CN108658953A - A kind of compound based on dibenzofurans and carbazole and application thereof and luminescent device - Google Patents

A kind of compound based on dibenzofurans and carbazole and application thereof and luminescent device Download PDF

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CN108658953A
CN108658953A CN201810468720.9A CN201810468720A CN108658953A CN 108658953 A CN108658953 A CN 108658953A CN 201810468720 A CN201810468720 A CN 201810468720A CN 108658953 A CN108658953 A CN 108658953A
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layer
compound
carbazole
dibenzofurans
electroluminescence device
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黄锦海
苏建华
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Shanghai Taoe Chemical Technology Co Ltd
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Shanghai Taoe Chemical Technology Co Ltd
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Abstract

The compound based on dibenzofurans and carbazole that the present invention provides a kind of, has the following structure formula：The compound has preferable thermal stability, it can be applied to organic electroluminescence device, solar cell, Organic Thin Film Transistors or organophotoreceptorswith field, when applied to organic electroluminescence device, operating voltage can be reduced, device efficiency is improved, the organic electroluminescence device of preparation has high efficiency and optical purity.

Description

A kind of compound based on dibenzofurans and carbazole and application thereof and luminescent device
Technical field
The present invention relates to field of organic electroluminescent materials, and in particular to a kind of chemical combination based on dibenzofurans and carbazole Object and application thereof further relates to a kind of luminescent device.
Background technology
Organic electroluminescence device (OLEDs) is between two metal electrodes by spin coating or vacuum evaporation deposition one 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 generated by cathode is followed to be incorporated in through electron transfer layer through hole transmission layer in the hole generated by anode Luminescent layer forms exciton, then shines.Organic electroluminescence device can be adjusted as desired by the material for changing luminescent layer Section emits the light of various needs.
Organic electroluminescence device has self-luminous, wide viewing angle, low energy consumption, efficiency as a kind of novel display technology High, thin, rich in color, fast response time, Applicable temperature range be wide, low driving voltage, can make flexible with it is transparent Display panel and the particular advantages such as environmental-friendly can be applied on flat-panel monitor and a new generation's illumination, be can also be used as The backlight of LCD.
Since the invention at the bottom of the 1980s, organic electroluminescence device is industrially 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, especially large screen display.And it is exactly in organic electroluminescence device to restrict one of key factor The performance of electroluminescent organic material.Additionally, due to OLED device when applying voltage-operated, Joule heat will produce so that Organic material is easy to happen crystallization, affects service life and the efficiency of device, therefore, it is also desirable to develop the organic electroluminescence of stability and high efficiency Luminescent material.
Organic electrophosphorescenpolymer phenomenon, breaches theoretical limitation of the organic electroluminescent quantum efficiency less than 25%, and promotion is arrived 100% (Baldo M.A., Forrest S.R.Et al, Nature, 1998,395,151-154), application also greatly carry The high efficiency of organic electroluminescence device.Usually, electroluminescent phosphorescence needs to use host-guest system technology, is commonly used as phosphorus The CBP (4,4'-bis (9-carbazolyl)-biphenyl) of light material of main part has efficient and high triplet energy level, when its work Based on material when, triplet energy state effectively can be transferred to object phosphorescent light-emitting materials from light emitting host material.But by In the characteristic of the hole of CBP easily transmission and the flowing of electronics difficulty so that as a result the charge unbalance of luminescent layer reduces the effect of device Rate.
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 anode, improves efficiency and the thermostabilization of device.Traditional hole-injecting material, such as copper Phthalocyanine (CuPc), degradation 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., thermal stability is poor, also largely influences device lifetime.Thus, it needs Develop the electroluminescent organic material of efficient stable.
Invention content
The compound based on dibenzofurans and carbazole that the present invention provides a kind of, is the change for having the following structure Formulas I Close object：
Wherein, Ar is selected from substitution either unsubstituted aryl, the substitution of C3-C30 or the unsubstituted heteroaryl of C6-C30 Substitution either unsubstituted triaromatic amine base, the substitution of C12-C30 or the unsubstituted carbazyl of base, C18-C30.
Optionally, the Ar is further replaced by the alkyl of C1-C12.
Optionally, the aryl is selected from phenyl, diphenyl, naphthalene, phenyl napthyl, xenyl, three simultaneously phenyl, anthryl, phenanthrene Base, pyrenyl, base, fluoranthene base, acenaphthenyl, acenaphthylene base, (9,9- dialkyl group) fluorenyl, (9,9- bis- replaces or unsubstituted aryl) Fluorenyl, substitution either unsubstituted dibenzothiophene and substitution or unsubstituted dibenzofuran group.
Further alternative, the compound based on dibenzofurans and carbazole is the compound of following structural 1-48：
The compound based on dibenzofurans and carbazole of the present invention can be reacted by Buchwald-Hartwig and crow Germania is anti-, suzkui should be prepared.
