aromatic heterocycle group of identical or different type, and directly or by least one following group link together each other, as Sauerstoffatom, nitrogen-atoms, sulphur atom, Siliciumatom, phosphorus atom, boron atom, chain structure unit and aliphatic cyclic group.
In a preferential embodiment, singlet state substrate material is optional in the compound comprising at least one following group:
Ar 1ar in describing with above-mentioned HIM/HTM 1and Ar 2same meaning, R 1-R 7can select independently of each other in following group: hydrogen, alkyl, alkoxyl group, amino, alkene, alkynes, aralkyl, assorted alkyl, aryl and heteroaryl, when they be aryl or heteroaryl time, the Ar during they and above-mentioned HIM/HTM describe 1and Ar 2same meaning;
N be one from 0 to 20 integer; X 1-X 8select in CH or N; X 9, X 10select in CR 1r 2or NR 1.
5. hole barrier materials (HBM)
Hole blocking layer (HBL) is commonly used to stop from successive functional layers, the particularly hole of luminescent layer.Contrast the OLED that does not have blocking layer, the existence of HBL can cause the raising of luminous efficiency usually.The hole barrier materials (HBM) of hole blocking layer (HBL) needs and compares successive functional layers, HOMO. as lower in luminescent layer is in a preferential embodiment, HBM has the excited level larger than adjacent emissive layers, as singlet state or triplet state, depend on twinkler. in the embodiment that another is preferential, HBM has electric transmission function.
In the embodiment of, contain the molecule identical with luminescent layer mesostroma material as HBM.
In the embodiment that another is preferential, HBM is optional in the compound comprising at least one following group:
Wherein, n be one from 0 to 20 integer; L is an assistant ligand; M be one from 1 to 3 integer.
6. singlet emitters (Singlet Emitter)
Singlet emitters often has longer conjugated pi electron system.So far, existing many examples, such as styrylamine (styrylamine) and derivative thereof disclosed in JP2913116B and WO2001021729A1, and disclosed in WO2008/006449 and WO2007/140847 indenofluorene (indenofluorene) and derivative thereof.
In a preferential embodiment, singlet emitters can be selected from unitary styrylamine (monostyrylamines), binary styrylamine (distyrylamines), ternary styrylamine (tristyrylamines), quaternary styrylamine (tetrastyrylamines), vinylbenzene phosphine (styrylphosphines), vinylbenzene ether (styryl ethers) and arylamine (arylamines).
A unitary styrylamine refers to a compound, and it comprises one without the styryl group replaced or replace and at least one amine, preferably aromatic amine.A binary styrylamine refers to a compound, and it comprises two without the styryl group replaced or replace and at least one amine, preferably aromatic amine.A ternary styrylamine refers to a compound, and it comprises three without the styryl group replaced or replace and at least one amine, preferably aromatic amine.A quaternary styrylamine refers to a compound, and it comprises four without the styryl group replaced or replace and at least one amine, preferably aromatic amine.A preferred vinylbenzene is toluylene, and it may be substituted further.Corresponding phosphine class is similar to amine with the definition of ethers.Arylamines or aromatic amine refer to a kind of compound, the aromatic nucleus that the nothing comprising three direct connection nitrogen replaces or replaces or heterocyclic ring system.Have at least one preferentially to select in carbocyclic fused ring system in the loop systems of these aromatic series or heterocycle, and preferably have at least 14 aromatic ring atoms.Wherein preferred example has fragrant anthranylamine, fragrant anthradiamine, fragrant pyrene amine, fragrant pyrene diamines, and fragrance bends amine and fragrance bends diamines.A fragrant anthranylamine refers to a compound, and one of them binary arylamines group (diarylamino) is directly linked on anthracene, preferably on the position of 9.A fragrant anthradiamine refers to a compound, and wherein two binary arylamines groups (diarylamino) are directly linked on anthracene, preferably 9, on the position of 10.Fragrance pyrene amine, fragrant pyrene diamines, the definition that fragrance amine in the wrong and fragrance bend diamines is similar, and wherein binary arylamines group is preferably linked to 1 or 1 of pyrene, on 6 positions.
