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CN109265450A - A kind of organic electroluminescent compounds and luminescent device of the aphthofurans containing benzo - Google Patents

A kind of organic electroluminescent compounds and luminescent device of the aphthofurans containing benzo Download PDF

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Publication number
CN109265450A
CN109265450A CN201811238349.3A CN201811238349A CN109265450A CN 109265450 A CN109265450 A CN 109265450A CN 201811238349 A CN201811238349 A CN 201811238349A CN 109265450 A CN109265450 A CN 109265450A
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organic
aphthofurans
organic electroluminescent
electroluminescent compounds
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黄锦海
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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 present invention provides a kind of organic electroluminescent compounds of aphthofurans containing benzo, have the following structure formula:The compound has preferable thermal stability, high-luminous-efficiency, high luminance purity, can be applied to organic electroluminescence device, organic solar batteries, Organic Thin Film Transistors or organophotoreceptorswith field.The present invention also provides a kind of organic electroluminescence devices, the device includes anode, cathode and organic layer, organic layer includes at least one layer in luminescent layer, hole injection layer, hole transmission layer, hole blocking layer, electron injecting layer, electron transfer layer, the at least one layer compound containing such as structural formula I in organic layer has the advantages that electroluminescent efficiency is good and excitation purity is excellent and the service life is long using the organic electroluminescence device that the compound makes.