The compound based on dibenzofurans and carbazole of the present invention can be applied to organic electroluminescence device, solar energy Battery, Organic Thin Film Transistors or organophotoreceptorswith field.
The present invention also provides a kind of organic electroluminescence device, which includes anode, cathode and organic layer, organic layer Including at least one in luminescent layer, hole injection layer, hole transmission layer, hole blocking layer, exciton barrier-layer or electron transfer layer Layer, it is at least one layer of in the organic layer to contain the compound based on dibenzofurans and carbazole as described in claim 1.
Wherein organic layer is luminescent layer；
Or organic layer is luminescent layer and electron transfer layer；
Or organic layer is luminescent layer, electron transfer layer and electron injecting layer；
Or organic layer is hole transmission layer and luminescent layer；
Or organic layer is hole injection layer, hole transmission layer and luminescent layer；
Or organic layer is hole transmission layer, luminescent layer and electron transfer 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, barrier layer, luminescent layer, electron transfer layer and electron injection Layer；
Or organic layer is hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer and hole blocking layer；
Or organic layer is hole transmission layer, luminescent layer, electron injecting layer and hole blocking layer.
Preferably, wherein the layer where the compound based on dibenzofurans and carbazole as described in structural formula I is hole Transport layer.
Being used alone based on the compound of dibenzofurans and carbazole as described in structural formula I, or it is mixed with other compounds It closes and uses；The compound based on dibenzofurans and carbazole as described in structural formula I can be used alone one such chemical combination Object can also use two or more the compound in structural formula I simultaneously；It is used alone a kind of selected from structural formula 1-48 Compound based on dibenzofurans and carbazole, or simultaneously using two or more selected from structural formula 1-48 based on dibenzo furan The compound muttered with carbazole.
Still optionally further, organic electroluminescence device of the invention include anode, hole injection layer, hole transmission layer, In luminescent layer, electron transfer layer, electron injecting layer and cathode, wherein luminescent layer or hole transmission layer containing it is a kind of or it is a kind of with On structural formula I the compound based on dibenzofurans and carbazole；It is further preferred that in luminescent layer or hole transmission layer The compound based on dibenzofurans and carbazole containing one or more kinds of structural formula 1-48.
The overall thickness of the organic electroluminescence device organic layer of the present invention is 1-1000nm, preferably 50-500nm.
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 barrier layer Deng, 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.In addition to the present invention is with Compounds of structural formula I, Can also include other small molecules and macromolecular organic compound, including but not limited to carbazole compound, triaromatic amine chemical combination Object, benzidine compound, compound of fluorene class, phthalocyanine-like compound, six cyano, six miscellaneous triphen (hexanitrilehexaazatr Iphenylene tetra- cyanogen dimethyl-parabenzoquinone (F4-TCNQ) of), tetra- fluoro- 7,7' of 2,3,5,6-, 8,8'-, gathers at polyvinyl carbazole Thiophene, polyethylene or polyphenyl sulfonic acid.
The luminescent layer of the organic electroluminescence device of the present invention has the good characteristics of luminescence, can be adjusted according to the needs The range of visible light.In addition to the present invention is with Compounds of structural formula I, following compound can also be contained, but not limited to this, Naphthalene compounds, pyrene compound, compound of fluorene class, luxuriant and rich with fragrance class compound,Class compound, glimmering anthracene compound, anthracene class chemical combination Object, pentacene class compound, class compound, two aromatic ethylene class compounds, triphenylamine ethylene compounds, aminated compounds, Benzimidazoles compound, furfuran compound, organic metal chelate complex.
The Organic Electron Transport Material of organic electroluminescence device of the present invention requires good electronic transmission performance, energy In reaching effectively electronics from cathode transport to luminescent layer, there is prodigious 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 Object, 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 the compound selected from alkaline-earth metal or alkaline-earth metal or alkali 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.Metal motor can be made It is prepared with vapour deposition method or sputtering method.
Device experimental shows compound based on dibenzofurans and carbazole of the present invention as described in structural formula I, have compared with Good thermal stability, high-luminous-efficiency, high luminance purity.Using this based on the organic of the compound of dibenzofurans and carbazole making Electroluminescent device has the advantages that electroluminescent efficiency is good and excitation purity is excellent and long lifespan.
Description of the drawings
Fig. 1 is a kind of organic electroluminescence device structural schematic diagram of the present invention,
Wherein, 110 be glass substrate, and 120 be anode, and 130 be hole injection layer, and 140 be hole transmission layer, and 150 be hair Photosphere, 160 be electron transfer layer, and 170 be electron injecting layer, and 180 be cathode.
Specific implementation mode
In order to describe the present invention in more detail, spy lifts following example, and but not limited to this.
Embodiment 1
The synthetic route of compound 1
The synthetic method of intermediate A
