CN105778892B - Compound and its organic electroluminescence device based on fluorenes and indolyl radical - Google Patents

Compound and its organic electroluminescence device based on fluorenes and indolyl radical Download PDF

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CN105778892B
CN105778892B CN201610150542.6A CN201610150542A CN105778892B CN 105778892 B CN105778892 B CN 105778892B CN 201610150542 A CN201610150542 A CN 201610150542A CN 105778892 B CN105778892 B CN 105778892B
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electroluminescence device
fluorenes
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CN105778892A (en
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黄锦海
苏建华
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Shanghai Taoe Chemical Technology Co Ltd
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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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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
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    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
    • C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
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    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
    • C07D209/88—Carbazoles; Hydrogenated carbazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
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    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
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    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
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    • 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
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    • C09K2211/1025—Heterocyclic compounds characterised by ligands
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Abstract

The present invention provides a kind of organic electroluminescent compounds based on fluorenes and indolyl radical, the compound has preferable heat endurance, high-luminous-efficiency, high luminance purity, low driving voltage, it can be used for making organic electroluminescence device, applied to organic solar batteries, perovskite battery, Organic Thin Film Transistors or organophotoreceptorswith field.Present invention also offers a kind of organic electroluminescence device, it includes anode, cathode and organic layer, organic layer includes at least one layer in luminescent layer, hole injection layer, hole transmission layer, exciton barrier-layer, electron transfer layer, and at least one layer includes the compound just like structural formula I in organic layer.

Description

Compound and its organic electroluminescence device based on fluorenes and indolyl radical
Technical field
The present invention relates to field of organic electroluminescent materials, and in particular to a kind of organic electroluminescence based on fluorenes and indolyl radical Luminophor and its organic electroluminescence device, belong to organic electroluminescence device display technology field.
Background technology
Organic electroluminescence device (OLEDs) is by spin coating or vacuum evaporation deposition one between two metal electrodes The device that layer organic material is prepared, a classical three layer organic electroluminescence device include hole transmission layer, luminescent layer And electron transfer layer.The electronics produced by cathode is followed to be incorporated in through electron transfer layer through hole transmission layer by the hole that anode produces Luminescent layer forms exciton, then shines.Organic electroluminescence device can be adjusted as desired by the material for changing luminescent layer Section launches the light of various needs.
Organic electroluminescence device has self-luminous, wide viewing angle, low energy consumption, efficiency as a kind of new Display Technique High, thin, rich in color, fast response time, Applicable temperature scope are wide, low driving voltage, can make flexible with it is transparent Display panel and the particular advantages such as environmental-friendly, can apply on flat-panel monitor and a new generation's illumination, can also conduct The backlight of LCD.
Since the invention at the bottom of the 1980s, organic electroluminescence device has industrially been applied, such as As screens such as camera and mobile phones, but current OLED device, since efficiency is low, it is wider that the factors such as service life is short restrict it General application, particularly large screen display, it is therefore desirable to improve the efficiency of device.And restrict one of key factor just It is the performance of the electroluminescent organic material in organic electroluminescence device.It is voltage-operated in application additionally, due to OLED device When, Joule heat can be produced so that organic material easily crystallizes, and have impact on service life and the efficiency of device, therefore, it is also desirable to Develop the electroluminescent organic material of stability and high efficiency.
In organic electroluminescence device, the introducing of hole mobile material and injection material, can be effectively reduced positive electricity Lotus is transferred to the ability of luminescent layer from cathode, improves efficiency and the thermostabilization of device.Traditional hole-injecting material, such as copper Phthalocyanine (CuPc), degraded is slow, prepares energy consumption height, is unfavorable for environmental protection, and it can absorb light, influence device Efficiency.Hole mobile material original NPB etc., heat endurance is poor, also largely influences device lifetime.Thus, need Develop the electroluminescent organic material of efficient stable.
The content of the invention
Present invention firstly provides a kind of organic electroluminescent compounds based on fluorenes and indolyl radical, it is with following knot The compound of structure Formulas I：
Wherein, Ar is selected from triaromatic amine base, 9- aryl carbazoles and carbazyl.