Based on the example of the singlet emitters of vinyl-amine and arylamine, also be preferred example, can find in following patent document: WO 2006/000388, WO 2006/058737, WO 2006/000389, WO 2007/065549, WO 2007/115610, US 7250532 B2, DE 102005058557 A1, CN 1583691 A, JP 08053397 A, the full content of US 6251531 B1, US 2006/210830 A, EP 1957606 A1 and US 2008/0113101 A1 hereby in the above-mentioned patent document listed is incorporated to herein as a reference.
Example based on stibene (distyrylbenzene) the extremely singlet emitters of derivative has US5121029.
Further preferred singlet emitters is optional in indenofluorene-amine and indenofluorene-diamines, disclosed in WO 2006/122630, benzo indenofluorene-amine (benzoindenofluorene-amine) and benzo indenofluorene-diamines (benzoindenofluorene-diamine), disclosed in WO 2008/006449, dibenzo indenofluorene-amine (dibenzoindenofluorene-amine) and dibenzo indenofluorene-diamines (dibenzoindenofluorene-diamine), disclosed in WO 2007/140847.
Other materials that can be used as singlet emitters have polycyclic aromatic hydrocarbon compounds, the particularly derivative of following compound: anthracene is as 9, 10-bis-(2-naphthanthracene) (9, 10-di (2-naphthylanthracene)), naphthalene, four benzene, xanthene, luxuriant and rich with fragrance (phenanthrene), pyrene (perylene) is as 2, 5, 8, 11-tetra-t-butylperylene, indeno pyrene (indenoperylene), penylene (phenylenes) is as (4, 4 '-(bis (9-ethyl-3-carbazovinylene)-1, 1 '-biphenyl), periflanthene, decacyclene (decacyclene), coronene (coronene), fluorenes, spiral shell two fluorenes (spirofluorene), aryl pyrene (arylpyrene) (as US20060222886), arylene ethene (arylenevinylene) is (as US5121029, US5130603), cyclopentadiene is as tetraphenyl cyclopentadiene (tetraphenylcyclopentadiene), rubrene (rubrene), tonka bean camphor (coumarine), rhodamine (rhodamine), quinacridone (quinacridone), pyrans (pyrane) is as 4 (dicyanoethylene)-6-(4-dimethylaminostyryl-2-methyl)-4H-pyrane (DCM), thiapyran (thiapyran), bis (azinyl) imine-boron compound (US 2007/0092753 A1), bis (azinyl) methene compound, carbostyryl compound, oxazinone (oxazone), benzoxazoles (benzoxazole), benzothiazole (benzothiazole), benzoglyoxaline (benzimidazole) and diketopyrrolopyrrole.The material of some singlet emitters can find in following patent document: US 20070252517 A1, US 4769292, US 6020078, US 2007/0252517 A1, US 2007/0252517 A1.Hereby the full content in the above-mentioned patent document listed is incorporated to herein as a reference.
7. triplet emitters (Triplet Emitter)
Triplet emitters also claims phosphorescent emitter.In a preferential embodiment, triplet emitters is the metal complex having formula M (L) n, and wherein M is an atoms metal, can be identical or different when L occurs at every turn, it is an organic ligand, it is connected on atoms metal M by one or more positions keyed jointing or coordination, and n is an integer being greater than 1, and better choosing is 1,2,3,4,5 or 6.Alternatively, these metal complexs are connected on a polymkeric substance, preferably by organic ligand by one or more position.
In a preferential embodiment, atoms metal M selects in transition metal or lanthanon or actinide elements, prioritizing selection Ir, Pt, Pd, Au, Rh, Ru, Os, Sm, Eu, Gd, Tb, Dy, Re, Cu or Ag, special prioritizing selection Os, Ir, Ru, Rh, Re, Pd, Pt.
