CN107417677A - A kind of carbazole pyridines organic electroluminescent compounds and its organic electroluminescence device - Google Patents

A kind of carbazole pyridines organic electroluminescent compounds and its organic electroluminescence device Download PDF

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CN107417677A
CN107417677A CN201710676775.4A CN201710676775A CN107417677A CN 107417677 A CN107417677 A CN 107417677A CN 201710676775 A CN201710676775 A CN 201710676775A CN 107417677 A CN107417677 A CN 107417677A
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compound
carbazole
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黄锦海
苏建华
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Shanghai Taoe Chemical Technology Co Ltd
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Abstract

The invention provides a kind of carbazole pyridines organic electroluminescent compounds, and it has following structure：The compound has preferable heat endurance, high-luminous-efficiency, high luminance purity, it can apply in organic electroluminescence device, organic solar batteries, OTFT or organophotoreceptorswith field, operating voltage can be reduced for organic electroluminescence device, device efficiency is improved, is the phosphorescent light body material with premium properties.Present invention also offers a kind of organic electroluminescence device, the device includes anode, negative electrode 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, at least one layer of compound comprising just like structural formula I in organic layer, the organic electroluminescence device have that electroluminescent efficiency is good and excitation is excellent and the advantages of long lifespans.

Description

A kind of carbazole pyridines organic electroluminescent compounds and its organic electroluminescence device
Technical field
The present invention relates to field of organic electroluminescent materials, and in particular to a kind of carbazole pyridines electroluminescent organic material 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.Hole follows the electronics as caused by negative electrode to be incorporated in through electron transfer layer through hole transmission layer as caused by anode Luminescent layer forms exciton, then lights.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 environment-friendly, it can apply on flat-panel monitor and a new generation's illumination, can also conduct LCD backlight.
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, because 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 When, Joule heat can be produced so that organic material easily crystallizes, and have impact on life-span and the efficiency of device, therefore, it is also desirable to Develop the electroluminescent organic material of stability and high efficiency.
Organic electrophosphorescenpolymer phenomenon, breaches theoretical limitation of the organic electroluminescent quantum efficiency less than 25%, and lifting is arrived 100% (Baldo M.A., Forrest S.R.Et al, Nature, 1998,395,151-154), its application also greatly carry The high efficiency of organic electroluminescence device.Usually, electroluminescent phosphorescence needs to use host-guest system technology, and conventional is 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 For material of main part when, triplet energy state effectively can be transferred to object phosphorescent light-emitting materials from light emitting host material.But by Easily transmitted and the characteristic of the difficult flowing of electronics in CBP hole so that the charge unbalance of luminescent layer, as a result reduce the effect of device Rate.
The content of the invention
The invention provides a kind of carbazole pyridines organic electroluminescent compounds, and it is the change with following structural formula I Compound：
Wherein, A and B independently selected from
Ar1Aryl selected from substitution or unsubstituted C6-C30；
X is selected from O, S or CR9R10；
R1-R10Independently selected from hydrogen, deuterium, C1-C12 alkyl, C1-C8 alkoxy, substitution or unsubstituted C6- C30 aryl, substitution either unsubstituted C3-C30 heteroaryl, substitution or unsubstituted 5 or 6 circle heterocycles alkyl, substitution Or unsubstituted C7-C30 bicyclic alkyl.
Preferably, R1-R8Independently selected from hydrogen, phenyl or naphthyl；
R9-R10Independently selected from methyl, ethyl, phenyl or naphthyl；
Ar1Selected from hydrogen, phenyl, naphthyl, three and phenyl, anthryl, phenanthryl, pyrenyl, base, fluoranthene base, (9,9- dialkyl group) Fluorenyl, (9,9- bis- substitutes either unsubstituted aryl) fluorenyl, 9,9- be Spirofluorene-based, substitution or unsubstituted dibenzothiophenes base Or substitution or unsubstituted dibenzofuran group, or more aryl and heteroaryl further substituted by C1-C12 alkyl.
It is further preferred that Ar1Selected from phenyl, xenyl, naphthyl or fluorenyl.
It is further preferred that carbazole pyridines organic electroluminescent compounds are following structural 1-57 compound：
A kind of carbazole pyridines organic electroluminescent compounds of the present invention can be applied in organic electroluminescence device, had Machine solar cell, OTFT or organophotoreceptorswith field.
Present invention also offers a kind of organic electroluminescence device, the device includes anode, negative electrode 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, wherein at least one layer carbazole pyridines organic electroluminescent compounds contained as described in structural formula I in the organic layer：
Wherein R1-R3, A and B it is defined as described above.
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 carbazole pyridines organic electroluminescent compounds as described in structural formula I is luminous Layer.
Preferably, the carbazole pyridines organic electroluminescent compounds wherein described in structural formula I are structural formula 1-57 change Compound.
When carbazole pyridines organic electroluminescent compounds as described in structural formula I are used for luminescent device preparation, Ke Yidan Solely use, can also be used in mixed way with other compounds；Carbazole pyridines organic electroluminescent compounds as described in structural formula I A kind of compound therein is can be used alone, the two or more compounds in structural formula I can also be used simultaneously.
The organic electroluminescence device of the present invention, further preferred mode are that the organic electroluminescence device includes sun Contain in pole, hole injection layer, hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer and negative electrode, wherein luminescent layer More than one structural formula I compound；It is further preferred that the chemical combination containing more than one structural formula 1-57 in luminescent layer Thing.
The gross thickness of the organic electroluminescence device organic layer of the present invention is 1-1000nm, preferably 50-500nm.