Preferably, the aryl is selected from phenyl, xenyl, naphthyl, anthryl, phenanthryl, pyrenyl, base, fluoranthene base, (9,9- Dialkyl group) fluorenyl, (bis- substituted or unsubstituted aryl of 9,9-) fluorenyl, 9,9- be Spirofluorene-based, dibenzothiophene, dibenzofurans Base, or the alkyl-substituted above aryl by C1-C12.
It is further preferred that the organic electroluminescent compounds based on fluorenes and indolyl radical of the present invention are following structural The compound of 1-32：
A kind of organic electroluminescent compounds based on fluorenes and indolyl radical of the present invention can pass through Buchwald- Hartwig reacts and ullmann reaction is prepared.
A kind of organic electroluminescent compounds based on fluorenes and indolyl radical of the present invention can be applied to be sent out in organic electroluminescence Optical device, organic solar batteries, perovskite battery, Organic Thin Film Transistors or organophotoreceptorswith field.
Present invention also offers a kind of organic electroluminescence device, which includes anode, cathode and organic layer, organic layer Comprising at least one layer in luminescent layer, hole injection layer, hole transmission layer, exciton barrier-layer, electron transfer layer, wherein described have Contain the organic electroluminescent compounds as described in structural formula I at least one layer in machine layer：
Wherein Ar is defined as described above.
Wherein organic layer is hole transmission layer and luminescent layer；
Or organic layer is hole injection layer, hole transmission layer, luminescent layer and electron transfer layer；
Or organic layer is hole injection layer, hole transmission layer, luminescent layer, electron transfer layer and electron injecting layer；
Or organic layer is hole injection layer, hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer and exciton Barrier layer；
Or organic layer is hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer and exciton barrier-layer；
Or organic layer is hole transmission layer, luminescent layer, electron injecting layer and exciton barrier-layer.
Preferably, as described in structural formula I it is sky based on layer where the organic electroluminescent compounds of fluorenes and indolyl radical Cave transport layer.
Preferably, the organic electroluminescent compounds based on fluorenes and indolyl radical as described in structural formula I are structural formula 1- 32 compound.
The organic electroluminescent compounds based on fluorenes and indolyl radical as described in structural formula I are prepared for luminescent device When, it can be used alone, can also be used in mixed way with other compounds；As described in structural formula I based on fluorenes and indolyl radical Organic electroluminescent compounds can be used alone a kind of compound therein, can also use two kinds in structural formula I at the same time Compound above.
The organic electroluminescence device of the present invention, further preferred mode are that the organic electroluminescence device includes sun Pole, hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer and cathode, contain structural formula I in its hole-transporting layer Compound；It is further preferred that the compound containing structural formula 1-32 in hole transmission layer.
The gross thickness of the organic electroluminescence device organic layer of the present invention is 1-1000nm, preferably 50-500nm.
The film thickness of the organic electroluminescence device luminescent layer of the present invention is preferably 10-50nm.
When having the compound of structural formula I using the present invention, can arrange in pairs or groups makes the organic electroluminescence device of the present invention With other materials, such as in hole injection layer, hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer and exciton barrier-layer It is medium, and obtain blue and green light, yellow light, feux rouges or white light.
The hole transmission layer and hole injection layer of organic electroluminescence device of the present invention, material requested have good hole Transmission performance, can effectively be transferred to hole on luminescent layer from anode.There is compound described in structural formula I except above-mentioned Outside, other small molecules and macromolecular organic compound can be included, include but not limited to carbazole compound, triaromatic amine chemical combination Thing, benzidine compound, compound of fluorene class, phthalocyanine-like compound, six cyano group, six miscellaneous triphen (hexanitrilehexaazatriphenylene), tetra- cyanogen dimethyl-parabenzoquinone (F4- of tetra- fluoro- 7,7' of 2,3,5,6-, 8,8'- TCNQ), polyvinyl carbazole, polythiophene, polyethylene or polyphenyl sulfonic acid.