Description

A kind of organic electroluminescent compounds and luminescent device of the aphthofurans containing benzo
Technical field
The present invention relates to field of organic electroluminescent materials, and in particular to a kind of organic electroluminescence hair of the aphthofurans containing benzo Optical compounds further relate to a kind of organic electroluminescence device.
Background technique
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 according to need the material by changing luminescent layer to adjust 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 and 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, due to low efficiency, it is wider that the factors such as service life is short restrict it General application, especially large screen display.And restricting one of key factor is exactly in organic electroluminescence device The performance of electroluminescent organic material.Additionally, due to OLED device when applying voltage-operated, Joule heat can be generated, 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 lower than 25%, and promotion is arrived 100% (Baldo M.A., Forrest S.R.Et al, Nature, 1998,395,151-154), application also greatly mention The high efficiency of organic electroluminescence device.Generally, electroluminescent phosphorescence needs commonly to be used as phosphorus using host-guest system technology 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 It is easily transmitted and the characteristic of electronics difficulty flowing in the hole of CBP, so that the charge unbalance of luminescent layer, as a result reduces the effect of device Rate.
Summary of the invention
The present invention provides a kind of organic electroluminescent compounds of aphthofurans containing benzo, to have the following structure formula The compound of I:
Wherein, X is selected from O, S, Se, CR1R2And NR3；
R1-R3Aryl independently selected from hydrogen, the alkyl of C1-C12, substitution or unsubstituted C6-C30 replaces or not The heteroaryl of substituted C3-C30；
Ar1Carbazyl, C18-C30 selected from substitution or unsubstituted C12-C30 replace or unsubstituted three fragrance Amido, the substitution of C8-C30 or unsubstituted indyl；
Ar2And Ar3Heteroaryl independently selected from hydrogen or substitution or unsubstituted C3-C30, and Ar2And Ar3When different For hydrogen.
Preferably, X is selected from O and S.
Preferably, Ar2And Ar3Selected from hydrogen or following aryl or heteroaryl: pyridyl group, pyrimidine radicals, pyridazinyl, triazine radical, miaow Oxazolyl, oxazolyl, thiazolyl, thiadiazolyl group, quinolyl, isoquinolyl, quinazolyl, quinoxalinyl, azepine dibenzofurans Base, azepine dibenzothiophene, imidazole radicals.
It is further preferred that the aryl and heteroaryl are further replaced by the alkyl of C1-C12.
Preferably, the organic electroluminescent compounds of the aphthofurans containing benzo are the chemical combination of following structural 1-56 Object:
The organic electroluminescent compounds of the aphthofurans containing benzo of the invention can be applied to organic electroluminescence device, Solar 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 Include at least one in luminescent layer, hole injection layer, hole transmission layer, hole blocking layer, electron injecting layer, electron transfer layer Layer, at least one layer of organic electroluminescent compounds containing the aphthofurans containing benzo as described in structural formula I in the organic layer.
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, the layer where the organic electroluminescent compounds of the aphthofurans containing benzo is luminescent layer, hole At least one layer in transport layer, hole injection layer.
The organic electroluminescent compounds of the aphthofurans containing benzo as described in structural formula I are used alone, or with otherization Object is closed to be used in mixed way；The organic electroluminescent compounds of the aphthofurans containing benzo as described in structural formula I can be used alone it One of compound, can also be simultaneously using two or more the compound in structural formula I；A kind of choosing is used alone The organic electroluminescent compounds of the aphthofurans containing benzo of self-structure formula 1-56, or structural formula is selected from using two or more simultaneously The organic electroluminescent compounds of the aphthofurans containing benzo of 1-56.
It is further preferred that organic electroluminescence device of the invention include anode, hole injection layer, hole transmission layer, Luminescent layer, electron transfer layer, electron injecting layer and cathode wherein contain one or more kinds of structural formula I's in luminescent layer Compound；It is further preferred that the compound containing one or more kinds of structural formula 1-56 in luminescent layer.
The overall thickness of organic electroluminescence device organic layer of the 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 organic electroluminescence device of the 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 can be used with the compound of the present invention It outside, can also include other small molecules and macromolecular organic compound, including but not limited to carbazole compound, triaromatic amine Close object, benzidine compound, compound of fluorene class, phthalocyanine-like compound, the miscellaneous triphen (hexanitrilehexaaza of six cyano six Triphenylene), tetra- cyanogen dimethyl-parabenzoquinone (F4-TCNQ) of 2,3,5,6- tetra- fluoro- 7,7', 8,8'-, polyvinyl carbazole, Polythiophene, polyethylene or polyphenyl sulfonic acid.
The luminescent layer of organic electroluminescence device of the invention has the good characteristics of luminescence, can be adjusted according to the needs The range of visible light.Except it is of the invention there is Compounds of structural formula I in addition to, 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 It reaches in effectively electronics from cathode transport to luminescent layer, there is very big electron mobility.It can choose following compound, 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 from cathode by the electron injecting layer of organic electroluminescence device of the present invention In, it is mainly selected from the alkali metal perhaps compound of alkali metal or compound or alkali selected from alkaline-earth metal or alkaline-earth metal Metal complex can choose following compound, but not limited to this: alkali metal, alkaline-earth metal, rare earth metal, alkali metal Oxide or 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 that can also be used with mixture, can also be used cooperatively with other electroluminescent organic materials.