When having structural formula I compound 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, gold-tinted, 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, effectively hole can be transferred on luminescent layer from anode.Except the compound with I of the present invention can be used Outside, other small molecules and macromolecular organic compound, including but not limited to carbazole compound, triaromatic amine can also be included Compound, benzidine compound, compound of fluorene class, phthalocyanine-like compound, six cyano group, six miscellaneous triphen (hexanitrilehexaaza Triphenylene the cyanogen dimethyl-parabenzoquinone (F4-TCNQ) of), tetra- fluoro- 7,7' of 2,3,5,6-, 8,8'- tetra-, PVK, 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.In addition to the present invention is with Compounds of structural formula I, still not limited to this can also be contained：Naphthalene compounds, Pyrene compound, compound of fluorene class, luxuriant and rich with fragrance class compound,Class compound, glimmering anthracene compound, anthracene compound, pentacene class Compound, class compound, two aromatic ethylene class compounds, triphenylamine ethylene compounds, aminated compounds, benzimidazole 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 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.
The electron injecting layer of organic electroluminescence device of the present invention, electronics effectively can be injected into organic layer from negative electrode In, it is mainly selected from the compound of alkali metal or alkali metal, or compound or alkali selected from alkaline-earth metal either 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, it 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, carbazole pyridines organic electroluminescent compounds of the present invention as described in structural formula I, with compared with Good heat endurance, high-luminous-efficiency, high luminance purity.Made using the carbazole pyridines organic electroluminescent compounds organic Electroluminescent device has that electroluminescent efficiency is good and excitation is excellent and the advantages of long lifespan.
Brief description of the drawings
Fig. 1 is the hydrogen nuclear magnetic resonance spectrogram of compound 1；
Fig. 2 is the hydrogen nuclear magnetic resonance spectrogram of compound 26；
Fig. 3 is a kind of organic electroluminescence device structural representation of the present invention,
Wherein, 110 glass substrate is represented as, 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 negative electrode.
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
Intermediate 1-1 synthesis
In flask, the addition iodo- pyridines of the bromo- 2- of 5- (8g, 28mmol), dibenzothiophenes -4- boric acid (6.4g, 28mmol), potassium carbonate (7.7g, 28mmol), tetra-triphenylphosphine palladium (0.5g), tetrahydrofuran (100mL) and water (50mL), in nitrogen It is heated to reflux under gas shielded 5 hours, cools down, extracted with dichloromethane, dry concentration, crude product purifies to obtain product through column chromatography 6.4g, yield 68%.
The synthesis of compound 1
Synthetic method is as with intermediate 1-1, and raw materials used is intermediate 1-1 and 9- phenyl -3- carbazole boric acid, yield For 92%, its hydrogen nuclear magnetic resonance spectrogram such as Fig. 1.
Embodiment 2
The synthesis of compound 7
Intermediate 7-1 synthesis
For synthetic method as intermediate 1-1 synthesis, raw materials used is the iodo- pyridines of the bromo- 2- of 5- and 2- dibenzofurans Boric acid, yield 56%.
The synthesis of compound 7
For synthetic method as compound 1-1 synthesis, raw materials used is intermediate 7-1 and 9- phenyl -3- carbazole boric acid, Yield is 85%.
Embodiment 3
The synthesis of compound 15
Intermediate 15-1 synthesis
For synthetic method as intermediate 1-1 synthesis, raw materials used is the iodo- pyridines of the bromo- 2- of 5- and 9- phenyl -3- carbazoles Boric acid, yield 47%.
The synthesis of compound 15
For synthetic method as intermediate 1-1 synthesis, raw materials used is intermediate 15-1 and 4- dibenzothiophenes boric acid, Yield is 83%.
Embodiment 4
The synthesis of compound 26
Synthetic method is as intermediate 1-1 synthesis, and raw materials used is intermediate 15-1 and 9, the fluorenes boric acid of 9 '-spiral shell two, Yield is 69%, its hydrogen nuclear magnetic resonance spectrogram such as Fig. 2.
Embodiment 5
The synthesis of compound 33
For synthetic method as intermediate 1-1 synthesis, raw materials used is intermediate 1-1 and 9- (3- phenyl-benzene) -3- benzene Base carbazole boric acid, yield 84%.
Embodiment 6
The synthesis of compound 53
Intermediate 53-1 synthesis
Synthetic method as intermediate 1-1 synthesis, it is raw materials used for the iodo- pyridines of the bromo- 2- of 5- and 9- (4- xenyls)- 3- carbazole boric acid, yield 55%.
The synthesis of compound 53
For synthetic method as intermediate 1-1 synthesis, raw materials used is intermediate 53-1 and 9,9- diphenyl -2- fluorenes boron Acid, yield 71%.
Embodiment 7-12
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) pass through successively：Deionized water, ethanol, acetone and deionized water are cleaned, then with oxygen plasma treatment 30 seconds.
Then, the thick MnO of 3nm are deposited on ITO3(molybdenum oxide) is hole injection layer 130,
Then, it is hole mobile material 140 that the thick TAPC of 50nm are deposited on hole injection layer,
Then, TCTA is deposited, forms the thick electronic barrier layers 150 of 5nm.
Then, the thick luminescent layers 160 of 20nm are deposited on electronic barrier layer, wherein, the compounds of this invention lights for main body Material, and with 3% weight than Ir (ppy)3Guest materials is adulterated as phosphorescence.
Then, the thick BmPYPB of 40nm are deposited on luminescent layer as electron transfer layer 170.
Finally, evaporation 1nm LiF are electron injecting layer 180 and 80nm Al as device cathodes 190.
Prepared device (structural representation is shown in Fig. 3) with Photo Research PR650 spectrometers measure 5000cd/m2Brightness under current efficiency be such as table 1.
Comparative example 1
Device prepared by comparative example is as the preparation method of embodiment 7-12 devices, except replacing the present inventionization with CBP Compound as material of main part outside.
Table 1
Embodiment Compound Current efficiency (cd/A) Glow color
7 1 55 Green glow
8 4 54 Green glow
9 13 53 Green glow
10 19 56 Green glow
11 40 57 Green glow
12 49 56 Green glow
Comparative example 1 CBP 45 Green glow
The structural formula of compound described in device is as follows：
As can be seen from the table, carbazole pyridines organic electroluminescent compounds of the invention are used for organic electroluminescence Part, operating voltage can be reduced, improve device efficiency, be the phosphorescent light body material with premium properties.It is as described above, of the invention Compound there is high stability, the organic electroluminescence device of preparation has high efficiency and optical purity.
Preferred embodiment of the invention described in detail above.It should be appreciated that one of ordinary skill in the art without Creative work can is needed to make many modifications and variations according to the design of the present invention.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 scheme, all should be in the protection domain being defined in the patent claims.