The luminescent layer of the organic electroluminescence device of the present invention, has the good characteristics of luminescence, can adjust as needed The scope of visible ray.The compound of the present invention can be used as main body luminescent material, can also contain following compound, including still It is not limited to naphthalene compounds, pyrene compound, compound of fluorene class, luxuriant and rich with fragrance class compound, class compound in the wrong, glimmering anthracene compound, anthracene Class compound, pentacene class compound, class compound, two aromatic ethylene class compounds, triphenylamine ethylene compounds, amine Compound, carbazole compound, benzimidazoles compound, furfuran compound, metal organic fluorescence complex compound, metal organophosphor Light complex compound (such as Ir, Pt, Os, Cu, Au), polyvinylcarbazole, poly-organosilicon compound, polythiophene organic macromolecular LED material Material, they can be used alone, can also a variety of mixtures uses.
The Organic Electron Transport Material of organic electroluminescence device of the present invention requires good electronic transmission performance, energy It is enough effectively electronics from cathode transport to luminescent layer in, there is very big electron mobility.Following compound can be selected, but It is not limited to this：Oxa- oxazole, thiazole compound, triazole compound, three nitrogen piperazine class compounds, triazine class chemical combination Thing, quinoline class compound, phenodiazine anthracene compound, siliceous heterocycle compound, quinolines, ferrosin class compound, Metallo-chelate (such as Alq3), fluorine substituted benzene compound, benzimidazoles compound.
Electronics, effectively can be injected into organic layer by the electron injecting layer of organic electroluminescence device of the present invention from cathode In, it is mainly selected from the alkali metal either compound of alkali metal or compound or alkali selected from alkaline-earth metal or alkaline-earth metal Metal complex, can select following compound, but not limited to this：Alkali metal, alkaline-earth metal, rare earth metal, alkali metal Oxide either halide, the oxide of alkaline-earth metal or halide, the oxide of rare earth metal or halide, alkali metal Or the organic complex of alkaline-earth metal；Preferably lithium, lithium fluoride, lithia, lithium nitride, 8-hydroxyquinoline lithium, caesium, carbonic acid Caesium, 8-hydroxyquinoline caesium, calcium, calcirm-fluoride, calcium oxide, magnesium, magnesium fluoride, magnesium carbonate, magnesia, these compounds can individually make With can also mixture use, can also be used cooperatively with other electroluminescent organic materials.
Each layer of organic layer in the organic electroluminescence device of the present invention, can be steamed by vacuum vapour deposition, molecular beam It is prepared by the modes such as plating method, the dip coating for being dissolved in solvent, spin-coating method, stick coating method or inkjet printing.It can make for metal motor Prepared with vapour deposition method or sputtering method.
Device experimental shows, organic electroluminescent compounds based on fluoranthene of the present invention as described in structural formula I, with compared with Good heat endurance, high-luminous-efficiency, high luminance purity, low driving voltage.Had using what the organic electroluminescent compounds made Organic electroluminescence devices have the advantages that electroluminescent efficiency is good and excitation purity is excellent and long lifespan.
Brief description of the drawings
Fig. 1 is the mass spectrogram of compound 1；
Fig. 2 is the mass spectrogram of compound 30；
Fig. 3 is a kind of organic electroluminescence device structure diagram of the present invention；
Wherein, 110 glass substrate is represented as, 120 are represented as anode, and 130 are represented as hole transmission layer, and 140 are represented as sending out Photosphere, 150 are represented as electron transfer layer, and 160 are represented as electron injecting layer, and 170 are represented as cathode.
Embodiment
In order to describe the present invention in more detail, especially exemplified by example below, but not limited to this.