Each layer of organic layer in organic electroluminescence device of the 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 the organic electroluminescent compounds of containing benzo aphthofurans of the present invention as described in structural formula I, With preferable thermal stability, high-luminous-efficiency, high luminance purity.Had using the organic electroluminescence device that the compound makes The advantage that electroluminescent efficiency is good and excitation purity is excellent and the service life is long.
Detailed description of the invention
Fig. 1 is a kind of organic electroluminescence device structural schematic diagram of the invention,
Wherein, 110 it is represented as glass substrate, 120 are represented as anode, and 130 are represented as hole injection layer, and 140 are represented as sky Cave transport layer, 150 are represented as barrier layer, and 160 are represented as luminescent layer, and 170 are represented as electron transfer layer, and 180 are represented as electronics note Enter layer, 190 are represented as cathode.
Specific embodiment
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 9
The synthetic method of intermediate 9-1
In flask, bromo benzo aphthofurans (5g, 17mmol) is sequentially added, 3- boric acid -9- phenyl carbazole (5.4g, 18.6mmol), potassium carbonate (5.4g, 40mmol), palladium acetate (0.05g), X-phos (0.1g), tetrahydrofuran (50mL) and water (20mL) is heated to reflux 10 hours under nitrogen protection, cooling, is extracted with dichloromethane, dry, and concentration, crude product is through column layer Analysis purifying obtains 6.6g, yield 85%.
The synthetic method of intermediate 9-2
It in flask, is added intermediate 9-1 (6g, 13mmol), dry tetrahydrofuran (70mL) is cold under nitrogen protection But -78 DEG C are arrived, the hexane solution (15.6mmol) of the n-BuLi of 2.5M is slowly added to, is slowly warming up to that be stirred at room temperature 2 small When, -78 DEG C are again cooled to, triisopropyl borate ester (4g, 15.6mmol) is slowly added to, is added dropwise, then be to slowly warm up to room Temperature is reacted 5 hours, and the dilute hydrochloric acid that 1N is added adjusts pH to 7, is extracted with dichloromethane, dry, and concentration is obtained through column chromatographic purifying To 2.8g, yield 43%.
The synthetic method of compound 9
In flask, sequentially add intermediate 9-2 (2g, 4mmol), chloro- 4, the 6- diphenyl -1,3,5-triazines of 2- (1g, 4mmol), potassium carbonate (1.4g, 10mmol), palladium acetate (0.05g), X-phos (0.1g), tetrahydrofuran (20mL) and water (10mL) is heated to reflux 10 hours under nitrogen protection, cooling, is extracted with dichloromethane, dry, and concentration, crude product is through column layer Analysis purifying obtains 1.6g, yield 59%.
Embodiment 2
The synthetic route of compound 20
Its synthetic method is such as compound 9, and raw materials used is intermediate 9-2 and bromo benzimidazole, yield are 78%.
Embodiment 3
The synthetic route of compound 24
For the synthetic method of intermediate 24-1 such as intermediate 9-1, raw materials used is 9- phenyl -2- carbazole boric acid, is produced Rate is 79%.
The synthetic method of intermediate 24-2 is such as intermediate 9-2, and raw materials used is intermediate 24-1, and yield is 38%.
The synthetic method of compound 24 is such as compound 9, yield 73%.
Embodiment 4
The synthetic route of compound 34
For the synthetic method of intermediate 34-1 such as intermediate 9-1, raw materials used is 4- carbazyl-phenyl-boronic acid, is produced Rate is 74%.
The synthetic method of intermediate 34-2 is such as intermediate 9-2, and raw materials used is intermediate 34-1, and yield is 30%.
The synthetic method of compound 34 is such as compound 9, yield 76%.
Embodiment 5
The synthetic route of compound 35
For the synthetic method of compound 35 such as compound 9, raw materials used is intermediate 34-2, yield 76%.
Embodiment 6-10
The preparation of organic electroluminescence device
OLED is prepared using the compound of embodiment
Firstly, by electrically conducting transparent ito glass substrate 110 (having anode 120 above) (the limited public affairs of South China glass group share Department) successively pass through: deionized water, ethyl alcohol, acetone and deionized water were cleaned, then with oxygen plasma treatment 30 seconds.
Then, the PEDOT:PSS (Polyglycolic acid fibre-is poly- (styrene sulfonate)) of spin coating 45nm thickness is on ITO It is 30 minutes dry at 130,150 DEG C of hole injection layer.
Then, the TAPC that 45nm thickness is deposited on hole injection layer is hole mobile material 140.
Then, TCTA is deposited, forms the electronic barrier layer 150 of 5nm thickness.
Then, the luminescent layer 160 of 20nm thickness is deposited on electronic barrier layer, wherein shine based on the compounds of this invention Material, and the Ir (pq) for being 5% with weight ratio2Acac adulterates guest materials as phosphorescence.
Then, the TmPYPB of 55nm thickness is deposited on the light-emitting layer as electron transfer layer 170.
Finally, vapor deposition 0.6nm LiF is electron injecting layer 180 and 80nm Al as device cathodes 190.
Prepared device (structural schematic diagram is shown in Fig. 1) with Photo Research PR650 spectrometer measure 10000cd/m2Brightness under external quantum efficiency be such as table 1.
Comparative example 1
Device prepared by comparative example 1 is as embodiment 6-10 device preparation method, in addition to replacing chemical combination of the present invention with CBP Object as material of main part outside.
1 experimental result of table
The structural formula of compound described in device is as follows:
From table 1 it follows that new Organic Electro Luminescent Materials of the invention are used for organic electroluminescence device, it can be with Operating voltage is reduced, device efficiency is improved, is the phosphorescent light body material with excellent performance.As described above, chemical combination of the invention Object has high stability, and the organic electroluminescence device of preparation has 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 within the scope of protection determined by the claims.