In flask, 4- (4- dibenzofuran groups)-aniline (10g, 28.6mmol), 9- (3- (4- bromophenyls) benzene) is added Carbazole (11.4g, 28.6mmol), sodium tert-butoxide (3.3g, 34.3mmol), palladium (0.1g), X-phos (0.3g), toluene (150mL) is heated to reflux 5 hours under nitrogen protection, and cooling, removing solvent, crude by column chromatography purifies to obtain 10.7g productions Object, yield 65%.
The synthetic method of compound 1
For synthetic method as the synthetic method of intermediate A, raw materials used is intermediate A and iodobenzene, yield 73%.
The synthetic method of other embodiment as the synthetic method of compound 1, be all use intermediate A as raw material, then It is reacted with other bromo-derivatives and iodo object, it is specific such as table 1：
Table 1
Embodiment 17-32
The preparation of organic electroluminescence device
OLED is prepared using the compound of embodiment
First, by electrically conducting transparent ito glass substrate 110 (carrying anode 120 above) (the limited public affairs of South China glass group share Department) it passes through successively：Deionized water, ethyl alcohol, acetone and deionized water were cleaned, then with oxygen plasma treatment 30 seconds.
Then, on ITO spin coating 45nm thickness PEDOT:PSS (Polyglycolic acid fibre-is poly- (styrene sulfonate)) is It is 30 minutes dry at 130,150 DEG C of hole injection layer.
Then, the compounds of this invention of 40nm thickness is deposited on hole injection layer as hole mobile material 140.
Then, the luminescent layer 150 of 30nm thickness is deposited on electronic barrier layer, wherein luminescent material based on CBP, and with The Ir (ppy) that weight ratio is 8%3Guest materials is adulterated as phosphorescence.
Then, the TMPYPB of 40nm thickness is deposited on the light-emitting layer as electron transfer layer 160.
Finally, vapor deposition 1nm LiF are electron injecting layer 170 and 80nm Al as device cathodes 180.
Prepared device (structural schematic diagram is shown in Fig. 1) with Photo Research PR650 spectrometers measure 100mA/cm2Current density under external quantum efficiency be such as table 2.
Comparative example 1
In addition to use NPB replace the compounds of this invention as hole mobile material other than, comparative example prepares the method and reality of device It is the same to apply a 17-32.
Table 2
The structural formula of compound described in device is as follows：
From Table 2, it can be seen that the compound based on dibenzofurans and carbazole of the present invention is used for organic electroluminescent Device can reduce operating voltage, improve device efficiency, be the hole mobile material with excellent performance.As described above, this hair There is bright compound high stability, the organic electroluminescence device of preparation to have high efficiency and optical purity.
The preferred embodiment of the present invention has been described in detail above.It should be appreciated that those skilled in the art without It needs creative work according to the present invention can conceive and makes 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 compound based on dibenzofurans and carbazole, which is characterized in that be the compound for having the following structure Formulas I：
Wherein, Ar be selected from C6-C30 substitution either unsubstituted aryl, the substitution of C3-C30 or unsubstituted heteroaryl, The substitution of C18-C30 either unsubstituted triaromatic amine base, the substitution of C12-C30 or unsubstituted carbazyl.
2. the compound of dibenzofurans as described in claim 1 and carbazole, which is characterized in that the Ar is further by C1- The alkyl of C12 replaces.
3. the compound based on dibenzofurans and carbazole as described in claim 1, which is characterized in that the aryl is selected from benzene Base, diphenyl, naphthalene, phenyl napthyl, xenyl, three and phenyl, anthryl, phenanthryl, pyrenyl, base, fluoranthene base, acenaphthenyl, acenaphthylene Base, (9,9- dialkyl group) fluorenyl, (9,9- bis- replaces either unsubstituted aryl) fluorenyl, substitution or unsubstituted dibenzo thiophene Pheno base and substitution or unsubstituted dibenzofuran group.
4. the compound based on dibenzofurans and carbazole as described in claim 1, which is characterized in that be following structural 1- 48 compound：
5. application of the compound described in claim 1 based on dibenzofurans and carbazole in organic electroluminescence device.
6. a kind of organic electroluminescence device, which includes anode, cathode and organic layer, and organic layer includes luminescent layer, hole At least one layer in implanted layer, hole transmission layer, hole blocking layer, exciton barrier-layer or electron transfer layer, which is characterized in that institute It states at least one layer of containing the compound based on dibenzofurans and carbazole as described in claim 1 in organic layer.
7. organic electroluminescence device as claimed in claim 6, which is characterized in that described in claim 1 to be based on dibenzo Layer where the compound of furans and carbazole is hole transmission layer.
8. organic electroluminescence device as claimed in claim 6, which is characterized in that described in claim 1 to be based on dibenzo The compound of furans and carbazole is used alone, or is used in mixed way with other compounds.
9. organic electroluminescence device as claimed in claim 6, which is characterized in that be used alone a kind of selected from such as claim The compound based on dibenzofurans and carbazole of structural formula 1-48 described in 4, or simultaneously using two or more selected from such as right It is required that the compound based on dibenzofurans and carbazole of the structural formula 1-48 described in 4.
10. organic electroluminescence device as claimed in claim 6, which is characterized in that the overall thickness of the organic layer is 1- 1000nm。
CN201810468720.9A 2018-05-16 2018-05-16 A kind of compound based on dibenzofurans and carbazole and application thereof and luminescent device Pending CN108658953A (en)

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KR20200088704A (en) * 2019-01-15 2020-07-23 머티어리얼사이언스 주식회사 Organic compound and organic electroluminescent device comprising the same
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