Embodiment 1
The synthesis of compound 1
The synthesis of intermediate 1-1
In the single-necked flask of 500mL, 5- bromo indoles (20.00g, 0.1mol), connection boric acid pinacol ester are sequentially added (51.80g, 0.2mmol), potassium acetate (22.80g, 0.2mol), [double (diphenylphosphino) ferrocene of 1,1'-] palladium chloride (1.50g) and 350mL dioxane, flow back 8h under nitrogen protection, and revolving removes dioxane after cooling, is distilled with 200mL Extracted 3 times with dichloromethane after water washing.Product 21.8g is recrystallized to give with methanol dichloromethane, yield is 90%.
The synthesis of intermediate 1-2
In the single-necked flask of 50mL, intermediate 1-1 (2.4g, 10mmol), 9- phenyl -9- (4- bromobenzenes are sequentially added Base)-fluorenes (4.4g, 11mmoleq), potassium carbonate (2.7g, 20mmol), four triphenyl phosphorus palladiums (50mg), dioxane (20.0mL) With water (4.0mL), flow back 5h under nitrogen protection.Revolving removes dioxane after cooling, is distilled with 20mL after water washing with two Chloromethanes extracts 3 times.Crude product purifies to obtain product 3.5g through column chromatography, and yield is 80%.
The synthesis of compound 1
In flask, intermediate 1-2 (0.5g, 1.15mmol), 4- bromines triphenylamine (0.5g, 1.56mmol), tertiary fourth are added Potassium alcoholate (0.2g, 1.78mmol), ortho-xylene (30ml), palladium (30mg) and X-phos (90mg), add under nitrogen protection When heat reflux 10 is small, cooling removes solvent, and crude product purifies to obtain product 0.5g, yield 64% through column chromatography.
Embodiment 2
The synthesis of compound 9
Synthetic method is as compound 1, in addition to replacing 4- bromine triphenylamines with the bromo- 9- phenyl-carbazoles of 3-, yield 73%.
Embodiment 3
The synthesis of compound 13
Synthetic method is as compound 1, in addition to replacing 4- bromine triphenylamines with 9- (4- bromophenyls) carbazole, yield 80%.
Embodiment 4
The synthesis of compound 15
The synthesis of intermediate 15-1
Synthetic method is as with intermediate 1-2, except being yield 86% outside raw material with bromo- 9, the 9- diphenylfluorenes of 2-.
The synthesis of compound 15
Synthetic method is as the synthesis of compound 1, in addition to replacing intermediate 1-2 with intermediate 15-1, yield 72%.
Embodiment 5
The synthesis of compound 18
Synthetic method is as compound 15, in addition to replacing 4- bromine triphenylamines with the bromo- 9- phenyl-carbazoles of 3-, yield 67%.
Embodiment 6
The synthesis of compound 21
Synthetic method is as compound 15, in addition to replacing 4- bromine triphenylamines with 9- (4- bromophenyls) carbazole, yield 74%.
Embodiment 7
The synthesis of compound 23
The synthesis of intermediate 23-1
Synthetic method is as intermediate 1-2, outside with bromo- 9, the 9- diphenylfluorenes of 4- as raw material, yield 90%.
The synthesis of compound 23
Synthetic method is as the synthesis of compound 1, in addition to replacing intermediate 1-2 with intermediate 23-1, yield 77%.
Embodiment 8
The synthesis of compound 27
Synthetic method is as compound 23, in addition to replacing 4- bromine triphenylamines with the bromo- 9- phenyl-carbazoles of 3-, yield 85%.
Embodiment 9
The synthesis of compound 30
Synthetic method is as compound 23, in addition to replacing 4- bromine triphenylamines with the bromo- 9- phenyl-carbazoles of 3-, yield 83%.
Embodiment 10-18
The preparation of organic electroluminescence device
OLED is prepared using the compound of embodiment 1-9 and comparative example.
First, by electrically conducting transparent ito glass substrate 110 (carrying anode 120 above) (the limited public affairs of South China glass group share Department) pass through successively：Deionized water, ethanol, acetone and deionized water are cleaned, then with oxygen plasma treatment 30 seconds.
Then, the compounds of this invention and comparative compound (such as following table) is deposited, forms the hole transmission layer 130 of 60nm thickness.