Claims (10)

1. a kind of organic electroluminescent compounds of aphthofurans containing benzo, which is characterized in that be the change for having the following structure Formulas I Close object:
Wherein, X is selected from O, S, Se, CR1R2And NR3；
R1-R3Aryl, substitution or unsubstituted independently selected from hydrogen, the alkyl of C1-C12, substitution or unsubstituted C6-C30 C3-C30 heteroaryl；
Ar1Selected from replace or the carbazyl of unsubstituted C12-C30, C18-C30 replace or unsubstituted triaromatic amine base, The substitution of C8-C30 or unsubstituted indyl；
Ar2And Ar3Heteroaryl independently selected from hydrogen or substitution or unsubstituted C3-C30, and Ar2And Ar3It is not simultaneously hydrogen.
2. the organic electroluminescent compounds of the aphthofurans containing benzo as described in claim 1, which is characterized in that X be selected from O and S。
3. the organic electroluminescent compounds of the aphthofurans containing benzo as described in claim 1, which is characterized in that Ar2And Ar3 Selected from hydrogen or following aryl or heteroaryl: pyridyl group, pyrimidine radicals, pyridazinyl, triazine radical, imidazole radicals, oxazolyl, thiazolyl, thiophene Di azoly, quinolyl, isoquinolyl, quinazolyl, quinoxalinyl, azepine dibenzofuran group, azepine dibenzothiophene, miaow Oxazolyl.
4. the organic electroluminescent compounds of the aphthofurans containing benzo as claimed in claim 3, which is characterized in that the aryl Further replaced by the alkyl of C1-C12 with heteroaryl.
5. the organic electroluminescent compounds of the aphthofurans containing benzo as described in claim 1, which is characterized in that be following knot The compound of structure formula 1-56:
6. the organic electroluminescent compounds of the aphthofurans described in claim 1 containing benzo are in organic electroluminescence device Using.
7. a kind of organic electroluminescence device, which includes anode, cathode and organic layer, and organic layer includes luminescent layer, hole Implanted layer, hole transmission layer, hole blocking layer, electron injecting layer, at least one layer in electron transfer layer, which is characterized in that institute State at least one layer of organic electroluminescent compounds containing the aphthofurans containing benzo as described in claim 1 in organic layer.
8. organic electroluminescence device as claimed in claim 7, which is characterized in that naphtho- containing benzo described in claim 1 Layer where the organic electroluminescent compounds of furans is luminescent layer.
9. organic electroluminescence device as claimed in claim 7, which is characterized in that naphtho- containing benzo described in claim 1 The organic electroluminescent compounds of furans are used alone, or are used in mixed way with other compounds.
10. organic electroluminescence device as claimed in claim 7, which is characterized in that be used alone a kind of selected from as right is wanted The organic electroluminescent compounds of the aphthofurans containing benzo of structural formula 1-56 described in asking 5, or two or more choosings are used simultaneously From the organic electroluminescent compounds of the aphthofurans containing benzo of structural formula 1-56 as claimed in claim 5.
CN201811238349.3A 2018-10-23 2018-10-23 A kind of organic electroluminescent compounds and luminescent device of the aphthofurans containing benzo Pending CN109265450A (en)

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Application publication date: 20190125