Claims (9)

1. a kind of carbazole pyridines organic electroluminescent compounds, it is characterised in that be the compound with following structural formula I：
Wherein, A and B independently selected from
Ar1Aryl selected from substitution or unsubstituted C6-C30；
X is selected from O, S or CR9R10；
R1-R10Independently selected from hydrogen, deuterium, C1-C12 alkyl, C1-C8 alkoxy, substitution or unsubstituted C6-C30 Aryl, substitution either unsubstituted C3-C30 heteroaryl, substitution or unsubstituted 5 or 6 circle heterocycles alkyl, substitution or not Substituted C7-C30 bicyclic alkyl.
2. carbazole pyridines organic electroluminescent compounds as claimed in claim 1, it is characterised in that R1-R8Independently selected from Hydrogen, phenyl, naphthyl；
R9-R10Independently selected from methyl, ethyl, phenyl or naphthyl；
Ar1Selected from hydrogen, phenyl, naphthyl, three and phenyl, anthryl, phenanthryl, pyrenyl, base, fluoranthene base, (9,9- dialkyl group) fluorenyl, (9,9- bis- substitutes either unsubstituted aryl) fluorenyl, 9,9- be Spirofluorene-based, substitution or unsubstituted dibenzothiophenes base or takes Generation or unsubstituted dibenzofuran group, or more aryl and heteroaryl further substituted by C1-C12 alkyl.
3. carbazole pyridines organic electroluminescent compounds as claimed in claim 2, it is characterised in that Ar1Selected from phenyl, connection Phenyl, naphthyl or fluorenyl.
4. carbazole pyridines organic electroluminescent compounds as claimed in claim 1, it is characterised in that it is following structural 1-57 compound：
5. a kind of organic electroluminescence device, the device includes anode, negative electrode and organic layer, and organic layer includes luminescent layer, hole At least one layer in implanted layer, hole transmission layer, hole blocking layer, electron injecting layer, electron transfer layer, it is characterised in that institute State at least one layer carbazole pyridines organic electroluminescent contained as described in any one in Claims 1-4 in organic layer Compound.
6. organic electroluminescence device as claimed in claim 5, it is characterised in that the carbazole pyridines as described in structural formula I Layer where organic electroluminescent compounds is luminescent layer.
7. organic electroluminescence device as claimed in claim 5, it is characterised in that the carbazole pyridines as described in structural formula I Class organic electroluminescent compounds are structural formula 1-57 compound.
8. organic electroluminescence device as claimed in claim 5, it is characterised in that the carbazole pyridines as described in structural formula I A kind of compound therein is used alone in organic electroluminescent compounds, or uses the two or more changes in structural formula I simultaneously Compound.
9. organic electroluminescence device as claimed in claim 5, it is characterised in that organic electroluminescence device organic layer it is total Thickness is 1-1000nm.
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