Then, the Alq of 30nm thickness is deposited on hole transmission layer3As luminescent layer 140.
Then, the Alq of 20nm thickness is deposited on the light-emitting layer3As electron transfer layer 150.
Finally, evaporation 1nm LiF are electron injecting layer 160 and 100nm Al as device cathodes 170.
Prepared device (structure diagram is shown in Fig. 1) with Photo Research PR650 spectrometers measure 150mA/cm2Current density under efficiency it is as shown in the table.
Table 1
Embodiment Compound Current efficiency (cd/A) Color
10 1 1.9 Green
11 9 1.3 Green
12 13 1.6 Green
13 15 1.7 Green
14 18 1.3 Green
15 21 1.5 Green
16 23 2.6 Green
17 27 1.4 Green
18 30 1.7 Green
Comparative example 1 NPB 1.2 Green
Under the same conditions, the organic electroluminescence device prepared using the organic electroluminescent compounds of the present invention Driving voltage is less than comparative example, as described above, the compound of the present invention has high stability, organic electroluminescence prepared by the present invention Luminescent device has low driving voltage, high efficiency and optical purity.
The structural formula of compound described in device is as follows：
Preferred embodiment of the invention described in detail above.It should be appreciated that those of ordinary skill in the art without Need creative work to conceive according to the present invention and make many modifications and variations.Therefore, all technologies in the art Personnel are available by logical analysis, reasoning, or a limited experiment on the basis of existing technology under this invention's idea Technical solution, all should be in the protection domain being defined in the patent claims.

Claims (10)

1. a kind of organic electroluminescent compounds based on fluorenes and indolyl radical, it is characterised in that it is with following structural formula I Compound：
Wherein, Ar is selected from triaromatic amine base, 9- aryl carbazoles and carbazyl.
2. the organic electroluminescent compounds according to claim 1 based on fluorenes and indolyl radical, it is characterised in that described Aromatic radical is selected from phenyl, xenyl, naphthyl, anthryl, phenanthryl, pyrenyl, base, fluoranthene base, (9,9- dialkyl group) fluorenyl, (9,9- Two substituted or unsubstituted aryl) fluorenyl, 9,9- be Spirofluorene-based, dibenzothiophene, dibenzofuran group, or by C1-C12's Alkyl-substituted above aryl.
3. the organic electroluminescent compounds according to claim 1 based on fluorenes and indolyl radical, it is characterised in that it is The compound of following structural 1-32：
4. a kind of organic electroluminescence device, it includes anode, cathode and organic layer, and organic layer includes luminescent layer, hole is injected At least one layer in layer, hole transmission layer, exciton barrier-layer, electron transfer layer, it is characterised in that in the organic layer at least One layer contains the organic electroluminescent compounds based on fluorenes and indolyl radical as claimed in claim 1.
5. organic electroluminescence device according to claim 4, it is characterised in that as described in structural formula I based on fluorenes and Yin Layer where the organic electroluminescent compounds of diindyl group is hole transmission layer.
6. organic electroluminescence device according to claim 4, it is characterised in that as described in structural formula I based on fluorenes and Yin The organic electroluminescent compounds of diindyl group are the compound of structural formula 1-32.
7. organic electroluminescence device according to claim 4, it is characterised in that as described in structural formula I based on fluorenes and Yin The organic electroluminescent compounds of diindyl group are used alone, or are used in mixed way with other compounds.
8. organic electroluminescence device according to claim 4, it is characterised in that as described in structural formula I based on fluorenes and Yin A kind of compound therein is used alone in the organic electroluminescent compounds of diindyl group, or uses two kinds in structural formula I at the same time Compound above.
9. organic electroluminescence device according to claim 4, it is characterised in that the gross thickness of the organic layer is 1- 1000nm。
10. organic electroluminescence device according to claim 4, it is characterised in that the film thickness 10- of the luminescent layer 50nm。
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KR20110064726A (en) * 2009-12-08 2011-06-15 제일모직주식회사 Manufacturing method for organic photoelectric device, organic photoelectric device using the same

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