Preferentially, triplet emitters includes chelating ligand, i.e. part, and by least two basic change point and metal-complexing, what give special priority for is that triplet emitters includes two or three identical or different bidentate or polydentate ligands.Chelating ligand is conducive to the stability improving metal complex.
The example of organic ligand can be selected from phenylpyridine (phenylpyridine) derivative, 7,8-benzoquinoline (7,8-benzoquinoline) derivative, 2 (2-thienyl) pyridine (2 (2-thienyl) pyridine) derivative, 2 (1-naphthyl) pyridine (2 (1-naphthyl) pyridine) derivative, or 2 phenylquinolines (2phenylquinoline) derivative.All these organic ligands all may be substituted, such as, replaced by fluorine-containing or trifluoromethyl.Assistant ligand preferentially can be selected from acetic acid acetone (acetylacetonate) or picric acid.
In a preferential embodiment, the metal complex that can be used as triplet emitters has following form:
Wherein M is a metal, selects in transition metal or lanthanon or actinide elements;
Ar 1can be identical or different at every turn when occurring, be a cyclic group, wherein at least include a donor atom, namely have the atom of lone-pair electron, as nitrogen or phosphorus, be connected with metal-complexing by its cyclic group; Ar 2can be identical or different at every turn when occurring, be a cyclic group, wherein at least include a C atom, be connected with metal by its cyclic group; Ar 1and Ar 2be connected together by covalent bond, can carry one or more substituted radical separately, they also can be linked together by substituted radical again; Can be identical or different at every turn when L occurs, be an assistant ligand, be preferable over double-tooth chelate ligand, preferably monoanionic, bidentate chelating ligand; M is 1,2 or 3, is preferentially 2 or 3, is especially preferentially 3; N is 0,1, or 2, being preferentially 0 or 1, is especially preferentially 0.
The example of phosphorescent emitter or triplet emitters has, but is not limited to:
The example that the material of some triplet emitters is extremely applied can find in following patent document and document: WO 200070655, WO 200141512, WO 200202714, WO 200215645, EP 1191613, EP 1191612, EP 1191614, WO 2005033244, WO 2005019373, US 2005/0258742, WO 2009146770, WO 2010015307, WO 2010031485, WO 2010054731, WO 2010054728, WO 2010086089, WO 2010099852, WO 2010102709, US 20070087219 A1, US 20090061681 A1, US 20010053462 A1, Baldo, Thompson et al.Nature 403, (2000), 750-753, US 20090061681 A1, US 20090061681 A1, Adachi et al.Appl.Phys.Lett.78 (2001), 1622-1624, J.Kido et al.Appl.Phys.Lett.65 (1994), 2124, Kido et al.Chem.Lett.657, 1990, US 2007/0252517 A1, Johnson et al., JACS 105, 1983, 1795, Wrighton, JACS 96, 1974, 998, Ma et al., Synth.Metals 94, 1998, 245, US 6824895, US 7029766, US 6835469, US 6830828, US 20010053462 A1, WO 2007095118 A1, US 2012004407 A1, WO 2012007088 A1, WO 2012007087 A1, WO 2012007086 A1, US 2008027220 A1, WO 2011157339 A1, CN 102282150 A, WO 2009118087 A1.Hereby the full content in the above-mentioned patent document listed and document is incorporated to herein as a reference.
8. dyestuff (Dye)
In principle, all for organic photovoltaic battery, comprise DSSC, organic functions dyestuff, in electron device all used in the present invention.Suitable dyestuff is selected from the multi-pyridine ligand of transition metal, preferred ruthenium, osmium, the metal complex dyes of copper.In a preferred embodiment, the general structure ML2 (X) 2 of metal complex dyes, wherein L is preferentially selected from 2, in 2'-dipyridyl-4,4'-dicarboxylic acid, M is transition metal, excellent dyestuff is selected from Ru, Os, Fe, V and Cu, X is selected from halogenide, prussiate, thiocyanate-, acetylacetonate compound, the substituting group of thiocarbamate or water.These metallized dyes are disclosed The Journal of Physical Chemistry C 2009,113,2966-2973 in the following literature, US2009000658, WO2009107100, WO2009098643, US6245988, WO2010055471, JP2010084003, EP1622178, WO9850393, WO9529924, WO9404497, WO9214741, WO9116719.Hereby the full content in the above-mentioned patent document listed and document is incorporated to herein as a reference.
Describe the present invention below in conjunction with preferred embodiment, but the present invention is not limited to following embodiment, be to be understood that, claims it should be appreciated by one skilled in the art that under summarising the guiding that scope of the present invention conceives in the present invention, to certain change that various embodiments of the present invention are carried out, all by cover by the spirit and scope of claims of the present invention.
Embodiment
1. compou nd synthesis
Compound 1-4 is reference compound, and their synthesis can referenced patent application WO2011137922A1.1a-4a is according to compound of the present invention, and their synthesis can in conjunction with patent application WO2011137922A1 and WO2005068583A1.
2. solubleness
The solubleness of compound 1-4 in toluene is very little, and the solubleness of compound 1a-4a in toluene has very large raising, all at more than 15mg/ml.
The preparation of 3.OLEDs and measurement
The solvability that compound 3a goes with 4a makes from solution, prepare OLED becomes possibility.Other materials for the preparation of OLED are as follows.
TFB (poly [(9,9-dioctylfluorenyl-2,7-diyl)-co-(4,4'-(N-(4-sec-butylphenyl)) diphenylamine)], H.W.Sands Corp) be a kind of organic hole transport material, the method synthesis that it also can be known in document, as disclosed in the patent application of WO99/54385.
PEDOT:PSS (Clevios P VP AI4083, Hereaus AG, Germany) is as HIM.
Twinkler 1 is blue phosphor twinkler, and it synthesizes see WO2008006449,
OLED1-2 has following structure:
OLED1:ITO(50nm)/PEDOT(80nm)/TFB(20nm)/2a:3a(15wt％)(80nm)/Ba(2nm)Al(100nm)
OLED2:ITO(50nm)/PEDOT(80nm)/TFB(20nm)/4a:Emitter1(5wt％)(60nm)/Ba(2nm)Al(100nm)
OLED1-2 follows these steps to preparation:
1. substrate prepares: the ITO conductive glass substrate of patterning uses all kinds of SOLVENTS (chloroform → acetone → Virahol) to clean first, then carries out UV ozone plasma treatment.
Rotary coating is at ITO conductive glass substrate in atmosphere in clean room for 2.HIL:PEDOT:PSS (Clevios P VP AI4083), and obtaining thickness is 80nm.Then at 120 DEG C, unwatering in 10 minutes is toasted in atmosphere.
TFB, as hole transmission layer, is first dissolved in toluene with the concentration of 0.5wt% by 3.HTL:TFB, this solution rotary coating in nitrogen glove box on PEDOT:PSS film, is then annealed 60 minutes at 180 DEG C.The thickness obtaining TFB is 10-20nm.
4.EML: be dissolved in toluene according to corresponding ratio by material of main part and twinkler, the concentration of solution is 24mg/ml, solution rotary coating in nitrogen glove box on TFB film, is then annealed 10 minutes at 180 DEG C.
5. negative electrode: all negative electrodes are all 10 -7in the vacuum atmosphere of Torr, by the method for vacuum thermal evaporation, and by use metal mask, deposition forms.
6. encapsulate: all devices in nitrogen glove box with the in addition glass cover-plate encapsulation of a kind of ultraviolet hardening resin.
Current/voltage (I-V) characteristic of LED carrys out record by computer-controlled (Keithley 2400 source measurement unit) and (Keithley 2000 multimeter), simultaneously, brightness is measured by using the silicon photoelectric diode (Newport 2112) calibrated.Electroluminescent spectrum is measured by spectrograph (Ocean Optics USB2000).The performance of OLED1-2 is summarised in table 1 below, and wherein EQE (External Quantum Efficiency) represents external quantum efficiency.
Table 1
Device Ignition voltage (V) Maximum EQE (%)
OLED1 2.92 10.0％
OLED2 3.00 4.0％

Claims (10)

1. the compound according to following general formula 1:
Wherein: A is an organic functions structural unit, and n is the integer from 1 to 10, and SLG is solubilising structural unit, SLG at least includes an electroneutral inorganic planar ring, and described inorganic planar ring includes 4m+2 π-electronics, and wherein m is the integer of 1 to 6.
2. compound according to claim 1, the SLG wherein narrated can be selected from following general formula:
Wherein
Ar 1, Ar 2be independently from each other aryl or heteroaryl groups separately, described group can be replaced by the group of one or more any type;
R 1, R 2hydrogen independently of one another separately; there is the straight chained alkyl of 1 to 20 C atom, alkoxyl group or thio alkoxy group; or there is the alkyl of the side chain of 3 to 20 C atoms or ring-type, alkoxyl group or thio alkoxy group or silyl-group; or there is the keto group of replacement of 1 to 20 C atom; there is the alkoxycarbonyl groups of 2 to 20 C atoms; there is the aryloxycarbonyl group of 7 to 20 C atoms; cyano group (-CN), carbamoyl group (-C (=O) NH 2); halogen formyl group (-C (=O)-X wherein X represents halogen atom); formyl group (-C (=O)-H); isocyano-group; isocyanate groups; thiocyanic ester group or lsothiocyanates group, oh group, nitryl group; CF3 group; Cl, Br, F; crosslinkable group or there is substituted or unsubstituted aromatics or the heteroaromatic ring system of 5 to 40 annular atomses; or there is aryloxy or the heteroaryloxy group of 5 to 40 annular atomses, or the combination of these systems, wherein one or more radicals R 1, R 2can each other and/or with described radicals R 1the ring of bonding forms aliphatic series or the aromatics ring system of monocycle or many rings; And
M is 0,1,2,3 or 4;
Wherein said dotted line key represents the key with functional architecture unit A bonding.
3., according to the one or more described compound in claim 1-2, wherein solubilising structural unit SLG can independently be selected from following general formula:
Wherein
R 1, R 2and m is as defined in claim 1,
O, p are 0,1,2,3,4 or 5 separately independently of one another, and
Wherein said dotted line key represents the key with functional architecture unit A bonding.
4., according to the one or more described compound in claim 1-3, its molecular weight is at least 800g/mol.
5. according to the one or more described compound in claim 1-4, wherein said organic functions structural unit A is selected from hole and injects or transport material (HIM/HTM), hole barrier materials (HBM), electron injection or transport material (EIM/ETM), electron-blocking materials (EBM), organic host materials (Host), singlet emitters (fluorescent illuminant), triplet emitters (phosphorescent emitter), particularly luminescent organometallic complex compound, the corresponding structural units of functional materials such as thermal excitation delayed fluorescence material (TADF material) and dyestuff.
6. a mixture, includes at least one according to the one or more described compound in claim 1-5, and at least another kind of organic functional material.
7. a composition, includes at least one according to the one or more described compound in claim 1-5 or at least one according to the mixture described in claim 6, and at least one organic solvent.
8. according to the one or more described application of compound in organic electronic devices in claim 1-5, electron device comprises Organic Light Emitting Diode, organic light emission battery, organic photovoltaic battery, organic field-effect tube, organic light-emitting field effect pipe, organic sensor and organic phasmon emitting diode (Organic Plasmon Emitting Diode).
9. an organic electronic devices, at least includes a kind of according to the one or more described compound in claim 1-6.
10. organic electronic devices according to claim 9, optional from Organic Light Emitting Diode, organic light emission battery, organic photovoltaic battery, organic field-effect tube, organic light-emitting field effect pipe, organic sensor and organic phasmon emitting diode (Organic Plasmon Emitting Diode).
CN201410289149.6A 2013-07-07 2014-06-25 Compound containing solubilization structure unit and application of compound in electronic device Pending CN104277064A (en)

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